Pub Date : 2024-06-10DOI: 10.3390/chemistry6030027
A. Mallikarjunaswamy, Gouthami Kuruvalli, K. Syed, Vaddi Damodara Reddy, Vipin A. Nair
Thiocyanates form an important class of organic compounds commonly found in natural products that exhibit excellent antimicrobial activity. The electrophilic thiocyanation is one of the most effective methods of introducing a -SCN functional group to the parent organic molecule. In this work, we explored an eco-friendly and highly efficient method for thiocyanation of anilines and 1-(substituted benzylidene)-2-phenylhydrazines using commercially available N-bromoscuccinimide (NBS) and potassium thiocyanate (KSCN). The optimized protocol afforded thiocyanates with good regioselectivity and excellent yields in comparison to the available methods.
{"title":"An Efficient and Eco-Friendly Procedure for Electrophilic Thiocyanation of Anilines and 1-(Substituted benzylidene)-2-phenyl Hydrazines","authors":"A. Mallikarjunaswamy, Gouthami Kuruvalli, K. Syed, Vaddi Damodara Reddy, Vipin A. Nair","doi":"10.3390/chemistry6030027","DOIUrl":"https://doi.org/10.3390/chemistry6030027","url":null,"abstract":"Thiocyanates form an important class of organic compounds commonly found in natural products that exhibit excellent antimicrobial activity. The electrophilic thiocyanation is one of the most effective methods of introducing a -SCN functional group to the parent organic molecule. In this work, we explored an eco-friendly and highly efficient method for thiocyanation of anilines and 1-(substituted benzylidene)-2-phenylhydrazines using commercially available N-bromoscuccinimide (NBS) and potassium thiocyanate (KSCN). The optimized protocol afforded thiocyanates with good regioselectivity and excellent yields in comparison to the available methods.","PeriodicalId":502867,"journal":{"name":"Chemistry","volume":"103 8","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-06-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141361313","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A visible-light photochromic hybrid film was synthesized based on combining phosphomolybdic acid (PMoA) with the polythiophene (PTh) matrix. The microstructure and photochromic properties of the materials were analyzed through atomic force microscopy (AFM), Fourier transform infrared spectroscopy (FTIR), X-ray photoelectron spectroscopy (XPS) and ultraviolet-visible spectra (UV-vis). According to FTIR spectra, the geometries of PMoA and PTh were well preserved in hybrid film and there exists a strong interaction at the interface of PMoA and PTh. The XPS spectra revealed the change in the chemical microenvironment and the reduction of Mo6+ atoms in the photoreduction reaction. Under visible light irradiation, the composite film changed from transparent to blue and deepened gradually, generating heteropoly blue. The hybrid film also shows reversibility in the presence of oxygen. The results indicated that the photochromic reaction was inconsistent with photoinduced electron transfer mechanism.
{"title":"Visible-Light Photochromic Properties of an Inorganic-Organic Phosphomolybdic Acid/Polythiophene Hybrid Thin Film","authors":"Wanqing Zhao, Hongmei Zhao, Wei Feng, Honggang Zhao","doi":"10.3390/chemistry6030026","DOIUrl":"https://doi.org/10.3390/chemistry6030026","url":null,"abstract":"A visible-light photochromic hybrid film was synthesized based on combining phosphomolybdic acid (PMoA) with the polythiophene (PTh) matrix. The microstructure and photochromic properties of the materials were analyzed through atomic force microscopy (AFM), Fourier transform infrared spectroscopy (FTIR), X-ray photoelectron spectroscopy (XPS) and ultraviolet-visible spectra (UV-vis). According to FTIR spectra, the geometries of PMoA and PTh were well preserved in hybrid film and there exists a strong interaction at the interface of PMoA and PTh. The XPS spectra revealed the change in the chemical microenvironment and the reduction of Mo6+ atoms in the photoreduction reaction. Under visible light irradiation, the composite film changed from transparent to blue and deepened gradually, generating heteropoly blue. The hybrid film also shows reversibility in the presence of oxygen. The results indicated that the photochromic reaction was inconsistent with photoinduced electron transfer mechanism.","PeriodicalId":502867,"journal":{"name":"Chemistry","volume":" 16","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-06-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141373878","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-05-10DOI: 10.3390/chemistry6030023
Alexander I. Dalinger, Sabina F. Mamedova, J. Burykina, Evgeniy O. Pentsak, Sergey Z Vatsadze
The aim of this work was the investigation of novel organocatalysts for the Michael addition of diethyl malonate to β-nitrostyrene. The methodology of the study included NMR titration, reaction monitoring by NMR spectroscopy and electrospray ionization mass spectrometry (ESI-MS), product characterization by MALDI, IR spectroscopy, scanning electron microscopy (SEM), thermal gravimetric analysis (TGA), and elemental analysis. As a result, evidence of supramolecular interactions between two pairs of components of the reaction was found. In addition to the supramolecular complexes, an unusual reaction, i.e., the Michael addition of NH-bispidines to β-nitrostyrene, was found, which led to previously unknown oligomers of β-nitrostyrene. A new mechanism for the catalytic action of NH-bispidine was proposed, which involved catalysis not by the initial organocatalyst but rather by its adduct with β-nitrostyrene. Thus, in this reaction, N-benzylbispidine acted as an initiator, and the real catalyst was the betaine formed during the initiation stage.
{"title":"Reaction of β-Nitrostyrene with Diethyl Malonate in the Presence of Bispidines: The Unusual Role of the Organocatalyst","authors":"Alexander I. Dalinger, Sabina F. Mamedova, J. Burykina, Evgeniy O. Pentsak, Sergey Z Vatsadze","doi":"10.3390/chemistry6030023","DOIUrl":"https://doi.org/10.3390/chemistry6030023","url":null,"abstract":"The aim of this work was the investigation of novel organocatalysts for the Michael addition of diethyl malonate to β-nitrostyrene. The methodology of the study included NMR titration, reaction monitoring by NMR spectroscopy and electrospray ionization mass spectrometry (ESI-MS), product characterization by MALDI, IR spectroscopy, scanning electron microscopy (SEM), thermal gravimetric analysis (TGA), and elemental analysis. As a result, evidence of supramolecular interactions between two pairs of components of the reaction was found. In addition to the supramolecular complexes, an unusual reaction, i.e., the Michael addition of NH-bispidines to β-nitrostyrene, was found, which led to previously unknown oligomers of β-nitrostyrene. A new mechanism for the catalytic action of NH-bispidine was proposed, which involved catalysis not by the initial organocatalyst but rather by its adduct with β-nitrostyrene. Thus, in this reaction, N-benzylbispidine acted as an initiator, and the real catalyst was the betaine formed during the initiation stage.","PeriodicalId":502867,"journal":{"name":"Chemistry","volume":" 6","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-05-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140993701","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-05-09DOI: 10.3390/chemistry6030022
Carlos E. Castillo-Espinoza, M. Gonzalez-Rivera, Alberto Medina-Ortiz, Juan Carlos Barragan-Galvez, Sergio Hidalgo-Figueroa, David Cruz Cruz, M. Devezé-Álvarez, Gerardo González-García, Clarisa Villegas Gómez, Á. Alonso-Castro
Depressive and anxiety disorders constitute some of the most prevalent mental disorders around the world. For years, the development of new lead compounds for drug discovery in this field has been an area of great attention. Recently, a series of tetrahydrocarbazole derivatives have demonstrated important anxiolytic-like activity, associated with their structures and stereochemistry. Here, we present a study of the antidepressant effect and anxiolytic-like activity of a fused thiopyrano-piperidone-tetrahydrocarboline (compound 4). The antidepressant and anxiolytic-like effects of 4 (1–50 mg/kg p.o.) were assessed with the tail suspension test and the hole-board test, respectively. This study determined the possible mechanisms involved in the anxiolytic-like actions of 4 using inhibitors or neurotransmission and evaluated its interaction with 5HT2A receptors using a molecular docking study. As an analog to the tetrahydrocarbazole core, the tetrahydrocarboline derivative showed anxiolytic-like activity (ED50 = 13 mg/kg p.o.) in the hole-board test, with a comparable effect to the reference drug, 1.5 mg/kg clonazepam, with the possible participation of the serotonergic system.
{"title":"Anxiolytic-Like and Antidepressant Effects of a 13H-indolo[2,3-a]thiopyrano[2,3-g]quinolizine Derivative","authors":"Carlos E. Castillo-Espinoza, M. Gonzalez-Rivera, Alberto Medina-Ortiz, Juan Carlos Barragan-Galvez, Sergio Hidalgo-Figueroa, David Cruz Cruz, M. Devezé-Álvarez, Gerardo González-García, Clarisa Villegas Gómez, Á. Alonso-Castro","doi":"10.3390/chemistry6030022","DOIUrl":"https://doi.org/10.3390/chemistry6030022","url":null,"abstract":"Depressive and anxiety disorders constitute some of the most prevalent mental disorders around the world. For years, the development of new lead compounds for drug discovery in this field has been an area of great attention. Recently, a series of tetrahydrocarbazole derivatives have demonstrated important anxiolytic-like activity, associated with their structures and stereochemistry. Here, we present a study of the antidepressant effect and anxiolytic-like activity of a fused thiopyrano-piperidone-tetrahydrocarboline (compound 4). The antidepressant and anxiolytic-like effects of 4 (1–50 mg/kg p.o.) were assessed with the tail suspension test and the hole-board test, respectively. This study determined the possible mechanisms involved in the anxiolytic-like actions of 4 using inhibitors or neurotransmission and evaluated its interaction with 5HT2A receptors using a molecular docking study. As an analog to the tetrahydrocarbazole core, the tetrahydrocarboline derivative showed anxiolytic-like activity (ED50 = 13 mg/kg p.o.) in the hole-board test, with a comparable effect to the reference drug, 1.5 mg/kg clonazepam, with the possible participation of the serotonergic system.","PeriodicalId":502867,"journal":{"name":"Chemistry","volume":" 28","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-05-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140995604","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-02-07DOI: 10.3390/chemistry6010011
Purti Patel, Mannanthara Kunhumon Noushija, S. Shanmugaraju
The design and development of useful chemosensors for the ultra-trace detection of environmental pollutants and contaminants is a topical area of research. Herein, we report a new nanoscale emissive Zn(II) coordination polymer (TB-Zn-CP) for differential fluorescence sensing of various antibiotics in water. TB-Zn-CP was synthesized using a unique V-shaped green emitting 4-amino-1,8-naphthalimide Tröger’s base (TBNap) fluorophore. The structural and morphological features of TB-Zn-CP were characterized by various standard spectroscopic and microscopy techniques. The fluorescence titration studies in water demonstrated a remarkable sensitivity and differential fluorescence sensing properties of TB-Zn-CP for the fast detection of different antibiotics. Among different antibiotics, chloramphenicol (CRP), 1,2-dimethyl-5-nitroimidazole (DMZ), and sulfamethazine (SMZ) displayed the highest fluorescence-quenching efficiency and superior sensitivity in their detection. The differential sensing capability of TB-Zn-CP was also indicated by visualizable color changes. The Stern–Volmer quenching constant KSV was determined to be in the order of 103–104 M−1, and the sensitivity was shown to be at a nanomolar (10−9 M) level. All these results confirm that TB-Zn-CP can be a potential and practically useful polymeric sensor for differential fluorescence and visual detection of different antibiotics in water.
{"title":"Differential Fluorescent Chemosensing of Antibiotics Using a Luminescent Zn(II) Coordination Polymer Based on a 4-Amino-1,8-naphthalimide Tröger’s Base Fluorophore","authors":"Purti Patel, Mannanthara Kunhumon Noushija, S. Shanmugaraju","doi":"10.3390/chemistry6010011","DOIUrl":"https://doi.org/10.3390/chemistry6010011","url":null,"abstract":"The design and development of useful chemosensors for the ultra-trace detection of environmental pollutants and contaminants is a topical area of research. Herein, we report a new nanoscale emissive Zn(II) coordination polymer (TB-Zn-CP) for differential fluorescence sensing of various antibiotics in water. TB-Zn-CP was synthesized using a unique V-shaped green emitting 4-amino-1,8-naphthalimide Tröger’s base (TBNap) fluorophore. The structural and morphological features of TB-Zn-CP were characterized by various standard spectroscopic and microscopy techniques. The fluorescence titration studies in water demonstrated a remarkable sensitivity and differential fluorescence sensing properties of TB-Zn-CP for the fast detection of different antibiotics. Among different antibiotics, chloramphenicol (CRP), 1,2-dimethyl-5-nitroimidazole (DMZ), and sulfamethazine (SMZ) displayed the highest fluorescence-quenching efficiency and superior sensitivity in their detection. The differential sensing capability of TB-Zn-CP was also indicated by visualizable color changes. The Stern–Volmer quenching constant KSV was determined to be in the order of 103–104 M−1, and the sensitivity was shown to be at a nanomolar (10−9 M) level. All these results confirm that TB-Zn-CP can be a potential and practically useful polymeric sensor for differential fluorescence and visual detection of different antibiotics in water.","PeriodicalId":502867,"journal":{"name":"Chemistry","volume":"17 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-02-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139854956","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-02-07DOI: 10.3390/chemistry6010011
Purti Patel, Mannanthara Kunhumon Noushija, S. Shanmugaraju
The design and development of useful chemosensors for the ultra-trace detection of environmental pollutants and contaminants is a topical area of research. Herein, we report a new nanoscale emissive Zn(II) coordination polymer (TB-Zn-CP) for differential fluorescence sensing of various antibiotics in water. TB-Zn-CP was synthesized using a unique V-shaped green emitting 4-amino-1,8-naphthalimide Tröger’s base (TBNap) fluorophore. The structural and morphological features of TB-Zn-CP were characterized by various standard spectroscopic and microscopy techniques. The fluorescence titration studies in water demonstrated a remarkable sensitivity and differential fluorescence sensing properties of TB-Zn-CP for the fast detection of different antibiotics. Among different antibiotics, chloramphenicol (CRP), 1,2-dimethyl-5-nitroimidazole (DMZ), and sulfamethazine (SMZ) displayed the highest fluorescence-quenching efficiency and superior sensitivity in their detection. The differential sensing capability of TB-Zn-CP was also indicated by visualizable color changes. The Stern–Volmer quenching constant KSV was determined to be in the order of 103–104 M−1, and the sensitivity was shown to be at a nanomolar (10−9 M) level. All these results confirm that TB-Zn-CP can be a potential and practically useful polymeric sensor for differential fluorescence and visual detection of different antibiotics in water.
{"title":"Differential Fluorescent Chemosensing of Antibiotics Using a Luminescent Zn(II) Coordination Polymer Based on a 4-Amino-1,8-naphthalimide Tröger’s Base Fluorophore","authors":"Purti Patel, Mannanthara Kunhumon Noushija, S. Shanmugaraju","doi":"10.3390/chemistry6010011","DOIUrl":"https://doi.org/10.3390/chemistry6010011","url":null,"abstract":"The design and development of useful chemosensors for the ultra-trace detection of environmental pollutants and contaminants is a topical area of research. Herein, we report a new nanoscale emissive Zn(II) coordination polymer (TB-Zn-CP) for differential fluorescence sensing of various antibiotics in water. TB-Zn-CP was synthesized using a unique V-shaped green emitting 4-amino-1,8-naphthalimide Tröger’s base (TBNap) fluorophore. The structural and morphological features of TB-Zn-CP were characterized by various standard spectroscopic and microscopy techniques. The fluorescence titration studies in water demonstrated a remarkable sensitivity and differential fluorescence sensing properties of TB-Zn-CP for the fast detection of different antibiotics. Among different antibiotics, chloramphenicol (CRP), 1,2-dimethyl-5-nitroimidazole (DMZ), and sulfamethazine (SMZ) displayed the highest fluorescence-quenching efficiency and superior sensitivity in their detection. The differential sensing capability of TB-Zn-CP was also indicated by visualizable color changes. The Stern–Volmer quenching constant KSV was determined to be in the order of 103–104 M−1, and the sensitivity was shown to be at a nanomolar (10−9 M) level. All these results confirm that TB-Zn-CP can be a potential and practically useful polymeric sensor for differential fluorescence and visual detection of different antibiotics in water.","PeriodicalId":502867,"journal":{"name":"Chemistry","volume":"9 32","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-02-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139795027","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-12-25DOI: 10.3390/chemistry6010004
Rodolphe Kinghat, A. Khatyr, M. Knorr, Carsten Strohmann, M. Kubicki
The thioether-functionalized 2-azabutadiene (iPrS)2C=C(H)-N=CPh2 L ligates to CdI2 and HgI2 to form the chelate compounds [CdI2{(iPrS)2C=C(H)-N=CPh2] (1) and [HgI2(iPrS)2C=C(H)-N=CPh2] (2). Their crystal structures were solved via X-ray diffraction. Both crystallize in the non-centrosymmetric space groups: monoclinic P21 (1) and orthorhombic P212121 (2), respectively. The closed-shell d10 metal centers are four-coordinated (two iodides and S and N coordinating atoms from the ligand L) in both complexes. The geometrical indexes τ indicate that a highly distorted trigonal pyramidal is adopted for 1 and a seesaw geometry for 2. The comparative nature of metal–ligand bonds is discussed on the basis of metric parameters and of QT-AIM (quantum theory of atoms in molecules) calculations. L was also treated with CuI to obtain the dinuclear species [LCu(μ2-I2)CuL] (3), in which the two Cu(I) centers are linked by a short metal–metal bond. The geometric and electronic properties of 3 are compared with those of 1 and 2.
硫醚官能化的 2-azabutadiene (iPrS)2C=C(H)-N=CPh2 L 与 CdI2 和 HgI2 连接，形成螯合物 [CdI2{(iPrS)2C=C(H)-N=CPh2] (1) 和 [HgI2(iPrS)2C=C(H)-N=CPh2] (2)。通过 X 射线衍射解决了它们的晶体结构。两者都在非中心对称空间群中结晶：分别为单斜 P21（1）和正交 P2121（2）。在这两种配合物中，闭壳 d10 金属中心均为四配位（两个碘化物以及配体 L 的 S 和 N 配位原子）。几何指数 τ 表明，1 采用了高度畸变的三叉金字塔形，而 2 则采用了跷跷板几何。根据度量参数和 QT-AIM（分子中原子的量子理论）计算，讨论了金属-配体键的比较性质。L 还与 CuI 一起处理，得到了双核物种 [LCu(μ2-I2)CuL] (3)，其中两个 Cu(I)中心通过短金属-金属键相连。我们将 3 的几何和电子特性与 1 和 2 进行了比较。
{"title":"4,4-Bis(isopropylthio)-1,1-diphenyl-2-azabuta-1,3-diene Adducts with Cadmium(II), Mercury(II) and Copper(I) Iodides: Crystal, Molecular and Electronic Structures of d10 Transition Metal Chelate Complexes","authors":"Rodolphe Kinghat, A. Khatyr, M. Knorr, Carsten Strohmann, M. Kubicki","doi":"10.3390/chemistry6010004","DOIUrl":"https://doi.org/10.3390/chemistry6010004","url":null,"abstract":"The thioether-functionalized 2-azabutadiene (iPrS)2C=C(H)-N=CPh2 L ligates to CdI2 and HgI2 to form the chelate compounds [CdI2{(iPrS)2C=C(H)-N=CPh2] (1) and [HgI2(iPrS)2C=C(H)-N=CPh2] (2). Their crystal structures were solved via X-ray diffraction. Both crystallize in the non-centrosymmetric space groups: monoclinic P21 (1) and orthorhombic P212121 (2), respectively. The closed-shell d10 metal centers are four-coordinated (two iodides and S and N coordinating atoms from the ligand L) in both complexes. The geometrical indexes τ indicate that a highly distorted trigonal pyramidal is adopted for 1 and a seesaw geometry for 2. The comparative nature of metal–ligand bonds is discussed on the basis of metric parameters and of QT-AIM (quantum theory of atoms in molecules) calculations. L was also treated with CuI to obtain the dinuclear species [LCu(μ2-I2)CuL] (3), in which the two Cu(I) centers are linked by a short metal–metal bond. The geometric and electronic properties of 3 are compared with those of 1 and 2.","PeriodicalId":502867,"journal":{"name":"Chemistry","volume":"18 2","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-12-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139157841","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-12-23DOI: 10.3390/chemistry6010003
A. K. Gatiatulin, Ilya S. Balakhontsev, Sofia M. Talashmanova, M. Ziganshin, V. Gorbatchuk
A new polymorph of anhydrous β-cyclodextrin (polymorph III) was obtained and characterized for the first time using powder X-ray diffraction, infrared spectroscopy, and thermal analysis. The solution enthalpy and time of dissolution in water were determined using solution calorimetry for this polymorph and compared with those of the dried commercial form of β-cyclodextrin (polymorph I), its amorphous form, and 2-hydroxypropyl-β-cyclodextrin. The specific heat capacities of polymorphs I and III were determined using differential scanning calorimetry across a wide range of temperatures, providing enthalpy and Gibbs energy values for the polymorphic transition at 298 K. The affinities of polymorph III and 2-hydroxypropyl-β-cyclodextrin for water were characterized by determining their hydration isotherms, which provided values of hydration Gibbs energy. Being energy-rich, the new-found polymorph of β-cyclodextrin has a significantly higher dissolution rate and an increased affinity for water compared with the dried commercial form of β-cyclodextrin. These properties render the new polymorph promising in industrial applications for guest inclusion in aqueous solutions and pastes, and may be a desirable alternative for water-soluble β-cyclodextrin derivatives.
通过粉末 X 射线衍射、红外光谱和热分析，首次获得了无水 β-环糊精的一种新的多晶体（多晶体 III），并对其进行了表征。利用溶液热量计测定了这种多晶体在水中的溶解焓和溶解时间，并将其与β-环糊精的干燥商品形式（多晶体 I）、其无定形形式以及 2-羟丙基-β-环糊精的溶解焓和溶解时间进行了比较。利用差示扫描量热法测定了多晶体 I 和 III 在较大温度范围内的比热容，从而得出了 298 K 时多晶体转变的焓和吉布斯能值。由于能量丰富，新发现的 β-环糊精多晶体与干燥的商用 β-环糊精相比，溶解速率明显更高，对水的亲和力也更强。这些特性使得这种新的多晶体在水溶液和糊剂中的客体工业应用中大有可为，并可能成为水溶性 β-环糊精衍生物的理想替代品。
{"title":"New Polymorph of β-Cyclodextrin with a Higher Bioavailability","authors":"A. K. Gatiatulin, Ilya S. Balakhontsev, Sofia M. Talashmanova, M. Ziganshin, V. Gorbatchuk","doi":"10.3390/chemistry6010003","DOIUrl":"https://doi.org/10.3390/chemistry6010003","url":null,"abstract":"A new polymorph of anhydrous β-cyclodextrin (polymorph III) was obtained and characterized for the first time using powder X-ray diffraction, infrared spectroscopy, and thermal analysis. The solution enthalpy and time of dissolution in water were determined using solution calorimetry for this polymorph and compared with those of the dried commercial form of β-cyclodextrin (polymorph I), its amorphous form, and 2-hydroxypropyl-β-cyclodextrin. The specific heat capacities of polymorphs I and III were determined using differential scanning calorimetry across a wide range of temperatures, providing enthalpy and Gibbs energy values for the polymorphic transition at 298 K. The affinities of polymorph III and 2-hydroxypropyl-β-cyclodextrin for water were characterized by determining their hydration isotherms, which provided values of hydration Gibbs energy. Being energy-rich, the new-found polymorph of β-cyclodextrin has a significantly higher dissolution rate and an increased affinity for water compared with the dried commercial form of β-cyclodextrin. These properties render the new polymorph promising in industrial applications for guest inclusion in aqueous solutions and pastes, and may be a desirable alternative for water-soluble β-cyclodextrin derivatives.","PeriodicalId":502867,"journal":{"name":"Chemistry","volume":"172 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-12-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139163120","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-11-21DOI: 10.3390/chemistry5040170
Nicholas C. Norman, Paul G. Pringle
The dn number or configuration is a very useful parameter in transition metal chemistry because it conveys information about the expected properties of a d-block metal complex, including its shape, magnetism, thermodynamic stability, kinetic lability, and spectroscopic properties. The dn number can be determined from either the oxidation state (OS) or valence number (VN) of the metal centre, and since, in most cases, these are numerically equal, the derived dn value is the same. However, examples are discussed where the OS and VN are not equal, which results in unavoidable ambiguities in dn values. Following a discussion of these examples, a revised definition of dn is proposed based on the occupation of the frontier molecular orbitals of the complex.
在过渡金属化学中，dn 数或构型是一个非常有用的参数，因为它传递了有关 d 块金属复合物预期特性的信息，包括其形状、磁性、热力学稳定性、动力学稳定性和光谱特性。dn 数可以通过金属中心的氧化态（OS）或价数（VN）来确定，由于在大多数情况下，它们在数值上是相等的，因此得出的 dn 值也是相同的。不过，我们也讨论了一些 OS 和 VN 不相等的例子，这导致了 dn 值不可避免的模糊性。在对这些例子进行讨论后，提出了基于复合物前沿分子轨道占据情况的 dn 修订定义。
{"title":"The dn Number in Transition Metal Chemistry: Its Utility and Limitations","authors":"Nicholas C. Norman, Paul G. Pringle","doi":"10.3390/chemistry5040170","DOIUrl":"https://doi.org/10.3390/chemistry5040170","url":null,"abstract":"The dn number or configuration is a very useful parameter in transition metal chemistry because it conveys information about the expected properties of a d-block metal complex, including its shape, magnetism, thermodynamic stability, kinetic lability, and spectroscopic properties. The dn number can be determined from either the oxidation state (OS) or valence number (VN) of the metal centre, and since, in most cases, these are numerically equal, the derived dn value is the same. However, examples are discussed where the OS and VN are not equal, which results in unavoidable ambiguities in dn values. Following a discussion of these examples, a revised definition of dn is proposed based on the occupation of the frontier molecular orbitals of the complex.","PeriodicalId":502867,"journal":{"name":"Chemistry","volume":"115 11","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-11-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139253386","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-11-21DOI: 10.3390/chemistry5040169
Saber Abu-Jabal, Ahmad Ghareeb, Derar Smadi, Othman Hamed, M. Assali, Avni Berisha, N. Abutaha, Waseem Mansour, Ameed Omairah, Alaa Janem, Ataa Jaser
Finding an effective anticancer drug to combat cancer cell resistance remains a challenge. Herein, we synthesized a new series of imidazolone derivatives 4a–4i and assessed their anticancer activities against liver cancer cells (Hep3B), Hela cells, and normal LX2 cells. The imidazolne derivatives were synthesized by the condensation cyclization reaction using the natural product vanillin as a starting material. Among the synthesized imidazolones are those with an alkyl sulfate moiety that are water-soluble and showed enhanced anticancer activity against the tested cancer cells. The anticancer testing results showed that compound 4d with the NO2 group at position 4 of the benzene ring was superior to the other compounds; it showed an IC50 value of 134.2 ± 4.4 µM against Hep3B cells, while compound 4h with the pyridyl moiety showed the highest cytotoxicity against Hela cells with an IC50 of 85.1 ± 2.1 µM. The anticancer activity of some imidazolones was greatly enhanced by adding to them the zwitterionic properties that made them more polar and water-soluble. DNA binding studies with compounds 4a1, 4d, and 4g indicated a docking score ranging from approximately −6.8 to −8.7 kcal/mol. This could be attributed to the outstanding interaction between the molecule and the DNA binding sites, which primarily relies on its inherent capability to establish hydrogen bonds, facilitated by the electron pair present at the oxygen atoms and the drug’s amino group. In conclusion, water-soluble imidazolone with zwitterionic functionality could be a promising tool for the development of anticancer medication. To outline the general idea and the relationships for the effect of the developed compounds under study, as well as their mechanism of action, further extensive research is also necessary.
{"title":"New Zwitterionic Imidazolones with Enhanced Water Solubility and Bioavailability: Synthesis, Anticancer Activity, and Molecular Docking","authors":"Saber Abu-Jabal, Ahmad Ghareeb, Derar Smadi, Othman Hamed, M. Assali, Avni Berisha, N. Abutaha, Waseem Mansour, Ameed Omairah, Alaa Janem, Ataa Jaser","doi":"10.3390/chemistry5040169","DOIUrl":"https://doi.org/10.3390/chemistry5040169","url":null,"abstract":"Finding an effective anticancer drug to combat cancer cell resistance remains a challenge. Herein, we synthesized a new series of imidazolone derivatives 4a–4i and assessed their anticancer activities against liver cancer cells (Hep3B), Hela cells, and normal LX2 cells. The imidazolne derivatives were synthesized by the condensation cyclization reaction using the natural product vanillin as a starting material. Among the synthesized imidazolones are those with an alkyl sulfate moiety that are water-soluble and showed enhanced anticancer activity against the tested cancer cells. The anticancer testing results showed that compound 4d with the NO2 group at position 4 of the benzene ring was superior to the other compounds; it showed an IC50 value of 134.2 ± 4.4 µM against Hep3B cells, while compound 4h with the pyridyl moiety showed the highest cytotoxicity against Hela cells with an IC50 of 85.1 ± 2.1 µM. The anticancer activity of some imidazolones was greatly enhanced by adding to them the zwitterionic properties that made them more polar and water-soluble. DNA binding studies with compounds 4a1, 4d, and 4g indicated a docking score ranging from approximately −6.8 to −8.7 kcal/mol. This could be attributed to the outstanding interaction between the molecule and the DNA binding sites, which primarily relies on its inherent capability to establish hydrogen bonds, facilitated by the electron pair present at the oxygen atoms and the drug’s amino group. In conclusion, water-soluble imidazolone with zwitterionic functionality could be a promising tool for the development of anticancer medication. To outline the general idea and the relationships for the effect of the developed compounds under study, as well as their mechanism of action, further extensive research is also necessary.","PeriodicalId":502867,"journal":{"name":"Chemistry","volume":"145 ","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-11-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139250651","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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