D. Stoitsov, M. Marinov, P. Penchev, P. Marinova, Neyko Stoyanov
The structure verification of 5′-oxospiro-(fluorene-9,4′-imidazolidine)-2′-thione by NMR is reported. Toward this aim, 2D NMR techniques including 1H-1H COSY, HMQC, and HMBC experiments were used to assist with the assignment of the 1H and 13C chemical shifts for the corresponding structure. The mutual interpretation of the 1D and 2D NMR spectra ensured a complete and accurate 1H and 13C NMR data assignment for 5′-oxospiro-(fluorene-9,4′-imidazolidine)-2′-thione.
{"title":"5′-Oxospiro-(fluorene-9,4′-imidazolidine)-2′-thione","authors":"D. Stoitsov, M. Marinov, P. Penchev, P. Marinova, Neyko Stoyanov","doi":"10.3390/m1864","DOIUrl":"https://doi.org/10.3390/m1864","url":null,"abstract":"The structure verification of 5′-oxospiro-(fluorene-9,4′-imidazolidine)-2′-thione by NMR is reported. Toward this aim, 2D NMR techniques including 1H-1H COSY, HMQC, and HMBC experiments were used to assist with the assignment of the 1H and 13C chemical shifts for the corresponding structure. The mutual interpretation of the 1D and 2D NMR spectra ensured a complete and accurate 1H and 13C NMR data assignment for 5′-oxospiro-(fluorene-9,4′-imidazolidine)-2′-thione.","PeriodicalId":509184,"journal":{"name":"Molbank","volume":"58 9","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-08-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141928911","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}
Indole derivatives are key components of natural products and possess a wide range of biological and pharmaceutical applications. Here, we present the synthesis of a new indole derivative, namely 2-(1-ethyl-5-nitro-1H-indole-7-carbonyl)butyl 4-methylbenzenesulfonate. The structural elucidation of this compound was accomplished through comprehensive spectroscopic analysis, including Fourier-transform infrared spectroscopy (FTIR), nuclear magnetic resonance (NMR), and high-resolution mass spectrometry (HRMS). Our molecular docking study revealed that this compound exhibits strong affinity towards tyrosinase, making it a promising candidate as an antioxidant agent.
{"title":"Synthesis, Characterization, and Docking Study of a Novel Indole Derivative Containing a Tosyl Moiety as Anti-Oxidant Agent","authors":"Abdelali Chihab, N. El Brahmi, S. El Kazzouli","doi":"10.3390/m1857","DOIUrl":"https://doi.org/10.3390/m1857","url":null,"abstract":"Indole derivatives are key components of natural products and possess a wide range of biological and pharmaceutical applications. Here, we present the synthesis of a new indole derivative, namely 2-(1-ethyl-5-nitro-1H-indole-7-carbonyl)butyl 4-methylbenzenesulfonate. The structural elucidation of this compound was accomplished through comprehensive spectroscopic analysis, including Fourier-transform infrared spectroscopy (FTIR), nuclear magnetic resonance (NMR), and high-resolution mass spectrometry (HRMS). Our molecular docking study revealed that this compound exhibits strong affinity towards tyrosinase, making it a promising candidate as an antioxidant agent.","PeriodicalId":509184,"journal":{"name":"Molbank","volume":"19 3","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141800900","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}
In this study, we report the synthesis of N-(2-(benzylamino)ethyl)-4-(naphthalene-1-sulfonamido)benzamide, designed on the basis of the structures of the PPARγ partial agonist SR2067 and of the commercial acetylcholinesterase inhibitor drug donepezil, aiming for a multi-target approach for the therapy of elderly diseases, such as diabetes and Alzheimer’s disease. The compound was fully characterized by using 1H and 13C NMR, FT-IR and HRMS.
{"title":"N-(2-(Benzylamino)ethyl)-4-(naphthalene-1-sulfonamido)benzamide","authors":"Rosalba Leuci, Fulvio Loiodice, L. Piemontese","doi":"10.3390/m1856","DOIUrl":"https://doi.org/10.3390/m1856","url":null,"abstract":"In this study, we report the synthesis of N-(2-(benzylamino)ethyl)-4-(naphthalene-1-sulfonamido)benzamide, designed on the basis of the structures of the PPARγ partial agonist SR2067 and of the commercial acetylcholinesterase inhibitor drug donepezil, aiming for a multi-target approach for the therapy of elderly diseases, such as diabetes and Alzheimer’s disease. The compound was fully characterized by using 1H and 13C NMR, FT-IR and HRMS.","PeriodicalId":509184,"journal":{"name":"Molbank","volume":"8 2","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141803239","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}
Pyridinium salts of 2-piperidinyl-6-triazolylpurine derivatives were obtained by the introduction of pyridinium moieties into the propane-1,3-diol fragment at the N(9) position of purine to enhance the solubility of 2-amino-6-triazolylpurine derivatives in water. Target structures were obtained using the tosylation of hydroxyl groups of 2-(6-(4-(4-methoxyphenyl)-1H-1,2,3-triazol-1-yl)-2-(piperidin-1-yl)-9H-purin-9-yl)propane-1,3-diol, the subsequent introduction of pyridine, and ion exchange. The compounds were characterized using 1H- and 13C-NMR spectra, FTIR, UV–Vis, and HRMS data.
{"title":"Synthesis of Pyridinium Moiety Containing Triazolyl Purines","authors":"Aleksejs Burcevs, M. Turks, Irina Novosjolova","doi":"10.3390/m1855","DOIUrl":"https://doi.org/10.3390/m1855","url":null,"abstract":"Pyridinium salts of 2-piperidinyl-6-triazolylpurine derivatives were obtained by the introduction of pyridinium moieties into the propane-1,3-diol fragment at the N(9) position of purine to enhance the solubility of 2-amino-6-triazolylpurine derivatives in water. Target structures were obtained using the tosylation of hydroxyl groups of 2-(6-(4-(4-methoxyphenyl)-1H-1,2,3-triazol-1-yl)-2-(piperidin-1-yl)-9H-purin-9-yl)propane-1,3-diol, the subsequent introduction of pyridine, and ion exchange. The compounds were characterized using 1H- and 13C-NMR spectra, FTIR, UV–Vis, and HRMS data.","PeriodicalId":509184,"journal":{"name":"Molbank","volume":"20 2","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141807919","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}
Hugo Pilotzi-Xahuentitla, Gabriela Canche-Naal, Rolffy Ortiz-Andrade, Gabriel Navarrete-Vázquez, Emanuel Hernández-Núñez
Benzazoles, such as benzoxazoles and benzothiazoles, are compounds with important biological and pharmacological activities and important intermediaries in synthesis. This report presents the synthesis of a butanamide derived from linking 5-chloro-2-aminobenzoxazole and 2-aminobenzothiazole via 4-chlorobutanoyl chloride. The corresponding compound N-(benzothiazol-2-yl)-4-((5-chlorobenzoxazol-2-yl)aminobutanamide was obtained at a 76% global yield using accessible starting materials and a methodology in two reaction steps. Furthermore, we conducted docking studies of this compound on 3-TOP protein to explore its potential as an antidiabetic agent.
{"title":"N-(Benzothiazol-2-yl)-4-((5-chlorobenzoxazol-2-yl)amino)butanamide","authors":"Hugo Pilotzi-Xahuentitla, Gabriela Canche-Naal, Rolffy Ortiz-Andrade, Gabriel Navarrete-Vázquez, Emanuel Hernández-Núñez","doi":"10.3390/m1854","DOIUrl":"https://doi.org/10.3390/m1854","url":null,"abstract":"Benzazoles, such as benzoxazoles and benzothiazoles, are compounds with important biological and pharmacological activities and important intermediaries in synthesis. This report presents the synthesis of a butanamide derived from linking 5-chloro-2-aminobenzoxazole and 2-aminobenzothiazole via 4-chlorobutanoyl chloride. The corresponding compound N-(benzothiazol-2-yl)-4-((5-chlorobenzoxazol-2-yl)aminobutanamide was obtained at a 76% global yield using accessible starting materials and a methodology in two reaction steps. Furthermore, we conducted docking studies of this compound on 3-TOP protein to explore its potential as an antidiabetic agent.","PeriodicalId":509184,"journal":{"name":"Molbank","volume":"56 6","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141813406","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}
The synthesis of phosphate receptors represents an important avenue of research given the ubiquity of phosphate in biological and environmental systems. While many molecular scaffolds suitable for smaller anions are available either commercially or via reported synthetic routes, scaffolds suitable for larger anions such as phosphate are less common. In this work, we present a clear and straightforward synthesis of the basic molecular scaffold 3,6-diaminophenanthrene and of a novel 3,6-bisureidophenanthrene anion receptor prepared from this scaffold. Of the seven synthetic steps using readily available starting materials and reagents, only a single chromatographic purification step was required. The different interactions of the 3,6-bisureidophenanthrene-based anion receptor with phosphate and chloride are demonstrated. We expect that this convenient synthesis of the 3,6-diaminophenanthrene building block will pave the way for applications in many different fields of research, from materials science to supramolecular chemistry.
{"title":"Synthesis of an Anion Receptor Using 3,6-Diaminophenanthrene as a Scaffold","authors":"Lau Halgreen, Hennie Valkenier","doi":"10.3390/m1853","DOIUrl":"https://doi.org/10.3390/m1853","url":null,"abstract":"The synthesis of phosphate receptors represents an important avenue of research given the ubiquity of phosphate in biological and environmental systems. While many molecular scaffolds suitable for smaller anions are available either commercially or via reported synthetic routes, scaffolds suitable for larger anions such as phosphate are less common. In this work, we present a clear and straightforward synthesis of the basic molecular scaffold 3,6-diaminophenanthrene and of a novel 3,6-bisureidophenanthrene anion receptor prepared from this scaffold. Of the seven synthetic steps using readily available starting materials and reagents, only a single chromatographic purification step was required. The different interactions of the 3,6-bisureidophenanthrene-based anion receptor with phosphate and chloride are demonstrated. We expect that this convenient synthesis of the 3,6-diaminophenanthrene building block will pave the way for applications in many different fields of research, from materials science to supramolecular chemistry.","PeriodicalId":509184,"journal":{"name":"Molbank","volume":" 17","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141822523","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}
Brandon Quillian, Kennedy Musso, Elizabeth M. Vinson, J. Bazemore, Allison R. Marks, Clifford W. Padgett
Diisoamyl (1R,4S)-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate (2) was prepared by reacting exo-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride (1) with isoamyl alcohol in the presence of a sulfuric acid catalyst under sonication conditions. Compound 2 was characterized by 1H, 13C NMR, DEPT-135, infrared, and UV-vis spectroscopy. Gas chromatography–mass spectrometry, elemental analysis, and melting point determination were used to assess purity. The structure of compound 2 was also determined by single-crystal X-ray diffraction. It crystallizes in the monoclinic space group P21/c (14) with cell values of a = 15.5647(3) Å, b = 12.8969(2) Å, c = 9.0873(2) Å; β= 99.3920(10)°.
{"title":"Diisoamyl (1R, 4S)-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate","authors":"Brandon Quillian, Kennedy Musso, Elizabeth M. Vinson, J. Bazemore, Allison R. Marks, Clifford W. Padgett","doi":"10.3390/m1852","DOIUrl":"https://doi.org/10.3390/m1852","url":null,"abstract":"Diisoamyl (1R,4S)-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate (2) was prepared by reacting exo-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride (1) with isoamyl alcohol in the presence of a sulfuric acid catalyst under sonication conditions. Compound 2 was characterized by 1H, 13C NMR, DEPT-135, infrared, and UV-vis spectroscopy. Gas chromatography–mass spectrometry, elemental analysis, and melting point determination were used to assess purity. The structure of compound 2 was also determined by single-crystal X-ray diffraction. It crystallizes in the monoclinic space group P21/c (14) with cell values of a = 15.5647(3) Å, b = 12.8969(2) Å, c = 9.0873(2) Å; β= 99.3920(10)°.","PeriodicalId":509184,"journal":{"name":"Molbank","volume":" 27","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141823971","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}
Markus Lang, Richard Goddard, Michael Patzer, Uday S. Ganapathy, Thomas Dick, A. Richter, R. W. Seidel
In view of the rise of drug-resistant tuberculosis and difficult-to-treat related diseases caused by non-tuberculous mycobacteria, there is an urgent need for antimycobacterial drug discovery. Nα-aroyl-N-aryl-phenylalanine amides (AAPs) have been identified as antimycobacterial agents and are subject to lead optimization. The aim of the present study is to evaluate the impact of N-aryl ortho cyano substitution in a lead compound on the crystal and molecular structure and its in vitro activity against Mycobacterium abscessus. The title AAP can be conveniently synthesized from N-Boc-protected d-phenylalanine in two amide coupling steps using a previously established racemization-free method. Two polymorphic forms in the solid-state are described, as discovered by X-ray and electron diffraction. The introduction of a cyano group in the ortho position of the AAP N-aryl ring, however, leads to loss of in vitro activity against M. abscessus subsp. abscessus.
{"title":"Polymorphism of an Nα-Aroyl-N-Aryl-Phenylalanine Amide: An X-ray and Electron Diffraction Study","authors":"Markus Lang, Richard Goddard, Michael Patzer, Uday S. Ganapathy, Thomas Dick, A. Richter, R. W. Seidel","doi":"10.3390/m1851","DOIUrl":"https://doi.org/10.3390/m1851","url":null,"abstract":"In view of the rise of drug-resistant tuberculosis and difficult-to-treat related diseases caused by non-tuberculous mycobacteria, there is an urgent need for antimycobacterial drug discovery. Nα-aroyl-N-aryl-phenylalanine amides (AAPs) have been identified as antimycobacterial agents and are subject to lead optimization. The aim of the present study is to evaluate the impact of N-aryl ortho cyano substitution in a lead compound on the crystal and molecular structure and its in vitro activity against Mycobacterium abscessus. The title AAP can be conveniently synthesized from N-Boc-protected d-phenylalanine in two amide coupling steps using a previously established racemization-free method. Two polymorphic forms in the solid-state are described, as discovered by X-ray and electron diffraction. The introduction of a cyano group in the ortho position of the AAP N-aryl ring, however, leads to loss of in vitro activity against M. abscessus subsp. abscessus.","PeriodicalId":509184,"journal":{"name":"Molbank","volume":" 2","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141829204","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}
Noël Pinaud, Y. Danten, Mathieu Marchivie, Marcel Besnard, Isabel Cabaço, Jean Guillon
Bis(1-butyl-1-methypyrrolidinium) perthiodicarbonate was obtained by the reaction of carbon disulfide with 1-butyl-1-methypyrrolidinium acetate ([BmPyrro][Ac]) in the liquid phase. Structural characterization of this original complex was achieved by single-crystal X-ray diffraction (SCXRD) analysis. The asymmetric unit of the title compound, C2S6·2C9H20N, consisted of two crystallographically 1-methyl-1-butyl pyrrolidinium cations and one perthiodicarbonate anion. The complex C2S6·2C9H20N crystallized in the monoclinic space group, C 2/c, and possessed the following cell parameters: a = 16.0970(10) Å, b = 14.7140(9) Å, c = 12.3280(8) Å, α = 90°, β = 112.3730(12)°, γ = 90°, V = 2700.11 Å3, and Z = 8, Z’ = 0.5.
{"title":"Crystal Structure of Bis(1-butyl-1-methypyrrolidinium) Perthiodicarbonate Complex","authors":"Noël Pinaud, Y. Danten, Mathieu Marchivie, Marcel Besnard, Isabel Cabaço, Jean Guillon","doi":"10.3390/m1849","DOIUrl":"https://doi.org/10.3390/m1849","url":null,"abstract":"Bis(1-butyl-1-methypyrrolidinium) perthiodicarbonate was obtained by the reaction of carbon disulfide with 1-butyl-1-methypyrrolidinium acetate ([BmPyrro][Ac]) in the liquid phase. Structural characterization of this original complex was achieved by single-crystal X-ray diffraction (SCXRD) analysis. The asymmetric unit of the title compound, C2S6·2C9H20N, consisted of two crystallographically 1-methyl-1-butyl pyrrolidinium cations and one perthiodicarbonate anion. The complex C2S6·2C9H20N crystallized in the monoclinic space group, C 2/c, and possessed the following cell parameters: a = 16.0970(10) Å, b = 14.7140(9) Å, c = 12.3280(8) Å, α = 90°, β = 112.3730(12)°, γ = 90°, V = 2700.11 Å3, and Z = 8, Z’ = 0.5.","PeriodicalId":509184,"journal":{"name":"Molbank","volume":"14 5","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141646538","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}
(1R,3R,5S,Z)-2-ethylidene-6,6-dimethyl-3-vinylbicyclo[3.1.1]heptane was prepared by hydrovinylation of nopadiene catalyzed by a cationic Ru complex. The structure was fully characterized by 1H- and 13C-NMR spectroscopy, including 2D-COSY and 2D-NOESY spectra, optical rotation, and combustion analysis. In contrast to the previously reported 1,2-hydrovinylation of 1-vinylcycloalkenes by this catalyst, the reaction with nopadiene proceeds by 1,4-addition of ethylene.
{"title":"(1R,3R,5S,Z)-2-Ethylidene-6,6-dimethyl-3-vinylbicyclo[3.1.1]-heptane","authors":"Zhengjie He, William A. Donaldson","doi":"10.3390/m1850","DOIUrl":"https://doi.org/10.3390/m1850","url":null,"abstract":"(1R,3R,5S,Z)-2-ethylidene-6,6-dimethyl-3-vinylbicyclo[3.1.1]heptane was prepared by hydrovinylation of nopadiene catalyzed by a cationic Ru complex. The structure was fully characterized by 1H- and 13C-NMR spectroscopy, including 2D-COSY and 2D-NOESY spectra, optical rotation, and combustion analysis. In contrast to the previously reported 1,2-hydrovinylation of 1-vinylcycloalkenes by this catalyst, the reaction with nopadiene proceeds by 1,4-addition of ethylene.","PeriodicalId":509184,"journal":{"name":"Molbank","volume":"47 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141648648","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}
京公网安备 11010802042870号
京ICP备2023020795号-1
扫码关注我们
求助内容：
应助结果提醒方式：