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Thermoresponsive sustainable release of anticancer drugs using cyto-compatible pyrenylated hydrogel as vehicle 以细胞相容性苯乙烯化水凝胶为载体的抗癌药热反应性可持续释放
IF 1.7 4区 化学 Q3 Chemistry Pub Date : 2023-01-18 DOI: 10.1007/s12039-022-02124-3
Dipen Biswakarma, Nilanjan Dey, Santanu Bhattacharya

Pyrene-based fluorogenic amphiphilic probe (1) has been synthesized, which can form a thixotropic (injectable) hydrogel in the aqueous medium. The biocompatible hydrogel, so formed, is involved in the thermoresponsive, sustainable delivery of two anticancer drugs, Doxorubicin (DOX) and Mitoxantrone (MT). A substantial difference in the extent of drug release is noticed at 25 and 37 °C, even at physiological pH. The cumulative releases of ~80% and ~70% for DOX and MT, respectively, from the drug-loaded hydrogel samples, are observed for 72 h. In both cases, drug molecule release follows zero-order kinetics and non-Fickian diffusion pathways. The excellent stability of 1 against proteinase enzyme suggests that the present system can be used for sustainable, targeted release of drug molecules under in-vivo conditions. As expected, DOX-loaded hydrogels kill cancer cells more efficiently than the free drug (i.e., DOX).

Graphical abstract

A pyrene-based amphiphilic probe has been synthesized, which can form a thixotropic hydrogel in the aqueous medium. The biocompatible hydrogel was involved in the thermoresponsive, sustainable delivery of two anticancer drugs, Doxorubicin (DOX) and Mitoxantrone (MT). Moreover, the DOX-loaded hydrogel could kill cancer cells more efficiently than the free drug.

合成了基于比利牛斯的荧光两亲探针(1),它可以在水介质中形成触变性(可注射)水凝胶。形成的生物相容性水凝胶参与了两种抗癌药物阿霉素(DOX)和米托蒽醌(MT)的热响应性可持续递送。在25°C和37°C时,即使在生理ph下,药物释放程度也存在显著差异。在72小时内,从载药的水凝胶样品中,DOX和MT的累积释放量分别为~80%和~70%。在这两种情况下,药物分子释放遵循零级动力学和非菲克扩散途径。1对蛋白酶的优异稳定性表明,该系统可用于体内条件下药物分子的持续靶向释放。正如预期的那样,负载DOX的水凝胶比游离药物(即DOX)更有效地杀死癌细胞。合成了一种吡啶基两亲性探针,该探针可在水介质中形成触变性水凝胶。该生物相容性水凝胶参与了两种抗癌药物阿霉素(DOX)和米托蒽醌(MT)的热响应性可持续递送。此外,含有dox的水凝胶可以比游离药物更有效地杀死癌细胞。
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引用次数: 1
Hydrophobic Hydration: A Theoretical Investigation of Structure and Dynamics 疏水水合作用:结构和动力学的理论研究
IF 1.7 4区 化学 Q3 Chemistry Pub Date : 2023-01-12 DOI: 10.1007/s12039-022-02123-4
Kambham Devendra Reddy, Rajib Biswas

The presence of external solutes alters the local structures, and dynamics of water. The nature and extent of these structural modifications depend on several factors. Particularly, the chemical nature of the solute is very crucial. The alteration of water structure and dynamics in the presence of hydrophobic substances draws considerable attention in biological systems. The present work is focused on exploring the microscopic arrangement of solvation shells of tiny hydrophobic solute methane. We explore the tetrahedral order, local structural index, and van Hove self-correlation function to get a quantitative understanding. We observe a slight increase in the structural order of water molecules in methane’s first solvation shell, similar to that of the low-temperature water. We also find that water facing the methane have lower structural order than bulk water. Furthermore, the water molecules in the first solvation shell around methane show relatively slower orientational relaxation.

The hydrophobicity-induced alterations of water structural and dynamical properties are investigated using solvation shell decomposition. We observe the slower relaxation of selected water molecules staying longer time in methane first solvation shell. We find enhanced structural order in the methane first solvation shell and some dangling water molecules.

外部溶质的存在改变了水的局部结构和动力学。这些结构变化的性质和程度取决于几个因素。特别是,溶质的化学性质是非常关键的。疏水物质存在时水结构和动力学的改变在生物系统中引起了相当大的关注。本文主要研究了微疏水溶质甲烷溶剂化壳的微观排列。我们探索了四面体序、局部结构指数和van Hove自相关函数,以获得定量的认识。我们观察到甲烷第一层溶剂化层中水分子的结构顺序略有增加,与低温水的结构顺序相似。我们还发现,面对甲烷的水比散装水具有更低的结构秩序。此外,甲烷周围第一溶剂化层的水分子表现出相对较慢的取向弛豫。采用溶剂化壳分解法研究了疏水性对水结构和动力学性质的影响。我们观察到某些水分子在甲烷第一溶剂化壳中停留时间较长,弛豫较慢。我们发现在甲烷第一溶剂化壳层和一些悬垂的水分子中有增强的结构秩序。
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引用次数: 0
Metal-free C(sp3)-H Bromination: Synthesis of Phenacyl bromide and Benzyl bromide derivatives 无金属C(sp3)-H溴化:苯那基溴和苯溴衍生物的合成
IF 1.7 4区 化学 Q3 Chemistry Pub Date : 2022-12-03 DOI: 10.1007/s12039-022-02107-4
Sourav Mal, Satinath Sarkar, Manoranjan Jana

A metal-free C(sp3)-H bromination methodology has been developed for aromatic ketones and some substituted toluenes under ambient conditions. The reaction for the toluenes is mediated by PhI(OAc)2 (iodobenzene diacetate) in presence of KBr, while the bromination in aromatic ketones requires additional assistance of p-TsOH.H2O and BF3.Et2O.

Graphical abstract

Synopsis: Synthesis of phenacyl bromides has been achieved under transition metal-free conditions. Some observations on substituted toluene systems have also been reported. In both cases, C(sp3)-H bromination has taken place at room temperature in the presence of phenyliodine diacetate (PIDA).

本文建立了一种无金属的C(sp3)-H溴化方法,用于芳香酮和某些取代甲苯的环境反应。甲苯的反应是在KBr存在下由PhI(OAc)2(二乙酸碘苯)介导的,而芳香酮的溴化则需要对tsoh的辅助。H2O和bf3, et2o。摘要:在无过渡金属的条件下合成了苯那基溴化物。还报道了对取代甲苯体系的一些观察结果。在这两种情况下,C(sp3)-H溴化都是在室温下,在二乙酸苯碘(PIDA)的存在下发生的。
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引用次数: 0
Thermally stable complexes of Fe(III), Co(II), Ni(II) and Cu(II) with Schiff base derived from 4-aminoacetophenone and salicylaldehyde 以4-氨基苯乙酮和水杨醛为原料制备了具有席夫碱的Fe(III)、Co(II)、Ni(II)和Cu(II)的热稳定配合物
IF 1.7 4区 化学 Q3 Chemistry Pub Date : 2022-11-25 DOI: 10.1007/s12039-022-02113-6
Rasheeda M Ansari, Dileep Ramakrishna, Badekai Ramachandra Bhat

The Schiff base ligand 1-(4-((2-hydroxybenzylidene)amino)phenyl)ethan-1-one, obtained from 4-aminoacetophenone and salicylaldehyde, and its complexes with Fe(III), Co(II), Ni(II) and Cu(II) have been synthesized. These complexes were characterized by FTIR spectroscopy, elemental, and SCXRD analysis. FTIR spectra of complexes show the bidentate coordination of metal ions with ligands where O and N are electron-donating sites of the azomethine group. The electronic absorption spectra of these complexes show the characteristics of absorption bands involved in the Fe, Co, and Ni complexes due to their π→π*, n→π* transitions. Further, the geometry of the complexes was deduced from the calculated magnetic moment values and single crystal XRD analysis.

Graphical abstract

A Schiff base derived from the condensation reaction between 2-aminoacetophenone and salicylaldehyde was involved in the formation of four different metal complexes, i.e., with Nickel, Cobalt, Iron, and Copper. The synthetic route to forming these complexes followed an easy process, and the complexes were obtained in good yields.

以4-氨基苯乙酮和水杨醛为原料合成了希夫碱配体1-(4-(2-羟基苄基)氨基)苯基)乙二酮及其与Fe(III)、Co(II)、Ni(II)和Cu(II)的配合物。这些配合物通过FTIR光谱、元素分析和SCXRD分析进行了表征。配合物的FTIR光谱显示金属离子与配体的双齿配位,其中O和N是亚甲基的给电子位点。这些配合物的电子吸收光谱显示出Fe、Co和Ni配合物由于π→π*、n→π*跃迁所涉及的吸收带特征。通过计算得到的磁矩值和单晶XRD分析,推导出配合物的几何形状。由2-氨基苯乙酮与水杨醛缩合反应生成的希夫碱与镍、钴、铁、铜等四种不同的金属配合物形成。合成这些配合物的方法简单,产率高。
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引用次数: 0
Transformation of refinery cracked naphtha stream into efficient lubricity improvers for ULSD 炼油裂解石脑油转化为高效ULSD润滑改进剂的研究
IF 1.7 4区 化学 Q3 Chemistry Pub Date : 2022-10-12 DOI: 10.1007/s12039-022-02102-9
H SRUTHI, D UDAYA KUMAR, PRAMOD HEGDE, M G MANJUNATHA, R KARTHICK, V NANDAKUMAR

A new route for the conversion of refinery light cracked naphtha (LCN) stream into lubricity improvers for ultra-low sulphur diesel (ULSD) was developed through a simple chemical process involving olefin epoxidation and esterification reactions. Two different methods viz., H2O2/glacial acetic acid and m-chloroperbenzoic acid (m-CPBA), were found to be suitable for the epoxidation of LCN. The LCN epoxide was subjected to an esterification reaction via epoxide ring opening using different long chain (C4 - C18 alkyl groups) organic acids to get the hydroxy ester derivatives of LCN. The lubricating property of the newly synthesized hydroxy esters was studied by dosing them with ULSD at 300 and 150 ppm (wt/vol) concentrations. Amongst them, LCN hydroxy ester derived from stearic acid showed the best lubrication-enhancing property at both dosage levels. The scanning electron microscope (SEM) image and energy dispersive spectra (EDS) of the high-frequency reciprocating rig (HFRR) specimen support the lubricating action of the LCN esters through the formation of a protective layer between the metallic surfaces. The synergy of simple chemical processes and efficient lubricity action makes these LCN esters as promising materials for low-cost and scalable additives for ULSD.

Graphical abstract

The olefin-rich light cracked naphtha obtained from the fluidized catalytic cracker unit of the oil refinery was converted into hydroxy esters through an epoxidation reaction followed by the esterification with different carboxylic acids. The hydroxy esters at low dosage levels (150/300 ppm) enhance the lubricating property of ultra-low sulfur diesel.

通过烯烃环氧化和酯化反应,开发了炼油轻裂化石脑油(LCN)流转化为超低硫柴油(ULSD)润滑改进剂的新工艺。发现H2O2/冰醋酸和间氯过苯甲酸(m-CPBA)两种不同的方法适合于LCN的环氧化反应。采用不同的长链(C4 - C18烷基)有机酸,通过开环环氧化反应得到LCN的羟基酯衍生物。用300 ppm和150 ppm (wt/vol)浓度的ULSD对新合成的羟基酯的润滑性能进行了研究。其中,硬脂酸衍生的LCN羟基酯在两种剂量下均表现出最佳的润滑性能。高频往复钻具(HFRR)试样的扫描电镜(SEM)图像和能量色散谱(EDS)证实了LCN酯通过在金属表面之间形成保护层而起润滑作用。简单的化学过程和高效的润滑作用的协同作用使这些LCN酯成为低成本和可扩展的ULSD添加剂。摘要炼油厂流化催化裂化装置生产的富烯烃轻裂化石脑油,经环氧化反应,再与不同的羧酸酯化反应,制得羟基酯。低剂量(150/300 ppm)的羟基酯提高了超低硫柴油的润滑性能。
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引用次数: 0
In silico studies of 6-phenyl-3-(pyridin-2-yl)-1,2,4-triazine as a corrosion inhibitor for some important metals used in implants 6-苯基-3-(吡啶-2-基)-1,2,4-三嗪作为植入物中一些重要金属的缓蚀剂的硅片研究
IF 1.7 4区 化学 Q3 Chemistry Pub Date : 2022-10-11 DOI: 10.1007/s12039-022-02104-7
Maria G Babashkina, Tatyana M Burkhanova, Damir A Safin

In this work detailed DFT-based computational studies of 6-phenyl-3-(pyridin-2-yl)-1,2,4-triazine (PhPyTrz) are reported. The global reactivity descriptors and molecular electrostatic potential (MEP) were also revealed to probe the reactivity and determine the reactive centers of PhPyTrz. Some biological properties of PhPyTrz were evaluated using online tools. Corrosion inhibition properties of PhPyTrz both in the gas phase and in the aqueous medium for some important metals used in implants were also estimated by means of DFT calculations. It was established that PhPyTrz exhibits the best corrosion inhibition towards Ni and Co. It was also revealed that the corrosion inhibition power of PhPyTrz decreases in water.

Graphical abstract

We report DFT-based computational studies of 6-phenyl-3-(pyridin-2-yl)-1,2,4-triazine (PhPyTrz). Some biological properties of PhPyTrz were predicted. Corrosion inhibition properties of PhPyTrz both in gas phase and in the aqueous medium for some important metals used in implants were also estimated by DFT calculations.

本文报道了基于dft的6-苯基-3-(吡啶-2-基)-1,2,4-三嗪(PhPyTrz)的计算研究。利用全局反应性描述符和分子静电势(MEP)来探测PhPyTrz的反应性并确定其反应中心。利用在线工具对PhPyTrz的一些生物学特性进行了评价。通过DFT计算,估计了PhPyTrz在气相和水介质中对一些重要金属植入物的缓蚀性能。结果表明,PhPyTrz对Ni和Co的缓蚀性能最好,在水中PhPyTrz的缓蚀能力有所下降。本文报道了基于dft的6-苯基-3-(吡啶-2-基)-1,2,4-三嗪(PhPyTrz)的计算研究。预测了PhPyTrz的一些生物学特性。通过DFT计算,估计了PhPyTrz在气相和水相介质中对一些重要金属的缓蚀性能。
{"title":"In silico studies of 6-phenyl-3-(pyridin-2-yl)-1,2,4-triazine as a corrosion inhibitor for some important metals used in implants","authors":"Maria G Babashkina,&nbsp;Tatyana M Burkhanova,&nbsp;Damir A Safin","doi":"10.1007/s12039-022-02104-7","DOIUrl":"10.1007/s12039-022-02104-7","url":null,"abstract":"<div><p>In this work detailed DFT-based computational studies of 6-phenyl-3-(pyridin-2-yl)-1,2,4-triazine (<b>PhPyTrz</b>) are reported. The global reactivity descriptors and molecular electrostatic potential (MEP) were also revealed to probe the reactivity and determine the reactive centers of <b>PhPyTrz</b>. Some biological properties of <b>PhPyTrz</b> were evaluated using online tools. Corrosion inhibition properties of <b>PhPyTrz</b> both in the gas phase and in the aqueous medium for some important metals used in implants were also estimated by means of DFT calculations. It was established that <b>PhPyTrz</b> exhibits the best corrosion inhibition towards Ni and Co. It was also revealed that the corrosion inhibition power of <b>PhPyTrz</b> decreases in water.</p><h3>Graphical abstract</h3><p>We report DFT-based computational studies of 6-phenyl-3-(pyridin-2-yl)-1,2,4-triazine (<b>PhPyTrz</b>). Some biological properties of <b>PhPyTrz</b> were predicted. Corrosion inhibition properties of <b>PhPyTrz</b> both in gas phase and in the aqueous medium for some important metals used in implants were also estimated by DFT calculations.</p><figure><div><div><div><picture><source><img></source></picture></div></div></div></figure></div>","PeriodicalId":50242,"journal":{"name":"Journal of Chemical Sciences","volume":"134 4","pages":""},"PeriodicalIF":1.7,"publicationDate":"2022-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4478462","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Palladium(II) complex bearing benzothiazole based O,N,S donor pincer ligand: Study of in-vitro cytotoxicity, interaction with CT-DNA and BSA protein 含苯并噻唑O,N,S供体螯配体钯配合物:体外细胞毒性、与CT-DNA和BSA蛋白相互作用的研究
IF 1.7 4区 化学 Q3 Chemistry Pub Date : 2022-09-30 DOI: 10.1007/s12039-022-02101-w
RAHUL NASKAR, PARAMITA GHOSH, SUBRATA MANDAL, SUBRATA JANA, NABENDU MURMU, TAPAN KUMAR MONDAL

A new palladium(II) complex, [Pd(LSEt)Cl] (C1) with benzothiazole based ONS donor pincer ligand (HLSEt) was synthesized (where, HLSEt = 2-(benzothiazol-2-yl)-6-(((2-(ethylthio)phenyl)imino)methyl)phenol). Interaction of C1 with CT DNA was investigated, and its binding constant was found to be 4.0×105 M−1. The proficiency of ethidium bromide (EB) displacement from its EB-CTDNA complex by C1 was performed by the fluorescence quenching method, and Stern-Volmer quenching constant (Ksv) was found to be 4.3×105 M−1. Similarly, the interaction of C1 with BSA protein was investigated by UV-Vis and fluorescence methods. The apparent association constant (Ka) and Ksv were determined (Ka = 2.8×104 M−1 and Ksv = 5.5×104 M−1). In vitro cytotoxicity of the complex, [Pd(LSEt)Cl] (C1), towards human gastric cancer cell lines (AGS) was assessed by the MTT assay method. The half maximal inhibitory concentration (IC50) of C1 (9.55 ± 1.23 µM) towards AGS cancer lines was found to be lower than cisplatin (23.13 ± 1.03 µM).

Graphical abstract

Herein, new palladium(II) complex, [Pd(LSEt)Cl] (C1) with benzothiazole-based ONS donor pincer ligand (HLSEt) was synthesized and characterized by several spectroscopic techniques. Interaction of C1 with CT DNA and BSA protein was investigated by UV-Vis and fluorescence methods. In vitro cytotoxicity of the complex toward human gastric cancer cell lines (AGS) was evaluated by the MTT assay method. The half maximal inhibitory concentration (IC50) of the palladium(II) complex (9.55±1.23 µM) was found to be less compared to cisplatin (23.13±1.03 µM) towards AGS cancer lines.

合成了一种新的钯(II)配合物[Pd(LSEt)Cl] (C1)与基于苯并噻唑的ONS供体钳形配体(HLSEt) (HLSEt = 2-(苯并噻唑-2-基)-6-((2-(乙基噻唑)苯基)亚氨基)甲基)苯酚)。研究了C1与CT DNA的相互作用,发现其结合常数为4.0×105 M−1。用荧光猝灭法测定了溴化乙啶(EB)从EB- ctdna络合物中被C1取代的能力,得到了Stern-Volmer猝灭常数(Ksv)为4.3×105 M−1。同样,用紫外可见和荧光方法研究了C1与BSA蛋白的相互作用。测定表观关联常数(Ka)和Ksv (Ka = 2.8×104 M−1,Ksv = 5.5×104 M−1)。采用MTT法测定复合物[Pd(LSEt)Cl] (C1)对人胃癌细胞株(AGS)的体外细胞毒性。C1对AGS的半数最大抑制浓度(IC50)(9.55±1.23µM)低于顺铂(23.13±1.03µM)。在此基础上,合成了新的钯(II)配合物[Pd(LSEt)Cl] (C1)与苯并噻唑基ONS供体钳形配体(HLSEt)配合物,并用多种光谱技术对其进行了表征。用紫外可见和荧光法研究了C1与CT DNA和BSA蛋白的相互作用。采用MTT法评价该复合物对人胃癌细胞株的体外细胞毒性。钯(II)配合物对AGS癌细胞的半最大抑制浓度(IC50)为9.55±1.23µM,低于顺铂(23.13±1.03µM)。
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引用次数: 0
New cyclam based Zn(II) complexes: effect of flexibility and para substitution on DNA binding, in vitro cytotoxic studies and antimicrobial activities 新型环环霉素Zn(II)配合物:柔韧性和对取代对DNA结合的影响,体外细胞毒性研究和抗菌活性
IF 1.7 4区 化学 Q3 Chemistry Pub Date : 2022-09-29 DOI: 10.1007/s12039-022-02091-9
B Archana, S Sreedaran

A series of macrobicyclic binuclear Zn(II) complexes were synthesized from their macrocyclic ligand (L1 and L2) by Schiff base condensation with appropriate aliphatic or aromatic diamines, ZnCl2.4H2O, and triethylamine. All the complexes were characterized by elemental and spectral analysis. The enhanced DNA binding affinity of complexes [Zn2L1a], [Zn2L1c], and [Zn2L1d] is due to the existence of the electron-donating CH3 group, which leads to hydrophobic interaction with the hydrophobic DNA surface. The existence of electron-withdrawing Br atom in complex [Zn2L2a], [Zn2L2c], and [Zn2L2e] leads to lesser DNA binding affinity. The fluorescence quenching of the Zn(II) complex at 370 nm indicates the strong coordination of metal ions with N and O atoms of the ligand. The 3D fluorescence spectrum of [Zn2L2d] complex has been quenched more compared to [Zn2L2a] due to the planarity of aromatic system. DNA cleavage of Zn(II) complexes begins at a low concentration (25 μM) and reaches the maximum cleavage with a successive increase in concentration (100 μM). All the complexes were screened for antimicrobial and anticancer activity.

Graphical abstract

Macrobicyclic binuclear zinc(II) complexes synthesized from their macrocyclic ligands by Schiff base condensation were characterized by elemental and spectral analysis. The enhanced DNA binding affinity (CH3 group) and lesser DNA binding affinity (Br group) have been explained. The 3D fluorescence spectrum shows quenching due to the planarity of aromatic system. DNA cleavage and in vitro activities have been discussed.

以大环配体(L1和L2)与相应的脂肪族或芳香族二胺、ZnCl2.4H2O和三乙胺通过席夫碱缩合反应合成了一系列大双环双核Zn(II)配合物。所有配合物均通过元素分析和光谱分析进行了表征。配合物[Zn2L1a]、[Zn2L1c]和[Zn2L1d]的DNA结合亲和力增强是由于给电子CH3基团的存在,导致与疏水DNA表面发生疏水相互作用。配合物[Zn2L2a]、[Zn2L2c]和[Zn2L2e]中吸电子的Br原子的存在导致DNA结合亲和力降低。Zn(II)配合物在370 nm处的荧光猝灭表明金属离子与配体的N和O原子有很强的配位作用。由于芳香体系的平面性,[Zn2L2d]配合物的三维荧光光谱比[Zn2L2a]更猝灭。Zn(II)配合物的DNA切割始于低浓度(25 μM),随着浓度的增加达到最大(100 μM)。所有的配合物都进行了抗菌和抗癌活性筛选。摘要用希夫碱缩合法制备了大环双核锌(II)配合物,并用元素和光谱分析对其进行了表征。DNA结合亲和力(CH3基团)增强,DNA结合亲和力(Br基团)减弱。由于芳香族体系的平面性,三维荧光光谱呈现猝灭现象。讨论了DNA裂解和体外活性。
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引用次数: 0
An efficient and expeditious synthesis of 1,2,4-triazolidine-3-thiones using meglumine as a reusable catalyst in water 以三聚氰胺为可重复使用催化剂在水中高效快速合成1,2,4-三唑烷-3-硫酮
IF 1.7 4区 化学 Q3 Chemistry Pub Date : 2022-09-03 DOI: 10.1007/s12039-022-02087-5
Liklesha B Masram, Simren S Salim, Angad B Barkule, Yatin U Gadkari, Vikas N Telvekar

A simple, convenient, and eco-friendly procedure has been developed using meglumine (15 mol%) as a green catalyst for the synthesis of 1,2,4-triazolidine-3-thiones under one-pot condition. Variously substituted aldehydes or ketones reacted well with thiosemicarbazide to give desired compounds in extremely good quantity. The developed protocol offers several advantages such as shorter reaction times, mild reaction conditions, easy workup, simple purification procedures, water as a solvent, and wide substrate scope tolerance. Further, the catalyst was recycled (up to 4 cycles) without compromising the yield of the final products.

Graphical abstract

The current protocol demonstrates the synthesis of 1,2,4-triazolidine-3-thiones from variously substituted aldehydes or ketones with thiosemicarbazide under aqueous conditions. A simple stirring of the reaction at room temperature in the presence of the catalytic amount of meglumine quickly gave the desired product an excellent yield. The method is operationally simple and eco-friendly.

研究了一种简单、方便、环保的新工艺,以十五摩尔%的三聚氨胺为绿色催化剂,在一锅条件下合成1,2,4-三唑烷-3-硫酮。各种取代的醛或酮与硫代氨基脲反应良好,得到大量所需的化合物。该方案具有反应时间短、反应条件温和、易于处理、纯化程序简单、水作为溶剂、底物范围宽等优点。此外,催化剂可循环使用(多达4次循环),而不会影响最终产品的收率。图解摘要:目前的程序演示了在水条件下由不同取代的醛或酮与硫脲基氨基脲合成1,2,4-三唑烷-3-硫酮。在室温下,在催化量的聚氨胺的存在下,简单的搅拌反应,很快就得到了理想的产物,收率很高。该方法操作简单,环保。
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引用次数: 3
Disodium Anacardate: A Bio-based Catalyst for Room Temperature Synthesis of New, Fluorescent 1, 4-Benzoxazinone and Benzophenoxazinone Derivatives 负氧水二钠:室温合成新型荧光1,4 -苯并恶嗪酮及苯并恶嗪酮衍生物的生物基催化剂
IF 1.7 4区 化学 Q3 Chemistry Pub Date : 2022-08-30 DOI: 10.1007/s12039-022-02082-w
Rahul A Nagarkar, Sudhir E Dapurkar

The first report of room temperature synthesis of new, fluorescent 1, 4-benzoxazinone derivatives using disodium anacardate as a bio-based catalyst is discussed here. Disodium anacardate was derived from cashew nut shell liquid (CNSL) which is a renewable but underutilized agro by-product of the cashew industry. The synthesis of 1, 4-benzoxazinone derivatives were derived through a one-pot three-component reaction of 2-aminophenol, diethyl acetylenedicarboxylate, and trans 1, 2-dibenzoylethylene. Further, the utility of disodium anacardate as a base catalyst is tested effectively for the room temperature synthesis of benzophenoxazinone derivatives synthesized from 2-aminophenol and dichloro-1,4-naphthoquinones. In a solvent effect study, the catalyst activity of disodium anacardate was found excellent in green solvents. The fluorescence activity was studied for the synthesized molecules. Our efforts through this study are to explore the novel applications of anacardic acid in organic transformations and establish its utility in new synthetic methodologies.

Graphical abstract

Herein, we report room temperature synthesis of new fluorescent 1,4-benzoxazinone and benzophenoxazinones derivatives using disodium anacardate as a bio-based catalyst which was also synthesized at room temperature from Cashew nut shell liquid (CNSL). The fluorescence activity was studied for the synthesized molecules.

本文首次报道了以负氧水二钠为生物基催化剂,室温合成新型荧光1,4 -苯并恶嗪酮衍生物。腰果壳液是腰果工业的一种可再生但未充分利用的农业副产品。以2-氨基苯酚、乙酰二羧酸二乙酯和反式1,2 -二苯甲酰基乙烯为原料,通过一锅三组分反应,合成了1,4 -苯并恶嗪酮衍生物。此外,本文还有效地测试了负氧水二钠作为碱催化剂在室温下由2-氨基苯酚和二氯-1,4-萘醌合成二苯并恶嗪酮衍生物的作用。在溶剂效应研究中发现,在绿色溶剂中,醋酐二钠具有良好的催化活性。研究了合成分子的荧光活性。我们通过这项研究的努力是探索无心酸在有机转化中的新应用,并在新的合成方法中建立其效用。本文以腰果壳液(CNSL)为原料,在室温下合成了新型荧光1,4-苯并恶嗪酮和二苯并恶嗪酮衍生物。研究了合成分子的荧光活性。
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