Synthesis, characterization and biological study of some new substituted pyrazolo[3,4-d] thiazolo[3,2-a] pyrimidine derivatives

Q2 Chemistry

Current Chemistry Letters Pub Date : 2023-01-01 DOI:10.5267/j.ccl.2023.3.010

M. Chavda, M. F. Dhaduk, J. Upadhyay

{"title":"Synthesis, characterization and biological study of some new substituted pyrazolo[3,4-d] thiazolo[3,2-a] pyrimidine derivatives","authors":"M. Chavda, M. F. Dhaduk, J. Upadhyay","doi":"10.5267/j.ccl.2023.3.010","DOIUrl":null,"url":null,"abstract":"Fused pyrimidines play an imperative role in our life due to their biological importance in the struggle of microorganisms. A series of 4-aryl-3-methyl-1-phenyl-1,4,6,7-tetrahydropyrazolo[3,4-d] thiazolo[3,2-a]pyrimidine (4a-j) were synthesized by cyclization of 3-methyl-1-phenyl-4-aryl-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-d]pyrimidine-6-thiones (3a-j) with 1,2-dibromoethane in presence of anhydrous potassium carbonate. Earlier, compounds (3a-j) were synthesized by the condensation of 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one (2), different substituted benzaldehyde and thiourea with catalytic amount of con. HCl in methanol. Compound 2 was synthesized by condensation of ethyl acetoacetate (1) and phenylhydrezine in presence of a catalytic amount of acetic acid at reflux temperature. The constitution of the synthesized products has been characterized by using elemental analysis, Infrared, 1H-NMR spectroscopy and further supported by Mass spectroscopy. All the products have been screened for their in-vitro biological assay like antibacterial and antifungal activity at concentration of 500 μg/ml. It was exposed that most of the compounds displayed inspiring antibacterial and antifungal activity compared to the used reference standard.","PeriodicalId":10942,"journal":{"name":"Current Chemistry Letters","volume":"111 1","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Current Chemistry Letters","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.5267/j.ccl.2023.3.010","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"Chemistry","Score":null,"Total":0}

引用次数: 0

Abstract

Fused pyrimidines play an imperative role in our life due to their biological importance in the struggle of microorganisms. A series of 4-aryl-3-methyl-1-phenyl-1,4,6,7-tetrahydropyrazolo[3,4-d] thiazolo[3,2-a]pyrimidine (4a-j) were synthesized by cyclization of 3-methyl-1-phenyl-4-aryl-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-d]pyrimidine-6-thiones (3a-j) with 1,2-dibromoethane in presence of anhydrous potassium carbonate. Earlier, compounds (3a-j) were synthesized by the condensation of 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one (2), different substituted benzaldehyde and thiourea with catalytic amount of con. HCl in methanol. Compound 2 was synthesized by condensation of ethyl acetoacetate (1) and phenylhydrezine in presence of a catalytic amount of acetic acid at reflux temperature. The constitution of the synthesized products has been characterized by using elemental analysis, Infrared, 1H-NMR spectroscopy and further supported by Mass spectroscopy. All the products have been screened for their in-vitro biological assay like antibacterial and antifungal activity at concentration of 500 μg/ml. It was exposed that most of the compounds displayed inspiring antibacterial and antifungal activity compared to the used reference standard.

查看原文本刊更多论文

一些新的取代吡唑[3,4-d]噻唑[3,2-a]嘧啶衍生物的合成、表征及生物学研究

融合嘧啶在我们的生活中扮演着重要的角色，因为它们在微生物的斗争中具有重要的生物学意义。以3-甲基-1-苯基-4-芳基-1,4,5,7-四氢- 6h -吡唑[3,4-d]嘧啶-6-硫酮(3a-j)为原料，在无水碳酸钾存在下与1,2-二溴乙烷环化，合成了一系列4-芳基-3-甲基-1-苯基-1,4,6,7-四氢吡唑[3,4-d]噻唑[3,2- A]嘧啶(4a-j)。在此之前，用催化量盐酸在甲醇中以5-甲基-2-苯基-2,4-二氢- 3h -吡唑-3-酮(2)、不同取代苯甲醛和硫脲缩合反应合成了化合物(3a-j)。在回流温度下，以乙酸乙酯(1)和苯肼为原料，在一定量的乙酸催化下缩合合成化合物2。通过元素分析、红外光谱、核磁共振谱和质谱对合成产物的结构进行了表征。所有产品在浓度为500 μg/ml时进行了体外抑菌和抗真菌活性的筛选。结果表明，与标准对照品相比，大多数化合物具有较强的抗菌和抗真菌活性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

Current Chemistry Letters Chemistry-Chemistry (all)

CiteScore

4.90

自引率

0.00%

发文量

审稿时长

20 weeks

期刊介绍： The "Current Chemistry Letters" is a peer-reviewed international journal which aims to publish all the current and outstanding research articles, reviews and letters in chemistry including analytical chemistry, green chemistry, inorganic chemistry, organic chemistry, physical chemistry, etc. This journal is dedicated to serve all academic and industrial researchers and scientists who are expert in all major advances in chemistry research. The journal aims to provide the most complete and reliable source of information on current developments in these fields. The emphasis will be on publishing quality articles rapidly and openly available to researchers worldwide. Please note readers are free to read, download, copy, distribute, print, search, or link to the full texts of articles published on this journal. Current Chemistry Letters is an open access journal, which provides instant access to the full text of research papers without any need for a subscription to the journal where the papers are published. Therefore, anyone has the opportunity to copy, use, redistribute, transmit/display the work publicly and to distribute derivative works, in any sort of digital form for any responsible purpose, subject to appropriate attribution of authorship. Authors who publish their articles may also maintain the copyright of their articles.