[BMIM]BF4介导的苯基-4-（1H-吡唑-5-基）-1H-吡唑并[3,4-b]喹啉-5（4H）-酮的多组分合成及其抗癌活性评价

IF 0.7 4区化学 Q4 CHEMISTRY, ORGANIC

Letters in Organic Chemistry Pub Date : 2023-08-31 DOI:10.2174/1570178620666230831162320

Areveli Srinivas, A. Shree, S. Goud

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引用次数: 0

摘要

吡唑桥联喹诺酮类支架是许多具有药用活性的新型化学实体的重要组成部分。本工作以[BMIM]BF4为绿色反应介质，通过3-甲基-1-苯基-1H-吡唑-5-胺1、5，5-二甲基环己烷-1，3-二酮2和1H-吡唑-5-甲醛3的一锅三组分反应，合成了与1H-吡嗪并[3，4-b]喹啉-5（4H）-酮衍生物共轭的苯基-4-（1H-吡噻唑-5-基），产率较高。此外，评估了合成的化合物对HeLa和DU145细胞的细胞毒性潜力。在八种衍生物中，化合物4d表现出良好的细胞毒性，对DU145和HeLa细胞的IC50值分别为8.5和8.9µM。分子对接研究表明，化合物4d对人检查点激酶1表现出良好的结合能（-8.4kcal/mol）。

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[BMIM]BF4 Mediated Multi-component Synthesis of Phenyl-4-(1H-pyrazol-5-yl)-1H-pyrazolo[3,4-b]quinolin-5(4H)-ones and Evaluation of their Anti-cancer Activity

Pyrazolo bridged quinolones scaffolds are an important building block in many of the medicinally active new chemical entities. In the current work, synthesis of phenyl-4-(1H-pyrazol-5-yl) conjugated with 1H-pyrazolo[3,4-b]quinolin-5(4H)-ones derivatives has been achieved by one-pot three-component reaction of 3-methyl-1-phenyl-1H-pyrazol-5-amine 1, 5,5-dimethylcyclohexane-1,3-diones 2, and 1H-pyrazole-5-carbaldehydes 3 using [BMIM]BF4 as green reaction medium with good yields. Furthermore, the synthesized compounds were evaluated for cytotoxic potential towards HeLa and DU145 cells. Of the eight derivatives, compound 4d exhibited good cytotoxicity with an IC50 value of 8.5 and 8.9 µM against DU145 and HeLa cells, respectively. The molecular docking studies revealed that compound 4d displayed good binding energy (-8.4 kcal/mol) against human checkpoint kinase 1.

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来源期刊

Letters in Organic Chemistry 化学-有机化学

CiteScore

1.30

自引率

12.50%

发文量

135

审稿时长

7 months

期刊介绍： Aims & Scope Letters in Organic Chemistry publishes original letters (short articles), research articles, mini-reviews and thematic issues based on mini-reviews and short articles, in all areas of organic chemistry including synthesis, bioorganic, medicinal, natural products, organometallic, supramolecular, molecular recognition and physical organic chemistry. The emphasis is to publish quality papers rapidly by taking full advantage of latest technology for both submission and review of the manuscripts. The journal is an essential reading for all organic chemists belonging to both academia and industry.