咪唑[2,1-b]噻唑- 1h -吡唑基膦酸盐的一锅合成及抗结核活性研究

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI:10.1002/ajoc.202400724

Nagaraju Chirra , Varshitha Shanigarapu , Balasubramanian Sridhar , Srinivas Kantevari

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引用次数: 0

摘要

本文提出了以5-咪唑[2,1-b]噻唑羧醛为原料，一锅法合成咪唑[2,1-b]噻唑-吡唑膦酸盐的有效方法。该反应涉及原位生成的α，β-不饱和酮与Bestmann-Ohira试剂（BOR）之间的1,3-偶极环加成，在碱的促进下形成吡唑膦酸盐作为唯一的区域异构体，收率很高。对新合成的化合物4（a-x）体外抗结核分枝杆菌H37Rv （Mtb）的评价表明，化合物4 0为最有效的类似物(MIC: 6.25 μg/mL；10.40μM)。

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One‐pot Synthesis and Antitubercular Activity of Imidazo[2,1‐b]thiazol‐1H‐pyrazolylphosphonates

Herein, we present an effective one‐pot method for the synthesis of imidazo[2,1‐b]thiazole‐pyrazole phosphonates from 5‐imidazo[2,1‐b] thiazole carboxaldehydes. The reaction involves a 1,3‐dipolar cycloaddition between in situ generated α,β‐unsaturated ketones and the Bestmann–Ohira reagent (BOR), facilitated by a base, leading to the formation of pyrazole phosphonates as the sole regioisomer with excellent yields. The in vitro evaluation of the newly synthesized compounds 4(a–x) against Mycobacterium tuberculosis H37Rv (Mtb) identified compound 4 o as the most effective analogue (MIC: 6.25 μg/mL; 10.40 μM).

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来源期刊

Asian Journal of Organic Chemistry CHEMISTRY, ORGANIC-

CiteScore

4.70

自引率

3.70%

发文量

372

期刊介绍： Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.