Synthesis and evaluation of novel substituted 1,2,3-triazolyldihydroquinolines as promising antitubercular agents

[Display omitted] A series of novel substituted 1,2,3-triazolyldihydroquinolines 6a–o was designed and synthesized from 2-acetylthiophene in five-step reaction sequence involving modified Boltzmann-Rahtz reaction of β-Enaminone; Vilsmeier-Haack chloroformylation using DMF/POCl3; Ohira-Bestmann homol...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2019-02, Vol.29 (4), p.529-533
Main Authors: Marvadi, Sandeep Kumar, Krishna, Vagolu Siva, Sriram, Dharmarajan, Kantevari, Srinivas
Format: Article
Language:English
Subjects:
Antitubercular Agents - chemical synthesis
Antitubercular Agents - pharmacology
Dihydroquinoline
Microbial Sensitivity Tests
Mycobacterium tuberculosis
Mycobacterium tuberculosis - drug effects
Quinolines - chemical synthesis
Quinolines - chemistry
Quinolines - pharmacology
Thiophene
Triazole
Triazoles - chemistry
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Summary:[Display omitted] A series of novel substituted 1,2,3-triazolyldihydroquinolines 6a–o was designed and synthesized from 2-acetylthiophene in five-step reaction sequence involving modified Boltzmann-Rahtz reaction of β-Enaminone; Vilsmeier-Haack chloroformylation using DMF/POCl3; Ohira-Bestmann homologation of aldehyde to alkyne as key steps. The reaction of alkyne 4 with various aryl azides in the presence of copper sulfate and sodium ascorbate resulted desired new 1,2,3-triazolyldihydroquinolines 6a–o in excellent yields. In vitro screening of new compounds for anti-mycobacterial activity against Mycobacterium tuberculosis H37Rv (Mtb), resulted in three derivatives 6a (MIC:1.56 µg/mL) and 6d, 6l (MIC:3.12 µg/mL) as promising antitubercular agents with lower cytotoxicity profiles.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2019.01.004