Click-based synthesis and antitubercular evaluation of dibenzofuran tethered thiazolyl-1,2,3-triazolyl acetamides

Bioorganic & Medicinal Chemistry Letters
2016.0

Abstract

A series of novel dibenzofuran tethered thiazolyl-1,2,3-triazolyl acetamides, designed by assembling antitubercular pharmacophoric fragments, dibenzofuran, 2-aminothiazole and substituted triazoles in one molecular architecture, were evaluated against Mycobacterium tuberculosis. The new analogues 6a-p accomplished in four step synthetic sequence utilizing click chemistry in the penultimate step, was fully characterized by their NMR and mass spectral data. Among the compounds 6a-p screened for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv, three compounds 6j (MIC: 1.56μg/mL); 6a and 6p (MIC: 3.13μg/mL) was found to be most active and exhibited lower cytotoxicity. Among these three, 6j could be a candidate to consider as a drug like hit analogue for further development.

Knowledge Graph

Similar Paper

Click-based synthesis and antitubercular evaluation of dibenzofuran tethered thiazolyl-1,2,3-triazolyl acetamides
Bioorganic & Medicinal Chemistry Letters 2016.0
Click-based synthesis and antitubercular evaluation of novel dibenzo[ b , d ]thiophene-1,2,3-triazoles with piperidine, piperazine, morpholine and thiomorpholine appendages
Bioorganic & Medicinal Chemistry Letters 2016.0
Rational design and synthesis of novel dibenzo[b,d]furan-1,2,3-triazole conjugates as potent inhibitors of Mycobacterium tuberculosis
European Journal of Medicinal Chemistry 2014.0
Design, synthesis and evaluation of 6-(4-((substituted-1H-1,2,3-triazol-4-yl)methyl)piperazin-1-yl)phenanthridine analogues as antimycobacterial agents
Bioorganic & Medicinal Chemistry Letters 2013.0
Design, synthesis and evaluation of 1,2,3-triazole-adamantylacetamide hybrids as potent inhibitors of Mycobacterium tuberculosis
Bioorganic & Medicinal Chemistry Letters 2014.0
One-pot synthesis of new triazole—Imidazo[2,1-b][1,3,4]thiadiazole hybrids via click chemistry and evaluation of their antitubercular activity
Bioorganic & Medicinal Chemistry Letters 2015.0
Synthesis and biological evaluation of novel 1,2,3-triazole derivatives as anti-tubercular agents
Bioorganic & Medicinal Chemistry Letters 2017.0
Dibenzofuran, dibenzothiophene and N-methyl carbazole tethered 2-aminothiazoles and their cinnamamides as potent inhibitors of Mycobacterium tuberculosis
Bioorganic & Medicinal Chemistry Letters 2018.0
1,2,3-Triazole derivatives as antitubercular agents: synthesis, biological evaluation and molecular docking study
MedChemComm 2015.0
Rational design, synthesis and antitubercular evaluation of novel 2-(trifluoromethyl)phenothiazine-[1,2,3]triazole hybrids
Bioorganic & Medicinal Chemistry Letters 2014.0