Synthesis and biological evaluation of new 2-aryl-4-((4-aryl-1H-1,2,3-triazol-1-yl)methyl)thiazole derivatives

Shinde, Vikas; Mahulikar, Pramod P.; Mhaske, Pravin C.; Nawale, Laxman; Sarkar, Dhiman

doi:10.1007/s11164-017-3164-4

Cited by 22 publications

(9 citation statements)

References 57 publications

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“…Ethyl 3-bromo-2-oxopropanoate 1 was refluxed with arylthioamide 2 to afford ethyl 2-arylthiazole-4-carboxylate 3 which in turn was utilized by Shinde team 17 to synthesize a group of 2-aryl-4-((4-aryl-1H-1,2,3-triazol-1-yl)methyl)thiazoles (Scheme 1). 4 had showed antitubercular activity against Mycobacterium tuberculosis (IC50 4.85 µg/mL) and it was more potent than Rifampicin against Mycobacterium bovis as presented by (IC50 0.03 µg/mL).…”

Section: Synthesis Of 2-arylthiazolesmentioning

confidence: 99%

Synthetic Approaches toward Certain Structurally Related Antimicrobial Thiazole Derivatives (2010-2020)

Abuo‐Rahma¹,

Hassan²,

Hassan³

et al. 2021

HETEROCYCLES

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In the present literature review, we comprehensively discuss different methods of synthesis of published antimicrobial thiazole derivatives in the last decade mainly those which showed antibacterial, antimycobacterial and/or antifungal activity. Owing to the great diversity of thiazole-derived antimicrobial agents, we organized most of them chemically in stipulated classes. In each class, we mentioned common methods of thiazole ring closure and indicated antimicrobial activity of the most active derivatives in clear and simple way. CONTENTS1.

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Section: Synthesis Of 2-arylthiazolesmentioning

confidence: 99%

Synthetic Approaches toward Certain Structurally Related Antimicrobial Thiazole Derivatives (2010-2020)

Abuo‐Rahma¹,

Hassan²,

Hassan³

et al. 2021

HETEROCYCLES

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“…Quinoline tethered azole hybrids are important pharmacophores that possess a wide range of biological activities . The 1,2,3‐triazole nucleus containing compounds are important pharmacophore for drug development as they also exhibit significant biological activities …”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of New 1,2,3‐Triazolyl‐Pyrazolyl‐Quinoline Derivatives as Potential Antimicrobial Agents

et al. 2020

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A new series of 4-{1-phenyl-4-[(4-phenyl-1,2,3-triazol-1-yl)methyl]pyrazol-3-yl}quinoline (7a-l) have been synthesized by a click reaction of 4-(4-(azidomethyl)-1-phenyl-1H-pyrazol-3-yl) quinoline (5a-d) with a substituted ethynylbenzene. The newly synthesized 1,2,3-triazolyl-pyrazolyl-quinoline derivatives were evaluated for biological activity against Escherichia coli (NCIM 2574), Proteus mirabilis (NCIM 2388), (Gram negative strains), Bacillus subtilis (NCIM 2063), Staphylococcus albus (NCIM 2178) (Gram positive strains) and in vitro antifungal activity against Candida albicans (NCIM 3100) and Aspergillus niger (ATCC 504). Five 1,2,3-triazolyl-pyrazolyl-quinoline derivatives, 7d, 7 g, 7 h, 7k and 7 l exhibited good antifungal activity against A. niger with MIC 62.5 μg/mL. The compounds 7 h, 7k and 7 l were further evaluated for ergosterol inhibition assay against A. niger cell sample at 62.5 μg/mL concentration. Upon analysis of the sterol inhibition assay, it was revealed that, the ergosterol biosynthesis has decreased in the fungal samples treated with the 1,2,3-triazolyl-pyrazolyl-quinoline derivatives. Thus antimicrobial activity suggested that, these compounds could aid and assist in the development of lead compounds to treat microbial infections.

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“…Pyrazole containing compounds are known for broad spectrum of biological activities [ 17,18 ] against infectious diseases such as antibacterial and antifungal, [ 19–22 ] antitubercular, [ 23,24 ] anticancer, [ 25 ] and anti‐inflammatory [ 26 ] activities. 1,2,3‐Triazole is also an important pharmacophore for drug development, [ 27,28 ] that show significant activities such as antimicrobial, [ 29–32 ] antifungal, [ 33,34 ] antitubercular, [ 35–37 ] antimalarial, [ 38 ] anticancer, [ 39 ] and antiviral [ 40 ] activities. Clubbed pyrazole, quinoline and triazole nucleus together is an important pharmacophore that possess wide range of biological activities [ 41,42 ] (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antimycobacterial screening of new 4‐(4‐(1‐benzyl‐1H‐1,2,3‐triazol‐4‐yl)‐1‐phenyl‐1H‐pyrazol‐3‐yl)quinoline derivatives

Thakare

Walunj

Chavan

et al. 2020

Journal of Heterocyclic Chem

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A new series of 4‐(4‐(1‐benzyl‐1H‐1,2,3‐triazol‐4‐yl)‐1‐phenyl‐1H‐pyrazol‐3‐yl)quinoline (6a‐t) have been synthesized by a click reaction of 4‐(4‐ethynyl‐1‐phenyl‐1H‐pyrazol‐3‐yl)quinoline (4a‐d) with a substituted benzyl azide (5a‐e). The starting alkyne derivatives 4a‐d are obtained from Bestmann‐Ohira reaction of 1‐phenyl‐3‐(quinolin‐4‐yl)‐1H‐pyrazole‐4‐carbaldehyde and dimethyl(1‐diazo‐2‐oxopropyl)phosphonate. The newly synthesized compounds are screened against M. tuberculosis H37Ra dormant and active, Escherichia coli, Pseudomonas fluorescence, Staphylococcus aureus and Bacillus subtilis strains at 30 μg/mL concentration. Most of the screened compounds showed good to moderate antibacterial activity against S. aureus, B. subtilis, and Mycobacterium tuberculosis H37Ra strains. The synthesized derivatives of quinolinyl‐pyrazole‐4‐carbaldehyde and quinolinyl‐pyrazole‐4‐ethyne reportd good to moderate activity against both strains of M. tuberculosis H37Ra. Ten derivatives of quinolinyl‐pyrazole presented good activity against B. subtilis. These results suggested that further optimization and development of quinolinyl‐pyrazolyl‐1,2,3‐triazole moeity could serve as lead compounds for antimycobacterial activity.

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Synthesis and biological evaluation of new 2-aryl-4-((4-aryl-1H-1,2,3-triazol-1-yl)methyl)thiazole derivatives

Cited by 22 publications

References 57 publications

Synthetic Approaches toward Certain Structurally Related Antimicrobial Thiazole Derivatives (2010-2020)

Synthetic Approaches toward Certain Structurally Related Antimicrobial Thiazole Derivatives (2010-2020)

Synthesis and Biological Evaluation of New 1,2,3‐Triazolyl‐Pyrazolyl‐Quinoline Derivatives as Potential Antimicrobial Agents

Synthesis and antimycobacterial screening of new 4‐(4‐(1‐benzyl‐1H‐1,2,3‐triazol‐4‐yl)‐1‐phenyl‐1H‐pyrazol‐3‐yl)quinoline derivatives

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