Design, synthesis and evaluation of 6-(4-((substituted-1H-1,2,3-triazol-4-yl)methyl)piperazin-1-yl)phenanthridine analogues as antimycobacterial agents

Nagesh, Hunsur Nagendra; Naidu, Kalaga Mahalakshmi; Rao, D. H. Sreenivasa; Sridevi, Jonnalagadda Padma; Sriram, Dharmarajan; Yogeeswari, Perumal; Sekhar, Kondapalli Venkata Gowri Chandra

doi:10.1016/j.bmcl.2013.10.016

Cited by 51 publications

(17 citation statements)

References 26 publications

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“…Compound 3 on reacting with propargyl amine in the presence of K 2 CO 3 formed N ‐alkyl product ( 4 ). The free acetylene group was converted to various N ‐((1‐substituted phenyl‐1 H ‐1,2,3‐triazol‐4‐yl)methyl)‐9 H ‐fluoren‐9‐amines ( 5a–p ) using different aromatic azides via click chemistry method …”

Section: Resultsmentioning

confidence: 99%

Design and synthesis of 9H‐fluorenone based 1,2,3‐triazole analogues as Mycobacterium tuberculosis InhA inhibitors

et al. 2018

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We prepared fifty various 9H-fluorenone based 1,2,3-triazole analogues varied with NH, -S-, and -SO - groups using click chemistry. The target compounds were characterized by routine analytical techniques, H, CNMR, mass, elemental, single-crystal XRD (8a) and screened for in vitro antitubercular activity against Mycobacterium tuberculosis (MTB) H37Rv strain and two "wild" strains Spec. 210 and Spec. 192 and MIC was determined. Further, the compounds were evaluated for MTB InhA inhibition study as well. The final analogues exhibited minimum inhibitory concentration (MIC) ranging from 52.35 to >295 μm. Among the -NH- analogues, one compound 5p (MIC 58.34 μm), among -S- containing analogues four compounds 8e (MIC 66.94 μm), 8f (MIC 74.20 μm), 8g (MIC 57.55 μm), and 8q (MIC 56.11 μm), among -SO - containing compounds one compound 10p (MIC 52.35 μm) showed less than MTB MIC 74.20 μm: Compound 4-(((9H-fluoren-9-yl)sulfonyl)methyl)-1-(3,4,5-trimethoxyphenyl)-1H-1,2,3-triazole (10p) was found to be the most active compound with 73% InhA inhibition at 50 μm; it inhibited MTB with MIC 52.35 μm. Further, 10f and 10p were docked to crystal structure of InhA to know binding interaction pattern. Most active compounds were found to be non-cytotoxic against HEK 293 cell lines at 50 μm.

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Section: Resultsmentioning

confidence: 99%

Design and synthesis of 9H‐fluorenone based 1,2,3‐triazole analogues as Mycobacterium tuberculosis InhA inhibitors

et al. 2018

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“…Several series of FQs‐isatin hybrids with remarkable improvement in lipophilicity have been evaluated for their anti‐TB activities, and some of them such as gatifloxacin (GTFX)‐isatin hybrid 1 exhibited promising in vitro and in vivo activities than the parent drugs . Further investigation indicated that the anti‐TB activity of these hybrids was greatly influenced by the linkers between FQs and isatin . 1,2,3‐Triazole fragment not only can act as the isostere of amide, ester, carboxylic acid, and other heterocycles, but also can serve as a useful tool to manipulate lipophilicity, polarity, and hydrogen bonding capacity of molecules, and consequently improved pharmacological, property of drug candidates, and ultimately drugs .…”

Section: Introductionmentioning

confidence: 99%

1H‐1,2,3‐Triazole tethered isatin‐moxifloxacin: Design, synthesis and in vitro anti‐mycobacterial evaluation

Jiang

Qian

2019

Archiv der Pharmazie

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A series of novel 1H-1,2,3-triazole tethered isatin-moxifloxacin (MXF) hybrids 5a-l with greater lipophilicity compared with the parent MXF were designed, synthesized and screened for their in vitro antimycobacterial activities against Mycobacterium tuberculosis (MTB) H 37 Rv and multidrug-resistant MTB (MDR-MTB) as well as their cytotoxicity on the VERO cell line. All the synthesized hybrids (MIC: 0.025-0.78 μg/ml) showed considerable activities against MTB H 37 Rv and MDR-MTB, and the most active conjugate 5c (MIC: 0.025 and 0.06 μg/ml) was 2 to >2048 times more potent in vitro than the three references MXF (MIC: 0.10 and 0.12 μg/ml), rifampicin (MIC: 0.39 and 32μg/ml) and isoniazid (MIC: 0.05 and >128 μg/ml) against the two tested strains. All hybrids (CC 50 : 4-64 μg/ml) were much more cytotoxic than the parent MXF (CC50: 128 μg/ml), but the most active hybrid 5c (CC 50 : 32 μg/ml) also displayed acceptable cytotoxicity, warranting further investigation.

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“…Nagesh et al developed piperazine substituted derivatives and screened them for antimycobacterial activity. Compound 167 was reported as the most active compound with MIC of 1.56 µg/mL against H37Rv strain[271]. Amongst the compounds synthesized by Agrawal et al, compound 168 displayed highest antimycobacterial activity with MIC of 0.5 µg/mL against H 37 Rv strain of M. tuberculosis[272].…”

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confidence: 98%

Piperazine scaffold: A remarkable tool in generation of diverse pharmacological agents

Shaquiquzzaman

Verma

Marella

et al. 2015

European Journal of Medicinal Chemistry

198

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Design, synthesis and evaluation of 6-(4-((substituted-1H-1,2,3-triazol-4-yl)methyl)piperazin-1-yl)phenanthridine analogues as antimycobacterial agents

Cited by 51 publications

References 26 publications

Design and synthesis of 9H‐fluorenone based 1,2,3‐triazole analogues as Mycobacterium tuberculosis InhA inhibitors

Design and synthesis of 9H‐fluorenone based 1,2,3‐triazole analogues as Mycobacterium tuberculosis InhA inhibitors

1H‐1,2,3‐Triazole tethered isatin‐moxifloxacin: Design, synthesis and in vitro anti‐mycobacterial evaluation

Piperazine scaffold: A remarkable tool in generation of diverse pharmacological agents

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