Design, synthesis and biological evaluation of novel 1,2,3-triazole analogues of Imidazo-[1,2-a]-pyridine-3-carboxamide against Mycobacterium tuberculosis

Nandikolla, Adinarayana; Srinivasarao, Singireddi; Khetmalis, Yogesh Mahadu; Kumar, Banoth Karan; Murugesan, Sankaranarayanan; Shetye, Gauri; Ma, Rui; Franzblau, Scott G.; Sekhar, Kondapalli Venkata Gowri Chandra

doi:10.1016/j.tiv.2021.105137

Cited by 22 publications

(23 citation statements)

References 34 publications

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“…As a pre-selection step for testing the docking protocols for the final compounds, we followed the protocols already established in our previous studies. 21,33 In accordance with Fig. 6, the RMSD for the target protein was 0.4 Å, signifying that the docking protocol was both reliable and ready for subsequent comparative studies (Table 4).…”

Section: Resultssupporting

confidence: 74%

“…21 It also possesses a conserved active site and lacks apparent homologs in mammals. 28 A few reports mentioned above 21,26 also suggested the mode of action of antimycobacterial imidazopyridines through inhibition of InhA of MTB. Hence, based on the reported rationale, targeting the InhA enzyme followed by disruption of mycobacterial cellular homeostasis may be the most appropriate strategy for the current molecular docking study, and hence we docked our compounds at the active site of enoyl acyl carrier protein reductase from Mycobacterium tuberculosis (PDB 4TZK).…”

Section: Introductionmentioning

confidence: 99%

“…Among all the compounds, 8 emerged to be the most potent with MIC of 13.74 μg mL −1 . 21 Literature-reported IPA-based anti-tubercular agents are showcased in Fig. 2.…”

Section: Introductionmentioning

confidence: 99%

“…26,27 It contains around 269 amino acid residues (single A chain) with one co-crystal ligand (( R )-1-cyclohexyl- N -(3,5-dichlorophenyl)-5-oxopyrrolidine-3-carboxamide) and one co-factor NAD in its 3D structure. 21 It also possesses a conserved active site and lacks apparent homologs in mammals. 28 A few reports mentioned above 21,26 also suggested the mode of action of antimycobacterial imidazopyridines through inhibition of InhA of MTB.…”

Section: Introductionmentioning

confidence: 99%

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Design, synthesis and anti-mycobacterial evaluation of imidazo[1,2-a]pyridine analogues

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Section: Resultssupporting

confidence: 74%

Section: Introductionmentioning

confidence: 99%

“…Among all the compounds, 8 emerged to be the most potent with MIC of 13.74 μg mL −1 . 21 Literature-reported IPA-based anti-tubercular agents are showcased in Fig. 2.…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Design, synthesis and anti-mycobacterial evaluation of imidazo[1,2-a]pyridine analogues

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“… 58 Compounds with activity >90% of inhibition of the growth of MT in MABA were further tested against M. abscessus ATCC 19977, M. chelonae ATCC 35752, M. marinum ATCC 927, M. avium ATCC 15769, and M. kansasii ATCC 12478, using MABA 58 and a cytotoxicity assay against Vero cell line ATCC CCL-81. 60 For the latter, 0.6 mM of resazurin was used and the absorbance was recorded at 530 nm (excitation) and 590 nm (emission). Positive controls for all assays are indicated in Tables 3 and 4 .…”

Section: Methodsmentioning

confidence: 99%

Insights into the Chemical Diversity of Selected Fungi from the Tza Itzá Cenote of the Yucatan Peninsula

et al. 2022

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Cenotes are habitats with unique physical, chemical, and biological features. Unexplored microorganisms from these sinkholes represent a potential source of bioactive molecules. Thus, a series of cultivable fungi ( Aspergillus spp. NCA257, NCA264, and NCA276, Stachybotrys sp. NCA252, and Cladosporium sp. NCA273) isolated from the cenote Tza Itzá were subjected to chemical, coculture, and metabolomic analyses. Nineteen compounds were obtained and tested for their antimicrobial potential against ESKAPE pathogens, Mycobacterium tuberculosis , and nontuberculous mycobacteria. In particular, phenylspirodrimanes from Stachybotrys sp. NCA252 showed significant activity against MRSA, MSSA, and mycobacterial strains. On the other hand, the absolute configuration of the new compound 17-deoxy-aspergillin PZ ( 1 ) isolated from Aspergillus sp. NCA276 was established via single-crystal X-ray crystallography. Also, the chemical analysis of the cocultures between Aspergillus and Cladosporium strains revealed the production of metabolites that were not present or were barely detected in the monocultures. Finally, molecular networking analysis of the LC-MS-MS/MS data for each fungus was used as a tool for the annotation of additional compounds, increasing the chemical knowledge on the corresponding fungal strains. Overall, this is the first systematic chemical study on fungi isolated from a sinkhole in Mexico.

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Design, Synthesis and Biological Evaluation of Novel Spiro‐[Chroman‐2,4′‐Piperidin]‐4‐One Analogs as Anti‐Tubercular Agents

Chitti

Nandikolla

Khetmalis

et al. 2022

Chemistry & Biodiversity

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A series of novel spiro‐[chromane‐2,4′‐piperidin]‐4(3H)‐one derivatives were designed, synthesized and structures were confirmed by analytical methods, viz., 1H‐NMR, 13C‐NMR and mass spectrometry. The synthetic derivatives were evaluated for their anti‐tuberculosis (anti‐TB) activity against Mycobacterium tuberculosis (Mtb) strain H37Ra. Among all the evaluated Compounds, PS08 exhibited significant inhibition with MIC value of 3.72 μM while MIC values of the remaining Compounds ranged from 7.68 to 230.42 μM in comparison to the standard drug INH (MIC 0.09 μM). The two most active Compounds however showed acute cytotoxicity towards the human MRC‐5 lung fibroblast cell lines. The in silico ADMET profiles of the titled Compounds were predicted and found within the prescribed limits of the Lipinski and Jorgenson rules. Molecular docking study of the notably active Compound (PS08) was also carried out after performing validation in order to understand the putative binding position of the test ligand at the active site of selected target protein Mtb tyrosine phosphatase (PtpB).

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Design, synthesis and biological evaluation of novel 1,2,3-triazole analogues of Imidazo-[1,2-a]-pyridine-3-carboxamide against Mycobacterium tuberculosis

Cited by 22 publications

References 34 publications

Design, synthesis and anti-mycobacterial evaluation of imidazo[1,2-a]pyridine analogues

Design, synthesis and anti-mycobacterial evaluation of imidazo[1,2-a]pyridine analogues

Insights into the Chemical Diversity of Selected Fungi from the Tza Itzá Cenote of the Yucatan Peninsula

Design, Synthesis and Biological Evaluation of Novel Spiro‐[Chroman‐2,4′‐Piperidin]‐4‐One Analogs as Anti‐Tubercular Agents

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