@article {46016, title = {Thiazolyl-pyrazole derivatives as potential antimycobacterial agents}, journal = {Bioorganic \& Medicinal Chemistry Letters}, volume = {29}, year = {2019}, month = {MAY}, pages = {1199-1202}, type = {Article}, abstract = {

Mycobacterium tuberculosis (Mtb) is an obligate aerobe that is capable of long-term persistence under conditions of low oxygen tension. A series of thiazolyl-pyrazole derivatives (6a-f, 7a-f, 8c, 8e) were screened for antimycobacterial activity against dormant M. tuberculosis H37Ra (D-MTB) and M. bovis BCG (D-BCG). Nine thiazolyl- pyrazole analogs, 6c, 6e, 7a, 7b, 7c, 7e, 7f, 8c and 8e exhibited promissing minimum inhibitory concentration (MIC) values (0.20-28.25 mu g/mL) against D-MTB and D-BCG strains of Mtb. Importantly, six compounds (7a, 7b, 7e, 7f, 8c and 8e) exhibited excellent antimycobacterial activity and low cytotoxicity at the maximum evaluated concentration of \> 250 mu g/mL. Finally, the promising antimycobacterial activity and lower cytotoxicity profile suggested that, these compounds could be further subjected for optimization and development as a lead, which could have the potential to treat tuberculosis.

}, keywords = {antimycobacterial activity, Cytotoxicity, Pyrazole, thiazoles}, issn = {0960-894X}, doi = {10.1016/j.bmcl.2019.03.020}, author = {Takate, Sushma J. and Shinde, Abhijit D. and Karale, Bhausaheb K. and Akolkar, Hemant and Nawale, Laxman and Sarkar, Dhiman and Mhaske, Pravin C.} } @article {46623, title = {Synthesis of new thiazole and pyrazole clubbed 1,2,3-triazol derivatives as potential antimycobacterial and antibacterial agents}, journal = {Polycyclic Aromatic Compounds}, volume = {42}, year = {2022}, month = {JUL}, pages = {3216-3237}, type = {Article}, abstract = {

New series of 4-methyl-2-(4-substituted phenyl)-5-(4-((4-(4-substituted phenyl)-1H-1,2,3-triazol-1-yl)methyl)-1-phenyl-1H-pyrazol-3-yl)thiazole, 6a-t and 4-(1,3-diphenyl-1H-pyrazol-4-yl)-1-((1,3-diphenyl-1H-pyrazol-4-yl)methyl )-1H-1,2,3-triazole, 11a-o derivatives have been synthesized by applying copper-catalyzed [3 + 2] cycloaddition reaction. The newly synthesized 1,3-thiazolyl-pyrazolyl-1,2,3-triazole (6a-t) and bis-pyrazolyl-1,2,3-triazole (11a-o) derivatives were screened for in vitro antimycobacterial activity against M. Tuberculosis H37Ra dormant and active and antibacterial activity against four pathogenic bacteria, E. coli (NCIM 2576), P. flurescence (NCIM 2059), S. aureus (NCIM 2602) and B. subtilis (NCIM 2162). Compounds 6a, 6f, 6j, 11e and 11m showed good activity against M tuberculosis H37Ra Active strain, also compounds 6g, 6h, 11f, 11n and 11o showed good activity against M tuberculosis H37Ra Dormant strain. Compounds 6b, 6i, 6l, 6o, 6r, 11k, 11l and 11m showed good activity against B. subtilis with IC50 1.99-2.96 mu g/mL. The antibacterial activity of thiazolyl-pyrazolyl-1,2,3-triazole and bis-pyrazolyl-1,2,3-triazole derivatives suggested that, these derivatives could lead to new compounds for treatment against bacterial infection.

}, keywords = {123-Triazole, antibacterial activity, antimycobacterial activity, Pyrazole, Thiazole}, issn = {1040-6638}, doi = {10.1080/10406638.2020.1857272}, author = {Jagadale, Shivaji M. and Abhale, Yogita K. and Pawar, Hari R. and Shinde, Abhijit and Bobade, Vivek D. and Chavan, Abhijit P. and Sarkar, Dhiman and Mhaske, Pravin C.} } @article {49921, title = {Regio selective synthesis of pyrazole derivatives of 5-chloro-2-methoxy phenyl hydrazide and their biological evaluation}, journal = {Journal of Heterocyclic Chemistry}, volume = {62}, year = {2025}, month = {APR}, pages = {325-329}, type = {Article}, abstract = {

Present study involves synthesis of derivatives of (5-chloro-2-methoxyphenyl) (5-alkyl-3-(substituted) (phenyl/alkyl)-1H-pyrazol-1-yl) methanones. Structural elucidation of the synthesized compounds was depicted by the data of 1H and 13C NMR, IR, and Mass spectral analysis. The newly synthesized compounds 1a-1d and 2a-2i were screened in vitro against Mycobacterium tuberculosis H37Ra using an established XRMA protocol. Among the screened compounds, 2d, 2f, and 2h showed good percent inhibition against the active stage of M. tuberculosis H37Ra 80.77, 55.70, and 79.54, respectively, at 30 mu g/mL of inhibitor concentration. Further in secondary screening, compound 2d exhibited significant antitubercular activity on the active stage of M. tuberculosis H37Ra with IC50 of 0.208 mu g/mL. The synthesized compounds were also screened for antibacterial activity and found no significant activity against Gram-positive Bacteria Bacillus subtitles and Staphylococcus aureus and Gram negative bacteria Pseudomonas aeruginosa and Escherichia coli at 30 mu g/mL, which confirms the specificity of inhibitory activity against M. tuberculosis and more selectively against the active stage. The present study will be helpful for the further development of these molecules into antitubercular lead candidates.

}, keywords = {5-chloro-2-methoxy phenyl hydrazide, antibacterial activity, Antitubercular activity, Biological evaluation, H37Ra, hydrazide, Pyrazole}, issn = {0022-152X}, doi = {10.1002/jhet.4941}, author = {Bavishi, Abhay and Vala, Hardev and Swami, Sagar and Thakrar, Shailesh and Shah, Anamik and Sarkar, Dhiman} } @article {49558, title = {Synthesis, biological screening, and molecular docking of hybrid pyrazole scaffolds for antitubercular and antimicrobial activity}, journal = {ChemistrySelect}, volume = {10}, year = {2025}, month = {JAN}, pages = {e202404830}, type = {Article}, abstract = {

This study reports the synthesis, characterization, and docking analysis of 21 novel compounds, including asymmetric dihydropyridines (4a-4o) and chalcones (6a-6f), derived from coupling 1,3-(substituted)-diphenyl-1H-pyrazole-4-carbaldehyde with active methylene compounds and 3-acetyl-4-hydroxycoumarin, respectively. Structural confirmation was achieved through 1H and 13C NMR, IR, and mass spectrometry. Biological screening against mycobacterium tuberculosis H37Ra identified compounds 4b, 4d, 4f, 4g , 4i, 4k, 6e, and 6f as significant antitubercular agents. Antibacterial evaluation at 30 mu g/mL showed selective inhibition of gram-positive bacteria, with compound 6e active against Staphylococcus aureus and Bacillus subtilis, and 6f showing activity specifically against S. aureus. Docking studies indicated effective InhA binding (Delta G = -3.52 to -7.27 kcal/mol) and inhibition constants ranging from 2640 to 4.71 mu M. Key binding interactions with residues TYR156 and ILE192 were observed, enhancing affinity, particularly for compound 6e. The SAR analysis emphasized the enhanced antitubercular potency of 2-chloroacetyl and 2,4-dichlorobenzoyl substitutions in the dihydropyridine series, while in the chalcone series, specific substitutions, such as the 3-nitro substitution in 6e, enhance antitubercular and antimicrobial potency due to stronger hydrogen bonding and increased polar surface area, while the 4-fluoro substitution in 6f confers selective activity against S. aureus.

}, keywords = {1, 4-dihydropyridine, 4-hydroxy coumarin, Biological activity, In silco studies, Pyrazole}, issn = {2365-6549}, doi = {10.1002/slct.202404830}, author = {Bavishi, Abhay and Vala, Hardev and Radadiya, Ashish and Swami, Sagar and Thakrar, Shailesh and Sarkar, Dhiman and Shah, Anamik} }