A novel series of 5‐(p‐(prop‐2‐ynyloxy)phenyl)‐3‐aryl‐4,5‐dihydropyrazole‐1‐carbothioamides 2a‐f and functionalized 2‐(3‐(aryl)‐5‐(4‐(prop‐2‐ynyloxy)phenyl)‐4,5‐dihydropyrazol‐1‐yl)‐4‐(3‐arylsydnone‐4‐yl)thiazoles 4a‐l were synthesized. The newly synthesized compounds were elucidated by analytical and spectral analysis. From the single‐crystal X‐ray diffraction method, it was observed that 2d crystallizes in a monoclinic crystal system with P21/n space group. The compounds 2d crystallized with cell parameters a = 15.0614 (19) Å, b = 6.0805 (7) Å, c = 20.903 (7) Å, α = 114.136 (6)o, β = 110.709 (14) o, γ = 96.553 (5) o, V = 1790.6 (4) Å3, Z = 4. From the Hirshfeld surface computational method, the major intercontacts present in these molecules are H…H (31.6%), C…H (18.2%) and S…H (12.2%), respectively. The newly synthesized compounds were tested for their ability to bleach 2,2'‐diphenyl‐1‐picrylhydrazyl (DPPH) radical using DPPH scavenging assay. Among the synthesized compounds carbothioamide compounds 2c (90.7%) and 2b (89.8%) exhibited good DPPH scavenging activity compared to the rest of the compounds. Most of the synthesized carbothioamide molecules (2a‐f) found to be potent compared to the thiazole derivatives (4a‐l).
A series of hybrid molecules containing pyrazolines and 1,2,3‐triazoles have been synthesized via Cu(I) mediated 1,3‐dipolar cycloaddition reactions bearing para substituted azides and dipolarophile (acetylenes) as a reactive precursors. Structure of all the synthesized derivatives were confirmed by 1HNMR, 13C NMR, LC–MS and IR spectral analysis and they are screened for α‐glucosidase and α‐amylase inhibitory and antioxidant activities by DPPH (2,2‐diphenyl‐1‐picrylhydrazyl) and ABTS (2,2‐azinobis (3‐ethylbenzothiazoline‐6‐sulfonic acid)) methods. Among the synthesized compounds, 3‐(4‐((1‐(4‐chlorophenyl)‐1H‐1,2,3‐triazol‐4‐yl)methoxy)phenyl)‐5‐(4‐fluorophenyl)‐4,5‐dihydropyrazole‐1‐carbaldehyde (5 k) showed promising inhibition of the antidiabetic enzymes with IC50=0.81±0.20 μM for α‐glucosidase and IC50=1.00±0.05 μM for α‐amylase compared with the standard therapeutic drug acarbose which shows IC50=1.30±0.06 μM and IC50=0.75±0.08 μM for α‐glucosidase and α‐amylase. Compared to all the synthesized compounds, the bleeching ability of 3‐(4‐((1‐(4‐chlorophenyl)‐1H‐1,2,3‐triazol‐4‐yl)methoxy)phenyl)‐5‐(4‐fluorophenyl)‐4,5‐dihydropyrazole‐1‐carbaldehyde (5 k) showed promising antioxidant activity in comparison with standard Butylated hydroxyl anisole. The molecular docking studies revealed the compound 3‐(4‐((1‐(4‐chlorophenyl)‐1H‐1,2,3‐triazol‐4‐yl)methoxy)phenyl)‐5‐(4‐fluorophenyl)‐4,5‐dihydropyrazole‐1‐carbaldehyde having lower binding energy with the maximum efficacy.
A new class of functionalized pyrazole bearing 1,2,3-triazole has been synthesized via Cu(I) mediated 1,3-dipolar cycloaddition of pyrazole bearing azide with various aromatic/heteroaromatic bearing terminal dipolarophile (acetylene). Structures of the newly synthesized compounds were explicated by analytical and spectral analysis. All the newly synthesized compounds were evaluated for their in-vitro antibacterial and antioxidant activity. Among the synthesized compound, triazole bearing 2,5-thiazolidinone 5b (20 ± 0.70) and triazole bearing thiocarboamide 5e (19 ± 0.70) showed good antibacterial activity against Escherichia coli and Pseudomonas aeruginosa, respectively. The newly synthesized compounds further tested for their ability to bleach DPPH radical using DPPH scavenging assay. Among the synthesized compounds 1,2,3-triazole bearing 2,5-thiazolidinone 5b (58.81%) exhibited good DPPH scavenging activity compared to the rest of the compounds. From the X-ray and Hirshfield analysis, it was observed that compound 3, crystallizes in a triclinic crystal system with a P-1 space group. The major intercontacts present in these molecules are H…H (39.7%), C…H (23.9%), N…H (20.3%).
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