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%).
Two new chalcones containing both pyrazole and thiophene substituents have been prepared and structurally characterized. 3-(3-Methyl-5-phenoxy-1-phenyl-1H-pyrazol-4-yl)-1-(thiophen-2-yl)prop-2-en-1-one, C23H18N2O2S (I), and 3-[3-methyl-5-(2-methylphenoxy)-1-phenyl-1H-pyrazol-4-yl]-1-(thiophen-2-yl)prop-2-en-1-one, C24H20N2O2S (II), are isomorphous as well as isostructural, and in each the thiophene substituent is disordered over two sets of atomic sites having occupancies 0.844 (3) and 0.156 (3) in (I), and 0.883 (2) and 0.117 (2) in (II). In each structure, the molecules are linked into sheets by a combination of C—H...N and C—H...O hydrogen bonds. Comparisons are made with some related compounds.
In the title compound, C 16 H 20 N 4 O, the dihedral angle between the pyrazole and phenyl rings is 53.86 (12) . The piperazine ring adopts a chair conformation with the exocyclic N-C bonds in equatorial orientations. In the crystal, molecules are linked by very weak C-HÁ Á ÁO hydrogen bonds to generate [010] C(8) chains, with adjacent molecules related by translation.
Structure descriptionPiperazine derivatives are found in biologically active compounds across many therapeutic areas and display antipsychotic (Chaudhary et al., 2006) and antifungal (Upadhayaya et al., 2004) behaviours. As part of our ongoing studies in this area (Girisha et al., 2010), herein we report the synthesis and structure of the title compound (Fig. 1).The dihedral angle between the pyrazole (r.m.s. deviation = 0.012 Å ) and phenyl rings is 53.86 (12) . The piperazine ring adopts a chair conformation with the exocyclic N-C bonds in equatorial orientations. The piperazine ring bisects the plane of the pyrazole ring which is evident from the dihedral angle value of 53.57 (10) between the mean planes of the pyrazole and piperazine (all atoms) rings.In the crystal, the molecules are linked by weak C-HÁ Á ÁO hydrogen bonds (Table 1) to generate [010] C(8) chains, with adjacent molecules related by translation (Fig. 2).
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