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.
Two new 1-(thiazol-2-yl)-4,5-dihydropyrazoles have been synthesized from simple precursors, and characterized both spectroscopically and structurally. In addition, two intermediates in the reaction pathway have been isolated and characterized, one of them structurally. The molecules of the intermediate (E)-1-(4-methoxyphenyl)-3-[4-(prop-2-ynyloxy)phenyl]prop-2-en-1-one, C19H16O3 (I), are linked by a combination of C—H...O and C—H...π(arene) hydrogen bonds to form ribbons. The products (RS)-5-(4-methoxyphenyl)-1-(4-phenythiazol-2-yl)-3-[4-(prop-2-ynyloxy)phenyl]-4,5-dihydro-1H-pyrazole, C28H23N3O2S (II), and (RS)-5-(4-methoxyphenyl)-1-[4-(4-methylphenyl)thiazol-2-yl]-3-[4-(prop-2-ynyloxy)phenyl]-4,5-dihydro-1H-pyrazole, C29H25N3O2S (III), are closely related – differing only by presence or absence of a methyl group at the arylthiazolyl substituent – and crystallize in an isomorphous setting. Both molecules contain an effectively planar dihydro-pyrazole ring, and possess an overall T-shaped structure, which is a characteristic of triaryl-substituted 4,5-dihydro-1-(thiazol-2-yl)pyrazole compounds. The crystal packing is characterized by intermolecular C—H...S and C—H...π (aryl/alkyne) interactions. A combination of two C—H...π(arene) hydrogen bonds links the product molecules into sheets.
In the title compound, C18H16N2O2, the phenyl and pyrazole rings subtend a dihedral angle of 22.68 (8)°. The packing of the title compound features aromatic π–π stacking and weak C—H...π interactions.
The title compound, C29H25N3O3S, crystallizes in the monoclinic space group P21/n. The molecule contains a central four-ring system in which all of the rings are almost coplanar. Both the 4-methoxyphenyl ring and the prop-2-ynyloxy substituent are disordered over two equivalent conformations with occupancy ratios of 0.903 (2):0.097 (2) and 0.776 (5):0.224 (5), respectively. In the crystal, π–π interactions [centroid–centroid distance = 3.7327 (11) Å] between the dihydropyrazole ring and the 4-methoxyphenyl ring link the molecules into centrosymmetric dimers. In addition, there are weak C—H...S, C—H...N and C—H...O interactions, which link the molecules into a complex three-dimensional array.
Crystal structures are reported for three amides containing N-benzo[d]thiazole substituents. In N-(benzo[d]thiazol-6-yl)-3-bromobenzamide, C14H9BrN2OS, where the two ring systems are nearly parallel to one another [dihedral angle = 5.8 (2)°], the molecules are linked by N—H...O and C—H...N hydrogen bonds to form ribbons of R
3
3(19) rings, which are linked into sheets by short Br...Br interactions [3.5812 (6) Å]. N-(6-Methoxybenzo[d]thiazol-2-yl)-2-nitrobenzamide, C15H11N3O4S, crystallizes with Z′ = 2 in space group Pna21: the dihedral angles between the ring systems [46.43 (15) and 66.35 (13)°] are significantly different in the independent molecules and a combination of two N—H...N and five C—H...O hydrogen bonds links the molecules into a three-dimensional network. The molecules of 5-cyclopropyl-N-(6-methoxybenzo[d]thiazol-2-yl)isoxazole-3-carboxamide, C15H13N3O3S, exhibit two forms of disorder, in the methoxy group and in the cyclopropylisoxazole unit; symmetry-related pairs of molecules are linked into dimers by pairwise N—H...N hydrogen bonds. Comparisons are made with the structures of some related compounds.
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