Crystal structure of 4-(benzo[d]thiazol-2-yl)-1,2-dimethyl-1H-pyrazol-3(2H)-one

Elboshi, Heba A.; Azzam, Rasha A.; Elgemeie, Galal H.; Jones, Peter G.

doi:10.1107/s2056989024001257

Cited by 2 publications

References 18 publications

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Crystal structures of four thioglycosides involving carbamimidothioate groups

Abu-Zaied,

Nawwar,

Elgemeie

et al. 2024

Acta Crystallogr E Cryst Commun

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The compounds 2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosyl N′-cyano-N-phenylcarbamimidothioate (C22H25N3O9S, 5a), 2′,3′,4′,6′-tetra-O-acetyl-β-D-galactopyranosyl N′-cyano-N-phenylcarbamimidothioate, (C22H25N3O9S, 5b), 2′,3′,4′,6′-tetra-O-acetyl-β-D-galactopyranosyl N′-cyano-N-methylcarbamimidothioate (C17H23N3O9S, 5c), and 2′,3′,4′,6′-tetra-O-acetyl-β-D-galactopyranosyl N′-cyano-N-p-tolylcarbamimidothioate (C23H27N3O9S, 5d) all crystallize in P212121 with Z = 4. For all four structures, the configuration across the central (formal) C=N(CN) double bond of the carbamimidothioate group is Z. The torsion angles C5—O1—C1—S (standard sugar numbering) are all close to 180°, confirming the β position of the substituent. Compound 5b involves an intramolecular hydrogen bond N—H...O1; in 5c this contact is the weaker branch of a three-centre interaction, whereas in 5a and 5d the H...O distances are much longer and do not represent significant interactions. The C—N bond lengths at the central carbon atom of the carbamimidothioate group are almost equal. All C—O—C=O torsion angles of the acetyl groups correspond to a synperiplanar geometry, but otherwise all four molecules display a high degree of conformational flexibility, with many widely differing torsion angles for equivalent groups. In the crystal packing, 5a, 5c and 5d form layer structures involving the classical hydrogen bond N—H...Ncyano and a variety of ‘weak’ hydrogen bonds C—H...O or C—H...S. The packing of 5b is almost featureless and involves a large number of borderline ‘weak’ hydrogen bonds. In an appendix, a potted history of wavelength preferences for structure determination is presented and it is recommended that, even for small organic crystals in non-centrosymmetric space groups, the use of Mo radiation should be considered.

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Crystal structures of four thioglycosides involving carbamimidothioate groups

Abu-Zaied,

Nawwar,

Elgemeie

et al. 2024

Acta Crystallogr E Cryst Commun

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Novel 2-Substituted Benzothiazole Derivatives: Synthesis, In-vitro and In- silico Evaluations as Potential Anticancer Agents

Azzam,

Seif,

El-Demellawy

et al. 2024

Preprint

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Cancer remains a global health concern, demanding the development of new therapeutic medicines. This research focuses on the synthesis, in vitro evaluation, and in silico analysis of new 2-substituted benzothiazole derivatives as possible anticancer drugs. Hybrid molecules comprising benzothiazole and pyridinone rings 10a-d and 14a-d were also synthesized. Several compounds were produced and characterized, using NMR, IR and elemental analysis, with promising anticancer activity against lung H1299, liver Hepg2 and breast MCF7 cancer cell lines. Structure-activity connection investigations identified crucial structural characteristics that influence potency, with particular benzylidine derivatives 7a-g demonstrating higher activity. In-silico ADME research revealed favorable drug-like features for chosen compounds, such as high gastrointestinal absorption and selective CYP inhibition. Toxicological projections indicated few side effects, confirming their potential as medication candidates. Docking studies revealed their binding mechanisms and interactions with protein tyrosine kinases PTK, identifying intriguing candidates for further study.

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Crystal structure of 4-(benzo[d]thiazol-2-yl)-1,2-dimethyl-1H-pyrazol-3(2H)-one

Cited by 2 publications

References 18 publications

Crystal structures of four thioglycosides involving carbamimidothioate groups

Crystal structures of four thioglycosides involving carbamimidothioate groups

Novel 2-Substituted Benzothiazole Derivatives: Synthesis, In-vitro and In- silico Evaluations as Potential Anticancer Agents

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