Mn(II) catalyzed synthesis of 5(4-hydroxyphenyl)-2-(N-phenylamino)-1,3,4-oxadiazole: Crystal structure, DFT, molecular docking, Hirshfeld surface analysis, and in vitro anticancer activity on DL cells

Gond, M.K.; Shukla, Alok; Pandey, Shivendra Kumar; Bharty, M.K.; Maiti, Biswajit; Acharya, Arbind; Tiwari, Neeraj; Katiyar, Diksha; Butcher, Ray J.

doi:10.1016/j.molstruc.2021.131547

Cited by 16 publications

(3 citation statements)

References 55 publications

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“…We have previously reported the cyclo-desulfurization of several N-acylhydrazine carbodithioates into the corresponding 1,3,4-oxadiazole in the presence of manganese(II) acetate via the loss of H 2 S where the Mn II ion presumably behaves as a weak Lewis acid (Paswan et al, 2015(Paswan et al, , 2016Gond et al, 2022). In the present work, a similar reaction is reported in presence of Co II chloride.…”

Section: Chemical Contextsupporting

confidence: 78%

Co^II-catalysed synthesis of N-(4-methoxyphenyl)-5-(pyridin-4-yl)-1,3,4-oxadiazol-2-amine hemihydrochloride monohydrate

Gautam,

Sonkar,

Yadav

et al. 2024

Acta Cryst E

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The title compound, C14H12N4O2·0.5HCl·H2O or H(C14H12N4O2)2 +·Cl−·2H2O, arose from the unexpected cyclization of isonicotinoyl-N-phenyl hydrazine carbothioamide catalysed by cobalt(II) acetate. The organic molecule is almost planar and a symmetric N...H+...N hydrogen bond links two of them together, with the H atom lying on a crystallographic twofold axis. The extended structure features N—H...O and O—H...Cl hydrogen bonds, which generate [001] chains. Weak C—H...Cl interactions cross-link the chains. The chloride ion has site symmetry 2. The major contributions to the Hirshfeld surface are from H...H (47.1%), Cl...H/H...Cl (total 10.8%), O...H/H...O (7.4%) and N...H/H...N (6.7%) interactions.

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Section: Chemical Contextsupporting

confidence: 78%

Co^II-catalysed synthesis of N-(4-methoxyphenyl)-5-(pyridin-4-yl)-1,3,4-oxadiazol-2-amine hemihydrochloride monohydrate

Gautam,

Sonkar,

Yadav

et al. 2024

Acta Cryst E

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“…synthesised a 5–(4-hydroxyphenyl)-2-(N-phenylamino)-1,3,4- oxadiazole (compound 21 , Figure 2 ) and determined the cytotoxic activity against Dalton’s lymphoma cells using an MTT assay. Compound 21 showed good anticancer activity (IC 50 = 50 μg/mL), superior to many reported compounds 29 .…”

Section: Oxadiazolementioning

confidence: 84%

Research progress on the synthesis and pharmacology of 1,3,4-oxadiazole and 1,2,4-oxadiazole derivatives: a mini review

Wang

Sun

Jia

et al. 2022

Journal of Enzyme Inhibition and Medicinal Chemistry

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Oxadiazole is a five-membered heterocyclic compound containing two nitrogen atoms and one oxygen atom. The 1,3,4-oxadiazole and 1,2,4-oxadiazole have favourable physical, chemical, and pharmacokinetic properties, which significantly increase their pharmacological activity via hydrogen bond interactions with biomacromolecules. In recent years, oxadiazole has been demonstrated to be the biologically active unit in a number of compounds. Oxadiazole derivatives exhibit antibacterial, anti-inflammatory, anti-tuberculous, anti-fungal, anti-diabetic and anticancer activities. In this paper, we report a series of compounds containing oxadiazole rings that have been published in the last three years only (2020–2022) as there was no report or their activities described in any article in 2019, which will be useful to scientists in research fields of organic synthesis, medicinal chemistry, and pharmacology.

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“…Thiosemicarbazide and its derivatives are also utilized as intermediates for the synthesis of a wide range of ve-membered heterocyclic compounds [20][21][22][23]. Thus, due to their diverse applications, interest has been rapidly growing in the chemistry of thiosemicarbazide derivatives.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterizations, Crystal structure, DFTand Hirshfeld surface analysis of4-cyclohexyl-1-(thiophene-2-carbonyl)thiosemicarbazide

Pandey

Gupta

Jaiswal

et al. 2022

Preprint

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The crystal structure of the thiosemicarbazide derivative 4-cyclohexyl-1-(thiophene-2-carbonyl)thiosemicarbazide (ChtcTSC), C12H17N3OS2, is reported here. The title compound ChtcTSC has been characterized by various physicochemical techniques viz UV-vis., Infrared, and NMR. It crystallizes in the monoclinic system having space group P 21/c. The dihedral angle between the thiophene and cyclohexyl rings is 60.7(4)°. The crystal packing is established by intermolecular N-H∙∙∙O packing interactions involving a three-center donor hydrogen bond between the keto oxygen atom of the thiophene group and H atoms belonging to the hydrazine group which links the molecules into chains along the (011) plane of the unit cell. Hydrogen bonds between the hydrazine hydrogen atom and one of the thiophene groups and C-H∙∙∙Cg π-ring interactions provide added stability to the crystal packing. The fingerprint plots associated with Hirshfeld surface analysis indicate that there are different types of weak interactions viz. O···H-C, O···H-N and S···H-C. The geometry optimization has been performed using the DFT method, and geometrical parameters thus obtained for ChtcTSC correlate with the single-crystal X-ray data. The TD-DFT studied showed a small HOMO and LUMO energy gap of 2.869 eV. The electronic transition from the ground state to the excited state due to a transfer of electrons from HOMO to LUMO levels is mainly associated with the n→π* transition.

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Mn(II) catalyzed synthesis of 5(4-hydroxyphenyl)-2-(N-phenylamino)-1,3,4-oxadiazole: Crystal structure, DFT, molecular docking, Hirshfeld surface analysis, and in vitro anticancer activity on DL cells

Cited by 16 publications

References 55 publications

Co^II-catalysed synthesis of N-(4-methoxyphenyl)-5-(pyridin-4-yl)-1,3,4-oxadiazol-2-amine hemihydrochloride monohydrate

Co^II-catalysed synthesis of N-(4-methoxyphenyl)-5-(pyridin-4-yl)-1,3,4-oxadiazol-2-amine hemihydrochloride monohydrate

Research progress on the synthesis and pharmacology of 1,3,4-oxadiazole and 1,2,4-oxadiazole derivatives: a mini review

Synthesis, Characterizations, Crystal structure, DFTand Hirshfeld surface analysis of4-cyclohexyl-1-(thiophene-2-carbonyl)thiosemicarbazide

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Mn(II) catalyzed synthesis of 5(4-hydroxyphenyl)-2-(N-phenylamino)-1,3,4-oxadiazole: Crystal structure, DFT, molecular docking, Hirshfeld surface analysis, and in vitro anticancer activity on DL cells

Cited by 16 publications

References 55 publications

CoII-catalysed synthesis of N-(4-methoxyphenyl)-5-(pyridin-4-yl)-1,3,4-oxadiazol-2-amine hemihydrochloride monohydrate

CoII-catalysed synthesis of N-(4-methoxyphenyl)-5-(pyridin-4-yl)-1,3,4-oxadiazol-2-amine hemihydrochloride monohydrate

Research progress on the synthesis and pharmacology of 1,3,4-oxadiazole and 1,2,4-oxadiazole derivatives: a mini review

Synthesis, Characterizations, Crystal structure, DFTand Hirshfeld surface analysis of4-cyclohexyl-1-(thiophene-2-carbonyl)thiosemicarbazide

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Co^II-catalysed synthesis of N-(4-methoxyphenyl)-5-(pyridin-4-yl)-1,3,4-oxadiazol-2-amine hemihydrochloride monohydrate

Co^II-catalysed synthesis of N-(4-methoxyphenyl)-5-(pyridin-4-yl)-1,3,4-oxadiazol-2-amine hemihydrochloride monohydrate