2-{[5-(Adamantan-1-yl)-4-methyl-4H-1,2,4-triazol-3-yl]sulfanyl}-N,N-dimethylethanamine

El-Emam, Ali A.; Lahsasni, Siham; Asiri, Hanadi H.; Quah, Ching Kheng; Fun, Hoong‐Kun

doi:10.1107/s160053681201464x

Cited by 5 publications

(3 citation statements)

References 13 publications

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“…The structure assignment of compounds 9a–d and 10a–d were based on the 1 H NMR and 13 C NMR data, which were consistent with the previously reported results and supported by X-ray studies,43–45 in addition to the X-ray spectrum of compound 9a (Figure 6). 46…”

Section: Resultsmentioning

confidence: 99%

Synthesis, antimicrobial, and anti-inflammatory activity, of novel S-substituted and N-substituted 5-(1-adamantyl)-1,2,4-triazole-3-thiols

Al‐Abdullah¹,

Asiri²,

Lahsasni³

et al. 2014

DDDT

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The reaction of 5-(1-adamantyl)-4-phenyl-1,2,4-triazoline-3-thione (compound 5) with formaldehyde and 1-substituted piperazines yielded the corresponding N-Mannich bases 6a–f. The reaction of 5-(1-adamantyl)-4-methyl-1,2,4-triazoline-3-thione 8 with various 2-aminoethyl chloride yielded separable mixtures of the S-(2-aminoethyl) 9a–d and the N-(2-aminoethyl) 10a–d derivatives. The reaction of compound 5 with 1-bromo-2-methoxyethane, various aryl methyl halides, and ethyl bromoacetate solely yielded the S-substituted products 11, 12a–d, and 13. The new compounds were tested for activity against a panel of Gram-positive and Gram-negative bacteria and the pathogenic fungus Candida albicans. Compounds 6b, 6c, 6d, 6e, 6f, 10b, 10c, 10d, 12c, 12d, 12e, 13, and 14 displayed potent antibacterial activity. Meanwhile, compounds 13 and 14 produced good dose-dependent anti-inflammatory activity against carrageenan-induced paw edema in rats.

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Section: Resultsmentioning

confidence: 99%

Synthesis, antimicrobial, and anti-inflammatory activity, of novel S-substituted and N-substituted 5-(1-adamantyl)-1,2,4-triazole-3-thiols

Al‐Abdullah¹,

Asiri²,

Lahsasni³

et al. 2014

DDDT

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“…The structures of the three compounds consist of three basic fragments; the adamantane cage, the triazole ring and the arylmethylsulfanyl moiety ( Figure 3 ). A search in the CSD database version 5.41 (1 November 2019 with three updates; accessed on 1 November 2020), through the ConQuest software version 2020.2.0, for molecules with a similar core gave four related structures [ 29 , 30 , 31 , 32 ], but the crystal structures of compounds 1 , 2 and 3 have not been reported.…”

Section: Resultsmentioning

confidence: 99%

Structural Insights and Docking Analysis of Adamantane-Linked 1,2,4-Triazole Derivatives as Potential 11β-HSD1 Inhibitors

et al. 2021

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The solid-state structural analysis and docking studies of three adamantane-linked 1,2,4-triazole derivatives are presented. Crystal structure analyses revealed that compound 2 crystallizes in the triclinic P-1 space group, while compounds 1 and 3 crystallize in the same monoclinic P21/c space group. Since the only difference between them is the para substitution on the aryl group, the electronic nature of these NO2 and halogen groups seems to have no influence over the formation of the solid. However, a probable correlation with the size of the groups is not discarded due to the similar intermolecular disposition between the NO2/Cl substituted molecules. Despite the similarities, CE-B3LYP energy model calculations show that pairwise interaction energies vary between them, and therefore the total packing energy is affected. HOMO-LUMO calculated energies show that the NO2 group influences the reactivity properties characterizing the molecule as soft and with the best disposition to accept electrons. Further, in silico studies predicted that the compounds might be able to inhibit the 11β-HSD1 enzyme, which is implicated in obesity and diabetes. Self- and cross-docking experiments revealed that a number of non-native 11β-HSD1 inhibitors were able to accurately dock within the 11β-HSD1 X-ray structure 4C7J. The molecular docking of the adamantane-linked 1,2,4-triazoles have similar predicted binding affinity scores compared to the 4C7J native ligand 4YQ. However, they were unable to form interactions with key active site residues. Based on these docking results, a series of potentially improved compounds were designed using computer aided drug design tools. The docking results of the new compounds showed similar predicted 11β-HSD1 binding affinity scores as well as interactions to a known potent 11β-HSD1 inhibitor.

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“…The compound consists of one triazole and two benzene rings. When examining the bond lengths under the X-ray parameters of compound (3) in Table 3, it can be seen that especially C38-N32 [1.136 (2) [23][24][25][26]. The dihedral angles between the 1,2,4 triazole ring and the C31-C36 and C51-C56 rings are 76.92º and 27.53º respectively.…”

Section: Measurements and Calculationsmentioning

confidence: 99%

Experimental and theoretical studies of 4-[(4-methyl-5-phenyl- 4H1,2,4-triazol-3-yl)sulfanyl]benzene-1,2-dicarbonitrile

Çoruh

Ustabaş

Akçay

et al. 2016

Maced. J. Chem. Chem. Eng.

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In this study, 4-[(4-methyl-5-phenyl-4H-1,2,4-triazol-3-yl)sulfanyl]benzene-1,2-dicarbonitrile was synthesized and its molecular structure was characterized by means of FT-IR and X-ray diffraction methods. The crystal is monoclinic and belongs to the P21/n space group. There are three weak intermolecular C-H…N type hydrogen bonds in the molecular structure. The geometrical parameters, vibration frequencies, HOMO-LUMO energies, and molecular electrostatic potential (MEP) map of the compound (3) in ground state were calculated by using density functional theory (DFT/B3LYP) with the 6-311G(d) basis set. Calculated geometrical parameters were compared with X-ray diffraction geometric parameters. On the other hand, theoretical and experimental FT-IR results were also compared.Keywords: crystal structure; 1,2,4-triazole; DFT calculations; molecular electrostatic potential; frontier orbitals ЕКСПЕРИМЕНТАЛНИ И ТЕОРЕТСКИ ИСПИТУВАЊА НА 4-[(4-МЕТИЛ-5-ФЕНИЛ-4H1,2,4-ТРИАЗОЛ-3-ИЛ)СУЛФАНИЛ]БЕНЗЕН-1,2-ДИКАРБОНИТРИЛВо ова истражување беше синтетизиран 4-[(4-метил-5-фенил-4Н1,2,4-триазол-3-ил)сул-фанил]бензен-1,2-дикарбонитрил, а неговата структура беше карактеризирана со помош на FT-IR и рендгенска дифракција. Кристалот е моноклиничен и припаѓа на просторната група P21/n. Во молекулската структура постојат три слаби интермолекулски водородни врски од типот на C-H…N. Геометриските параметри, вибрациските фреквенции, енергиите на HOMO-LUMO и мапата на молекулскиот електростатички потенцијал (MEP) на соединението (3) во основна состојба беа пресметани со теоријата на функционалот на густината (DFT/B3LYP) и основен сет 6-311G(d). Пресметаните геометриски параметри беа споредени со геометриските параметри добиени со рендгенската дифракција. Исто така беа споредени и теоретските и експерименталните резултати добиени со FT-IR.Клучни зборови: кристална структура; 1,2,4-триазол; DFT пресметки; молекулски електростатички потенцијал; гранични орбитали U. Çoruh, R. Ustabaş, H. T. Akçay, E. Menteşe, E. M. V. Lopez Maced.

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2-{[5-(Adamantan-1-yl)-4-methyl-4H-1,2,4-triazol-3-yl]sulfanyl}-N,N-dimethylethanamine

Cited by 5 publications

References 13 publications

Synthesis, antimicrobial, and anti-inflammatory activity, of novel S-substituted and N-substituted 5-(1-adamantyl)-1,2,4-triazole-3-thiols

Synthesis, antimicrobial, and anti-inflammatory activity, of novel S-substituted and N-substituted 5-(1-adamantyl)-1,2,4-triazole-3-thiols

Structural Insights and Docking Analysis of Adamantane-Linked 1,2,4-Triazole Derivatives as Potential 11β-HSD1 Inhibitors

Experimental and theoretical studies of 4-[(4-methyl-5-phenyl- 4H1,2,4-triazol-3-yl)sulfanyl]benzene-1,2-dicarbonitrile

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