5-(Adamantan-1-yl)-3-[(2-methoxyethyl)sulfanyl]-4-phenyl-4H-1,2,4-triazole

Abstract

Key indicators: single-crystal X-ray study; T = 296 K; mean (C-C) = 0.003 Å; disorder in main residue; R factor = 0.045; wR factor = 0.130; data-to-parameter ratio = 14.3.In the title adamantyl derivative, C 21 H 27 N 3 OS, the terminal methoxyethyl unit is disordered over two orientations with a refined site-occupancy ratio of 0.846 (6):0.154 (6). The 1,2,4-triazole ring is statistically planar [r.m.s. deviation = 0.002 (2) Å ] and the phenyl substituent is almost perpendicular to its mean plane [dihedral angle = 83.57 (11) ]. No directional intermolecular interactions were observed in the crystal structure. Related literature

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

“…47 Similarly, reaction of compound 5 with various aryl methyl halides or ethyl bromoacetate in dry acetone in the presence of anhydrous potassium carbonate at reflux temperature yielded the corresponding S -substituted derivatives, 12a–e and 13. Compound 13 was subjected to alkaline hydrolysis via heating in 10% aqueous sodium hydroxide solution for 30 minutes followed by acidification to yield the corresponding carboxylic acid derivative 14 in 73% yield (Figure 8 and Table 1).…”

“…The reaction of compound 5 with 1-bromo-2-methoxyethane in N,N-dimethylformamide in the presence of anhydrous potassium carbonate at room temperature yielded the corresponding S -(2-methoxyethyl) derivative 11 as confirmed by 1 H NMR, 13 C NMR, and X-ray spectrum ( Figure 7 ). 47 Similarly, reaction of compound 5 with various aryl methyl halides or ethyl bromoacetate in dry acetone in the presence of anhydrous potassium carbonate at reflux temperature yielded the corresponding S -substituted derivatives, 12a–e and 13. Compound 13 was subjected to alkaline hydrolysis via heating in 10% aqueous sodium hydroxide solution for 30 minutes followed by acidification to yield the corresponding carboxylic acid derivative 14 in 73% yield ( Figure 8 and Table 1 ).…”

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

“…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.…”

“…In the two related molecules 5-(adamantan-1-yl)-3-(benzylsulfanyl)- 4-methyl-4 H -1,2,4-triazole [ 29 ], and 5-(adamantan-1-yl)-3-[(4-chlorobenzyl)- sulfanyl]-4-methyl-4 H -1,2,4-triazole [ 30 ], the equivalent to the C20/C25 ring is parallel to the triazole-sulfanyl fragment due to the absence of an aromatic ring in the N3 position of the triazole group. However, observing the conformational behavior in 3-(adamantan-1-yl)-5-[(2-methoxyethyl)sulfanyl]-4-phenyl-4 H -1,2,4-triazole [ 31 ], a phenyl ring in N3 would constantly be orthogonal due to its steric effect with the adamantane cage.…”