A comparative study of two novel unsymmetrically substituted triazacyclohexanes
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Date
2017-02-27
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Abstract
Novel unsymmetrically N-substituted N,N0-R1N00-R2-1,3,5-triazacyclohexanes (1b and 2b; R1 ¼ p-chlorophenyl or p-methoxyphenyl and R2 ¼ butyl or cyclohexyl) have been synthesized in a good yield from
condensation reaction by excess amine. Both triazacyclohexane rings have chair conformation. However,
1b adopts diaxial orientation of aryl groups and an equatorial form of alkyl group whereas 2b prefers an
axial orientation of the alkyl group and diequatorial forms of aryl groups. 1b is consolidated by weak CH/p interactions. Intra-molecular C-H/O or C-H/N hydrogen bonds and C-H/p may be effective in
the stabilization of 2b. Both compounds have showed moderate antimicrobial activity, but 1b exhibits
higher activity than 2b. All experimental results are found in good support to theoretical data. Findings of
research may be helpful guide for the medicinal chemists and the field is further open for pharmacokinetics studies.