SYNTHESIS OF NOVEL γ-CARBOLINE DERIVATIVES AND THEIR IN SILICO STUDIES ON 5HT1, H1 AND CCR2 ANTAGONIST RECEPTORS
Journal Title: International Journal of Pharmacy and Pharmaceutical Sciences - Year 2014, Vol 6, Issue 10
Abstract
Objective: Synthesis of novel γ-carboline precursor 4 by using mild, inexpensive and eco friendly T3Methods: The reaction was carried out by taking mixture of 1 equiv. of phenyl hydrazine hydrochloride, 1 equiv. of N-Boc piperidone and 0.25equiv. of TP as catalyst and synthesis of γ-carbolinesulfonamides, amides and tertiary amines 5a-l from compound 4 as a key intermediate. In silico docking studies against 5HT1, H1 andCCR2 antagonist receptors of all 5a-l compounds.Results: An excellent yield of γ-carboline precursor 4 was obtained by using mild, inexpensive and eco friendly TP(50% in EtOAc) in toulene at 90 °C. After 6hr the product γ-carboline 4 was obtained by water workup followed boc deprotection byHCl in dioxane treatment. Further, the sulfonation, amidation and reductive amination were carried out to γ-carboline 4 to get derivatives of γ-carboline 5a-l. The synthesized compounds were docked against 5HT1, H1 and CCR2 antagonist receptors using AutoDock v 4.2.3Conclusion: An eco friendly procedure to prepare γ-carboline 4 using mild and inexpensive TP catalyst. Among the synthesizedcompounds, the 5b and 5c were shown three hydrogen bonding interaction having-10.1082 and-13.9105 kcal/mol of interaction energy with H1protein at the active site amino acids ARG175, TYR185 and SER128 respectively. The inhibitory constants were found to be 88.7015 and 56.2123µM respectively.3
Authors and Affiliations
E Siddalingamurthy, K. M. Mahadevan, N. M. Jagadeesh, M. N Kumara
Keywords
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