Synthesis, spectroscopic and X-ray crystallographic analysis of N-(2-(2-(4-chlorophenoxy)acetamido)phenyl)-1H-indole-2-carboxamide
Open Access
- 30 September 2019
- journal article
- Published by European Journal of Chemistry in European Journal of Chemistry
- Vol. 10 (3), 234-238
- https://doi.org/10.5155/eurjchem.10.3.234-238.1874
Abstract
Medicinal chemistry of indole analogs constitutes important therapeutic agents with anti-oxidant, anti-HIV and anti-cancer activities. Indole nucleus is frequently found in synthetic and natural products, pharmaceuticals, functional materials, agrochemicals, etc. The title compound, N-(2-(2-(4-chlorophenoxy)acetamido)phenyl)-1H-indole-2-carboxamide (5), has been synthesized in good yield by stirring the compound N-(2-aminophenyl)-2-(4-chlorophenoxy)acetamide (3) with 1H-indole-2-carboxylic acid (4), in dry dichloromethane followed by the addition of 2,6-lutidine, and o-(benzotriazol-1-yl)-N,N,N',N'-tetramethyl uraniumtetrafluoroborate in cooled condition. Compound 5 was synthesized and characterized by the conventional spectroscopic techniques (1H NMR, 13C NMR and LC-MS) and the three-dimensional structure was elucidated by using single crystal X-ray diffraction methods. It crystallizes in the monoclinic crystal system with space group P21/c. The structure was solved by direct methods and refined by full matrix least square procedure to a final R value of 0.043 for 2490 observed reflections. Three intra-molecular interactions of the type N-H···N and C-H···N were observed. The packing of molecules in the unit cell is governed by N-H···O and C-H···O intermolecular H-boned interactions which leads to the formation of infinite staking chain along [001] direction. In addition, two weak C-H···π interactions also contribute to molecular packing.Keywords
This publication has 35 references indexed in Scilit:
- The Novel 4-Phenyl-2-Phenoxyacetamide Thiazoles modulates the tumor hypoxia leading to the crackdown of neoangiogenesis and evoking the cell deathEuropean Journal of Medicinal Chemistry, 2018
- Design, synthesis and pharmacophoric model building of new 3‐alkoxymethyl/3‐phenyl indole‐2‐carboxamides with potential antiproliferative activityChemical Biology & Drug Design, 2017
- Indoles — A promising scaffold for drug developmentEuropean Journal of Pharmaceutical Sciences, 2016
- Indole-3-carbinol induces tumor cell death: function follows formJournal of Surgical Research, 2016
- Synthesis, anticancer activities and molecular modeling studies of novel indole retinoid derivativesEuropean Journal of Medicinal Chemistry, 2012
- 2-Arylindoles: a privileged molecular scaffold with potent, broad-ranging pharmacological activity.Current Medicinal Chemistry, 2012
- Conformationally restricted homotryptamines. Part 5: 3-(trans-2-aminomethylcyclopentyl)indoles as potent selective serotonin reuptake inhibitorsBioorganic & Medicinal Chemistry Letters, 2009
- Metal complexes involving indole rings: Structures and effects of metal–indole interactionsCoordination Chemistry Reviews, 2009
- Anti-cancer activity studies of indolalthiohydantoin (PIT) on certain cancer cell linesIl Farmaco, 2000
- Evaluation of anti-HIV activity of 5- (2-phenyl-3′-indolal)-2-thiohydantoinIl Farmaco, 1998