Synthesis, spectroscopic and X-ray crystallographic analysis of N-(2-(2-(4-chlorophenoxy)acetamido)phenyl)-1H-indole-2-carboxamide

Abstract

Medicinal chemistry of indole analogs constitutes important therapeutic agents with antioxidant, 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-(4chlorophenoxy)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 ( 1 H NMR, 13 C 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.

Synthesis, Characterization of Novel N'(2-Phenoxyacetyl)Nicotinohydrazide and N'(2-Phenoxyacetyl)Isonicotinohydrazide Derivatives as Anti-Inflammatory and Analgesic Agents

“…Heterocycles containing nitrogen are known to possess various pharmaceuticals applications [12,13]. This has attracted many researchers attention in recent year and it is one of the most important division which have an amazing activities in pharmacy [14], agriculture [15], the polymer [16] and other elds [17]. The main biological activities of nitrogen-containing compounds are antiproliferative [18], antiviral [19], antimalarial [20], anti-in ammatory [1] and antimicrobial [21].…”

Synthesis, crystal structure elucidation, Hirshfeld surface analysis, 3D energy frameworks and DFT studies of 2-(4-fluorophenoxy) acetic acid

“…Azomethine and its phenoxy acetic acid-derived complexes have reported biological importance including pyridoxal phosphate anti-metabolites, bacteriostatic activity, and antitumor activity [21][22][23][24][25][26]. In view of their broad spectrum of medicinal properties and as a part of our ongoing work on the synthesis and characterization of novel compounds [27][28][29], the title compound was synthesized. The compound obtained was characterized spectroscopically, and the structure was confirmed by X-ray diffraction studies.…”