N-Silylmethyl-2-(1-Naphthyl)Acetamides: Synthesis, Structure and Computational Screening-Reference-Cited by-同舟云学术

N-Silylmethyl-2-(1-Naphthyl)Acetamides: Synthesis, Structure and Computational Screening

Published:2024-06 Issue:12 Volume:28 Page:959-966
ISSN:1385-2728
Container-title:Current Organic Chemistry
language:en
Short-container-title:COC

Author:

Soldatenko Anastasiya S.¹,Molokeev Maxim S.²³,Lazareva Nataliya F.¹^ORCID

Affiliation:

1. Siberian Division of the Russian Academy of Sciences, A.E. Favorsky Irkutsk Institute of Chemistry, 1 Favorsky Street, Irkutsk 664033, Russia

2. Laboratory of Crystal Physics, Federal Research Center KSC SB RAS, Kirensky Institute of Physics, Krasnoyarsk 660036, Russia

3. Institute of Engineering Physics and Radio Electronic, Siberian Federal University, Krasnoyarsk 660041, Russia

Abstract

Abstract: Synthesis of new hybrid organosilicon compounds based on the amides 1- naphthylacetic acid was described. N-Organyl-2-(1-naphthyl)-N-[(triethoxysilyl)methyl]- acetamides were obtained by the reaction of 1-naphthylacetyl chloride with α-silylamines RNHCH2Si(OEt)3 (R = Me, i-Pr and Ph). Their subsequent interaction with N(CH2CH2OH)3 led to the formation of N-organyl-2-(1-naphthyl)-N-(silatranylmethyl)acetamides. The structure of these hybrid compounds was characterized by 1H, 13C, and 29Si NMR spectroscopy. The structure of N-methyl- and N-isopropyl-2-(1-naphthyl)-N-(silatranylmethy)acetamides was confirmed by X-ray diffraction analysis. Results of computational screening showed that these silatranes are bioavailable and have drug-likeness.

Funder

Russian Science Foundation

Publisher

Bentham Science Publishers Ltd.

Reference75 articles.

1. Yang C.; Sheng X.; Zhang L.; Yu J.; Huang D.; Arylacetic acids in organic synthesis. Asian J Org Chem 2020,9(1),23-41

2. Gröger H.; Enzymatic routes to enantiomerically pure aromatic α-hydroxy carboxylic acids: A further example for the diversity of biocatalysis. Adv Synth Catal 2001,343(6-7),547-558

3. Sakakibara Y.; Ito E.; Fukushima T.; Murakami K.; Itami K.; Late-stage functionalization of arylacetic acids by photoredox-catalyzed decarboxylative carbon–heteroatom bond formation. Chemistry 2018,24(37),9254-9258

4. Hadjipavlou-Litina D.; Pontiki E.; Aryl-acetic and cinnamic acids as lipoxygenase inhibitors with antioxidant, anti-inflammatory, and anticancer activity. Advanced Protocols in Oxidative Stress III Methods in Molecular Biology 2015,1208

5. Chan H.C.; Kuo S.C.; Huang L.J.; Liu C.H.; Hsu S.L.; A phenylacetate derivative, SCK6, inhibits cell proliferation via G1 cell cycle arrest and apoptosis. Eur J Pharmacol 2003,467(1-3),31-39