Abstract
Steiger N-acylation of a-alanine with 4-(4-bromophenylsulfonyl)benzoyl chloride led to 2-[4-(4-bromophenylsulfonyl)benzamido]propanoic acid. This compound underwent intramolecular cyclization in the presence of N-methylmorpholine and ethyl chloroformate or acetic anhydride to the corresponding saturated azlactone. Then acylaminoacylation of dry aromatic hydrocarbons with 2-[4-(4-bromophenylsulfonyl)phenyl]-4-methyloxazol-5(4H)-one or 2-[4-(4-bromophenylsulfonyl) benzamido ]propanoyl chloride in the presence of anhydrous aluminum chloride led to corresponding a-acylamino ketones. These new intermediates were heterocyclized under the action of phosphorus oxychloride or concentrated sulfuric acid in the presence of acetic anhydride to the corresponding oxazoles. The newly synthesized compounds were characterized by spectral studies (FT-IR, UV-Vis, MS, 1H- and 13C-NMR) and elemental analysis. The purity of the new compounds was evaluated by RP-HPLC. The experimental research regarding to the in vitro cytotoxic activity of the new compounds were performed using Daphnia magna bioassay.
Highlights
THEODORA-VENERA APOSTOL1, STEFANIA-FELICIA BARBUCEANU1*, OCTAVIAN TUDOREL OLARU2, CONSTANTIN DRAGHICI3, GABRIEL SARAMET4, BOGDAN SOCEA5, CRISTIAN ENACHE6, LAURA-ILEANA SOCEA1 1 Carol Davila University of Medicine and Pharmacy, Faculty of Pharmacy, Organic Chemistry Department, 6 Traian Vuia Str., 020956, Bucharest, Romania 2 Carol Davila University of Medicine and Pharmacy, Faculty of Pharmacy, Pharmaceutical Botany and Cell Biology Department, 6 Traian Vuia Str., 020956, Bucharest, Romania 3 Military Medical Scientific Research Center, 24-28 Gr
Ones and oxazoles, is seems of interest to synthesize new heterocyclic compounds from these classes and their acyclic intermediates using the reaction sequences from scheme 1
The key precursor, 4-(4-bromophenylsulfonyl) benzoic acid 1, and corresponding acyl chloride 2 were already described in literature [30,31]
Summary
FT-IR spectra were recorded in KBr pellets on a Bruker Vertex 70 spectrometer; intensity of IR bands are given as: weak (w), medium (m), strong (s), and very strong (vs). Mass spectra (ESI-MS/MS) were recorded on a Varian 1200 LC-MS/MS high performance liquid chromatograph coupled with a triple quadrupole mass spectrometer with electrospray interface (ESI), by positive and/or negative ionization. Compounds purity was checked by RP-HPLC using a Beckman System Gold 126 liquid chromatograph, equipped with a System Gold 166 UV-Vis detector; retention reported. Contents of time C, H, N(,tRa)ndofS compounds in min is were determined using a Costech ECS 4010 micro elemental analyzer
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