Synthesis, Characterization and Cytotoxicity Evaluation of New Compounds from Oxazol-5(4H)-ones and Oxazoles Class Containing 4-(4-Bromophenylsulfonyl)phenyl Moiety

被引：0

作者：

Apostol, Theodora-Venera ^{[1
]}

Barbuceanu, Stefania-Felicia ^{[1
]}

Olaru, Octavian Tudorel ^{[2
]}

Draghici, Constantin ^{[3
]}

Saramet, Gabriel ^{[4
]}

Socea, Bogdan ^{[5
]}

Enache, Cristian ^{[6
]}

Socea, Laura-Ileana ^{[1
]}

机构：

[1] Carol Davila Univ Med & Pharm, Organ Chem Dept, Fac Pharm, 6 Traian Vuia Str, Bucharest 020956, Romania

[2] Carol Davila Univ Med & Pharm, Fac Pharm, Pharmaceut Bot & Cell Biol Dept, 6 Traian Vuia Str, Bucharest 020956, Romania

[3] Mil Med Sci Res Ctr, 24-28 Gr Cobalcescu Str, Bucharest 010195, Romania

[4] Carol Davila Univ Med & Pharm, Fac Pharm, Pharmaceut Technol & Biopharmacy Dept, 6 Traian Vuia Str, Bucharest 020956, Romania

[5] Carol Davila Univ Med & Pharm, Fac Gen Med, St Pantelimon Emergency Hosp, 340-342 Pantelimon Rd, Bucharest 021659, Romania

[6] Cent Lab Phytosanitary Quarantine, 11 Afumati Rd, Bucharest 077190, Romania

来源：

REVISTA DE CHIMIE | 2019年 / 70卷 / 04期

关键词：

N-acyl-alpha-amino acid; 1,3-oxazol-5(4H)-one; alpha-acylamino ketone; 1,3-oxazole; cytotoxicity; S-ALKYLATED 1,2,4-TRIAZOLES; ACID-DERIVATIVES; THIAZOLE; GENERATION; AZLACTONE; IMIDAZOLE; MECHANISM; PRODUCTS; DESIGN;

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Steiger N-acylation of alpha-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 alpha-acylamino ketones. These new intermediates were heterocyclized under the action of phosphorus 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, H-1- and C-13-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.

引用

页码：1099 / 1107

页数：9

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