DESIGN, SYNTHESIS, CHARACTERIZATION, AND CYTOTOXICITY EVALUATION OF NEW 4-BENZYL-1,3-OXAZOLE DERIVATIVES BEARING 4-(4-CHLOROPHENYLSULFONYL)PHENYL MOIETY

被引：6

作者：

Apostol, Theodora-Venera ^{[1
]}

Socea, Laura-Ileana ^{[1
]}

Draghici, Constantin ^{[2
]}

Olaru, Octavian Tudorel ^{[3
]}

Saramet, Gabriel ^{[4
]}

Enache-Preoteasa, Cristian ^{[5
]}

Barbuceanu, Stefania-Felicia ^{[1
]}

机构：

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

[2] Romanian Acad, Costin D Nenitescu Inst Organ Chem, 202B Splaiul Independentei St, Bucharest 060023, Romania

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

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

[5] Natl Phytosanit Lab, 11 Voluntari Blvd, Voluntari 077190, Romania

来源：

FARMACIA | 2021年 / 69卷 / 02期

关键词：

N-acyl-alpha-amino acid; 1,3-oxazol-5(4H)-one; 1,3-oxazole; cytotoxicity; BIOLOGICAL EVALUATION; NATURAL-PRODUCTS; INHIBITORS; OXAZOLE; OXAZOL-5(4H)-ONES;

D O I：

10.31925/farmacia.2021.2.17

中图分类号：

R9 [药学];

学科分类号：

1007 ;

摘要：

This paper presents the design, synthesis, characterization, and cytotoxicity evaluation of eight organic compounds that have in their molecules the 4-(4-chlorophenylsulfonyl)phenyl moiety: four acyclic precursors derived from phenylalanine (one N-acyl-alpha-amino acid, one N-acyl-alpha-amino acyl chloride, and two N-acyl-alpha-amino ketones), and four cyclization products: one 1,3-oxazol-5(4H)-one, and three 1,3-oxazoles substituted in 5-position with phenyl, p-tolyl, and m-xylyl group, respectively. Structures of synthesized compounds were confirmed by elemental analysis and spectral methods (UV-Vis, FT-IR, MS, H-1 and C-13-NMR). The compounds purity determination was performed by RP-HPLC. Cytotoxic effect of synthesized compounds was evaluated on Daphnia magna crustacean.

引用

页码：314 / 324

页数：11

共 50 条

[41] Synthesis, characterization, and in vitro anticancer evaluation of 2-substituted 5-arylsulfonyl-1,3-oxazole-4-carbonitriles [J].

Kachaeva, Maryna V. ;

Pilyo, Stepan G. ;

Zhirnov, Victor V. ;

Brovarets, Volodymyr S. .

MEDICINAL CHEMISTRY RESEARCH, 2019, 28 (01) :71-80

[42] Synthesis, Characterization, and Biological Evaluation for New Derivatives Based on 2Сhloro-N-[4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl]acetamide [J].

Jamel, N. M. ;

Alheety, K. A. ;

Hassan, H. A. ;

Tomma, J. H. ;

Ahmed, H. S. ;

Baqir, R. K. .

RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2024, 94 (12) :3340-3347

[43] Synthesis and cytotoxicity evaluation of some new 6-nitro derivatives of thiazole-containing 4-(3H)-quinazolinone [J].

Hosseinzadeh, Leila ;

Aliabadi, Alireza ;

Kalantari, Masoud ;

Mostafavi, Abolfazl ;

Khajouei, Marzieh Rahmani .

RESEARCH IN PHARMACEUTICAL SCIENCES, 2016, 11 (03) :210-218

[44] Synthesis and Evaluation of Imidazole Derivatives Bearing Imidazo[2,1-b] [1,3,4]thiadiazole Moiety as Antibacterial Agents [J].

Xu, Wen-Bo ;

Li, Siqi ;

Zheng, Chang-Ji ;

Yang, Yu-Xuan ;

Zhang, Changhao ;

Jin, Cheng-Hua .

MEDICINAL CHEMISTRY, 2024, 20 (01) :40-51

[45] Design and Synthesis of New 4-(3,4,5-Trimethoxyphenyl)Thiazole-Pyrimidine Derivatives as Potential Antiproliferative Agents [J].

El-Damasy, Ashraf K. ;

Jin, Heewon ;

Sabry, Mohamed A. ;

Kim, Hyun Ji ;

Alanazi, Mohammed M. ;

Seo, Seon Hee ;

Bang, Eun-Kyoung ;

Keum, Gyochang .

MEDICINA-LITHUANIA, 2023, 59 (06)

[46] Design, Synthesis and Anticancer Activity of a New Series of N-aryl-N′-[4-(pyridin-2-ylmethoxy)benzyl]urea Derivatives [J].

Hou, Shicheng ;

Liang, Shishao ;

Zhang, Chao ;

Han, Yingmei ;

Liang, Jianhui ;

Hu, Hongyu ;

Zhang, Xingeng ;

Hu, Chun ;

Liu, Xiaoping ;

Zhang, Hong .

MOLECULES, 2021, 26 (12)

[47] Design, synthesis and biological evaluation of novel benzimidazole-derived p21-activited kinase 4 (PAK4) inhibitors bearing a 4-(4-methylpiperazin-1-yl)phenyl scaffold as potential antitumor agents [J].

Hao, Shuang ;

Hou, Liang ;

Wang, Jia-hui ;

Yan, Jing-han ;

Niu, Yi-fan ;

Cai, Zheng-hao ;

Li, Feng ;

Meng, Fan-hao .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2024, 280

[48] Synthesis and primary cytotoxicity evaluation of new 5-benzylidene-2, 4-thiazolidinedione derivatives [J].

Patil, Vijay ;

Tilekar, Kalpana ;

Mehendale-Munj, Sonali ;

Mohan, Rhea ;

Ramaa, C. S. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (10) :4539-4544

[49] Design, synthesis and biological evaluation of isochroman-4-one hybrids bearing piperazine moiety as antihypertensive agent candidates [J].

Xie, Shaowen ;

Li, Xinnan ;

Yu, Hao ;

Zhang, Pengfei ;

Wang, Jia ;

Wang, Chaolei ;

Xu, Shengtao ;

Wu, Zheng ;

Liu, Jie ;

Zhu, Zheying ;

Xu, Jinyi .

BIOORGANIC & MEDICINAL CHEMISTRY, 2019, 27 (13) :2764-2770

[50] Design, Synthesis, and Antitumor Activity Evaluation of Novel 2,4,7-Trisubstituted Quinazoline Derivatives Containing an Aminomethyl Piperidine Moiety [J].

Han, Jiahui ;

Wang, Shihao ;

Chen, Hongjing ;

Gu, Dongling ;

Yang, Zichen ;

Wang, Hao ;

Yu, Fuqiang ;

Chi, Lingling ;

Ke, Yu ;

Liu, Hongmin ;

Zhang, Qiurong .

RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2025, 51 (02) :869-885

← 1 2 3 4 5 →