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https://doi.org/10.37358/Rev.Chim.1949

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Revista de Chimie (Rev. Chim.), Year 2019, Volume 70, Issue 4, 1099-1107

https://doi.org/10.37358/RC.19.4.7073

Theodora-Venera Apostol, Stefania-Felicia Barbuceanu, Octavian Tudorel Olaru, Constantin Draghici, Gabriel Saramet, Bogdan Socea, Cristian Enache, Laura-Ileana Socea

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

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.
Keywords:
N-acyl-a--amino acid; 1;3-oxazol-5(4H)-one; a-acylamino ketone; 1;3-oxazole; cytotoxicity

Issue: 2019, Volume 70, Issue 4
Pages: 1099-1107
Publication date: 2019/5/15
https://doi.org/10.37358/RC.19.4.7073
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This article is published under the Creative Commons Attribution 4.0 International License
Citation Styles
Cite this article as:
APOSTOL, T., BARBUCEANU, S., OLARU, O.T., DRAGHICI, C., SARAMET, G., SOCEA, B., ENACHE, C., SOCEA, L., Synthesis, characterization and Cytotoxicity Evaluation of New Compounds from Oxazol-5(4H)-ones and Oxazoles Class Containing 4-(4-Bromophenylsulfonyl)phenyl Moiety, Rev. Chim., 70(4), 2019, 1099-1107.

Vancouver
Apostol T, Barbuceanu S, Olaru OT, Draghici C, Saramet G, Socea B, Enache C, Socea L. Synthesis, characterization and Cytotoxicity Evaluation of New Compounds from Oxazol-5(4H)-ones and Oxazoles Class Containing 4-(4-Bromophenylsulfonyl)phenyl Moiety. Rev. Chim.[internet]. 2019 Apr;70(4):1099-1107. Available from: https://doi.org/10.37358/RC.19.4.7073


APA 6th edition
Apostol, T., Barbuceanu, S., Olaru, O.T., Draghici, C., Saramet, G., Socea, B., Enache, C. & Socea, L. (2019). Synthesis, characterization and Cytotoxicity Evaluation of New Compounds from Oxazol-5(4H)-ones and Oxazoles Class Containing 4-(4-Bromophenylsulfonyl)phenyl Moiety. Revista de Chimie, 70(4), 1099-1107. https://doi.org/10.37358/RC.19.4.7073


Harvard
Apostol, T., Barbuceanu, S., Olaru, O.T., Draghici, C., Saramet, G., Socea, B., Enache, C., Socea, L. (2019). 'Synthesis, characterization and Cytotoxicity Evaluation of New Compounds from Oxazol-5(4H)-ones and Oxazoles Class Containing 4-(4-Bromophenylsulfonyl)phenyl Moiety', Revista de Chimie, 70(4), pp. 1099-1107. https://doi.org/10.37358/RC.19.4.7073


IEEE
T. Apostol, S. Barbuceanu, O.T. Olaru, C. Draghici, G. Saramet, B. Socea, C. Enache, L. Socea, "Synthesis, characterization and Cytotoxicity Evaluation of New Compounds from Oxazol-5(4H)-ones and Oxazoles Class Containing 4-(4-Bromophenylsulfonyl)phenyl Moiety". Revista de Chimie, vol. 70, no. 4, pp. 1099-1107, 2019. [online]. https://doi.org/10.37358/RC.19.4.7073


Text
Theodora-Venera Apostol, Stefania-Felicia Barbuceanu, Octavian Tudorel Olaru, Constantin Draghici, Gabriel Saramet, Bogdan Socea, Cristian Enache, Laura-Ileana Socea,
Synthesis, characterization and Cytotoxicity Evaluation of New Compounds from Oxazol-5(4H)-ones and Oxazoles Class Containing 4-(4-Bromophenylsulfonyl)phenyl Moiety,
Revista de Chimie,
Volume 70, Issue 4,
2019,
Pages 1099-1107,
ISSN 2668-8212,
https://doi.org/10.37358/RC.19.4.7073.
(https://revistadechimie.ro/Articles.asp?ID=7073)
Keywords: N-acyl-a--amino acid; 1;3-oxazol-5(4H)-one; a-acylamino ketone; 1;3-oxazole; cytotoxicity


RIS
TY - JOUR
T1 - Synthesis, characterization and Cytotoxicity Evaluation of New Compounds from Oxazol-5(4H)-ones and Oxazoles Class Containing 4-(4-Bromophenylsulfonyl)phenyl Moiety
A1 - Apostol, Theodora-Venera
A2 - Barbuceanu, Stefania-Felicia
A3 - Olaru, Octavian Tudorel
A4 - Draghici, Constantin
A5 - Saramet, Gabriel
A6 - Socea, Bogdan
A7 - Enache, Cristian
A8 - Socea, Laura-Ileana
JF - Revista de Chimie
JO - Rev. Chim.
PB - Revista de Chimie SRL
SN - 2668-8212
Y1 - 2019
VL - 70
IS - 4
SP - 1099
EP - 1107
UR - https://doi.org/10.37358/RC.19.4.7073
KW - N-acyl-a--amino acid
KW - 1
KW - 3-oxazol-5(4H)-one
KW - a-acylamino ketone
KW - 1
KW - 3-oxazole
KW - cytotoxicity
ER -


BibTex
@article{RevCh2019P1099,
author = {Apostol Theodora-Venera and Barbuceanu Stefania-Felicia and Olaru Octavian Tudorel and Draghici Constantin and Saramet Gabriel and Socea Bogdan and Enache Cristian and Socea Laura-Ileana},
title = {Synthesis, characterization and Cytotoxicity Evaluation of New Compounds from Oxazol-5(4H)-ones and Oxazoles Class Containing 4-(4-Bromophenylsulfonyl)phenyl Moiety},
journal = {Revista de Chimie},
volume = {70},
number = {4},
pages = {1099-1107},
year = {2019},
issn = {2668-8212},
doi = {https://doi.org/10.37358/RC.19.4.7073},
url = {https://revistadechimie.ro/Articles.asp?ID=7073}
}
 
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