2. Academic Validation
  3. The synthesis of 4,7-disubstituted-2H-benzo[b][1,4]-oxazin-3(4H)-ones using Smiles rearrangement and their in vitro evaluation as platelet aggregation inhibitors

The synthesis of 4,7-disubstituted-2H-benzo[b][1,4]-oxazin-3(4H)-ones using Smiles rearrangement and their in vitro evaluation as platelet aggregation inhibitors

  • Bioorg Med Chem Lett. 2014 Mar 15;24(6):1479-83. doi: 10.1016/j.bmcl.2014.02.014.
Shuai Xia 1,  Ji-Qiang Liu 1,  Xiu-Hua Wang 1,  Ye Tian 2,  Yu Wang 1,  Jing-Huan Wang 1,  Liang Fang 3,  Hua Zuo 4
Affiliations

Affiliations

  • 1 College of Pharmaceutical Sciences, Southwest University, Chongqing 400715, China.
  • 2 Department of Medicinal Chemistry and Key Laboratory of Chemical Biology, School of Pharmaceutical Sciences, Shandong University, Jinan 250012, China.
  • 3 Department of Oncology, The Ninth People's Hospital of Chongqing, Chongqing 400700, China. Electronic address: fangliangfranc@gmail.com.
  • 4 College of Pharmaceutical Sciences, Southwest University, Chongqing 400715, China. Electronic address: zuohua@swu.edu.cn.
PMID: 24565904 DOI: 10.1016/j.bmcl.2014.02.014
Abstract

A series of novel benzo[b][1,4]oxazin-3(4H)-one derivatives were synthesized as platelet aggregation inhibitors for structure-activity relationships (SAR) analysis. The synthetic pattern, involved Smiles rearrangement for the preparation of benzoxazine, was proven to be more efficient than the conventional methods. Biological evaluation demonstrated that among all the synthesized compounds, compound 9u (IC50=9.20μM) exhibited the most potent inhibition activity compared with aspirin, the positive control (IC50=7.07μM). Molecular docking revealed that these set of compounds could be the GPIIb/IIIa antagonist for that they could be situated in the binding site of GPIIb/IIIa receptor quite well.

Keywords

4,7-Disubstituted-2H-benzo[b][1,4]oxazin-3(4H)-one; Molecular docking; Platelet aggregation; Smiles rearrangement; Structure–activity relationships (SAR).

Figures
嗨！很高兴为您提供帮助！

尊敬的 MCE 客户您好，
请您选择所在区域，我们将转接对应客服为您服务！

热门区域

A

B

C

F

G

H

J

L

N

Q

S

T

X

Y

Z

热 A B C F G H J L N Q S T X Y Z