Synthesis of andrographolide derivatives:: A new family of α-glucosidase inhibitors

被引：82

作者：

Xu, Hai-Wei ^{[1
]}

Dai, Gui-Fu ^{[1
]}

Liu, Gai-Zhi ^{[1
]}

Wang, Jun-Feng ^{[1
]}

Liu, Hong-Min ^{[1
]}

机构：

[1] Zhengzhou Univ, New Drug Res & Dev Ctr, Zhengzhou 450052, Peoples R China

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2007年 / 15卷 / 12期

关键词：

synthesis; glucosidase inhibitor; andrographolide derivative;

D O I：

10.1016/j.bmc.2007.03.063

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Andrographolide (1), the cytotoxic agent of the plant Andrographis paniculata, was subjected to semi-synthetic studies leading to a series of new derivatives, a novel family of glucosidase inhibitors. Nicotination of 3,19-hydroxyls in 15-alkylidene andrographolide derivatives (9) was favorable to alpha-glucosidase inhibition activity. Among them, 15-p-chlorobenzylidene-14-deoxy-11,12-didehydro-3,19-dinicotinateandrographolide (11c) was a very potent inhibitor against alpha-glucosidase with an IC50 value of 6 mu M. However, all compounds concerned for beta-glucosidase showed no inhibition. All compounds synthesized were characterized by the analysis of NMR, IR, HRMS spectra and the stereochemistry of 2 was confirmed by X-ray analysis. (C) 2007 Published by Elsevier Ltd.

引用

页码：4247 / 4255

页数：9

共 50 条

[31] Synthesis and Biological Evaluation of Andrographolide C-Glycoside Derivatives as α-Glycosidase Inhibitors
Yan Lin
Xu Haiwei
Liu Fengwu
Zhao Jin
Liu Hongmin
CHINESE JOURNAL OF CHEMISTRY, 2012, 30 (04) : 914 - 918
[32] Synthesis, molecular structure, spectral analysis, and biological activity of new malonamide derivatives as α-glucosidase inhibitors
Barakat, Assem
Islam, Mohammad Shahidul
Al-Majid, Abdullah Mohammed
Soliman, Saied M.
Ghabbour, Hazem A.
Yousuf, Sammer
Choudhary, M. Iqbal
Ul-Haq, Zaheer
JOURNAL OF MOLECULAR STRUCTURE, 2017, 1134 : 253 - 264
[33] Synthesis of Bis-indolylmethane sulfonohydrazides derivatives as potent α-Glucosidase inhibitors
Gollapalli, Mohammed
Taha, Muhammad
Ullah, Hayat
Nawaz, Muhammad
AlMuqarrabun, Laode Muhammad Ramadhan
Rahim, Fazal
Qureshi, Faiza
Mosaddik, Ashik
Ahmat, Norizan
Khan, Khalid Mohammed
BIOORGANIC CHEMISTRY, 2018, 80 : 112 - 120
[34] Catalytic asymmetric synthesis of indole derivatives as novel α-glucosidase inhibitors in vitro
Islam, Mohammad Shahidul
Barakat, Assem
Al-Majid, Abdullah Mohammed
Alia, M.
Yousuf, Sammer
Choudhary, M. Iqbal
Khalil, Ruqaiya
Ul-Haq, Zaheer
BIOORGANIC CHEMISTRY, 2018, 79 : 350 - 354
[35] Synthesis and Biological Activity of Novel Deoxynojirimycin Derivatives as Potent α-Glucosidase Inhibitors
Yu, Dan
Hu, Fangfang
Zhang, Yu
Zheng, Xiaorui
Kuang, Chunxiang
Yang, Qing
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2013, 68 (04): : 383 - 390
[36] Rational Design and Synthesis of Novel Benzimidazole Derivatives as Potential β-Glucosidase Inhibitors
Liu, Xu
Sun, Ge
Li, Fengxing
Feng, Xia
Jia, Tongguan
Luo, Cheng
Chen, Shijie
Chen, Hua
LETTERS IN DRUG DESIGN & DISCOVERY, 2024, 21 (13) : 2674 - 2683
[37] Synthesis, inhibitory activities, and QSAR study of xanthone derivatives as α-glucosidase inhibitors
Liu, Yan
Ke, Zhuofeng
Cui, Jianfang
Chen, Wen-Hua
Ma, Lin
Wang, Bo
BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (15) : 7185 - 7192
[38] Molecular docking studies and synthesis of novel bisbenzimidazole derivatives as inhibitors of α-glucosidase
Ozil, Musa
Emirik, Mustafa
Belduz, Ali
Ulker, Serdar
BIOORGANIC & MEDICINAL CHEMISTRY, 2016, 24 (21) : 5103 - 5114
[39] Synthesis of activity evaluation of flavonoid derivatives as alpha-glucosidase inhibitors
Zhu, Hua
Zhong, Xin
FRONTIERS IN CHEMISTRY, 2022, 10
[40] Concise synthesis of a new triterpenoid saponin from the roots of Gypsophila oldhamiana and its derivatives as α-glucosidase inhibitors
Liu, Qingchao
Guo, Tiantian
Li, Fahui
Li, Dong
NEW JOURNAL OF CHEMISTRY, 2016, 40 (11) : 9537 - 9549

← 1 2 3 4 5 →