Synthesis and structure confirmation of 7-ester-8-aminomethylene-substituted baicalein derivatives

被引：1
作者：
Mou, Jiajia [1 ]
Wang, Qiang [2 ]
Deng, Yanru [1 ]
Chen, Danghui [1 ]
Qiu, Shuang [1 ]
机构：
[1] Tianjin Univ Tradit Chinese Med, Sch Chinese Mat Med, Dept Med Chem, Hlth Ind Pk, Tianjin 301617, Peoples R China
[2] South Cent Univ Nationalities, Coll Pharm, Wuhan, Peoples R China
来源：
JOURNAL OF THE CHINESE CHEMICAL SOCIETY | 2021年 / 68卷 / 09期
基金：
中国国家自然科学基金;
关键词：
baicalein derivatives; esterification reaction; Mannich reaction; strontium chloride identification reaction; BIOLOGICAL EVALUATION; CELL-CYCLE; FLAVONOIDS; GROWTH;
D O I：
10.1002/jccs.202100194
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Twelve baicalein derivatives, derivatized with 7-ester and 8-aminomethylene groups, were synthesized as cyclin-dependent kinase 1 (CDK1) inhibitors, by the addition of one of four secondary amines to C-8, using the Mannich reaction, followed by mono-esterification with one of three carboxylic acids. Analysis by H-1-, C-13-NMR, and HMBC spectra, as well as a chemical test, confirmed that the esterification occurred at the 7-phenolic hydroxyl position of baicalein but not at the 5- or 6-positions.
引用
收藏
页码：1598 / 1603
页数：6
相关论文
共 50 条
  • [31] Design, synthesis and investigation on the structure-activity relationships of N-substituted 2-aminothiazole derivatives as antitubercular agents
    Pieroni, Marco
    Wan, Baojie
    Cho, Sanghyun
    Franzblau, Scott G.
    Costantino, Gabriele
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 72 : 26 - 34
  • [32] Synthesis and crystal structure analysis of substituted 2-(3-(hydroxymethyl)quinolin-2-yl)phenol derivatives
    Rambabu, D.
    Krishna, G. Rama
    Basavoju, Srinivas
    Rao, M. V. Basaveswara
    Reddy, C. Malla
    Pal, Manojit
    JOURNAL OF MOLECULAR STRUCTURE, 2012, 1016 : 126 - 133
  • [33] Design, synthesis and structure-activity relationships of new triazole derivatives containing N-substituted phenoxypropylamino side chains
    Wang, Shengzheng
    Jin, Gang
    Wang, Wenya
    Zhu, Lingjian
    Zhang, Yongqiang
    Dong, Guoqiang
    Liu, Yang
    Zhuang, Chunlin
    Miao, Zhenyuan
    Yao, Jianzhong
    Zhang, Wannian
    Sheng, Chunquan
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 53 : 292 - 299
  • [34] Synthesis and evaluation of 8-oxoadenine derivatives as potent Toll-like receptor 7 agonists with high water solubility
    Nakamura, Tomoaki
    Wada, Hiroki
    Kurebayashi, Hirotaka
    McInally, Tom
    Bonnert, Roger
    Isobe, Yoshiaki
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (03) : 669 - 672
  • [35] Novel 8-deaza-5,6,7,8-tetrahydroaminopterin derivatives as dihydrofolate inhibitor: Design, synthesis and antifolate activity
    Zhang, Zhili
    Wu, Jun
    Ran, Fuxiang
    Guo, Ying
    Tian, Ran
    Zhou, Shouxin
    Wang, Xiaowei
    Liu, Zhenming
    Zhang, Liangren
    Cui, Jingrong
    Liu, Junyi
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (02) : 764 - 771
  • [36] Design, synthesis, molecular docking, molecular dynamic simulation, and MMGBSA analysis of 7-O-substituted 5-hydroxy flavone derivatives
    Patel, Kajalben B. B.
    Patel, Rahul V. V.
    Ahmad, Iqrar
    Rajani, Dhanji
    Patel, Harun
    Mukherjee, Sudipta
    Kumari, Premlata
    JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS, 2024, 42 (12) : 6378 - 6392
  • [37] 7-((4-Substituted)piperazin-1-yl) derivatives of ciprofloxacin: Synthesis and in vitro biological evaluation as potential antitumor agents
    Azema, Joelle
    Guidetti, Brigitte
    Dewelle, Janique
    Le Calve, Benjamin
    Mijatovic, Tatjana
    Korolyov, Alexander
    Vaysse, Julie
    Malet-Martino, Myriam
    Martino, Robert
    Kiss, Robert
    BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (15) : 5396 - 5407
  • [38] Synthesis and evaluation of 7-substituted coumarin derivatives as multimodal monoamine oxidase-B and cholinesterase inhibitors for the treatment of Alzheimer's disease
    Joubert, Jacques
    Foka, Germaine B.
    Repsold, Benjamin P.
    Oliver, Douglas W.
    Kapp, Erika
    Malan, Sarel F.
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 125 : 853 - 864
  • [39] Structure-based Design, Synthesis and Anti-influenza A Virus Activities of Substituted Phenyl-coupled Heterocyclic Ethylamide Derivatives
    Wang Yang
    Lei Fan
    Li Xiaolong
    He Yi
    Li Jue
    Qiu Rui
    Wu Xueying
    Hai Li
    Wu Yong
    CHEMICAL RESEARCH IN CHINESE UNIVERSITIES, 2015, 31 (06) : 942 - 951
  • [40] Structure-based design, synthesis and anti-influenza A virus activities of substituted phenyl-coupled heterocyclic ethylamide derivatives
    Yang Wang
    Fan Lei
    Xiaolong Li
    Yi He
    Jue Li
    Rui Qiu
    Xueying Wu
    Li Hai
    Yong Wu
    Chemical Research in Chinese Universities, 2015, 31 : 942 - 951
12345