Synthesis, Characterization, and Biological Evaluations of 1,3,5-Triazine Derivatives of Metformin Cyclization with Berberine and Magnolol in the Presence of Sodium Methylate

被引:22
|
作者
Cao, Han [1 ]
Liao, Shili [1 ]
Zhong, Wenjing [1 ]
Xiao, Xuerong [1 ]
Zhu, Jiancheng [1 ]
Li, Weimin [2 ]
Wu, Xia [1 ]
Feng, Yifan [1 ]
机构
[1] Pharmaceut Univ, Cent Lab Guangdong, Guangzhou 510000, Guangdong, Peoples R China
[2] Guangzhou Univ Chinese Med, Coll Chinese Mat Medica, Guangzhou 510000, Guangdong, Peoples R China
基金
中国国家自然科学基金;
关键词
cyclization triazine; anti-inflammatory activity; anti-insulin resistance; CANCER CELLS; INHIBITION; ACTIVATION; APOPTOSIS; PATHWAY; KINASE;
D O I
10.3390/molecules22101752
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
The novel target products were synthesized in the formation of a triazine ring from berberine, magnolol, and metformin catalyzed by sodium methylate. The structures of products 1-3 were firstly confirmed by extensive spectroscopic analyses and single-crystal X-ray diffraction. The crystal structures of the target product 2 and the intermediate product 7b were reported for the first time. All target products were evaluated for their anti-inflammatory and antidiabetic activities against INS-1 and RAW264.1 cells in vitro and all products showed excellent anti-inflammatory effects and anti-insulin resistance effects. Our studies indicated that new compounds 1-3 were found to be active against inflammation and insulin resistance.
引用
收藏
页数:11
相关论文
共 50 条
  • [41] SYNTHESIS OF COLOR METAL-COMPLEX UNSATURATED DERIVATIVES OF 1,3,5-TRIAZINE
    KONSTANTINOVA, TN
    SHOPOVA, SV
    DRAGANOV, AS
    DOKLADI NA BOLGARSKATA AKADEMIYA NA NAUKITE, 1978, 31 (07): : 889 - 891
  • [42] Synthesis and study of 1,3,5-triazine based thiazole derivatives as antimicrobial agents
    Desai, N. C.
    Makwana, Atul H.
    Rajpara, K. M.
    JOURNAL OF SAUDI CHEMICAL SOCIETY, 2016, 20 : S334 - S341
  • [43] SYNTHESIS OF 2-(PARA-AMINOPHENYLAZO)-1,3,5-TRIAZINE DERIVATIVES
    INOUE, Y
    HSU, YC
    KATO, Y
    HAMANO, M
    KAMO, Y
    KEUMI, T
    KITAJIMA, H
    NIPPON KAGAKU KAISHI, 1981, (12) : 1922 - 1928
  • [44] HETEROCYCLIC-COMPOUNDS - SYNTHESIS OF SOME FLUORINATED 1,3,5-TRIAZINE DERIVATIVES
    TYAGI, E
    VERMA, SS
    PRAKASH, L
    MITAL, RL
    REVUE ROUMAINE DE CHIMIE, 1990, 35 (10-12) : 1025 - 1029
  • [45] New Usage for Cyclotrimerization Reaction: a Facile Synthesis of 1,3,5-Triazine Derivatives
    Ouyang, Mi
    Yu, Chun-hui
    Zhang, Ning-yu
    Song, Qing-bao
    Sun, Jing-wei
    Hu, Bin
    Zhang, Cheng
    MATERIALS SCIENCE AND NANOTECHNOLOGY I, 2013, 531-532 : 32 - +
  • [46] 1,3,5-Triazine as Branching Connector for the Construction of Novel Antimicrobial Peptide Dendrimers: Synthesis and Biological Characterization
    Sheyi, Rotimi
    Mhlongo, Jessica T.
    Jorba, Marta
    Fuste, Ester
    Sharma, Anamika
    Vinas, Miguel
    Albericio, Fernando
    Espinal, Paula
    de la Torre, Beatriz G.
    INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2024, 25 (11)
  • [47] Synthesis, characterization and antimalarial activity of hybrid 4-aminoquinoline-1,3,5-triazine derivatives
    Bhat, Hans Raj
    Singh, Udaya Pratap
    Yadav, Pankaj S.
    Kumar, Vikas
    Gahtori, Prashant
    Das, Aparoop
    Chetia, Dipak
    Prakash, Anil
    Mahanta, J.
    ARABIAN JOURNAL OF CHEMISTRY, 2016, 9 : S625 - S631
  • [48] Synthesis and Biological Evaluation of New Dithiocarbamate Derivatives and New α-aminophosphonate Conjugates Containing 1,3,5-Triazine Nucleus
    Ghanim, Ibrahim M.
    El Gokha, Ahmed A.
    Aleem, Abdel Aleem Hassan Abdel
    El-Sayed, Ibrahim E. T.
    EGYPTIAN JOURNAL OF CHEMISTRY, 2023, 66 (10): : 69 - 77
  • [49] Design, Synthesis, and Anti-PVY Biological Activity of 1,3,5-Triazine Derivatives Containing Piperazine Structure
    Bai, Lian
    Wei, Chunle
    Zhang, Jian
    Song, Runjiang
    INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2023, 24 (09)
  • [50] SYNTHESIS AND TAUTOMERIC TRANSFORMATIONS OF 2-METHOXY-1,3,5-TRIAZINE AND 2,4-DIMETHOXY-1,3,5-TRIAZINE PHOSPHORYLATED DERIVATIVES
    ZIMIN, MG
    FOMAKHIN, EV
    GOLDFARB, EI
    PUDOVIK, AN
    ZHURNAL OBSHCHEI KHIMII, 1986, 56 (03): : 553 - 560