Synthesis of imidazo[1,2-a]pyridine-containing peptido- mimetics by tandem of Groebke-Blackburn-Bienayme and Ugi reactions

被引:5
|
作者
Kolomiiets, Oleksandr, V [1 ,2 ]
Tsygankov, Alexander, V [1 ,3 ]
Kornet, Maryna N. [4 ]
Brazhko, Aleksander A. [4 ]
Musatov, Vladimir I. [1 ]
Chebanov, Valentyn A. [1 ,2 ]
机构
[1] Natl Acad Sci Ukraine, State Sci Inst Inst Single Crystals, Div Chem Funct Mat, Nauky Ave, 60, UA-61072 Kharkiv, Ukraine
[2] Kharkov Natl Univ, Fac Chem, Svobody Sq, 4, UA-61022 Kharkiv, Ukraine
[3] Natl Tech Univ, Kharkiv Polytech Inst, Kyrpychova st, 2, UA-61002 Kharkiv, Ukraine
[4] Zaporizhzhya Natl Univ, Lab Biotechnol Physiol Act Subst, Zhukovsky Str 66, UA-69600 Zaporizhzhya, Ukraine
来源
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 19卷
基金
新加坡国家研究基金会;
关键词
Groebke-Blackburn-Bienayme reaction; imidazo[1; 2-a]pyridine; isocyanide; multicomponent reaction; peptidomimetic; Ugi reaction; MULTICOMPONENT REACTION; RECEPTOR; DERIVATIVES; DISCOVERY; PYRAZINES; BINDING;
D O I
10.3762/bjoc.19.53
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Peptidomimetics with a substituted imidazo[1,2-a ]pyridine fragment were synthesized by a tandem of Groebke-Black-burn-Bienayme and Ugi reactions. The target products contain substituted imidazo[1,2-a]pyridine and peptidomimetic moieties as pharmacophores with four diversity points introduced from readily available starting materials, including scaffold diversity. A small focused compound library of 20 Ugi products was prepared and screened for antibacterial activity.
引用
收藏
页码:727 / 735
页数:9
相关论文
共 49 条
  • [31] SYNTHESIS AND REACTIONS OF 1H-IMIDAZO[1,2-A]PYRROLO[3,2-E]PYRIDINE SYSTEM
    BANCROFT, KCC
    WARD, TJ
    BROWN, K
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (05): : 465 - 467
  • [33] Copper-catalyzed tandem cyclization of 2-(2-iodophenyl)imidazo[1,2-a] pyridine derivatives with selenium: Synthesis of benzo[b]selenophene-fused imidazo[1,2-a]pyridines
    Matsumura, Mio
    Sakata, Yumi
    Iwase, Atsuya
    Kawahata, Masatoshi
    Kitamura, Yuki
    Murata, Yuki
    Kakusawa, Naoki
    Yamaguchi, Kentaro
    Yasuike, Shuji
    TETRAHEDRON LETTERS, 2016, 57 (49) : 5484 - 5488
  • [34] Novel amide derivatives containing an imidazo[1,2-a]pyridine moiety: Design, synthesis as potential nematicidal and antibacterial agents
    Wei, Chengqian
    Huang, Junjie
    Luo, Yuqin
    Wang, Shaobo
    Wu, Sikai
    Xing, Zhifu
    Chen, Jixiang
    PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY, 2021, 175
  • [35] REACTIONS WITH NAPATHOYLHYDROXIMOYL CHLORIDES - SYNTHESIS OF DERIVATIVES OF ISOXAZOLE, PYRROLIDINO[3,4-D]ISOXAZOLIN-4,6-DIONE, IMIDAZO[1,2-A]PYRIDINE, IMIDAZO[1,2-A]PYRIMIDINE, BENZOTRIAZINE AND BENZOTHIADIAZINE
    ABDELHAMID, AO
    ALHAMIDI, AA
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1995, 42 (01) : 83 - 88
  • [36] One-pot oxidative Groebke-Blackburn-Bienayme reaction of alcohols: using bio-supported and magnetically recyclable Fe2O3@cellulose and Fe2O3@cellulose-SO3H nanocomposites for the synthesis of 3-aminoimidazo[1,2-a]pyridines
    Shaabani, Ahmad
    Nosrati, Hamed
    Hezarkhani, Zeinab
    Afshari, Ronak
    MONATSHEFTE FUR CHEMIE, 2018, 149 (08): : 1459 - 1467
  • [37] Synthesis of new hybrid compounds of imidazo[1,2-a]pyrimidine/pyridine based on quinoxaline through palladium-catalyzed coupling reactions and heteroannulation
    Enjilzadeh, Marzieh
    Keivanloo, Ali
    Bakherad, Mohammad
    TETRAHEDRON, 2025, 175
  • [38] Synthesis and Anti-acute Myeloid Leukemia Activity of Cyclopropane-1,1-diamide Derivatives Containing Imidazo[1,2-a]pyridine
    Wu, Luejia
    Li, Jiangdong
    Shi, Zhonghua
    Jin, Xin
    Wang, Xianheng
    Zhao, Changkuo
    Huang, Qiang
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2025, 45 (01) : 286 - 296
  • [39] Synthesis and anticancer activity evaluation of some novel imidazo[1,2-a]pyridine based heterocycles containing S-alkyl/aryl moiety
    Kaya, Betul
    Yurttas, Leyla
    Baysal, Merve
    Celikates, Buesra Korkut
    Kaplancikli, Zafer Asim
    Imamoglu, Rizvan
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2024, 199 (05) : 383 - 393
  • [40] Direct one-pot synthesis of zolimidine pharmaceutical drug and imidazo [1,2-a] pyridine derivatives via I2/CuO-promoted tandem strategy
    Qun Cai
    Mei-Cai Liu
    Bi-Ming Mao
    Xuan Xie
    Feng-Cheng Jia
    Yan-Ping Zhu
    An-Xin Wu
    ChineseChemicalLetters, 2015, 26 (07) : 881 - 884