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
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
  • [41] Direct one-pot synthesis of zolimidine pharmaceutical drug and imidazo[1,2-a]pyridine derivatives via I2/CuO-promoted tandem strategy
    Cai, Qun
    Liu, Mei-Cai
    Mao, Bi-Ming
    Xie, Xuan
    Jia, Feng-Cheng
    Zhu, Yan-Ping
    Wu, An-Xin
    CHINESE CHEMICAL LETTERS, 2015, 26 (07) : 881 - 884
  • [42] N-(2-Phenoxy)ethyl imidazo[1,2-a]pyridine-3-carboxamides containing various amine moieties: Design, synthesis and antitubercular activity
    Li, Linhu
    Wang, Apeng
    Wang, Bin
    Liu, Mingliang
    Lv, Kai
    Tao, Zeyu
    Ma, Chao
    Ma, Xican
    Han, Bing
    Wang, Aoyu
    Lu, Yu
    CHINESE CHEMICAL LETTERS, 2020, 31 (02) : 409 - 412
  • [43] N-(2-Phenoxy)ethyl imidazo[1,2-a]pyridine-3-carboxamides containing various amine moieties:Design,synthesis and antitubercular activity
    Linhu Li
    Apeng Wang
    Bin Wang
    Mingliang Liu
    Kai Lv
    Zeyu Tao
    Chao Ma
    Xican Ma
    Bing Han
    Aoyu Wang
    Yu Lu
    ChineseChemicalLetters, 2020, 31 (02) : 409 - 412
  • [44] Design, synthesis, molecular docking and anti-proliferative activity of novel phenothiazine containing imidazo[1,2-a]pyridine derivatives against MARK4 protein
    Bhakta, Avijit
    Mukhtar, Sayeed
    Anwar, Saleha
    Haider, Shaista
    Alahmdi, Mohammed Issa
    Parveen, Humaira
    Alsharif, Meshari A.
    Wani, Mohmmad Younus
    Chakrabarty, Anindita
    Hassan, Md. Imtaiyaz
    Ahmed, Naseem
    RSC MEDICINAL CHEMISTRY, 2024, 15 (06): : 1942 - 1958
  • [46] 2-Phenyl-imidazo[1,2-a]pyridine Compounds Containing Hydrophilic Groups as Potent and Selective Ligands for Peripheral Benzodiazepine Receptors: Synthesis, Binding Affinity and Electrophysiological Studies
    Denora, Nunzio
    Laquintana, Valentino
    Pisu, Maria Giuseppina
    Dore, Riccardo
    Murru, Luca
    Latrofa, Andrea
    Trapani, Giuseppe
    Sanna, Enrico
    JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (21) : 6876 - 6888
  • [47] 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
    Ahmad Shaabani
    Hamed Nosrati
    Zeinab Hezarkhani
    Ronak Afshari
    Monatshefte für Chemie - Chemical Monthly, 2018, 149 : 1459 - 1467
  • [48] Synthesis of indole alkaloid analogues containing the novel hexahydropyrrolo[1′,2′,3′:1,9a,9]imidazo[1,2-a]indole skeleton by ring-closing reactions of tryptophan-derived α-amino nitriles
    Gonzalez-Vera, Juan A.
    Garcia-Lopez, M. Teresa
    Herranz, Rosario
    TETRAHEDRON, 2007, 63 (37) : 9229 - 9234
  • [49] Reactions with hydrazonoyl halides: Part XVIII - Synthesis of pyrrolidino[3,4-c]pyrazole, pyrazolo[3,4-d]pyridazine, imidazo[1,2-a]pyridine, pyrazolo[3,4-d]pyrimidine and other heterocyclic derivatives
    Emam, HA
    Abdelhamid, AO
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1997, 36 (10): : 880 - 885