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
  • [21] p-Toluenesulfonic acid catalyzed, isocyanide-free, Groebke-Blackburn-Bienayme (GBB) type multicomponent synthesis of 3-anilino-imdazo[1,2-a]pyridines
    Jalani, Hitesh B.
    Jeong, Jin-Hyun
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2022, 59 (07) : 1266 - 1271
  • [22] MCM-41-SO3H-catalyzed synthesis of highly substituted 3-amino-imidazo[1,2-a]pyridines or pyrazines via the Groebke-Blackburn-Bienayme multicomponent reaction under grinding conditions at ambient temperature
    Naeimabadi, M.
    Javanshir, Sh.
    Maleki, A.
    Dekamin, M. G.
    SCIENTIA IRANICA, 2016, 23 (06) : 2724 - 2734
  • [23] Synthesis of imidazo[1,2-a]quinoxalines by double Groebke reactions and inhibitory effects on radicals and DNA oxidation
    Chen, Jia-Feng
    Liu, Zai-Qun
    TETRAHEDRON, 2016, 72 (15) : 1850 - 1859
  • [24] Synthesis of unsymmetrical bis-heterocycles containing the imidazo [2,1-b]thiazole framework and their benzo[d]fused analogues by an acid-free Groebke-Blackburn-Bienayme reaction
    Kishore, Kranthi G.
    Islas-Jacome, Alejandro
    Renteria-Gomez, Angel
    Conejo, Alain S.
    Basavanag, Unnamatla M. V.
    Wrobel, Kazimierz
    Gamez-Montano, Rocio
    TETRAHEDRON LETTERS, 2016, 57 (31) : 3556 - 3560
  • [25] Synthesis of imidazo[1,2-a]pyridines in a sequential one-pot Groebke-Blackburn modification using 2-aminopyridines, aldehydes and amines
    Flesch, D.
    Sciubert-Zsilavecz, M.
    PHARMAZIE, 2015, 70 (08): : 507 - 510
  • [26] Multicomponent Polymerizations of Isocyanides, Aldehydes, and 2-Aminopyridine toward Imidazo[1,2-a]pyridine-Containing Fused Heterocyclic Polymers
    Chen, Tingting
    Ye, Fan
    Hu, Rongrong
    Tang, Ben Zhong
    MACROMOLECULES, 2022, 55 (19) : 8590 - 8598
  • [27] REACTIONS WITH HYDROXAMOYL HALIDES - SYNTHESIS OF SEVERAL ISOXAZOLE, IMIDAZO[1,2-A]PYRIDINE, IMIDAZO[1,2-A]PYRIMIDINE AND BENZ-1,2,4-TRIAZINE DERIVATIVES
    ABDELHAMID, AO
    NEGM, AM
    ABDEEN, TMS
    ARCHIV DER PHARMAZIE, 1988, 321 (12) : 913 - 915
  • [28] Synthesis of 2,6-dichloro-5-(beta-D-ribofuranosyl)imidazo[1,2-a]pyridine, the first C-nucleoside containing an imidazo[1,2-a]pyridine heterocycle as the aglycon
    Gudmundsson, KS
    Drach, JC
    Townsend, LB
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 211 : 266 - ORGN
  • [29] Synthesis and biological study of some new chalcones and oxopyrimidines containing imidazo[1,2-a]pyridine nucleus
    Joshi, M. J.
    Vekariya, P. B.
    Dodiya, B. L.
    Ghetiya, R. M.
    Joshi, H. S.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2012, 49 (01) : 130 - 134
  • [30] Reactions with Hydrazonoyl Halides 62: Synthesis and Antimicrobial Evaluation of Some New Imidazo [1,2-a]pyrimidine, Imidazo [1,2-a]pyridine, Imdazo [1,2-b]pyrazole, and Quinoxaline Derivatives
    Abdelhamid, Abdou O.
    Abdelall, Eman K. A.
    Zaki, Yasser H.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2010, 47 (02) : 477 - 482