Solvent-free synthesis of novel steroidal 2-aminopyridines

被引:11
|
作者
Zhang, Yan-Ling [1 ,2 ,3 ]
Li, Ya-Fei [1 ,2 ]
Shi, Xiao-Li [1 ,2 ]
Yu, Bin [1 ,2 ]
Shi, Yun-Kai [1 ,2 ]
Liu, Hong-Min [1 ,2 ]
机构
[1] Zhengzhou Univ, Sch Pharmaceut Sci, 100 KeXue DaDao, Zhengzhou 450001, Henan Province, Peoples R China
[2] Collaborat Innovat Ctr New Drug Res & Safety Eval, 100 KeXue DaDao, Zhengzhou 450001, Henan Province, Peoples R China
[3] Xuchang Univ, Coll Chem & Chem Engn, Xuchang 461000, Henan Province, Peoples R China
关键词
Solvent-free; Steroidal pyridines; Synthesis; Enaminonitrile; PROSTATE-CANCER; DERIVATIVES; EFFICIENT; AGENTS; 3-CYANO-2-AMINOPYRIDINES; SPIROOXINDOLES; ABIRATERONE; GALETERONE; DIENAMIDES; INHIBITORS;
D O I
10.1016/j.steroids.2016.09.005
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 synthesis of novel steroidal 3-cyano-2-aminopyridines using enaminonitrile and various primary amines was established under solvent-free condition. Structures of the new compounds were characterized by MS,H-1 and C-13 NMR data and the structure of 2-aminopyridine of the product 5b was further confirmed by X-ray analysis. The reaction mechanism was proposed on the basis of the key intermediate obtained. The adjacent amine and nitrile groups existed in the final products have the potential for late stage functionalization, which would provide efficient access to steroidal compound collections with structural diversity and complexity. (C) 2016 Elsevier Inc. All rights reserved.
引用
收藏
页码:147 / 153
页数:7
相关论文
共 50 条
  • [1] A mild, catalyst-free synthesis of 2-aminopyridines
    Poola, Bhaskar
    Choung, Wonken
    Nantz, Michael H.
    TETRAHEDRON, 2008, 64 (48) : 10798 - 10801
  • [2] A catalyst- and solvent-free thermal multicomponent approach for the construction of diverse and polysubstituted 2-aminopyridines and their antibacterial activity
    Baral, Ek Raj
    Sharma, Kavita
    Akhtar, Muhammad Saeed
    Lee, Yong Rok
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (43) : 10285 - 10297
  • [3] Solvent-free ruthenium trichloride-mediated [2+2+2] cycloaddition of α,ω-diynes and cyanamides: a convenient access to 2-aminopyridines
    Ye, Fei
    Haddad, Mansour
    Michelet, Veronique
    Ratovelomanana-Vidal, Virginie
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (06): : 1063 - 1068
  • [4] 2-AMINOPYRIDINES
    ARNALL, P
    DACE, GR
    MANUFACTURING CHEMIST, 1970, 41 (02): : 21 - &
  • [5] A NEW ROUTE FOR THE SYNTHESIS OF 2-AMINOPYRIDINES
    Kibou, Zahira
    Cheikh, Nawel
    Choukchou-Braham, Noureddine
    Mostefa-Kara, Bachir
    Benabdellah, Mohammed
    Villemin, Didier
    SCIENTIFIC STUDY AND RESEARCH-CHEMISTRY AND CHEMICAL ENGINEERING BIOTECHNOLOGY FOOD INDUSTRY, 2011, 12 (02): : 121 - 126
  • [6] SOLVENT AND TEMPERATURE EFFECTS ON THE FLUORESCENCE OF 2-AMINOPYRIDINES, 3-AMINOPYRIDINES AND 4-AMINOPYRIDINES
    JAARINEN, S
    NIIRANEN, J
    KOSKIKALLIO, J
    FINNISH CHEMICAL LETTERS, 1987, 14 (3-4): : 160 - 161
  • [7] SYNTHESIS OF SUBSTITUTED 2-AMINOPYRIDINES - A VERSATILE APPROACH
    HUSSAINI, FA
    PRAGYA
    RAM, VJ
    SINGH, SK
    NATH, M
    SHOEB, A
    BHADURI, AP
    JOURNAL OF CHEMICAL RESEARCH-S, 1994, (03): : 86 - 86
  • [8] A one-pot synthesis of functionalized 1,3,5-triazine-2-thiones from ammonium thiocyanate, acid chlorides, and 2-aminopyridines under solvent-free conditions
    Mohebat, Razieh
    Saeedi, Farideh
    JOURNAL OF SULFUR CHEMISTRY, 2012, 33 (05) : 583 - 587
  • [9] Solvent-free synthesis of novel dihydropyrimidinones scaffolds
    Yu, Qiang
    Wei, Fengping
    Huang, Liangfu
    Fang, Zhiqiang
    Ma, Wuping
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U2595 - U2595
  • [10] REACTION OF ETHOXYMETHYLENEMALONONITRILE WITH 2-AMINOPYRIDINES
    OKAMOTO, Y
    KURASAWA, Y
    TAKAGI, K
    TAKADA, A
    UEDA, T
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1974, 22 (02) : 243 - 247