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
来源：
STEROIDS | 2016年 / 115卷
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 40 条
  • [1] Catalyst-free three-component reaction between 2-aminopyridines (or 2-aminothiazoles), aldehydes, and isocyanides in water
    Adib, Mehdi
    Mahdavi, Mohammad
    Noghani, Mahsa Alizadeh
    Mirzaei, Peiman
    [J]. TETRAHEDRON LETTERS, 2007, 48 (41) : 7263 - 7265
  • [2] Synthesis and evaluation of a series of aminocyanopyridines as antimicrobial agents
    Altundas, Aliye
    Ayvaz, Selcuk
    Logoglu, Elif
    [J]. MEDICINAL CHEMISTRY RESEARCH, 2011, 20 (01) : 1 - 8
  • [3] Anti-inflammatory profile of some synthesized heterocyclic pyridone and pyridine derivatives fused with steroidal structure
    Amr, Abdel-Galil E.
    Abdulla, Mohamed M.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (13) : 4341 - 4352
  • [4] Phase I clinical trial of a selective inhibitor of CYP17, abiraterone acetate, confirms that castration-resistant prostate cancer commonly remains hormone driven
    Attard, Gerhardt
    Reid, Alison H. M.
    Yap, Timothy A.
    Raynaud, Florence
    Dowsett, Mitch
    Settatree, Sarah
    Barrett, Mary
    Parker, Christopher
    Martins, Vanessa
    Folkerd, Elizabeth
    Clark, Jeremy
    Cooper, Colin S.
    Kaye, Stan B.
    Dearnaley, David
    Lee, Gloria
    de Bono, Johann S.
    [J]. JOURNAL OF CLINICAL ONCOLOGY, 2008, 26 (28) : 4563 - 4571
  • [5] HETEROCYCLIC-ANALOGS OF THE ANTIHYPERTENSIVE BETA-ADRENERGIC BLOCKING-AGENT (S)-2-[3-(TERT-BUTYLAMINO)-2-HYDROXYPROPOXY]-3-CYANOPYRIDINE
    BALDWIN, JJ
    ENGELHARDT, EL
    HIRSCHMANN, R
    PONTICELLO, GS
    ATKINSON, JG
    WASSON, BK
    SWEET, CS
    SCRIABINE, A
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1980, 23 (01) : 65 - 70
  • [6] Applications of 2-arylhydrazononitriles in synthesis: Preparation of new indole containing 1,2,3-triazole, pyrazole and pyrazolo[1,5-a]pyrimidine derivatives and evaluation of their antimicrobial activities
    Behbehani, Haider
    Ibrahim, Hamada Mohamed
    Makhseed, Saad
    Mahmoud, Huda
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (05) : 1813 - 1820
  • [7] Design, synthesis, and antipicornavirus activity of 1-[5-(4-arylphenoxy)alkyl]-3-pyridin-4-ylimidazolidin-2-one derivatives
    Chang, CS
    Lin, YT
    Shih, SR
    Lee, CC
    Lee, YC
    Tai, CL
    Tseng, SN
    Chern, JH
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (10) : 3522 - 3535
  • [8] New cytotoxic steroids from the soft coral Clavularia viridis
    Duh, Chang-Yih
    Lo, I-Wen
    Wang, Shang-Kwei
    Dai, Chang-Feng
    [J]. STEROIDS, 2007, 72 (6-7) : 573 - 579
  • [9] Synthesis of aminonicotinonitriles and diaminopyridines through base-catalyzed ring transformation of 2H-pyran-2-ones
    Farhanullah
    Agarwal, N
    Goel, A
    Ram, VJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (07) : 2983 - 2985
  • [10] Synthesis and evaluation of antifungal properties of a series of the novel 2-amino-5-oxo-4-phenyl-5,6,7,8-tetrahydroquinoline-3-carbonitrile and its analogues
    Gholap, Atul R.
    Toti, Kiran S.
    Shirazi, Fazal
    Kumari, Ratna
    Bhat, Manoj Kumar
    Deshpande, Mukund V.
    Srinivasan, Kumar V.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (21) : 6705 - 6715
1234