Synthesis and biological activities of camphor-based non-peptide growth hormone secretagogues

被引:20
|
作者
Nargund, RP [1 ]
Barakat, KH [1 ]
Cheng, K [1 ]
Chan, WWS [1 ]
Butler, BR [1 ]
Smith, RG [1 ]
Patchett, AA [1 ]
机构
[1] MERCK & CO INC,MERCK SHARP & DOHME RES LABS,DEPT PHYSIOL,RAHWAY,NJ 07065
关键词
D O I
10.1016/0960-894X(96)00213-2
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The synthesis and growth hormone (GH) releasing activities of a novel series of camphor-based non-peptide GH secretagogues is presented. Use of the (R)-nipecotic acid amino side-chain and N-terminal derivatization of it with an (R)-(2-hydroxy)propyl group provided a potent secretagogue 18 (EC(50) = 90 nM). An o-tolyl piperazine was identified as a good replacement for the spiroindanyl piperidine. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:1265 / 1270
页数:6
相关论文
共 50 条
  • [41] Non-peptide gonadotropin-releasing hormone receptor antagonists
    Betz, Stephen F.
    Zhu, Yun-Fei
    Chen, Chen
    Struthers, R. Scott
    JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (12) : 3331 - 3348
  • [42] Synthesis and structural characterization of enantiopure camphor-based di-, tri- and tetrasulfides
    Otten, S
    Fröhlich, R
    Haufe, G
    HETEROCYCLES, 1999, 51 (03) : 505 - 512
  • [43] Design and synthesis of nanomolar δ-opioid selective non-peptide mimetic agonists based on peptide leads
    Liao, SB
    Shenderovich, MD
    Alfaro-Lopez, J
    Stropova, D
    Hosohata, K
    Davis, P
    Jernigan, KA
    Porreca, F
    Yamamura, HI
    Hruby, VJ
    PEPTIDES: FRONTIERS OF PEPTIDES SCIENCE, 1999, : 214 - 215
  • [44] Design, Synthesis and Biological Evaluation of Novel Non-peptide Boronic Acid Derivatives as Proteasome Inhibitors
    Zhang, Jiankang
    Shen, Luqing
    Wang, Jincheng
    Luo, Peihua
    Hu, Yongzhou
    MEDICINAL CHEMISTRY, 2014, 10 (01) : 38 - 45
  • [45] Design, synthesis and biological evaluation of novel non-peptide boronic acid derivatives as proteasome inhibitors
    Ge, Ying
    Li, Aibo
    Wu, Jianwei
    Feng, Haiwei
    Wang, Letian
    Liu, Hongwu
    Xu, Yungen
    Xu, Qingxiang
    Zhao, Li
    Li, Yuyan
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 128 : 180 - 191
  • [46] Design, synthesis and biological evaluation of a novel series of pyrazolidone-piperidine growth hormone secretagogues.
    Carpino, PA
    Lefker, BA
    Toler, SM
    Pan, LC
    Cook, ER
    DiBrino, JN
    Hada, WA
    Inthavongsay, J
    Mangano, FM
    Mullins, MA
    Nickerson, DF
    Ragan, JA
    Rose, CR
    Tess, DA
    Wright, AS
    Zawistoski, MP
    Pirie, CM
    Chidsey-Frink, K
    Ng, OC
    DaSilva-Jardine, P
    Thompson, DD
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 216 : U284 - U284
  • [47] Design, synthesis, and SAR of novel imidazole-based growth hormone secretagogues.
    Cohen, JD
    Jungheim, LN
    Adrian, MD
    Bryant, HU
    Heiman, ML
    Osborne, JJ
    Seyler, DE
    Shetler, P
    Short, LL
    Surface, PL
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 218 : U955 - U955
  • [48] Synthesis and pharmacological profile of non-peptide vasopressin antagonists
    Galanski, ME
    Erker, T
    Studenik, CR
    Kamyar, M
    Rawnduzi, P
    Pabstova, M
    Lemmens-Gruber, R
    EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES, 2005, 24 (05) : 421 - 431
  • [49] Asymmetric synthesis of α,α-disubstituted α-amino acids by diastereoselective alkylation of camphor-based tricyclic iminolactone
    Xu, Peng-Fei
    Li, Shuo
    Lu, Ta-Jung
    Wu, Chen-Chang
    Fan, Botao
    Golfis, Georgia
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (12): : 4364 - 4373
  • [50] Structure Based Design of Non-Peptide Mimetics
    Herring, Robert H., III
    Haser, J. Colin
    Hada, Subin
    Eden, Mario R.
    23 EUROPEAN SYMPOSIUM ON COMPUTER AIDED PROCESS ENGINEERING, 2013, 32 : 175 - 180