Synthesis of (E)- and (Z)-fluoro-olefin analogues of potent dipeptidyl peptidase IV inhibitors

被引:34
|
作者
Van der Veken, P [1 ]
Kertèsz, I [1 ]
Senten, K [1 ]
Haemers, A [1 ]
Augustyns, K [1 ]
机构
[1] Univ Instelling Antwerp, Dept Med Chem, B-2610 Antwerp, Belgium
关键词
D O I
10.1016/S0040-4039(03)01542-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(E)- and (Z)-fluoro-olefin analogues of potent dipeptidyl peptidase IV inhibitors were synthesized. A WadsworthHorner-Eminons reaction, followed by amide formation and reduction of the amide were used for the construction of the alpha-fluoro-alpha,beta-unsaturated amine functionality. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6231 / 6234
页数:4
相关论文
共 50 条
  • [41] Design, Synthesis and SAR Studies of Novel and Potent Dipeptidyl Peptidase 4 Inhibitors
    Luo, Na
    Fang, Xiaoyu
    Su, Mingbo
    Zhang, Xinwen
    Li, Dan
    Li, Honglin
    Li, Shiliang
    Zhao, Zhenjiang
    CHINESE JOURNAL OF CHEMISTRY, 2021, 39 (01): : 115 - 120
  • [42] Synthesis and structure-activity relationships of potent 1-(2-substituted-aminoacetyl)-4-fluoro-2-cyanopyrrolidine dipeptidyl peptidase IV inhibitors
    Fukushima, Hiroshi
    Hiratate, Akira
    Takahashi, Masato
    Saito-Hori, Masako
    Munetomo, Eiji
    Kitano, Kiyokazu
    Saito, Hidetaka
    Takaoka, Yuji
    Yamamoto, Koji
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2008, 56 (08) : 1110 - 1117
  • [43] CoMFA and CoMSIA of diverse pyrrolidine analogues as dipeptidyl peptidase IV inhibitors: active site requirements
    Vanangamudi Murugesan
    Nidhi Sethi
    Yenamandra S. Prabhakar
    Seturam B. Katti
    Molecular Diversity, 2011, 15 : 457 - 466
  • [44] Fluropyrrolidines as novel, potent dipeptidyl peptidase inhibitors.
    Randhawa, SA
    Haffner, CD
    Lenhard, JM
    Osterhout, MH
    Stephenson, B
    Wright, LL
    Croom, DK
    Bass, JY
    Caldwell, RD
    Cowan, DJ
    Deaton, DN
    Dwornik, KA
    Fang, J
    Heyer, DO
    Kaldor, IW
    Larkin, AL
    McConn, DJ
    McDougald, DL
    McFadyen, RB
    Reister, SM
    Secosky, MB
    Thompson, BD
    Wells-Knecht, KJ
    Zhang, WH
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 226 : U17 - U17
  • [45] Development of potent and selective dipeptidyl peptidase II inhibitors
    Senten, K
    Van der Veken, P
    Bal, G
    De Meester, I
    Lambeir, AM
    Scharpé, S
    Bauvois, B
    Haemers, A
    Augustyns, K
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (20) : 2825 - 2828
  • [46] Rational design and synthesis of potent and long-lasting glutamic acid-based dipeptidyl peptidase IV inhibitors
    Tsai, Ting-Yueh
    Hsu, Tsu
    Chen, Chiung-Tong
    Cheng, Jai-Hong
    Chiou, Mei-Chun
    Huang, Chih-Hsiang
    Tseng, Ya-Ju
    Yeh, Teng-Kuang
    Huang, Chung-Yu
    Yeh, Kai-Chia
    Huang, Yu-Wen
    Wu, Ssu-Hui
    Wang, Min-Hsien
    Chen, Xin
    Chao, Yu-Sheng
    Jiaang, Weir-Torn
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (07) : 1908 - 1912
  • [47] 4-Aryleyelohexylaianine analogs as potent, selective, and orally active inhibitors of dipeptidyl peptidase IV
    Kaelin, David E.
    Smenton, Abigail L.
    Elermann, George J.
    He, Huaibing
    Leiting, Barbara
    Lyons, Kathryn A.
    Patel, Reshma A.
    Patel, Sangita B.
    Petrov, Alexsandr
    Scapin, Glovanna
    Wu, Joseph K.
    Thornberry, Nancy A.
    Weber, Ann E.
    Duffy, Joseph L.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (21) : 5806 - 5811
  • [48] Synthesis, Evaluation and Molecular Docking of Thiazolopyrimidine Derivatives as Dipeptidyl Peptidase IV Inhibitors
    Sharma, Mani
    Gupta, Monica
    Singh, Divya
    Kumar, Manoj
    Kaur, Punit
    CHEMICAL BIOLOGY & DRUG DESIGN, 2012, 80 (06) : 918 - 928
  • [49] Discovery of potent, selective beta-homophenylalanine based dipeptidyl peptidase IV inhibitors.
    Xu, JY
    Parmee, ER
    Leiting, B
    Marsilio, F
    Patel, RA
    Wu, JK
    Thornberry, NA
    Weber, AE
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 227 : U24 - U24
  • [50] Discovery of potent, selective, and orally bioavailable oxadiazole-based dipeptidyl peptidase IV inhibitors
    Xu, Jinyou
    Wei, Lan
    Mathvink, Robert J.
    Edmondson, Scott D.
    Eiermann, George J.
    He, Huaibing
    Leone, Joseph F.
    Leiting, Barbara
    Lyons, Kathryn A.
    Marsilio, Frank
    Patel, Reshma A.
    Patel, Sangita B.
    Petrov, Aleksandr
    Scapin, Giovanna
    Wu, Joseph K.
    Thornberry, Nancy A.
    Weber, Ann E.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (20) : 5373 - 5377