Cyclic cis-1,3-Diamines Derived from Bicyclic Hydrazines: Synthesis and Applications

被引:4
|
作者
Fleurisson, Claire [1 ]
Benedetti, Erica [1 ]
Micouin, Laurent [1 ]
机构
[1] Univ Paris, CNRS, UMR8601, Lab Chim & Biochim Pharmacol & Toxicol, 45 Rue St Peres, F-75006 Paris, France
关键词
cyclic cis-1,3-diamines; bicyclic hydrazines; fragments RNA ligands and probes; N-N bond cleavage; hydroxylation; fluorination; reductive amination; REVERSE-TRANSCRIPTION PRIMER; ACTING DPP-4 INHIBITOR; TARGETING RNA; CHEMICAL TRANSFORMATION; HEXAACETYL-STREPTAMINE; ASYMMETRIC-SYNTHESIS; BETA-AMINO; AMINOCYCLITOLS; 2-DEOXYSTREPTAMINE; DERIVATIVES;
D O I
10.1055/s-0040-1707324
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cyclic cis-1,3-diamines are versatile building blocks frequently found in natural molecules or biologically active compounds. In comparison with widely studied 1,2-diamines, and despite their chemical similarity, 1,3-diamines have been investigated less intensively probably because of a lack of general synthetic procedures giving access to these compounds with good levels of chemo-, regio-, and stereocontrol. In this Account we will give a general overview of the biological interest of cyclic cis-1,3-diamines. We will then describe the synthesis and potential applications of these compounds with a particular focus on the work realized in our laboratory.
引用
收藏
页码:858 / 874
页数:17
相关论文
共 50 条
  • [1] STEREOSELECTIVE SYNTHESIS OF (+/-)-CIS-INOS-1,3-DIAMINES
    BEIER, B
    SCHURRLE, K
    WERBITZKY, O
    PIEPERSBERG, W
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (08): : 2255 - 2262
  • [2] Diastereoselective Ring Homologation of Bicyclic Hydrazines: Access to cis-1,3-Diaminocyclohexitols
    Blond, Aurelie
    Turcaud, Serge
    Lecourt, Thomas
    Micouin, Laurent
    ACS OMEGA, 2018, 3 (11): : 15302 - 15307
  • [3] SYNTHESIS OF 1,3-DIAMINES
    CONSTANTINOUKOKOTOU, V
    KOKOTOS, G
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1994, 26 (05) : 599 - 602
  • [4] Synthesis of benzodiazepines from 1,3-diamines and organoboronic acids.
    Petasis, NA
    Raber, JC
    Patel, ZD
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 220 : U97 - U97
  • [5] Efficient synthesis of diastereomerically pure 1,3-diamines
    Merla, B
    Risch, N
    SYNTHESIS-STUTTGART, 2002, (10): : 1365 - 1372
  • [6] Recent Advances in the Catalytic Synthesis of 1,3-Diamines
    Yang, Beiqi
    Yu, Aiwen
    Wang, Yuanhua
    CHEMCATCHEM, 2023, 15 (11)
  • [7] Synthesis of Chiral 1,3-Diamines Derived from cis-2-Benzamidocyclohexanecarboxylic Acid and Their Application in the Cu-Catalyzed Enantioselective Henry Reaction
    Kodama, Koichi
    Sugawara, Kazuyuki
    Hirose, Takuji
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (48) : 13584 - 13592
  • [8] Asymmetric synthesis of densely functionalized pyrazolidines and 1,3-diamines
    Chauveau, A.
    Martens, T.
    Bonin, M.
    Micouin, L.
    Husson, H.-P.
    Synthesis, 2002, (13) : 1885 - 1890
  • [9] Asymmetric synthesis of densely functionalized pyrazolidines and 1,3-diamines
    Chauveau, A
    Martens, T
    Bonin, M
    Micouin, L
    Husson, HP
    SYNTHESIS-STUTTGART, 2002, (13): : 1885 - 1890
  • [10] 1,3-diphenylpropane-1,3-diamines .10. Synthesis and biochemical evaluation of highly substituted 1,3-diphenylpropane-1,3-diamines and preparation of their Pt(II) complexes
    Bielmeier, P
    Kaiser, A
    Gust, R
    Wiegrebe, W
    MONATSHEFTE FUR CHEMIE, 1996, 127 (10): : 1073 - 1080