Diversity-oriented synthesis of analogues of the novel macrocyclic peptide FR-225497 through late stage functionalization

被引:15
作者
Mukherjee, Jyotiprasad [1 ]
Sil, Suman [1 ]
Chattopadhyay, Shital Kumar [1 ]
机构
[1] Univ Kalyani, Dept Chem, Kalyani 741235, W Bengal, India
来源
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 11卷
关键词
cross metathesis; cyclic peptides; diversity oriented synthesis; macrocycle; HISTONE DEACETYLASE INHIBITORS; NATURAL-PRODUCTS; CHEMISTRY;
D O I
10.3762/bjoc.11.270
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A concise synthetic approach to a class of biologically interesting cyclic tetrapeptides is reported which involves a late-stage functionalization of a macrocyclic scaffold through cross metathesis in an attempt to create diversity. The utility of this protocol is demonstrated through the preparation of three structural analogues of the important naturally occurring histone deacetylase inhibitor FR-225497.
引用
收藏
页码:2487 / 2492
页数:6
相关论文
共 25 条
  • [1] Abe F., 2000, WO Patent, Patent No. [WO2000/008048 A2, 2000008048]
  • [2] Enantioselective synthesis of unsaturated amino acids using p-methoxybenzylamine as an ammonia equivalent
    Alcón, M
    Moyano, A
    Pericàs, MA
    Riera, A
    [J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (23) : 4639 - 4651
  • [3] Expanding medicinal chemistry space
    Barker, Andy
    Kettle, Jason G.
    Nowak, Thorsten
    Pease, J. Elizabeth
    [J]. DRUG DISCOVERY TODAY, 2013, 18 (5-6) : 298 - 304
  • [4] Anticancer activities of histone deacetylase inhibitors
    Bolden, Jessica E.
    Peart, Melissa J.
    Johnstone, Ricky W.
    [J]. NATURE REVIEWS DRUG DISCOVERY, 2006, 5 (09) : 769 - 784
  • [5] Histone deacetylases: salesmen and customers in the post-translational modification market
    Brandl, Andre
    Heinzel, Thorsten
    Kraemer, Oliver H.
    [J]. BIOLOGY OF THE CELL, 2009, 101 (04) : 193 - 205
  • [6] A planning strategy for diversity-oriented synthesis
    Burke, MD
    Schreiber, SL
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (01) : 46 - 58
  • [7] (R)-2,3-O-CYCLOHEXYLIDENEGLYCERALDEHYDE, A VERSATILE INTERMEDIATE FOR ASYMMETRIC-SYNTHESIS OF CHIRAL ALCOHOL
    CHATTOPADHYAY, A
    MAMDAPUR, VR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (03) : 585 - 587
  • [8] Efficient Construction of the Carbon Skeleton of the Novel Polyoxazole-Based Cyclopeptide IB-01211 via a Biomimetic Macrocyclisation
    Chattopadhyay, Shital K.
    Singha, Sovan K.
    [J]. SYNLETT, 2010, (04) : 555 - 558
  • [9] Natural products as an inspiration in the diversity-oriented synthesis of bioactive compound libraries
    Cordier, Christopher
    Morton, Daniel
    Murrison, Sarah
    Nelson, Adam
    O'Leary-Steele, Catherine
    [J]. NATURAL PRODUCT REPORTS, 2008, 25 (04) : 719 - 737
  • [10] Dandapani S, 2012, FUTURE MED CHEM, V4, P2279, DOI [10.4155/fmc.12.178, 10.4155/FMC.12.178]