The Chemistry of Mycophenolic Acid - Synthesis and Modifications Towards Desired Biological Activity

被引:21
作者
Cholewinski, G. [1 ]
Malachowska-Ugarte, M. [1 ]
Dzierzbicka, K. [1 ]
机构
[1] Gdansk Univ Technol, Fac Chem, Dept Organ Chem, PL-80233 Gdansk, Poland
关键词
Mycophenolic acid; MPA; MPA analogues; INOSINE MONOPHOSPHATE DEHYDROGENASE; ADENINE-DINUCLEOTIDE ANALOGS; CLAISEN REARRANGEMENT; MONOCYCLIC ANALOGS; INDOLE ANALOGS; INHIBITION; TRANSFORMATION; MOFETIL; AGENTS;
D O I
10.2174/092986710791163920
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
Mycophenolic acid (MPA) is a basis for the immunosuppressive drugs used in clinic against rejection in solid organs transplantations. Since its physiological activity is very promising, numerous studies have been performed to establish mechanism of action, structure-activity relationship (SAR), synthesis of MPA derivatives to improve or extent its clinical use to anticancer one, especially. The reported methods for preparation of MPA analogues have been achieved by semi-synthetic approaches or total synthesis and accomplished by in vitro or / and in vivo evaluations. In this review we would like to bring together chemical aspects of these compounds and their implementations within biological activity, their synthesis and structural modifications referred to the structure-activity relationship (SAR).
引用
收藏
页码:1926 / 1941
页数:16
相关论文
共 51 条
  • [31] Microbiological transformation of mycophenolic acid
    Jekkel, A
    Barta, I
    Kónya, A
    Süto, J
    Boros, S
    Horváth, G
    Ambrus, G
    [J]. JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2001, 11 (4-6) : 423 - 426
  • [32] Mycophenolic acid trough level monitoring in solid organ transplant recipients treated with mycophenolate mofetil: association with clinical outcome
    Kaplan, Bruce
    [J]. CURRENT MEDICAL RESEARCH AND OPINION, 2006, 22 (12) : 2355 - 2364
  • [33] KNOX M, 1993, Patent No. 5247083
  • [34] Synthesis of novel indole analogues of mycophenolic acid as potential antineoplastic agents
    Lai, G
    Anderson, WK
    [J]. TETRAHEDRON, 2000, 56 (17) : 2583 - 2590
  • [35] Inhibitory effect of mycophenolic acid on the replication of infectious pancreatic necrosis virus and viral hemorrhagic septicemia virus
    Marroqui, Laura
    Estepa, Amparo
    Perez, Luis
    [J]. ANTIVIRAL RESEARCH, 2008, 80 (03) : 332 - 338
  • [36] Synthesis of some monocyclic analogues of mycophenolic acid via the Johnson ortho ester Claisen rearrangement
    Meza-Aviña, ME
    Ordoñez, M
    Fernández-Zertuche, M
    Rodríguez-Fragoso, L
    Reyes-Esparza, J
    de los Ríos-Corino, AAM
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (23) : 6521 - 6528
  • [37] Structure-activity relationships for inhibition of inosine monophosphate dehydrogenase by nuclear variants of mycophenolic acid
    Nelson, PH
    Carr, SF
    Devens, BH
    Eugui, EM
    Franco, F
    Gonzalez, C
    Hawley, RC
    Loughhead, DG
    Milan, DJ
    Papp, E
    Patterson, JW
    Rouhafza, S
    Sjogren, EB
    Smith, DB
    Stephenson, RA
    Talamas, FX
    Waltos, AM
    Weikert, RJ
    Wu, JC
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (21) : 4181 - 4196
  • [38] NELSON PH, 1988, Patent No. 4753935
  • [39] Mycophenolate mofetil in dermatology
    Orvis, Alissa K.
    Wesson, Stanton K.
    Breza, Thomas S., Jr.
    Church, Ann A.
    Mitchell, Christina L.
    Watkins, Shannon W.
    [J]. JOURNAL OF THE AMERICAN ACADEMY OF DERMATOLOGY, 2009, 60 (02) : 183 - 199
  • [40] Novel mycophenolic adenine bis(phosphonate) analogues as potential differentiation agents against human leukemia
    Pankiewicz, KW
    Lesiak-Watanabe, KB
    Watanabe, KA
    Patterson, SE
    Jayaram, HN
    Yalowitz, JA
    Miller, MD
    Seidman, M
    Majumdar, A
    Prehna, G
    Goldstein, BM
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (03) : 703 - 712