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
  • [1] Abdurrazzaque M., 2008, Patent US, Patent No. 2008300404
  • [2] Mycophenolic acid production in solid-state fermentation using a packed-bed bioreactor
    Alani, Faiez
    Grove, Jason A.
    Anderson, William A.
    Moo-Young, Murray
    [J]. BIOCHEMICAL ENGINEERING JOURNAL, 2009, 44 (2-3) : 106 - 110
  • [3] Immunosuppressive drugs, the first 50 years and a glance forward
    Allison, AC
    [J]. IMMUNOPHARMACOLOGY, 2000, 47 (2-3): : 63 - 83
  • [4] Synthesis and modeling studies with monocyclic analogues of mycophenolic acid
    Anderson, WK
    Boehm, TL
    Makara, GM
    Swann, RT
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (01) : 46 - 55
  • [5] ANINDYA S, 2003, Patent No. 0164931
  • [6] Mycophenolic acid: A one hundred year odyssey from antibiotic to immunosuppressant
    Bentley, R
    [J]. CHEMICAL REVIEWS, 2000, 100 (10) : 3801 - 3825
  • [7] Birch A.J., 1969, J. Chem. Soc. D: Chem. Commun, P788
  • [8] STUDIES IN THE BIOCHEMISTRY OF MICRO-ORGANISMS .86. THE MOLECULAR CONSTITUTION OF MYCOPHENOLIC ACID, A METABOLIC PRODUCT OF PENICILLIUM BREVI-COMPACTUM DIERCKX .3. FURTHER OBSERVATIONS ON THE STRUCTURAL FORMULA FOR MYCOPHENOLIC ACID
    BIRKINSHAW, JH
    RAISTRICK, H
    ROSS, DJ
    [J]. BIOCHEMICAL JOURNAL, 1952, 50 (05) : 630 - 634
  • [9] TOTAL SYNTHESIS OF MYCOPHENOLIC ACID, SOME ANALOGS AND SOME BIOGENETIC INTERMEDIATES
    CANONICA, L
    RINDONE, B
    SCOLASTICO, C
    SANTANIELLO, E
    [J]. TETRAHEDRON, 1972, 28 (16) : 4395 - +
  • [10] Mycophenolic acid analogs with a modified metabolic profile
    Chen, Liqiang
    Wilson, Daniel J.
    Labello, Nicholas P.
    Jayaram, Hiremagalur N.
    Pankiewicz, Krzysztof W.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (20) : 9340 - 9345