Synthesis of 2-fluoronoraristeromycin and its inhibitory activity against Plasmodium falciparum S-adenosyl-L-homocysteine hydrolase

被引:39
|
作者
Kitade, Y
Kojima, H
Zulfiqur, F
Kim, HS
Wataya, Y
机构
[1] Gifu Univ, Fac Engn, Dept Biomol Sci, Gifu 5011193, Japan
[2] Okayama Univ, Fac Pharmaceut Sci, Okayama 7008530, Japan
关键词
D O I
10.1016/j.bmcl.2003.08.074
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Palladium-coupling reaction of (IS, 4 R)-cis-4-acetoxy-2-cyclopenten-1-ol with sodium salt of 2-fluoroadenine resulted in the formation of (IS,4R)-4-(6-amino-2-fluoro-9H-purin-9-yl)cyclopent-2-en-1-ol. Subsequent oxidation was carried out with osmium tetraoxide (OsO4) in the presence of 4-methylmorpholine N-oxide (NMO) to give 2-fluoronoraristeromycin, possessing significant inhibitory activity against recombinant Plasm odium falciparum SAH hydrolase. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3963 / 3965
页数:3
相关论文
共 50 条
  • [41] ENZYMATIC SYNTHESIS OF S-ADENOSYL-L-HOMOCYSTEINE FROM ADENOSINE AND HOMOCYSTEINE
    DELAHABA, G
    CANTONI, GL
    JOURNAL OF BIOLOGICAL CHEMISTRY, 1959, 234 (03) : 603 - 608
  • [42] SYNTHESIS AND ANTIVIRAL ACTIVITY OF SOME NEW S-ADENOSYL-L-HOMOCYSTEINE DERIVATIVES
    SERAFINOWSKI, P
    DORLAND, E
    HARRAP, KR
    BALZARINI, J
    DECLERCQ, E
    JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (24) : 4576 - 4583
  • [43] Synthesis of novel 4′-modified neplanocin A analogues and their inhibitory activity against S-adenosyl-L-I-homocysteine hydrolase
    Kumamoto, Hiroki
    Deguchi, Kazuki
    Takahashi, Nonoko
    Tanaka, Hiromichi
    Kitade, Yukio
    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2007, 26 (6-7): : 733 - 736
  • [44] S-Adenosyl-L-Homocysteine Hydrolase Inhibition by a Synthetic Nicotinamide Cofactor Biomimetic
    Kailing, Lyn L.
    Bertinetti, Daniela
    Paul, Caroline E.
    Manszewski, Tomasz
    Jaskolski, Mariusz
    Herberg, Friedrich W.
    Pavlidis, Ioannis V.
    FRONTIERS IN MICROBIOLOGY, 2018, 9
  • [45] ISOZYME AND DNA ANALYSIS OF HUMAN S-ADENOSYL-L-HOMOCYSTEINE HYDROLASE (AHCY)
    ARREDONDOVEGA, FX
    CHARLTON, JA
    EDWARDS, YH
    HOPKINSON, DA
    WHITEHOUSE, DB
    ANNALS OF HUMAN GENETICS, 1989, 53 : 157 - 167
  • [46] S-adenosyl-L-homocysteine hydrolase and methylation disorders: Yeast as a model system
    Tehlivets, Oksana
    Malanovic, Nermina
    Visram, Myriam
    Paykov-Keller, Tea
    Keller, Walter
    BIOCHIMICA ET BIOPHYSICA ACTA-MOLECULAR BASIS OF DISEASE, 2013, 1832 (01): : 204 - 215
  • [47] CDNA FOR S-ADENOSYL-L-HOMOCYSTEINE HYDROLASE FRONT CATHARANTHUS-ROSEUS
    SCHRODER, G
    WAITZ, A
    HOTZE, M
    SCHRODER, J
    PLANT PHYSIOLOGY, 1994, 104 (03) : 1099 - 1100
  • [48] S-ADENOSYL-L-HOMOCYSTEINE HYDROLASE INHIBITORS AS ANTIVIRAL AGENTS - 5'-DEOXYARISTEROMYCIN
    SIDDIQI, SM
    SCHNELLER, SW
    IKEDA, S
    SNOECK, R
    ANDREI, G
    BALZARINI, J
    DECLERCQ, E
    NUCLEOSIDES & NUCLEOTIDES, 1993, 12 (02): : 185 - 198
  • [49] S-ADENOSYL-L-HOMOCYSTEINE HYDROLASE - POTENTIAL BIOLOGICAL TARGET FOR MEDICINAL CHEMISTRY
    CHIANG, PK
    CANTONI, GL
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1979, (SEP): : 32 - 32
  • [50] Molecular properties and inhibitors of malarial S-adenosyl-L-homocysteine hydrolase (SAHH)
    Prigge, ST
    Caridha, D
    Zhang, P
    Kyle, DE
    Milhous, WK
    Chiang, PK
    PROCEEDINGS OF THE 10TH INTERNATIONAL CONGRESS OF PARASITOLOGY-ICOPA X: SYMPOSIA, WORKSHOPS AND CONTRIBUTED PAPERS, 2002, : 499 - 503