New neplanocin analogues. 12. Alternative synthesis and antimalarial effect of (6′R)-6′-C-methylneplanocin A, a potent AdoHcy hydrolase inhibitor

Journal of Medicinal Chemistry

Volumn 45, Issue 3, 2002, Pages 748-751

  Shuto, Satoshi ^a   Minakawa, Noriaki ^a   Niizuma, Satoshi ^a   Kim, Hye Sook ^b   Wataya, Yusuke ^b   Matsuda, Akira ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSYLHOMOCYSTEINASE; ADENOSYLHOMOCYSTEINASE INHIBITOR; ALDEHYDE DERIVATIVE; CHLOROQUINE; NEPLANOCIN A; NEPLANOCIN DERIVATIVE; ORGANOMETALLIC COMPOUND; TITANIUM DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIMALARIAL ACTIVITY; ARTICLE; CHELATION; CONTROLLED STUDY; DOSE RESPONSE; DRUG POTENCY; DRUG SYNTHESIS; ENZYME INHIBITION; GROWTH INHIBITION; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; MALARIA; MOUSE; NONHUMAN; PARASITE DEVELOPMENT; PLASMODIUM BERGHEI; STEREOCHEMISTRY;

ADENOSINE; ADENOSYLHOMOCYSTEINASE; ANIMALS; ANTIMALARIALS; ENZYME INHIBITORS; HYDROLASES; MALARIA; MICE; PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM;

EID: 0037204012     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm010374i     Document Type: Article

References (36)

1. Synthesis and properties of oligonucleotides containing 5-formyl-2′-deoxycytidine. In vitro DN′A polymerase reactions on DNA templates containing 5-formyl-2-deoxycytidine
2. Antimalarial drug resistance: An increasing problem
3. Chemotherapy and drug resistance in malaria
4. Chloroquine: Mechanism of drug action and resistance in Plasmodium falciparum
5. High-level chloroquine resistance of Plasmodium berghei is associated with multiple drug resistance and loss of reversal by calcium antagonists
6. Pharmacological and biochemical aspects of S-adenosylhomocysteine and S-adenosylhomocysteine hydrolase
7. S-Adenosyl-L-homocysteine hydrolase as a target for antiviral chemotherapy
8. Antimalarial activity of S-isobutyladenosine against Plasmodium falciparum in culture
9. Antimalarial activity of neplanocin A with perturbations in the metabolism of purines, polyamines and S-adenosylmethionine
10. Antimalarial activity of 4′,5′unsaturated 5′-fluoroadenosine mechanisms-based inhibitor of S-adenosyl-L-homocysteine hydrolase
11. Plasmodium falciparum S-adenosylhomocysteine hydrolase. cDNA identification, predicted protein sequence, and expression in Escherichia coli
12. Studies on neplanocin A, new antitumor antibiotic. I. Producing organism, isolation, and characterization
13. Studies on neplanocin A, new antitumor antibiotic. II. Structure determination
14. Neplanocin A. A potent inhibitor of S-adenosylhomocysteine hydrolase and of vaccinia virus multiplication in mouse L-020 cells
15. Antiviral and antimetabolic activities of neplanocins
16. Neplanocin A. A cyclopentenyl analog of adenosine with specificity for inhibiting RNA methylation
17. Biochemical mode of cytotoxic action of neplanocin A in L 1210 leukemic cells
18. Antitumor activity of derivatives of neplanocin A in vivo and in vitro
19. New neplanocin analogues. I. Synthesis of 6′-modified neplanocin A derivatives as broad-spectrum antiviral agents
20. Antiviral activities of ribavirin EICAR and (6′R)-6′-C-methylneplanocin A against several ortho- and paramyxoviruses
21. New neplanocin analogues. III. 6′R-Configuration is essential for the antiviral activity of 6′-C-methyl-3-deazaneplanocin A's
22. New neplanocin analogues. IV. An adenosine deaminase-resistant equivalent of neplanocin A
23. New neplanocin analogues. V. A potent adenosylhomocysteine hydrolase inhibitor lacking antiviral activity. Synthesis and antiviral activity of 6′-carboxylic acid derivatives of neplanocin A
24. New neplanocin analogues. 6. Synthesis and potent antiviral activity of 6′-homoneplanocin A
25. New neplanocin analogues. 7. Synthesis and antiviral activity of 2-halo derivatives of neplanocin A
26. New neplanocin analogues. VIII. Synthesis and biological activity of 6′-C-ethyl, ethenyl, and ethynyl derivatives of neplanocin A
27. 4 system. Synthesis of 6′-methylene derivatives of neplanocin A as potential antiviral nucleosides. New neplanocin analogues. 11
28. Potential inhibitors of S-adenosylmethionine-dependent methyltransferases. 11. Molecular dissections of neplanocin A as potential inhibitors of S-adenosylhomocysteine hydrolase
29. Synthesis of 3-deazaneplanocin A, a powerful inhibitor of S-adenosylhomocysteine hydrolase with potent and selective in vitro and in vivo antiviral activities
30. 9-(trans-2′, trans-3′-Dihydroxycyclopent-4′-enyl)-adenine and 3-deazaadenine: Analogs of neplanocin A which retain potent antiviral activity but exhibit reduced cytotoxicity
31. New neplanocin analogues. IX. A practical preparation of (6′R)-6′-C-methylneplanocin A (RMNPA), a potent antiviral agent, and the determination of its 6′-configuration. Diastereoselective deamination by adenosine deaminase
32. Synthesis and antimalarial activity of cyclic peroxides, 1,2,4,5,7-pentoxocanes and 1,2,4,5-tetroxanes
33. Synthesis and antimalarial activity of novel medium-sized 1,2,4,5-tetraoxacycloalkanes