Synthesis and antiviral activity of 5- and 5'-substituted thymidine analogs
Journal Article
·
· J. Med. Chem.; (United States)
The 5'-O-p-tolylsulfonyl derivatives of 5-chloro-, 5-bromo, and 5-iodo-2'-deoxyuridine were synthesized and converted into the corresponding 5-halo-5'-azido-2',5'-dideoxyuridines (5-7). Reduction of 5-chloro-5'-azido-2',5'-dideoxyuridine (5) afforded 5-chloro-5'-amino-2',5'-dideoxyuridine (10, AClU); however, similar efforts to prepare 5-bromo-5'-amino-2',5'-dideoxyuridine (11) and 5-iodo-5'-amino-2',5'-dideoxyuridine (12) by reduction of the corresponding 5'-azido precursor resulted in the formation of 5'-amino-2',5'-dideoxyuridine (9). 5-Bromo-5'-amino-2',5'-dideoxyuridine (11, ABrU) and 5-iodo-5'-amino-2',5'-dideoxyuridine (12, AIU) were prepared by halogenation of the 5-mercuriacetate of 5'-amino-2',5'-dideoxyuridine. The 5'-amino-2',5'-dideoxy analogs of 5-methyl-, 5-chloro-, 5-bromo-, and 5-iodo-2'-deoxyuridine possess antiviral activity against herpes simplex virus but exhibit no inhibitory activity against sarcoma 180 (murine) or Vero (monkey) cells in culture. 2 tables.
- Research Organization:
- Yale Univ., New Haven
- OSTI ID:
- 6855467
- Journal Information:
- J. Med. Chem.; (United States), Journal Name: J. Med. Chem.; (United States) Vol. 19:4; ISSN JMCMA
- Country of Publication:
- United States
- Language:
- English
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Wed Dec 31 23:00:00 EST 1975
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Synthesis and biological activities of 5-trifluoromethyl-5'-azido-2',5'-dideoxyuridine and 5-trifluoromethyl-5'-amino-2',5'-dideoxyuridine
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Wed Dec 31 23:00:00 EST 1975
· J. Med. Chem.; (United States)
·
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Successful therapy of herpes hominis keratitis in rabbits by 5-10D0-5'-amino-2'5'-dideoxyuridine (AIU): a novel analog of thymidine
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·
OSTI ID:6433733
Related Subjects
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
550600 -- Medicine
62 RADIOLOGY AND NUCLEAR MEDICINE
ACETATES
AMINES
AZIDES
AZINES
CARBOXYLIC ACID SALTS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
DEOXYURIDINE
DRUGS
ELEMENTS
HALOGENS
HETEROCYCLIC COMPOUNDS
HYDROXY COMPOUNDS
IODINE
MERCURY COMPOUNDS
NITROGEN COMPOUNDS
NONMETALS
NUCLEOSIDES
NUCLEOTIDES
ORGANIC BROMINE COMPOUNDS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC IODINE COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PYRIMIDINES
REDUCTION
RIBOSIDES
SYNTHESIS
URACILS
YIELDS
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
550600 -- Medicine
62 RADIOLOGY AND NUCLEAR MEDICINE
ACETATES
AMINES
AZIDES
AZINES
CARBOXYLIC ACID SALTS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
DEOXYURIDINE
DRUGS
ELEMENTS
HALOGENS
HETEROCYCLIC COMPOUNDS
HYDROXY COMPOUNDS
IODINE
MERCURY COMPOUNDS
NITROGEN COMPOUNDS
NONMETALS
NUCLEOSIDES
NUCLEOTIDES
ORGANIC BROMINE COMPOUNDS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC IODINE COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PYRIMIDINES
REDUCTION
RIBOSIDES
SYNTHESIS
URACILS
YIELDS