Document Detail

Structural studies on bioactive compounds. Part 27. Chemistry of the immunomodulatory agent bropirimine.
MedLine Citation:
PMID:  7748456     Owner:  NLM     Status:  MEDLINE    
The 2-amino-6-phenylpyrimidin-4(3H)-ones bropirimine (1) and the debrominated analogue (4) undergo electrophilic nitration and sulphonation in the meta-position of the 6-phenyl group in strongly acidic conditions. Subsequent electrophilic substitutions take place in the 5-position of the pyrimidine ring, if vacant. Rearrangement of the 2-nitramino-6-phenyl-pyrimidines (22) and (23) furnishes the 2-amino-6-(3-nitrophenyl)pyrimidines (9) and (18), respectively. Nucleophilic substitutions, in contrast, occur readily in the pyrimidine 2-, 4- and 6-positions. Debromination of bropirimine by hydrazine hydrate can be rationalized by invoking an initial attack by the nucleophile at the electron-deficient pyrimidine 6-position. The reactive 4-chloro group in 5-bromo-4-chloro-2-formylamino-6-phenylpyrimidine (25) can be displaced with a range of nucleophiles (azide ion, ethanol, hydrazine, and primary and secondary aliphatic amines), without loss of the bromo substituent.
M F Stevens; G U Baig; E N Gate; R T Wheelhouse
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Anti-cancer drug design     Volume:  10     ISSN:  0266-9536     ISO Abbreviation:  Anticancer Drug Des.     Publication Date:  1995 Apr 
Date Detail:
Created Date:  1995-06-20     Completed Date:  1995-06-20     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  8603523     Medline TA:  Anticancer Drug Des     Country:  ENGLAND    
Other Details:
Languages:  eng     Pagination:  215-26     Citation Subset:  IM    
Cancer Research Laboratories, University of Nottingham, UK.
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MeSH Terms
Adjuvants, Immunologic / chemistry*
Cytosine / analogs & derivatives*,  chemistry
Magnetic Resonance Spectroscopy
Mass Spectrometry
Molecular Structure
Spectrophotometry, Infrared
Reg. No./Substance:
0/Adjuvants, Immunologic; 56741-95-8/bropirimine; 71-30-7/Cytosine

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