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Synthesis of 4‐(2‐acetoxyethoxymethyl)‐6‐methyl‐1,2,4‐triazin‐3(4 H )‐one 1‐oxide as thymidine analogue
Author(s) -
Banijamali Ali R.,
Foye William O.
Publication year - 1986
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570230601
Subject(s) - chemistry , alkylation , moiety , triazine , benzyl bromide , bromide , medicinal chemistry , nucleoside , phosphoryl chloride , chloride , ring (chemistry) , stereochemistry , organic chemistry , catalysis
Alkylation of the sodium salt and the trimethyl silylated derivatives of 6‐methyl‐1,2,4‐triazin‐3(4 H )‐one 1‐oxide with chloromethoxyethyl acetate, n‐hexyl chloride and benzyl bromide gave the 4‐substituted products. However, attempts to achieve the ring closure of N 4 ‐(2‐acetoxyethoxymethyl)thiosemicarbazide with bicarbonyl compounds to the corresponding as ‐triazines under different reaction conditions was not possible without disruption of the acetoxyethoxymethyl moiety. Although the as ‐triazine nucleoside analog II did not show antileukemic activity, this and other 4‐alkylated as ‐triazine 1‐oxides revealed good growth inhibitory effects against a representative spectrum of microorganisms.