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Synthesis of N ‐[4‐[2‐(2,4‐Diamino‐1,6‐dihydro‐6‐oxo‐5‐pyrimidinyl)‐ethylamino]benzoyl]‐L‐glutamic acid. An acyclic analogue of 5,6,7,8‐tetrahydrofolic acid
Author(s) -
Kelley James L.,
Mclean Ed W.
Publication year - 1990
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.5570270264
Subject(s) - chemistry , acetal , acetaldehyde , stereochemistry , glutamic acid , medicinal chemistry , organic chemistry , amino acid , ethanol , biochemistry
The synthesis of N ‐[4‐[2‐(2,4‐diamino‐1,6‐dihydro‐6‐oxo‐5‐pyrimidinyl)ethylamino]benzoyl]‐L‐glutamic acid ( 2 ), a two carbon analogue of 5‐DACTHF ( 1 ) and an acyclic analogue of 5,6,7,8‐tetrahydrofolic acid, is reported. The pyrimidinylacetaldehyde diethyl acetal 3 , which was prepared in 2‐steps from 2‐chloro acetaldehyde diethyl acetal, was converted to 2 in four steps. Compound 2 was less cytotoxic toward Detroit 98 or L cells than 5‐DACTHF ( 1 ).