1968
DOI: 10.1021/jm00312a037
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Folic acid analogs. I. p-[[(2,4-Diamino-5-pyrimidinyl)methyl]amino]benzoyl-L-glutamic acid and related compounds

Abstract: The largest and most effective class of tyrosine hydroxylase inhibitors is made up of tyrosine analogs.

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Cited by 12 publications
(5 citation statements)
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“…The first representatives of this new class of N-substituted 5-(aminomethyl)-2,4-pyrimidinediamines were initially obtained by treating 5-(bromomethyl)-2,4-pyrimidinediamine dihydrobromide ( 5 ) with a number of primary, secondary, and cyclic amines, as shown in Scheme . The starting material 5 was prepared in four steps following essentially the procedures described in the literature. We soon realized that the insolubility of compound 5 in most usual solvents, including DMF and DMSO, and its high reactivity, often leading to complex mixtures of products, would probably limit the potential of the method. In contrast, the crystalline pyridinium salt 6 , obtained on treatment of compound 5 with pyridine in DMF, was found to be a very effective starting material for performing the nucleophilic substitutions described above.…”
Section: Resultsmentioning
confidence: 99%
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“…The first representatives of this new class of N-substituted 5-(aminomethyl)-2,4-pyrimidinediamines were initially obtained by treating 5-(bromomethyl)-2,4-pyrimidinediamine dihydrobromide ( 5 ) with a number of primary, secondary, and cyclic amines, as shown in Scheme . The starting material 5 was prepared in four steps following essentially the procedures described in the literature. We soon realized that the insolubility of compound 5 in most usual solvents, including DMF and DMSO, and its high reactivity, often leading to complex mixtures of products, would probably limit the potential of the method. In contrast, the crystalline pyridinium salt 6 , obtained on treatment of compound 5 with pyridine in DMF, was found to be a very effective starting material for performing the nucleophilic substitutions described above.…”
Section: Resultsmentioning
confidence: 99%
“…The starting material 5 was prepared in four steps following essentially the procedures described in the literature. [10][11][12][13] We soon realized that the insolubility of compound 5 in most usual solvents, including DMF and DMSO, and its high reactivity, often leading to complex mixtures of products, would probably limit the potential of the method. In contrast, the crystalline pyridinium salt 6, obtained on treatment of compound 5 with pyridine in DMF, was found to be a very effective starting material for performing the nucleophilic substitutions described above.…”
Section: Resultsmentioning
confidence: 99%
“…mentioned a 5-phenylethyl analogue of TMP [2,4-diamino-5-(3,4,5-trimethoxyphenylethyl)pyrimidine] and 2,4-diamino-5-(3,4-dimethoxyphenylethyl)pyrimidine (Ro12-6099, Table ), which is not described elsewhere. Weinstock et al described a 2,4-diaminopyrimidine with a −NHCH 2 − bridge between the heterocycle and the phenyl ring. The phenyl ring is substituted only by a carboxyl group.…”
Section: Methodsmentioning
confidence: 99%
“…In a review, Kompis et al 28 2), which is not described elsewhere. Weinstock et al 29 described a 2,4-diaminopyrimidine with a -NHCH 2 -bridge between the heterocycle and the phenyl ring. The phenyl ring is substituted only by a carboxyl group.…”
Section: Methodsmentioning
confidence: 99%
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