Potential Anticancer Agents.<sup>1</sup> LIII. Alkylating Agents Derived from Some Folic Reductase Inhibitors

DeGraw, Joseph I.; Ross, Leonard O.; Goodman, Leon; Baker, B. R.

doi:10.1021/jo01065a059

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1962

1984

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Cited by 6 publications

(3 citation statements)

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“…An analytical sample, m.p. 119-120°, was obtained similarly from another run; X"j¡i°¿, 3.00 (NH), 5.82 (ester C=0), 7.55 (N02), 8.36 (C-O-C).…”

Section: (Cooh)mentioning

confidence: 99%

Potential Anticancer Agents.¹ LXXIV. Alkylating Agents Derived from Indole. III. Synthesis of Some Indolealkanoic Acid Nitrogen Mustards

DeGraw¹,

Goodman²

1962

J. Org. Chem.

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“…An analytical sample, m.p. 119-120°, was obtained similarly from another run; X"j¡i°¿, 3.00 (NH), 5.82 (ester C=0), 7.55 (N02), 8.36 (C-O-C).…”

Section: (Cooh)mentioning

confidence: 99%

Potential Anticancer Agents.¹ LXXIV. Alkylating Agents Derived from Indole. III. Synthesis of Some Indolealkanoic Acid Nitrogen Mustards

DeGraw¹,

Goodman²

1962

J. Org. Chem.

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“…All aqueous layers were combined, washed with 20 ml. of ether, and adjusted to pH [7][8] with glacial acetic acid. The turbid solution was saturated with sodium chloride and extracted with four 20-ml.…”

mentioning

confidence: 99%

“…The residual solution was evaporated to dryness in vacuo (70°/5 mm. ), giving 5.8 g. (100%) of a sirup identified as XIII by its infrared spectrum; X"",w 4.52 (conjugated C=N), 6.10 (C=C), 8.85 and 9.3-9.5 (acetal C-0-C).…”

mentioning

confidence: 99%

Potential Anticancer Agents.¹ LXIX. Tetrahydroquinazoline Analogs of Tetrahydrofolic Acid. IV. The Synthesis of 5,8-Dideaza-5,6,7,8-tetrahydroaminopterin

DeGraw¹,

Goodman²,

Weinstein³

et al. 1962

J. Org. Chem.

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The direct fusion of 4-oxocyclohexanecarboxaldehyde dimethyl acetal (III) with cyanoguanidine provided the key intermediate, 2,4-diacetamido-5,6,7,8-tetrahydro-6-quinazolinecarboxaldehyde (XV), necessary for the synthesis of 5,8-dideaza-5,6,7,8-tetrahydroaminopterin (Ila). The conversion of XV to Ila was accomplished by the reductive alkylation of p-aminobenzoyl-L-glutamic acid with XV, followed by hydrolysis of the blocked intermediate XVIII to give the crystalline and chromatographically homogeneous Ila.

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Investigations into the synthesis of 6‐ethyl‐5‐(4‐pyridinyl)‐2,4‐pyrimidinediamine as a potential antimalarial agent

Hung

Werbel

1984

Journal of Heterocyclic Chem

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The synthesis of 6‐ethyl‐5‐(4‐pyridinyl)‐2,4‐pyrimidinediamine (2), the pyridine analog of pyrimethamine, is described. Condensation of 4‐pyridineacetonitrile (3) with methyl propionate afforded α‐(1‐oxopropyl)‐4‐pyridineacetonitrile (4). Treatment with triethyl orthopropionate gave primarily the undesired N‐alkylated material. However reaction of the crude mixture with guanidine afforded 2 in low yield. This material was devoid of significant antimalarial activity.

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Potential Anticancer Agents.¹ LIII. Alkylating Agents Derived from Some Folic Reductase Inhibitors

Cited by 6 publications

References 1 publication

Potential Anticancer Agents.¹ LXXIV. Alkylating Agents Derived from Indole. III. Synthesis of Some Indolealkanoic Acid Nitrogen Mustards

Potential Anticancer Agents.¹ LXXIV. Alkylating Agents Derived from Indole. III. Synthesis of Some Indolealkanoic Acid Nitrogen Mustards

Potential Anticancer Agents.¹ LXIX. Tetrahydroquinazoline Analogs of Tetrahydrofolic Acid. IV. The Synthesis of 5,8-Dideaza-5,6,7,8-tetrahydroaminopterin

Investigations into the synthesis of 6‐ethyl‐5‐(4‐pyridinyl)‐2,4‐pyrimidinediamine as a potential antimalarial agent

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Potential Anticancer Agents.1 LIII. Alkylating Agents Derived from Some Folic Reductase Inhibitors

Cited by 6 publications

References 1 publication

Potential Anticancer Agents.1 LXXIV. Alkylating Agents Derived from Indole. III. Synthesis of Some Indolealkanoic Acid Nitrogen Mustards

Potential Anticancer Agents.1 LXXIV. Alkylating Agents Derived from Indole. III. Synthesis of Some Indolealkanoic Acid Nitrogen Mustards

Potential Anticancer Agents.1 LXIX. Tetrahydroquinazoline Analogs of Tetrahydrofolic Acid. IV. The Synthesis of 5,8-Dideaza-5,6,7,8-tetrahydroaminopterin

Investigations into the synthesis of 6‐ethyl‐5‐(4‐pyridinyl)‐2,4‐pyrimidinediamine as a potential antimalarial agent

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Product

Resources

About

Potential Anticancer Agents.¹ LIII. Alkylating Agents Derived from Some Folic Reductase Inhibitors

Potential Anticancer Agents.¹ LXXIV. Alkylating Agents Derived from Indole. III. Synthesis of Some Indolealkanoic Acid Nitrogen Mustards

Potential Anticancer Agents.¹ LXXIV. Alkylating Agents Derived from Indole. III. Synthesis of Some Indolealkanoic Acid Nitrogen Mustards

Potential Anticancer Agents.¹ LXIX. Tetrahydroquinazoline Analogs of Tetrahydrofolic Acid. IV. The Synthesis of 5,8-Dideaza-5,6,7,8-tetrahydroaminopterin