ChemInform Abstract: 2‐ACETYLPYRIDINE THIOSEMICARBAZONES. 7. DERIVATIVES OF 2‐ACETYLQUINOLINE AS POTENTIAL ANTIMALARIAL AGENTS

Klayman, Daniel L.; Scovill, John P.; Bartosevich, J. F.; Bruce, J.; Massie, Samuel P.; Grant, Sharday; González, Anaisa Hernández

doi:10.1002/chin.198425213

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“…Anal. Pyridinyl 1-oxide )ethylidene]hydrazide (14). The preparation of thiosemicarbazones derived from 2-acetylpyridine 1-oxide is exemplified by the following reaction.…”

Section: Methodsmentioning

confidence: 99%

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2-Acetylpyridine thiosemicarbazones. 9. Derivatives of 2-acetylpyridine 1-oxide as potential antimalarial agents

Scovill¹,

Klayman²,

Lambros³

et al. 1984

J. Med. Chem.

111

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In view of the antimalarial activity in mice of 2-acetylpyridine thiosemicarbazones, a series of analogous 1-oxides was prepared for evaluation. Their synthesis was achieved by the reaction of 2-acetylpyridine 1-oxide with methyl hydrazinecarbodithioate to give methyl 3-[1-(2-pyridinyl 1-oxide)ethylidene]hydrazinecarbodithioate (II). Reaction of the latter intermediate with secondary amines afforded the desired 2-acetylpyridine 1-oxide thiosemicarbazones (III). Reduction of the azomethine linkage of II with NaBH4 gave methyl 3-[1-(2-pyridinyl 1-oxide)ethyl]-hydrazinecarbodithioate (IV) whose S-methyl group was then displaced by amines to give a 1-[1-(2-pyridinyl 1-oxide)ethyl]thiosemicarbazide, V. Antimalarial activity of III was evaluated against both Plasmodium berghei in the mouse and Plasmodium falciparum in an automated in vitro test system. In both cases, 2-acetylpyridine 1-oxide thiosemicarbazones were found to be less active than the corresponding de-1-oxide analogues. When compounds V were evaluated against Plasmodium berghei in the mouse, a diminution of activity was similarly seen in comparison to the analogues not bearing the 1-oxide moiety.

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“…Anal. Pyridinyl 1-oxide )ethylidene]hydrazide (14). The preparation of thiosemicarbazones derived from 2-acetylpyridine 1-oxide is exemplified by the following reaction.…”

Section: Methodsmentioning

confidence: 99%

“…The 2-acetylpyridine 1-oxide thiosemicarbazone, 3-azabicyclo[3.2.2]nonane-3-thiocarboxylic acid 2-[l-(2-pyridinyl 1oxide)ethylidene]hydrazide (14), was combined with CuCl2 to give a bronze-colored product, 15, which was shown by microanalysis to correspond to a 1:1:1 complex of ligand, metal ion, and gegenion.…”

mentioning

confidence: 99%

2-Acetylpyridine thiosemicarbazones. 9. Derivatives of 2-acetylpyridine 1-oxide as potential antimalarial agents

Scovill¹,

Klayman²,

Lambros³

et al. 1984

J. Med. Chem.

111

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ChemInform Abstract: 2‐ACETYLPYRIDINE THIOSEMICARBAZONES. 7. DERIVATIVES OF 2‐ACETYLQUINOLINE AS POTENTIAL ANTIMALARIAL AGENTS

Abstract: In Analogie zu entsprechenden, bekannten Pyridinderivaten werden ausgehend von Acetylchinolin (I) über den Dithioester(III) die Thiosemicarbazone (V) dargestellt, wobei im Falle von (Vb) das Thiadiazol (VI) als Nebenprodukt beobachtet wird.

Cited by 1 publication

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2-Acetylpyridine thiosemicarbazones. 9. Derivatives of 2-acetylpyridine 1-oxide as potential antimalarial agents

2-Acetylpyridine thiosemicarbazones. 9. Derivatives of 2-acetylpyridine 1-oxide as potential antimalarial agents

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