Synthesis of Some New 6,8‐Disubstituted 7,8‐Dihydropyrimido[2,3:4,3]pyrazolo[1,5‐a]pyrimidines and 6,7,8‐Trisubstituted Pyrimido[2,3:4,3]Pyrazolo[1,5‐a]Pyrimidine Derivatives

Ho, Yuh-Wen; Yao, Chia-Tseng

doi:10.1002/jccs.200300043

J Chinese Chemical Soc

2003

DOI: 10.1002/jccs.200300043

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Synthesis of Some New 6,8‐Disubstituted 7,8‐Dihydropyrimido[2,3:4,3]pyrazolo[1,5‐a]pyrimidines and 6,7,8‐Trisubstituted Pyrimido[2,3:4,3]Pyrazolo[1,5‐a]Pyrimidine Derivatives

Yuh-Wen Ho

Chia-Tseng Yao

Abstract: Cyclization of 5-cyano-1,6-dihydro-4-methyl-2-phenyl-6-thioxopyrimidine 4 with excess of 85% hydrazine hydrate afforded the 3-amino-4-methyl-6-phenylpyrazolo [3,4-d]pyrimidine 5, which can react with appropriate Mannich base derivatives 13a-c and chalcones 27a,b to yield the corresponding 6, 8-disubstituted 7,8-dihydropyrimido[2,3:4,3]pyrazolo[1,5-a]pyrimidines 15a-c and 30a,b, respectively. On the other hand, the 6,7,8-trisubstituted pyrimido [2,3:4,3]pyrazolo[1,5-a]pyrimidine derivatives 8a-g, 20a-e, 36 and… Show more

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Cited by 27 publications

References 23 publications

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Facile Synthesis and In‐Vitro Antitumor Activity of Some Pyrazolo[3,4‐b]pyridines and Pyrazolo[1,5‐a]pyrimidines Linked to a Thiazolo[3,2‐a]benzimidazole Moiety

Abdel‐Aziz¹,

Saleh

Elzahabi

2010

Archiv der Pharmazie

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The key precursor E-3-(N,N-dimethylamino)-1-(3-methylthiazolo[3,2-a]benzimidazol-2-yl)prop-2-en-1-one 4 was synthesized in good yield using Gold's reagent. The reaction of enaminone 4 with 5-amino-3-aryl-1-phenylpyrazoles 5a, b in refluxing acetic acid in the presence of sulphuric acid, yielded pyrazolo[3,4-b]pyridines 7a, b. Similarly, pyrazolo[1,5-a]pyrimidines 10a, b and 14a-f were prepared by reaction of enaminone 4 with 5-amino-1H-pyrazoles 8a, b and 12a-f, respectively. The structure of pyrazolo[1,5-a]pyrimidine 10b was determined by X-ray diffraction. The synthesized compounds were tested for their in-vitro antitumor activity against the colon cancer cell line CaCo-2; their cytotoxicity against the normal fibroblast cell line BHK was explored as well. Some of the tested compounds exhibited cell growth inhibitory activity. The significant antitumor activity of compound 14f against the CaCo-2 cell line (IC(50 )= 0.5 microg/mL) was coupled with a lower toxicity against BHK (IC(50 )= 2.3 microg/mL).

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Facile Synthesis and In‐Vitro Antitumor Activity of Some Pyrazolo[3,4‐b]pyridines and Pyrazolo[1,5‐a]pyrimidines Linked to a Thiazolo[3,2‐a]benzimidazole Moiety

Abdel‐Aziz¹,

Saleh

Elzahabi

2010

Archiv der Pharmazie

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A Novel Antifungal Agent with Broad Spectrum: 1‐(4‐Biphenylyl)‐3‐(1H‐imidazol‐1‐yl)‐1‐propanone

Roman¹,

Mareș

Nastasa

2012

Archiv der Pharmazie

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A series of (1-substituted aryl)-3-(1H-imidazol-1-yl)-1-propanones was synthesized through the N-alkylation of imidazole with 3-dimethylamino-1-(substituted aryl)-1-propanone hydrochlorides (ketonic Mannich bases). A second series of N(1) -substituted imidazoles was obtained by the reduction of the carbonyl function of the imidazole-ketones in the previous series by means of NaBH(4) . All of the compounds were evaluated for antifungal activity against 16 strains of Candida, and 3-(1H-imidazol-1-yl)-1-(4-biphenylyl)-1-propanone emerged as a broad-spectrum antifungal agent. Several 3-(1H-imidazol-1-yl)-1-(2'-(substituted benzyl)oxyphenyl)-1-propanones were also active towards Candida kefyr.

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Reaction of Pyrimidinonethione Derivatives: Synthesis of N‐Methyl‐2‐Hydrizinopyrimidine‐4‐One, Thiazolo[3,4‐b] N‐Methylpyrimidinone; 2‐(1‐Pyrazolonyl) N‐Methylpyrimidine‐4‐one and 2‐Hydrazino‐N‐Methyl Pyrimidine‐4‐One Derivatives

Al–Shara′ey

2004

J Chinese Chemical Soc

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6-Aryl-5-cyano-4-pyrimidinone-2-thion derivatives 1a-c reacted with methyl iodide (1:2) to give the corresponding 2-S,N-dimethyl pyrimidine-4-one derivatives 2a-c. Compounds 2a-c were in turn, reacted with hydrazine hydrate to give the sulfur free reaction products 3a-c. These reaction products were taken as the starting materials for the synthesis of several new heterocyclic derivatives. Reaction of 3a-c with acetic anhydride and formic acid gave pyrimido triazines 4a-c and 7a-c, respectively. Their reactions with active methylene containing reagents gave the corresponding 2-(1-pyrazonyl)-N-methyl pyrimidine derivatives 9a-c and 10a-c, respectively. Their reactions with aromatic aldehydes afforded the corresponding 2-hydrazono pyrimidine derivatives 11a-c. The structure of these reactions products were established based on both elemental analysis and spectral data studies.

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Synthesis of Some New 6,8‐Disubstituted 7,8‐Dihydropyrimido[2,3:4,3]pyrazolo[1,5‐a]pyrimidines and 6,7,8‐Trisubstituted Pyrimido[2,3:4,3]Pyrazolo[1,5‐a]Pyrimidine Derivatives

Cited by 27 publications

References 23 publications

Facile Synthesis and In‐Vitro Antitumor Activity of Some Pyrazolo[3,4‐b]pyridines and Pyrazolo[1,5‐a]pyrimidines Linked to a Thiazolo[3,2‐a]benzimidazole Moiety

Facile Synthesis and In‐Vitro Antitumor Activity of Some Pyrazolo[3,4‐b]pyridines and Pyrazolo[1,5‐a]pyrimidines Linked to a Thiazolo[3,2‐a]benzimidazole Moiety

A Novel Antifungal Agent with Broad Spectrum: 1‐(4‐Biphenylyl)‐3‐(1H‐imidazol‐1‐yl)‐1‐propanone

Reaction of Pyrimidinonethione Derivatives: Synthesis of N‐Methyl‐2‐Hydrizinopyrimidine‐4‐One, Thiazolo[3,4‐b] N‐Methylpyrimidinone; 2‐(1‐Pyrazolonyl) N‐Methylpyrimidine‐4‐one and 2‐Hydrazino‐N‐Methyl Pyrimidine‐4‐One Derivatives

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