Synthesis, antibacterial activity and cytotoxicity of new fused pyrazolo[1,5-a]pyrimidine and pyrazolo[5,1-c][1,2,4]triazine derivatives from new 5-aminopyrazoles

Wedad M. Al-Adiwish, M. I M Tahir, A. Siti-Noor-Adnalizawati, Siti Farah Hashim, Nazlina Ibrahim, Wan Yaacob Wan Ahmad

Research output: Contribution to journalArticle

57 Citations (Scopus)

Abstract

New 5-aminopyrazoles 2a-c were prepared in high yields from the reaction of known α,α-dicyanoketene-N,S-acetals 1a-c with hydrazine hydrate under reflux in ethanol. These compounds were utilized as intermediates to synthesize pyrazolo[1,5-a]-pyrimidines 3a-c, 4a-d, 5a-c, and 6a-c, as well as pyrazolo[5,1-c][1,2,4]triazines 7a-c and 8a-c, by the reaction of 2-[bis(methylthio)methylene]malononitrile, α,α-dicyanoketene-N,S- acetals 1a-b, acetylacetone, acetoacetanilide as well as acetylacetone, and malononitrile, respectively. Furthermore, cyclization of 2a-c with pentan-2,5-dione yielded the corresponding 5-pyrrolylpyrazoles 9a-c. Moreover, fusion of 2a-c with acetic anhydride resulted in the corresponding 1-acetyl-1H-pyrazoles 10a-c. The antibacterial activity and cytotoxicity against Vero cells of several selected compounds are also reported.

Original languageEnglish
Pages (from-to)464-476
Number of pages13
JournalEuropean Journal of Medicinal Chemistry
Volume64
DOIs
Publication statusPublished - 2013

Fingerprint

Acetals
hydrazine
Cytotoxicity
Pyrazoles
Derivatives
Dilatation and Curettage
Vero Cells
Cyclization
Ethanol
Fusion reactions
acetylacetone
dicyanmethane
5-aminopyrazole
pyrazolo(1,5-a)pyrimidine
1,2,4-triazine
acetoacetanilide
acetic anhydride

Keywords

  • 5-Aminopyrazoles
  • Antibacterial activity
  • Cytotoxicity
  • Pyrazolo[1,5-a]pyrimidines
  • Pyrazolo[5,1-c][1,2,4]triazines α,α-Dicyanoketene-S,S- and N,S-acetals

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Synthesis, antibacterial activity and cytotoxicity of new fused pyrazolo[1,5-a]pyrimidine and pyrazolo[5,1-c][1,2,4]triazine derivatives from new 5-aminopyrazoles. / Al-Adiwish, Wedad M.; Tahir, M. I M; Siti-Noor-Adnalizawati, A.; Hashim, Siti Farah; Ibrahim, Nazlina; Wan Ahmad, Wan Yaacob.

In: European Journal of Medicinal Chemistry, Vol. 64, 2013, p. 464-476.

Research output: Contribution to journalArticle

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abstract = "New 5-aminopyrazoles 2a-c were prepared in high yields from the reaction of known α,α-dicyanoketene-N,S-acetals 1a-c with hydrazine hydrate under reflux in ethanol. These compounds were utilized as intermediates to synthesize pyrazolo[1,5-a]-pyrimidines 3a-c, 4a-d, 5a-c, and 6a-c, as well as pyrazolo[5,1-c][1,2,4]triazines 7a-c and 8a-c, by the reaction of 2-[bis(methylthio)methylene]malononitrile, α,α-dicyanoketene-N,S- acetals 1a-b, acetylacetone, acetoacetanilide as well as acetylacetone, and malononitrile, respectively. Furthermore, cyclization of 2a-c with pentan-2,5-dione yielded the corresponding 5-pyrrolylpyrazoles 9a-c. Moreover, fusion of 2a-c with acetic anhydride resulted in the corresponding 1-acetyl-1H-pyrazoles 10a-c. The antibacterial activity and cytotoxicity against Vero cells of several selected compounds are also reported.",
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AU - Tahir, M. I M

AU - Siti-Noor-Adnalizawati, A.

AU - Hashim, Siti Farah

AU - Ibrahim, Nazlina

AU - Wan Ahmad, Wan Yaacob

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AB - New 5-aminopyrazoles 2a-c were prepared in high yields from the reaction of known α,α-dicyanoketene-N,S-acetals 1a-c with hydrazine hydrate under reflux in ethanol. These compounds were utilized as intermediates to synthesize pyrazolo[1,5-a]-pyrimidines 3a-c, 4a-d, 5a-c, and 6a-c, as well as pyrazolo[5,1-c][1,2,4]triazines 7a-c and 8a-c, by the reaction of 2-[bis(methylthio)methylene]malononitrile, α,α-dicyanoketene-N,S- acetals 1a-b, acetylacetone, acetoacetanilide as well as acetylacetone, and malononitrile, respectively. Furthermore, cyclization of 2a-c with pentan-2,5-dione yielded the corresponding 5-pyrrolylpyrazoles 9a-c. Moreover, fusion of 2a-c with acetic anhydride resulted in the corresponding 1-acetyl-1H-pyrazoles 10a-c. The antibacterial activity and cytotoxicity against Vero cells of several selected compounds are also reported.

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