Facile synthesis, cytotoxic and antimicrobial activity studies of a new group of 6-aryl-3-[4-(methylsulfonyl)benzyl]-7H-[1,2,4]triazolo[3,4-b][1,3,4] thiadiazines

V. Sumangala, Boja Poojary, N. Chidananda, T. Arulmoli, Shalini Shenoy

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

The reaction of 4-(methylsulfonyl)phenylacetohydrazide (3) with carbon disulfide and potassium hydroxide followed by hydrazine hydrate gave 4-amino-5-[4-(methylsulfonyl)benzyl]-4H-[1,2,4]triazole-3-thione (4). The resulting triazole was subjected to cyclocondensation reaction with different phenacyl bromides to afford 6-substituted-3-[4-(methylsulfonyl)benzyl]-7H-[1,2, 4]triazolo[3,4-b][1,3,4]thiadiazines (5a-i). All structures of the newly synthesized compounds were confirmed by IR, NMR, mass spectral studies and elemental analyses. The newly synthesized compounds were screened for their cytotoxic, antibacterial and antifungal activity. Some of the derivatives have exhibited promising biological activity.

Original languageEnglish
Pages (from-to)59-64
Number of pages6
JournalEuropean Journal of Medicinal Chemistry
Volume54
DOIs
Publication statusPublished - 01-08-2012

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hydrazine
Thiadiazines
Carbon Disulfide
Thiones
Triazoles
Bioactivity
Nuclear magnetic resonance
Derivatives
1,2,4-triazole
potassium hydroxide
phenacyl bromide

All Science Journal Classification (ASJC) codes

  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

Cite this

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abstract = "The reaction of 4-(methylsulfonyl)phenylacetohydrazide (3) with carbon disulfide and potassium hydroxide followed by hydrazine hydrate gave 4-amino-5-[4-(methylsulfonyl)benzyl]-4H-[1,2,4]triazole-3-thione (4). The resulting triazole was subjected to cyclocondensation reaction with different phenacyl bromides to afford 6-substituted-3-[4-(methylsulfonyl)benzyl]-7H-[1,2, 4]triazolo[3,4-b][1,3,4]thiadiazines (5a-i). All structures of the newly synthesized compounds were confirmed by IR, NMR, mass spectral studies and elemental analyses. The newly synthesized compounds were screened for their cytotoxic, antibacterial and antifungal activity. Some of the derivatives have exhibited promising biological activity.",
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Facile synthesis, cytotoxic and antimicrobial activity studies of a new group of 6-aryl-3-[4-(methylsulfonyl)benzyl]-7H-[1,2,4]triazolo[3,4-b][1,3,4] thiadiazines. / Sumangala, V.; Poojary, Boja; Chidananda, N.; Arulmoli, T.; Shenoy, Shalini.

In: European Journal of Medicinal Chemistry, Vol. 54, 01.08.2012, p. 59-64.

Research output: Contribution to journalArticle

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AU - Poojary, Boja

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AU - Arulmoli, T.

AU - Shenoy, Shalini

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AB - The reaction of 4-(methylsulfonyl)phenylacetohydrazide (3) with carbon disulfide and potassium hydroxide followed by hydrazine hydrate gave 4-amino-5-[4-(methylsulfonyl)benzyl]-4H-[1,2,4]triazole-3-thione (4). The resulting triazole was subjected to cyclocondensation reaction with different phenacyl bromides to afford 6-substituted-3-[4-(methylsulfonyl)benzyl]-7H-[1,2, 4]triazolo[3,4-b][1,3,4]thiadiazines (5a-i). All structures of the newly synthesized compounds were confirmed by IR, NMR, mass spectral studies and elemental analyses. The newly synthesized compounds were screened for their cytotoxic, antibacterial and antifungal activity. Some of the derivatives have exhibited promising biological activity.

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