Synthesis and antitumor activity studies of some new fused 1,2,4-triazole derivatives carrying 2,4-dichloro-5-fluorophenyl moiety

K. Subrahmanya Bhat, Boja Poojary, D. Jagadeesh Prasad, Prashantha Naik, B. Shivarama Holla

Research output: Contribution to journalArticle

89 Citations (Scopus)

Abstract

A series of 3-(2,4-dichloro-5-fluorophenyl)-6-(substituted phenyl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines (4) (Fig. 1) have been synthesized by the cyclization of 3-(2,4-dichloro-5-fluorophenyl)-1,2,4-triazol-5-thiol (3) with substituted phenacyl bromides. All the newly synthesized compounds were confirmed by IR, 1H NMR and mass spectral studies. Among the compounds tested for their antitumor activity three compounds exhibited in vitro antitumor activity with moderate to excellent growth inhibition against a panel of sixty cancer cell lines of leukemia, non-small cell lung cancer, melanoma, ovarian cancer, prostate and breast cancer. The compound 4d showed promising antiproliferative activity with GI50 values in the range of 1.06-25.4 μM.

Original languageEnglish
Pages (from-to)5066-5070
Number of pages5
JournalEuropean Journal of Medicinal Chemistry
Volume44
Issue number12
DOIs
Publication statusPublished - 12-2009

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Prostatic Neoplasms
Thiadiazines
Cells
Breast Neoplasms
Derivatives
Cyclization
Sulfhydryl Compounds
Non-Small Cell Lung Carcinoma
Ovarian Neoplasms
Melanoma
Leukemia
Nuclear magnetic resonance
Cell Line
Growth
Neoplasms
1,2,4-triazole
In Vitro Techniques
Proton Magnetic Resonance Spectroscopy
phenacyl bromide

All Science Journal Classification (ASJC) codes

  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Bhat, K. Subrahmanya ; Poojary, Boja ; Prasad, D. Jagadeesh ; Naik, Prashantha ; Holla, B. Shivarama. / Synthesis and antitumor activity studies of some new fused 1,2,4-triazole derivatives carrying 2,4-dichloro-5-fluorophenyl moiety. In: European Journal of Medicinal Chemistry. 2009 ; Vol. 44, No. 12. pp. 5066-5070.
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Synthesis and antitumor activity studies of some new fused 1,2,4-triazole derivatives carrying 2,4-dichloro-5-fluorophenyl moiety. / Bhat, K. Subrahmanya; Poojary, Boja; Prasad, D. Jagadeesh; Naik, Prashantha; Holla, B. Shivarama.

In: European Journal of Medicinal Chemistry, Vol. 44, No. 12, 12.2009, p. 5066-5070.

Research output: Contribution to journalArticle

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AB - A series of 3-(2,4-dichloro-5-fluorophenyl)-6-(substituted phenyl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines (4) (Fig. 1) have been synthesized by the cyclization of 3-(2,4-dichloro-5-fluorophenyl)-1,2,4-triazol-5-thiol (3) with substituted phenacyl bromides. All the newly synthesized compounds were confirmed by IR, 1H NMR and mass spectral studies. Among the compounds tested for their antitumor activity three compounds exhibited in vitro antitumor activity with moderate to excellent growth inhibition against a panel of sixty cancer cell lines of leukemia, non-small cell lung cancer, melanoma, ovarian cancer, prostate and breast cancer. The compound 4d showed promising antiproliferative activity with GI50 values in the range of 1.06-25.4 μM.

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