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Analgesic and antimicrobial studies of some 2,4-dichloro-5-fluorophenyl containing arylidenetriazolothiadiazines

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Abstract

2,4-Dichloro-5-fluorophenyl containing 7-arylidenetriazolothiadiazines were obtained by the reaction of 4-amino-3-(2,4-dichloro-5-fluorophenyl)-5-mercapto-1,2,4-triazole with 2,3-dibromo-1,3-diarylpropan-1-ones, and also by the reaction of 4-amino-3-(2,4-dichloro-5-fluorophenyl)-5-mercapto-1,2,4-triazole with α-bromopropenones in the presence of a base. The structure of the 7-arylidenetriazolothiadiazines was confirmed by an alternative synthesis. A plausible mechanism for the formation of 7-arylidenetriazolothiadiazines is proposed. All newly synthesized compounds were screened for their analgesic and antimicrobial activities. Compounds bearing 4-chlorophenyl or 3,4-methylenedioxyphenyl moieties at position 7 of the arylidenetriazolothiadiazines showed excellent analgesic activity. Arylidenetriazolothiadiazines carrying a phenyl, 4-chlorophenyl, 4-methylphenyl, 3,4-dimethoxyphenyl, and 2,4-dichlorophenyl moieties at position 7 showed excellent antibacterial and antifungal activities.

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Authors and Affiliations

  1. Department of Chemistry, Mangalore University, Mangalagangothri, Karnataka, India

    Mari S. Karthikeyan, Bantwal S. Holla & Shalini Shenoy

Authors
  1. Mari S. Karthikeyan
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  2. Bantwal S. Holla
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  3. Shalini Shenoy
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Correspondence to Mari S. Karthikeyan.

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Correspondence: Mari Sithambaram Karthikeyan, Department of Chemistry, Mangalore University, Mangalagangothri 574199, Karnataka, India.

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Karthikeyan, M., Holla, B. & Shenoy, S. Analgesic and antimicrobial studies of some 2,4-dichloro-5-fluorophenyl containing arylidenetriazolothiadiazines. Monatsh Chem 139, 707–716 (2008). https://doi.org/10.1007/s00706-007-0797-9

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