TY - JOUR
T1 - Analgesic and antimicrobial studies of some 2,4-dichloro-5-fluorophenyl containing arylidenetriazolothiadiazines
AU - Karthikeyan, Mari S.
AU - Holla, Bantwal S.
AU - Shenoy, Shalini
PY - 2008/6/1
Y1 - 2008/6/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=44549084219&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=44549084219&partnerID=8YFLogxK
U2 - 10.1007/s00706-007-0797-9
DO - 10.1007/s00706-007-0797-9
M3 - Article
AN - SCOPUS:44549084219
SN - 0026-9247
VL - 139
SP - 707
EP - 716
JO - Monatshefte fur Chemie
JF - Monatshefte fur Chemie
IS - 6
ER -