Synthesis and Biological Evaluation of Some New N1-[4-(4-Chlorophenylsulfonyl)benzoyl]-N 4-(aryl)-thiosemicarbazides and Products of Their Cyclization
Corresponding Author
Stefania-Felicia Barbuceanu
Organic Chemistry Department, Faculty of Pharmacy, 020956 Bucharest, Romania
Correspondence to: Stefania-Felicia Barbuceanu; e-mail: [email protected].Search for more papers by this authorGabriela Bancescu
Microbiology Department, Faculty of Dentistry, 050051 Bucharest, Romania
Search for more papers by this authorGabriel Saramet
Pharmaceutical Techniques Department, Faculty of Pharmacy, 020956 Bucharest, Romania
Search for more papers by this authorFlorica Barbuceanu
Institute for Diagnosis and Animal Health, 050557 Bucharest, Romania
Search for more papers by this authorConstantin Draghici
C. D. Nenitescu Institute of Organic Chemistry, Romanian Academy, 060023 Bucharest, Romania
Search for more papers by this authorFlavian Stefan Radulescu
Pharmaceutical Industry Department, Faculty of Pharmacy, 020956 Bucharest, Romania
Search for more papers by this authorAura Ionescu
Pharmacology and Clinical Pharmacy Department, Faculty of Pharmacy, 020956 Bucharest, Romania
Search for more papers by this authorSimona Negres
Pharmacology and Clinical Pharmacy Department, Faculty of Pharmacy, 020956 Bucharest, Romania
Search for more papers by this authorCorresponding Author
Stefania-Felicia Barbuceanu
Organic Chemistry Department, Faculty of Pharmacy, 020956 Bucharest, Romania
Correspondence to: Stefania-Felicia Barbuceanu; e-mail: [email protected].Search for more papers by this authorGabriela Bancescu
Microbiology Department, Faculty of Dentistry, 050051 Bucharest, Romania
Search for more papers by this authorGabriel Saramet
Pharmaceutical Techniques Department, Faculty of Pharmacy, 020956 Bucharest, Romania
Search for more papers by this authorFlorica Barbuceanu
Institute for Diagnosis and Animal Health, 050557 Bucharest, Romania
Search for more papers by this authorConstantin Draghici
C. D. Nenitescu Institute of Organic Chemistry, Romanian Academy, 060023 Bucharest, Romania
Search for more papers by this authorFlavian Stefan Radulescu
Pharmaceutical Industry Department, Faculty of Pharmacy, 020956 Bucharest, Romania
Search for more papers by this authorAura Ionescu
Pharmacology and Clinical Pharmacy Department, Faculty of Pharmacy, 020956 Bucharest, Romania
Search for more papers by this authorSimona Negres
Pharmacology and Clinical Pharmacy Department, Faculty of Pharmacy, 020956 Bucharest, Romania
Search for more papers by this authorContract grant sponsor: Sectoral Operational Programme Human Resources Development, European Social Fund.
Contract grant sponsor: Government of Romania.
Contract grant number: POSDRU/89/1.5/S/64109.
ABSTRACT
In the present study, new 1,2,4-triazoles, 1,3,4-thiadiazoles, and acylthiosemicarbaz-ides derived from 4-(4-chlorophenylsulfonyl)benzoic acid hydrazide were synthesized and screened for their antimicrobial and analgesic activities. Acylthiosemicarbazides 2–4 were synthesized by a reaction of 4-(4-chlorophenyl-sulfonyl)benzoic acid hydrazide 1 with different arylisothiocyanates.4,5-Disubstituted-2,4-dihydro-3H-1,2,4-triazol-3-thiones 5–7 and 2,5-disubstituted-1,3,4-thiadiazoles 8–10 were obtained by dehydrative cyclization of corresponding acylthiosemicarbazide derivatives 2–4 in basic media (8% aqueous sodium hydroxide) and in acidic media (sulfuric acid or phosphorous oxychloride), respectively. The structures of the newly synthesized compounds have been confirmed on the basis of elemental analysis and spectral studies (IR, 1H NMR, 13C NMR, MS). Their antimicrobial activities against some bacteria and yeasts were investigated. The analgesic activity of all compounds was performed with two pharmacological tests: the writhing test induced with acetic acid and hot-plate test. The results showed that triazole 7 had the best antimicrobial activity against Bacillus cereus. In the chemical stimulus test, triazoles 6 and 7 were the most active compounds whereas in the hot-plate test thiadiazoles 9 and 10 exhibited the highest analgesic activity.
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