13153-01-0Relevant articles and documents
Vibrational and quantum chemical investigation of cyclization of thiosemicarbazide group in 1-benzoyl-4-phenyl-3-thiosemicarbazide
Gautam, Priyanka,Prakash, Om,Dani,Singh,Singh, Ranjan K.
, p. 278 - 287 (2014)
1-Benzoyl-4-phenyl-3-thiosemicarbazide (H3bpt) was treated with acid - base in one sequence and base - acid in other sequence, both of which lead to ring formation of thiosemicarbazide group, giving N-phenyl-5-phenyl-1,3, 4-thiadiazol-2-amine (Hppta) in the first case and 4,5-diphenyl-2,4-dihydro-1,2, 4-triazole-3-thione (Hdptt) in the second case. The primary (H3bpt) as well as the resulting compounds (Hppta & Hdptt) has been characterized by elemental analyses, NMR, FTIR and Raman spectroscopic techniques. The quantum chemical calculations of the compounds are performed using DFT/B3LYP/6311G(d,p) method for geometry optimizations and also for prediction of the molecular properties. The cyclization is confirmed by disappearance of many bands belonging to the open chain subgroups of H3bpt such as; NH stretching, NH bending, CN stretching, NH puckering, CO stretching etc. The ring formation of 1-benzoyl-4-phenyl-3-thiosemicarbazide (H3bpt) has been further confirmed by the appearance of many bands belonging to the closed ring of thiosemicarbazide in the resulting compounds Hppta and Hdptt.
Synthesis, characterization and antioxidant activities of semicarbazide and thiosemicarbazide derivatives
Alam, Faima,Ali, Basharat,Ali, Mahboob,Khan, Khalid Mohammed,Khan, Momin,Manaf, Abdul,Zaman, Khair
, p. 475 - 483 (2021/08/21)
In this research work Semicarbazide, thiosemicarbazide derivatives 3 to 25 were synthesized by conventional methods with high percentage yield and reaction rate. 1H-NMR and EIMS spectroscopic techniques were used to elucidate the structure of t
Pharmacomodulations of the benzoyl-thiosemicarbazide scaffold reveal antimicrobial agents targeting D-alanyl-D-alanine ligase in bacterio
Ameryckx, Alice,Pochet, Lionel,Wang, Gang,Yildiz, Esra,Saadi, Bouazza Es,Wouters, Johan,Van Bambeke, Fran?oise,Frédérick, Rapha?l
supporting information, (2020/06/03)
D-Alanyl-D-alanine ligase (Ddl) is a validated and attractive target among the bacterial enzymes involved in peptidoglycan biosynthesis. In the present work, we investigated the pharmacomodulations of the benzoylthiosemicarbazide scaffold to identify new Ddl inhibitors with antibacterial potency. Five novel series of thiosemicarbazide analogues, 1,2,4-thiotriazole-3-thiones, 1,3,4-thiadiazoles, phenylthiosemicarbazones, diacylthiosemicarbazides and thioureas were synthesized via straightforward procedures, then tested against Ddl and on susceptible or resistant bacterial strains. Among these, the thiosemicarbazone and thiotriazole were identified as the most promising scaffolds with Ddl inhibition potency in the micromolar range. Antimicrobial evaluation of salicylaldehyde-4(N)-(3,4-dichlorophenyl) thiosemicarbazone 33, one of the best compounds in our study, revealed interesting antimicrobial activities with values of 3.12–6.25 μM (1.06–2.12 μg/mL) against VRE strains and 12.5–25.0 μM (4.25–8.50 μg/mL) towards MRSA and VRSA strains. A detailed mechanistic study was conducted on the Ddl inhibitors 4-(3,4-dichlorophenyl)-5-(2-hydroxyphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 20 and compound 33, and revealed a bactericidal effect at 5 × MIC concentration after 7 h and 24 h, respectively, and a bacteriostatic effect at 1 × MIC or 2 × MIC without any sign of bacterial membrane disruption at these lower concentrations. Finally, 20 and 33 were proved to target Ddl in bacterio via intracellular LC-MS dosage of D-Ala, L-Ala and D-Ala-D-Ala. Although, at this stage, our results indicate that other mechanisms might be involved to explain the antimicrobial potency of our compounds, their ability to inhibit the growth of strains resistant to usual antibiotics, as well as strains that express alternative ligases, sets the stage for the development of new antimicrobial agents potentially less sensitive to resistance mechanisms.
Development of 3,5-Dinitrophenyl-Containing 1,2,4-Triazoles and Their Trifluoromethyl Analogues as Highly Efficient Antitubercular Agents Inhibiting Decaprenylphosphoryl-β- d -ribofuranose 2′-Oxidase
Karabanovich, Galina,Du?ek, Jan,Savková, Karin,Pavli?, Oto,Pávková, Ivona,Korábe?ny, Jan,Ku?era, Tomá?,Ko?ová Vl?ková, Hana,Huszár, Stanislav,Konyariková, Zuzana,Kone?ná, Klára,Jand'Ourek, Ond?ej,Stola?íková, Ji?ina,Korduláková, Jana,Vávrová, Kate?ina,Pávek, Petr,Klime?ová, Věra,Hrabálek, Alexandr,Miku?ová, Katarína,Roh, Jaroslav
, p. 8115 - 8139 (2019/09/30)
We report herein the discovery of 3,5-dinitrophenyl 1,2,4-triazoles with excellent and selective antimycobacterial activities against Mycobacterium tuberculosis strains, including clinically isolated multidrug-resistant strains. Thorough structure-activity relationship studies of 3,5-dinitrophenyl-containing 1,2,4-triazoles and their trifluoromethyl analogues revealed the key role of the position of the 3,5-dinitrophenyl fragment in the antitubercular efficiency. Among the prepared compounds, the highest in vitro antimycobacterial activities against M. tuberculosis H37Rv and against seven clinically isolated multidrug-resistant strains of M. tuberculosis were found with S-substituted 4-alkyl-5-(3,5-dinitrophenyl)-4H-1,2,4-triazole-3-thiols and their 3-nitro-5-(trifluoromethyl)phenyl analogues. The minimum inhibitory concentrations of these compounds reached 0.03 μM, which is superior to all the current first-line anti-tuberculosis drugs. Furthermore, almost all compounds with excellent antimycobacterial activities exhibited very low in vitro cytotoxicities against two proliferating mammalian cell lines. The docking study indicated that these compounds acted as the inhibitors of decaprenylphosphoryl-β-d-ribofuranose 2′-oxidase enzyme, which was experimentally confirmed by two independent radiolabeling experiments.
