2349-67-9Relevant articles and documents
Synthesis, antibacterial and?antitubercular activities of?some?7-[4-(5-amino-[1,3,4]thiadiazole-2-sulfonyl)-piperazin -1-yl] fluoroquinolonic derivatives
Talath,Gadad
, p. 918 - 924 (2006)
In the present study, a series of 7-[4-(5-amino-1,3,4 thiadiazole-2-sulfonyl)]-1-piperazinyl fluoroquinolonic derivatives VIIa-d were synthesized in good yields and characterized by IR, 1H-NMR, 13C-NMR, FAB Mass spectral and elemental analyses. The compounds were evaluated for their preliminary in vitro antibacterial activity against some Gram-positive and Gram-negative bacteria and selected compounds VIIa, b were screened for antitubercular activity against Mycobacterium tuberculosis H37Rv strain by broth dilution assay method. The antibacterial data of the tested N-sulfonylfluoroquinolones VIIa-d indicated that all the synthesized compounds showed better activity against Gram-positive bacteria S.?aureus, E.?faecelis, Bacillus sp. (MIC = 1-5?μg?ml-1, respectively) compared to reference drugs. The MIC values of tested derivatives connotes that the sparfloxacin and gatifloxacin derivatives VIIc, d were most active against the tested Gram-positive bacterial strains (MIC = 1-5?μg?ml-1). All the tested compounds VIIa-d showed poor activity against the Gram-negative bacteria. The in vitro antitubercular activity reports of selected compounds VIIa, b against M.?tuberculosis strain H37Rv showed moderate activity at MIC of 10?μg?ml-1.
Synthesis and biological assessment of ciprofloxacin-derived 1,3,4-thiadiazoles as anticancer agents
Ahadi, Hamideh,Shokrzadeh, Mohammad,Hosseini-khah, Zahra,Ghassemi barghi, Nasrin,Ghasemian, Majid,Emadi, Elnaz,Zargari, Mehryar,Razzaghi-Asl, Nima,Emami, Saeed
, (2020)
The quinolone-3-carboxylic acid scaffold is essential structure for antibacterial activity of fluoroquinolones such as ciprofloxacin. Modification of 3-carboxylic functionality in this structure can be used for switching its activity from antibacterial to anticancer. Accordingly, a series of C-3 modified ciprofloxacin derivatives containing N-(5-(benzylthio)-1,3,4-thiadiazol-2-yl)-carboxamide moiety was synthesized as novel anticancer agents. Most of compounds showed significant activity against MCF-7, A549 and SKOV-3 cancer cells in the MTT assay. In particular, compounds 13a-e and 13g were found to be as potent as standard drug doxorubicin against MCF-7 cell line (IC50s = 3.26–3.90 μM). Furthermore, the 4-fluorobenzyl derivatives 13h and 14b with IC50 values of 3.58 and 2.79 μM exhibited the highest activity against SKOV-3 and A549 cells, being as potent as doxorubicin. Two promising compounds 13e and 13g were further tested for their apoptosis inducing activity and cell cycle arrest. Both compounds could significantly induce apoptosis in MCF-7 cells, while compound 13e was more potent apoptosis inducer resulting in an 18-fold increase in the proportion of apoptotic cells at the IC50 concentration in MCF-7 cells. The cell cycle analysis revealed that compounds 13e and 13g could increase cell portions in the sub-G1 phase, inducing oligonucleosomal DNA fragmentation and apoptosis confirmed by comet assay.
Design, synthesis, and docking studies of new 1,3,4-thiadiazole-2-thione derivatives with carbonic anhydrase inhibitory activity
Abdel-Hamid, Mohammed K.,Abdel-Hafez, Atef A.,El-Koussi, Nawal A.,Mahfouz, Nadia M.,Innocenti, Alessio,Supuran, Claudiu T.
, p. 6975 - 6984 (2007)
A new series of 1,3,4-thiadiazole-2-thione derivatives have been prepared and assayed for the inhibition of three physiologically relevant carbonic anhydrase (CA, EC 4.2.1.1) isozymes, the cytosolic human isozymes I and II, and the transmembrane, tumor-associated hCA IX. Against hCA I the investigated thiones, showed inhibition constants in the range of 2.55-222 μM, against hCA II in the range of 2.0-433 μM, and against hCA IX in the range of 1.25-148 μM. Compound 5c, 4-(4,5-dihydro-5-thioxo-1,3,4-thiadiazol-2-yl)-1-(5-nitro-2-oxoindolin-3 -ylidene)semicarbazide showed interesting inhibition of the tumor-associated hCA IX with KI value of 1.25 μM, being the first non-sulfonamide type inhibitor of such activity. This result is rather important taking into consideration the known antitumor activity of thiones. In addition, docking of the tested compounds into CA II active site was performed in order to predict the affinity and orientation of these compounds at the isozyme active site. The results showed similar orientation of the target compounds at CA II active site compared with reported sulfonamide type CAIs with the thione group acting as a zinc-binding moiety.
Ultrasound-assisted improved synthesis of 5-(benzylthio)-1,3,4-thiadiazol-2-amine derivatives: an experimental and computational study
Erdogan, Taner
, p. 899 - 912 (2019)
The main objects of this study are: (1) to propose alternative efficient methods for the synthesis of 5-amino-1,3,4-thiadiazole-2-thiol and 5-(benzylthio)-1,3,4-thiadiazol-2-amine derivatives, (2) to investigate the reactions and the chemical species which take place in the investigated reactions computationally via density functional theory (DFT) calculations, (3) to make a comparison between experimental and computationally obtained data, and (4) to make a comparison between the computational methods to find out the best computational technique to simulate the investigated molecules and reactions. The study consists of two parts. In the first part, synthesis of 5-amino-1,3,4-thiadiazole-2-thiol and 5-(benzylthio)-1,3,4-thiadiazol-2-amine derivatives have been carried out. For both syntheses, it has been proposed that the reactions can be carried out effectively with the use of ultrasound. To the best of our knowledge, this is the first use of ultrasound for both reactions. The results showed that ultrasound can increase the efficiency of the investigated reactions and can be a good alternative to conventional methods. In the second part of the study, some DFT calculations have been performed on the chemical species which take place in the investigated reactions. In computational studies, seven different basis sets have been used. In this second part, comparisons have been made (1) between experimental and computationally obtained data, and (2) between the computational techniques to reveal the best method for the investigated molecules.
Mercapto thiadiazole-based sensors with high selectivity and sensitivity for Hg2+ in aqueous solution
Zhang, You-Ming,Liu, Ming-Xia,Lin, Qi,Li, Qiao,Wei, Tai-Bao
, p. 619 - 621 (2010)
Two simple mercapto thiadiazole-based sensors have been synthesised by a convenient method and exhibit excellent sensitivity and selectivity for Hg 2+ in DMSO/H2O (1:1, v/v) aqueous solution. The sensors react with Hg2+ to form stable complexes and the association constants, Ka, are 4.4 × 104 M-1 and 1.0 × 103 M-1, respectively. Furthermore, the detection limit of one sensor towards Hg2+ is 8.0 × 10-7 M.
Synthesis of novel 2-acetamide-5-phenylthio-1,3,4-thiadiazole-containing phenyl urea derivatives as potential VEGFR-2 inhibitors
Ayati, Adileh,Fathi, Parnian,Foroumadi, Alireza,Foroumadi, Roham,Ketabforoosh, Shima H. M. E.,Moghimi, Setareh,Safari, Fatemeh,Salarinejad, Somayeh,Toolabi, Mahsa
, (2022/01/13)
A novel series of 2-acetamide-5-phenylthio-1,3,4-thiadiazol derivatives containing a phenyl urea warhead were synthesized and evaluated as antiproliferative agents. The cytotoxic activities of the newly synthesized compounds were evaluated toward three human cancer cell lines, including HT-29, A431, and PC3, as well as normal HDF cells, using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide assay. The biological results revealed the highest degree of cytotoxic effects for the 4-chloro-containing compound 9e against the A431 cell line. Further assessment by Western blot analysis assay confirmed the induction of apoptosis by compound 9e, with upregulation of Bax and downregulation of Bcl-2 proteins in A431 cancer cells. In addition, compound 9e inhibited the phosphorylation of vascular endothelial growth factor and its receptor (VEGFR-2) in A431 cancer cells while the total level of actin protein was unchanged. These results were confirmed by a three-dimensional cell culture method using the hanging drop technique.
Design, synthesis and evaluation of novel thienopyrimidine-based agents bearing diaryl urea functionality as potential inhibitors of angiogenesis
Faraji, Aram,Oghabi Bakhshaiesh, Tayebeh,Hasanvand, Zaman,Motahari, Rasoul,Nazeri, Elahe,Boshagh, Mohammad Amin,Firoozpour, Loghman,Mehrabi, Hossein,Khalaj, Ali,Esmaeili, Rezvan,Foroumadi, Alireza
, (2020/10/27)
Inhibition of angiogenesis is a promising strategy for the treatment of cancer. Herein, we describe the design and synthesis of thieno[2,3-d]pyrimidine-1,3,4-thiadiazole-aryl urea derivatives 11a-m to evaluate their efficacy in the chick chorioallantoic membrane (CAM) assay. Among target agents, 11i had a considerable activity against prostate cancer cell line, PC3 (IC50 = 3.6 μM). Moreover, induction of apoptosis, good inhibitory activity against the growth of capillary blood vessels, and inhibition of VEGFR-2 phosphorylation were noticeable parameters which convinced us that 11i could be considered as a promising candidate for the discovery of novel drugs to treat tumors, particularly prostate cancer.
