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 of thiodiazole copper microcapsules and release behavior of inhibiting R. solanacearum
Feng, Chao,Zhang, Chengsheng,Kong, Fanyu,Wang, Jing
, p. 4478 - 4486 (2014)
Microcapsules are one of the most useful devices to reduce the dosage of pesticides and prolong the duration of the active ingredient in target crops. In this study, thiadiazole copper (TDC) microcapsules were synthesized by in situ polymerization using p
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.
A simple colorimetric sensor with high selectivity for mercury cation in aqueous solution
Zhang, You-Ming,Li, Ping,Lin, Qi,Wei, Tai-Bao,Li, Jun-Qiang
, p. 2286 - 2294 (2011)
A simple and sensitive mercapto thiadiazole Schiff-base colorimetric chemosensor 2 was synthesized. It exhibits good selectivity and sensitivity for the mercury cation over other metal cations such as Zn2+, Pb 2+, Cd2+, Ni2+, Co2+, Ag+, Ca 2+, Mg2+, and Cr3+ in both aqueous solution and on paper-made test kits. The change in color is very easily observed by the naked eye for the presence of Hg2+ cation, whereas other metal cations do not induce such a change. The chemosensor 2 showed remarkably anti-interference ability toward other metal cations and the detection limit toward Hg2+ was 1.5 × 10-5 M. Copyright Taylor & Francis Group, LLC.
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.
Synthesis, bioactivity, and the anion-binding property of 2-sulfydryl-1,3,4-thiodiazole derivatives
Shang, Xuefang,Li, Wanli,Wei, Xiaofang,Zhang, Huanle,Fu, Zhiyuan,Zhang, Jinlian,Xu, Xiufang
, p. 142 - 149 (2015)
Two new compounds (1 and 2) containing 2-sulfydryl-1,3,4-thiodiazole have been synthesized and optimized. They both showed wide antibacterial activity for colon bacillus, Staphylococcus aureus, S. albus, dysentery bacillus and inferior activity for Bacillus subtilis. In addition, their binding properties were evaluated for biologically important anions (F-, Cl-, Br-, I-, AcO-, and H2PO4 -) by theoretical investigation, UV-vis, fluorescence, and 1H NMR titration experiments, and they displayed strong binding ability for H2PO4 - without the interference of other anions tested. Especially the binding ability of compound 2 containing anthracene with H2PO4- was 1000 times stronger than that of compound 1 containing nitrobenzene. Two compounds based on 2-sulfydryl-1,3,4-thiodiazole have both properties of anion recognition and antibacterial activity.
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.
Characterization of domain-specific interaction of synthesized dye with serum proteins by spectroscopic and docking approaches along with determination of in vitro cytotoxicity and antiviral activity
Rudra, Suparna,Dasmandal, Somnath,Patra, Chiranjit,Patel, Biman Kumar,Paul, Suvendu,Mahapatra, Ambikesh
, p. 3773 - 3790 (2018)
The interaction between a synthesized dye with proteins, bovine, and human serum albumin (BSA, HSA, respectively) under physiological conditions has been characterized in detail, by means of steady-state and time-resolved fluorescence, UV–vis absorption, and circular dichroism (CD) techniques. An extensive time-resolved fluorescence spectroscopic characterization of the quenching process has been undertaken in conjugation with temperature-dependent fluorescence quenching studies to divulge the actual quenching mechanism. From the thermodynamic observations, it is clear that the binding process is a spontaneous molecular interaction, in which van der Waals and hydrogen bonding interactions play the major roles. The UV–vis absorption and CD results confirm that the dye can induce conformational and micro-environmental changes of both the proteins. In addition, the dye binding provokes the functionality of the native proteins in terms of esterase-like activity. The average binding distance (r) between proteins and dye has been calculated using FRET. Cytotoxicity and antiviral effects of the dye have been found using Vero cell and HSV-1F virus by performing MTT assay. The AutoDock-based docking simulation reveals the probable binding location of dye within the sub-domain IIA of HSA and IB of BSA.
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.
Design, Synthesis, Antibacterial Activity, and Mechanisms of Novel 1,3,4-Thiadiazole Derivatives Containing an Amide Moiety
Wu, Zhibing,Shi, Jin,Chen, Jixiang,Hu, Deyu,Song, Baoan
, p. 8660 - 8670 (2021)
To discover novel antibacterial agents, a series of novel 1,3,4-thiadiazole derivatives containing an amide moiety were designed and synthesized, and their antibacterial activities were tested. Compound 30 was designed and synthesized according to the CoMFA model. Compound 30 exhibited higher antibacterial activities against Xanthomonas oryzae pv. oryzicola and Xanthomonas oryzae pv. oryzae, with EC50 values of 2.1 and 1.8 mg/L, respectively, which were superior to those of thiodiazole copper (99.6 and 92.5 mg/L). The protective and curative activities of compound 30 against rice bacterial leaf blight were 51.3 and 46.1%, respectively, which were better than those of thiodiazole copper (37.8 and 38.5%). The protective and curative activities of compound 30 against rice bacterial leaf streak were 45.9 and 40.5%, respectively, which were better than those of thiodiazole copper (36.2 and 31.1%). In addition, the protective activity of compound 30 against rice bacterial leaf streak was related to increased activities of related defense enzymes and upregulated the differentially expressed proteins of the glycolysis/gluconeogenesis pathway.
