14731-25-0

Usage

InChI:InChI=1/C9H9N3S2/c1-6-2-4-7(5-3-6)10-8-11-12-9(13)14-8/h2-5H,1H3,(H,10,11)(H,12,13)

Upstream product

• 125908-36-3 1-propyl-6-tolyl-2,5-dithiobiurea 
• 106-49-0 p-toluidine 
• 622-59-3 1-isothiocyanato-4-methylbenzene 
• 75-15-0 carbon disulfide 
• 13278-67-6 4-(4-methylphenyl)-3-thiosemicarbazide 
• 125908-37-4 1-butyl-6-tolyl-2,5-dithiobiurea 
• 125908-31-8 1-ethyl-6-tolyl-2,5-dithiobiurea 
• 125908-27-2 1-methyl-6-tolyl-2,5-dithiobiurea 
• 859084-32-5 3-p-tolylthiocarbamoyl-dithiocarbazic acid methyl ester 

Downstream Products

• 14731-49-8 (5-benzylsulfanyl-[1,3,4]thiadiazol-2-yl)-p-tolyl-amine 
• 52494-18-5 [5-(4-methyl-anilino)-[1,3,4]thiadiazol-2-ylsulfanyl]-acetic acid ethyl ester 
• 42238-71-1 6-methyl-N-(p-tolyl)benzo[d]thiazol-2-amine 
• 85063-53-2 N-(4-chlorophenyl)-6-methylbenzo[d]thiazol-2-amine 
• 17076-42-5 N,N'-di-p-tolyl-[1,3,4]thiadiazole-2,5-diamine 
• 17076-46-9 5-(4-methyl-anilino)-4-p-tolyl-2,4-dihydro-[1,2,4]triazole-3-thione 
• 27385-89-3 5-(4-methyl-anilino)-3H-[1,3,4]thiadiazole-2-thione; 4-methyl-aniline salt 
• 27385-96-2 N-benzyl-N'-p-tolyl-[1,3,4]thiadiazole-2,5-diamine 
• 21123-72-8 5-(4-methyl-anilino)-4-phenyl-2,4-dihydro-[1,2,4]triazole-3-thione 
• 21123-54-6 N-phenyl-N'-p-tolyl-[1,3,4]thiadiazole-2,5-diamine 
• 27385-90-6 5-(4-methyl-anilino)-3H-[1,3,4]thiadiazole-2-thione; 4-chloro-aniline salt 
• 27385-93-9 4-(4-chloro-phenyl)-5-(4-methyl-anilino)-2,4-dihydro-[1,2,4]triazole-3-thione 
• 27385-94-0 N-(4-chloro-phenyl)-N'-p-tolyl-[1,3,4]thiadiazole-2,5-diamine 
• 42254-17-1 3-benzylsulfanyl-7-methyl-benzo[4,5]thiazolo[2,3-c][1,2,4]triazole 

Relevant academic research and scientific papers

CERTAIN NEW 4-(2-((5-(SUBSTITUTEDAMINO)-1,3,4-THIADIAZOLE-2-YL)THIO)ACETYL)BENZENESULPHONEAMIDE DERIVATIVES AND A METHOD FOR THE SYNTHESIS OF SAID DERIVATIVES

The invention relates to a certain new 4-(2-((5-(substitutedamino)-1,3,4-thiadiazole-2-yl)thio)acetyl)benzenesulphonamide derivatives for use in pharmaceutics, chemical and pharmaceutical industry, and to a method for the synthesis of said derivatives.

Synthesis and antitumor activity of novel pyridazinone derivatives containing 1,3,4-thiadiazole moiety

A series of novel pyridazinone derivatives containing the 1,3,4-thiadiazole moiety were synthesized and characterized by 1H NMR, 13C NMR, spectroscopies HRMS and IR. Among them, the structure of compound 5c (2-(Tert-butyl)?4-chloro-5-((5-((2-ethylphenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One) was unambiguously confirmed via single crystal X-ray diffraction analysis. The inhibitory activity of all the target compounds against MGC-803 and Bcap-37 was determined by MTT assay, with doxorubicin (the inhibition rates were 95.5 ± 0.4% and 95.7 ± 1.0% respectively) as a control. The preliminary results showed that the inhibitory activity of compound 5n (2-(Tert-butyl)?4-chloro-5-((5-((3-fluorophenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One) was superior to the others. The inhibition rates of MGC-803 and Bcap-37 cells were 86.3 ± 2.2% and 92.3 ± 0.6% at a concentration of 10 μmol/L, respectively. The preliminary structure-activity relationship showed that when the 2-position of the benzene ring was substituted by a methyl group, such as compound 5j (2-(Tert-butyl)?4-chloro-5-((5-((2,3-dimethylphenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One), it exhibited good anticancer activity on MGC-803 cells. Besides, introducing fluorine, chlorine, or trifluoromethyl group onto the benzene ring, such as compound 5 m (2-(Tert-butyl)?4-chloro-5-((5-((4-(trifluoromethoxy)phenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One), displayed good anticancer activity on MGC-803 and Bcap-37 cells.

Synthesis and characterization of a new series of thiadiazole derivatives as potential anticancer agents

Cancer is one of the most common causes of death in the world. Despite the importance of combating cancer in healthcare systems and research centers, toxicity in normal tissues and the low efficiency of anticancer drugs are major problems in chemotherapy. Nowadays the aim of many medical research projects is to discover new safer and more effective anticancer agents. 1,3,4-Thiadiazole compounds are important fragments in medicinal chemistry because of their wide range of biological activities, including anticancer activities. The aim of this study was to determine the capacity of newly synthesized 1,3,4-thiadiazole compounds as chemotherapeutic agents. The structures of the obtained compounds were elucidated using 1H-NMR, 13C-NMR and mass spectrometry. Although the thiadiazole derivatives did not prove to be significantly cytotoxic to the tumour tissue cultures, compound 4i showed activity against the C6 rat brain cancer cell line (IC50 0.097 mM) at the tested concentrations.

Novel 1,3,4-thiadiazole compounds as potential MAO-A inhibitors-design, synthesis, biological evaluation and molecular modelling

Monoamine oxidases (MAOs) are important drug targets for the management of neurological disorders. Herein, a series of new 1,3,4-thiadiazole derivatives bearing various alkyl/arylamine moieties as MAO inhibitors were designed and synthesized. All of the compounds were more selective against hMAO-A than hMAO-B. The half maximal inhibitory concentration (IC50) values of most of the compounds were lower than that of the common drug moclobemide (IC50 = 4.664 μM) and compound 6b was proven to be the most active compound (IC50 = 0.060 μM). Moreover, it was seen that compound 6b showed a similar inhibition profile to that of clorgyline (IC50 = 0.048 μM). The inhibition profile was found to be reversible and competitive for compound 6b with MAO-A selectivity. Molecular modelling studies aided in the understanding of the interaction modes between compound 6b and MAO-A. Furthermore, this compound was predicted to have a good pharmacokinetic profile and high BBB penetration. Therefore, such compounds are of interest towards developing new MAO inhibitors.

Synthesis and antifungal activities of ω-(5-arylamino-1,3,4-thiadiazol-2-thio)-ω(1H-1,2,4-triazol-1-yl) acetophenones

Several ω-(5-arylamino-1,3,4-thiadiazol-2-thiol)-ω-(1H-1,2,4-triazol-1- yl)acetophenones 4a-i have been synthesized. The representative compounds exhibit some antifungal and plant growth regulatory activities. The structures of these compounds have been confirmed by elemental analyses, 1H NMR, IR and MS spectra.

an interesting isomerization: synthesis of mesoionic 5-arylamino-1,3,4-thiadiazolium-2-thiolates by using ω-bromo-ω-(1H-1,2,4-triazol-1-yl)acetophenone as catalyst

Mesoionic 5-arylamino-1,3,4-thiadiazolium-2-thiolates 7a-f were prepared by the isomerization of 5-arylamino-1,3,4-thiadiazol-2-thiones 5a-f by using ω-bromo-ω-(1H-1,2,4-triazol-1-yl)acetophenone 6 as catalyst. All the structures of mesoionic synthesized were confirmed by elemental analyses, 1H NMR, IR and MS spectral data. We have also determined the x-ray photoelectron spectroscopy (XPS) of the mesoionic and their precursors. A comparison of XPS spectra between the mesoionic and their precursors showed that the charge separation in mesoionic is distinctly larger than in their precursors.

Alkali catalyzed thermal cyclization of 1-substituted and 1,6-disubstituted 2,5-dithiobiureas: Formation of 1,2,4-triazolidine-3,5-dithiones and/or 1,3,4-thiadiazoline-5-thiones

Alkali catalyzed thermal cyclization of 1-alkyl and 1,6-dialkyl-2,5-dithiobiureas (I, R=alkyl, R'=H and R=R'=alkyl) results in the formation of 4-alkyl-1,2,4-triazolidine-3,5-dithiones (V) (alkyl=Me or Et) and 2-alkylamino-Δ2-1,3,4-thiadiazoline-5-thiones (VI) (alkyl=n-Pr or n-Bu).Under the same conditions, 1-alkyl-6-aryl-2,5-dithiobiureas (I, R=alkyl, R'=aryl) give 2-arylamino-Δ2-1,3,4-thiadiazoline-5-thiones (IX) (alkyl=Me, Et, n-Pr or n-Bu) and 4-alkyl-1,2,4-triazolidine-3,5-dithiones (V) also when the alkyl groups are Me or Et.