10253-83-5

Basic information

• Product Name: 5-(phenylamino)-1,3,4-thiadiazole-2(3h)-thione
• Synonyms: 4-thiadiazole-2(3h)-thione,5-(phenylamino)-3;4-thiadiazole-2(3h)-thione,5-anilino-3;5-(phenylamino)-1,3,4-thiadiazole-2(3h)-thione;5-anilino-1,3,4-thiadiazole-2(3H)-thione;2-(Phenylamino)-5-mercapto-1,3,4-thiadiazole;1,3,4-Thiadiazole-2(3H)-thione, 5-(phenylamino)-;1,3,4-Thiadiazole-2(3H)-thione, 5-anilino-;Einecs 233-592-6
• CAS NO: 10253-83-5
• Molecular Formula: C₈H₇N₃S₂
• Molecular Weight: 209.29128
• EINECS: 233-592-6
• Mol File: 10253-83-5.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 318.3°Cat760mmHg
• Flash Point: 146.3°C
• Appearance: /
• Density: 1.47g/cm³
• Vapor Pressure: 0.000364mmHg at 25°C
• Refractive Index: 1.765
• CAS DataBase Reference: 5-(phenylamino)-1,3,4-thiadiazole-2(3h)-thione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(phenylamino)-1,3,4-thiadiazole-2(3h)-thione(10253-83-5)
• EPA Substance Registry System: 5-(phenylamino)-1,3,4-thiadiazole-2(3h)-thione(10253-83-5)

Safety Data

• Hazardous Substances Data: 10253-83-5(Hazardous Substances Data)

Usage

General Description

5-(phenylamino)-1,3,4-thiadiazole-2(3h)-thione, also known as phenylaminothiadiazole, is a chemical compound with the molecular formula C7H6N4S. It is a heterocyclic nitrogen-sulfur compound with potential pharmaceutical applications. Phenylaminothiadiazole has been studied for its antimicrobial and anticancer properties, and it has shown potential as a therapeutic agent for the treatment of various diseases. Its molecular structure and chemical properties make it a versatile building block for the synthesis of various pharmaceutical compounds. More research is being conducted to explore the potential therapeutic applications of phenylaminothiadiazole in medicine and drug development.

InChI:InChI=1/C8H7N3S2/c12-8-11-10-7(13-8)9-6-4-2-1-3-5-6/h1-5H,(H,9,10)(H,11,12)

Upstream product

• 2209-59-8 1,6-diphenyl-dithiodiurea 
• 2209-60-1 4-phenyl-[1,2,4]triazolidine-3,5-dithione 
• 61784-88-1 1-ethyl-6-phenyl-2,5-dithiobiurea 
• 7647-01-0 hydrogenchloride 
• 64-19-7 acetic acid 
• 101277-86-5 bis-(anilino-[1,3,4]thiadiazol-2-yl)-disulfide 
• 875815-11-5 N-phenyl-N-(5-thioxo-4,5-dihydro-[1,3,4]thiadiazol-2-yl)-acetamide 
• 387361-80-0 3-phenylthiocarbamoyl-dithiocarbazic acid methyl ester 
• 103-72-0 phenyl isothiocyanate 
• 5351-69-9 4-Phenyl-3-thiosemicarbazide 
• 75-15-0 carbon disulfide 
• 670-54-2 ethenetetracarbonitrile 
• 7664-93-9 sulfuric acid 
• 125908-35-2 1-propyl-6-phenyl-2,5-dithiobiurea 

Downstream Products

• 5585-21-7 (5-methylsulfanyl-[1,3,4]thiadiazol-2-yl)-phenyl-amine 
• 14132-85-5 5-anilino-4-(4-methoxy-phenyl)-2,4-dihydro-[1,2,4]triazole-3-thione 
• 21123-55-7 N-(4-methoxy-phenyl)-N'-phenyl-[1,3,4]thiadiazole-2,5-diamine 
• 77643-06-2 2-anilino-5-phenylcarbamoylmethylthio-1,3,4-thiadiazole 
• 14731-48-7 5-benzylthio-2-phenylamino-1,3,4-thiadiazole 
• 21123-71-7 5-anilino-4-p-tolyl-2,4-dihydro-[1,2,4]triazole-3-thione 
• 21123-54-6 N-phenyl-N'-p-tolyl-[1,3,4]thiadiazole-2,5-diamine 
• 52494-15-2 ethyl 2-[[5-(phenylamino)-1,3,4-thiadiazol-2-yl]thio]acetate 

Relevant articles and documents

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.

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 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.

Synthesis and in vitro evaluation of thiadiazole derivatives as AChE, Bu-ChE and LOX inhibitors

N'-Benzylidene-2-[[5-(phenylamino)-1,3,4-thiadiazol-2-yl]thio]acetohydrazide derivatives (5a-p) were synthesized to screen for their AChE, BuChE and LOX inhibitory activity. The CCK-8 assay was also carried out to determine their cytotoxicity against NIH/3T3 cells. The most potent AChE inhibitors were found as compounds 5m (49.79% ± 3.08) and 5p (42.39% ± 3.19), whereas the most potent BuChE inhibitor was found as compound 5d (35.15% ± 2.21). Among these derivatives, N'-(3-methoxybenzylidene)-2-[[5-(phenylamino)-1,3,4-thiadiazol-2-yl]thio]acetohydrazide (5p) can be considered as the most promising AChE inhibitor due to its low cytotoxicity to NIH/3T3 cells (IC50 > 500 μg/mL). N'-(4-Methoxybenzylidene)-2-[[5-(phenylamino)-1,3,4-thiadiazol-2-yl]thio]a-cetohydrazide (5n) exhibited weak inhibition on LOX (%20.65 ± 0.08), whilst the other compounds were not active.