55774-34-0

Basic information

• Product Name: 5-(ETHYLAMINO)-1,3,4-THIADIAZOLE-2-THIOL
• Synonyms: 1,3,4-Thiadiazole-2-thiol,5-ethylamino- (6CI);2-Ethylamino-5-mercapto-1,3,4-thiadiazole;5-(Ethylamino)-1,3,4-thiadiazole-2(3H)-thione;5-(Ethylamino)-1,3,4-thiadiazole-2-thiol;5-Ethylamino-3H-[1,3,4]thiadiazole-2-thione
• CAS NO: 55774-34-0
• Molecular Formula: C₄H₇N₃S₂
• Molecular Weight: 161.25
• Mol File: 55774-34-0.mol

Chemical Properties

• Boiling Point: 224.9 °C at 760 mmHg
• Flash Point: 89.8 °C
• Appearance: /
• Density: 1.54 g/cm³
• Vapor Pressure: 0.0887mmHg at 25°C
• Refractive Index: 1.748
• CAS DataBase Reference: 5-(ETHYLAMINO)-1,3,4-THIADIAZOLE-2-THIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(ETHYLAMINO)-1,3,4-THIADIAZOLE-2-THIOL(55774-34-0)
• EPA Substance Registry System: 5-(ETHYLAMINO)-1,3,4-THIADIAZOLE-2-THIOL(55774-34-0)

Safety Data

• Hazardous Substances Data: 55774-34-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C4H7N3S2/c1-2-5-3-6-7-4(8)9-3/h2H2,1H3,(H,5,6)(H,7,8)

Upstream product

• 75-15-0 carbon disulfide 
• 13431-34-0 N-ethylthiosemicarbazide 

Downstream Products

• 79010-45-0 ethyl-(benzylmercapto-[1,3,4]thiadiazol-2-yl)-amine 

Relevant articles and documents

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 of new benzothiazole derivatives bearing thiadiazole as monoamine oxidase inhibitors

Monoamine oxidases (MAO) are enzymes that catalyze the oxidative deamination of monoamines such as dopamine, noradrenaline, adrenaline, and serotonin. Recent studies have shown that numerous benzothiazole derivatives exhibit hMAO inhibitory activity in the micromolar concentration range. In this study, a novel series of benzothiazole-thiadiazole (5a-5l) was synthesized and characterized their chemical structures by 1H-NMR, 13C-NMR, and Mass spectroscopy. These compounds were evaluated as inhibitors for types A and B MAO enzymes. Compounds 5f and 5l were the most active derivatives in the series with an IC50 values of 0.107 ± 0.003 and 0.128 ± 0.004, respectively. Furthermore, cytotoxicity of compounds 5f and 5l were investigated and found as non-cytotoxic.

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 optimization of thiadiazole derivatives as a novel class of substrate competitive c-Jun N-terminal kinase inhibitors

A series of thiadiazole derivatives has been designed as potential allosteric, substrate competitive inhibitors of the protein kinase JNK. We report on the synthesis, characterization and evaluation of a series of compounds that resulted in the identifica

Synthesis of a series of stromelysin-selective thiadiazole urea matrix metalloproteinase inhibitors

The synthesis and enzyme inhibition data for a series of thiadiazole urea matrix metalloproteinase (MMP) inhibitors are described. A broad screening effort was utilized to identify several thiadiazoles which were weak inhibitors of stromelysin. Optimization of the thiadiazole leads to include an α-amino acid side chain with variable terminal amide substituents provided a series of ureas which were moderately effective stromelysin inhibitors, with K(i)'s between 0.3 and 1.0 μM. The most effective analogues utilized an L-phenylalanine as the amino acid component. In particular, unsubstituted 46 had a K(i) of 710 nM, while the p-fluoro analogue 52 displayed increased potency (100 nM). Stromelysin inhibition was further improved using a pentafluorophenylalanine substituent which resulted in 70, a 14 nM inhibitor. While gelatinase inhibition was generally poor, the use of 1-(2-pyridyl)piperazine as the amide component usually provided for enhanced activity, with 71 inhibiting gelatinase with a K(i) of 770 nM. The combination of this heterocycle with a p-fluorophenylalanine substituent provided the only analogue, 69, with collagenase activity (13 μM). The SAR for analogues described within this series can be rationalized through consideration of the X-ray structure recently attained for 70 complexed to stromelysin. Uniquely, this structure showed the inhibitor to be completely orientated on the left side of the enzyme cleft. These results suggest that thiadiazole urea heterocycles which incorporate a substituted phenylalanine can provide selective inhibitors of stromelysin. Careful selection of the amide substituent can also provide for analogues with modest gelatinase inhibition.

Process for the production of 2-amino-5-mercapto-1,3,4-thiadiazole

2-Amino-5-mercapto-1,3,4-thiadiazoles can be produced in very high yields from thiosemicarbazides and carbon disulfide in aqueous phase by working in the presence of the corresponding ammonium salt of bis-2,5-mercapto-1,3,4-thiadiazole at a temperature above 40° C. Preferably the process is carried out in the presence of the mother liquor from a previous reaction.

2-Amino-5-hydrocarbyldithio-1,3,4-thiadiazole compounds

Thiadiazole derivatives characterized by the formula: EQU1 where R is hydrocarbyl of from 1 to 30 carbons and R' is hydrogen or hydrocarbyl of from 1 to 30 carbons prepared by the method of contacting a 2-amino-5-mercapto-1,3,4-thiadiazole characterized by the formula: EQU2 sequentially with an alkali metal hydroxide and a hydrocarbyl sulfenyl bromide characterized by the formula R-S-Br where R and R' are as heretofore defined. Hydrocarbon oil compositions comprising a hydrocarbon oil of lubricating viscosity containing between about 0.01 and 50 wt. % of said amino hydrocarbyldithio thiadiazole.