13431-39-5

Basic information

• Product Name: 4-TERT-BUTYL-3-THIOSEMICARBAZIDE
• Synonyms: 4-TERT-BUTYL-3-THIOSEMICARBAZIDE;N1-(TERT-BUTYL)HYDRAZINE-1-CARBOTHIOAMIDE;N-4-TERT-BUTYLTHIOSEMICARBAZIDE;N-(tert-butyl)hydrazinecarbothioamide
• CAS NO: 13431-39-5
• Molecular Formula: C₅H₁₃N₃S
• Molecular Weight: 147.24
• Mol File: 13431-39-5.mol

Chemical Properties

• Melting Point: 139-140°C
• Boiling Point: 211 °C at 760 mmHg
• Flash Point: 81.4 °C
• Appearance: /
• Density: 1.071 g/cm³
• Vapor Pressure: 0.187mmHg at 25°C
• Refractive Index: 1.541
• Water Solubility: Insoluble in water.
• BRN: 507219
• CAS DataBase Reference: 4-TERT-BUTYL-3-THIOSEMICARBAZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-TERT-BUTYL-3-THIOSEMICARBAZIDE(13431-39-5)
• EPA Substance Registry System: 4-TERT-BUTYL-3-THIOSEMICARBAZIDE(13431-39-5)

Safety Data

• Statements: R22:Harmful if swallowed.
• Safety Statements: S22:Do not inhale dust.; S36/37:Wear suitable protective clothing and gloves.
• RIDADR: 2811
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 13431-39-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-TERT-BUTYL-3-THIOSEMICARBAZIDE is used as a reagent in the synthesis of N-substituted 2-amino-5-(2, 4-dihydroxyphenyl)-1, 3, 4-thiadiazoles, which are compounds with demonstrated antiproliferative activity. These synthesized compounds have potential applications in the development of new drugs targeting the inhibition of cell proliferation, which is a crucial aspect in the treatment of various diseases, including cancer.
Used in Chemical Synthesis:
In the chemical industry, 4-TERT-BUTYL-3-THIOSEMICARBAZIDE can be utilized as a building block or intermediate for the synthesis of more complex organic molecules. Its unique structure and reactivity make it a valuable component in the creation of novel compounds with specific properties and applications, such as in materials science, agrochemicals, and other specialty chemicals.

InChI:InChI=1/C5H13N3S/c1-5(2,3)7-4(9)8-6/h6H2,1-3H3,(H2,7,8,9)

Upstream product

• 590-42-1 tert-butyl isothiocyanate 
• 75-15-0 carbon disulfide 
• 75-64-9 tert-butylamine 
• 21184-93-0 N-tert.-Butyl-thiocarbamoylmercaptoessigsaeure 

Downstream Products

• 193345-81-2 5-tert-butylimino-3-(2-chloro-phenyl)-thiazolo[5,4-d]isoxazol-6-ylamine 
• 883036-77-9 C₁₂H₁₇N₃OS 
• 193345-67-4 5-tert-butylimino-3-phenyl-thiazolo[5,4-d]isoxazol-6-ylamine 
• 164404-46-0 5-[(Z)-tert-Butylimino]-1,3-diphenyl-1H-pyrazolo[3,4-d]thiazol-6-ylamine 

Relevant articles and documents

Novel thiosemicarbazone derivatives: In vitro and in silico evaluation as potential mao-b inhibitors

MAO-B inhibitors are frequently used in the treatment of neurodegenerative diseases such as Parkinson’s and Alzheimer’s. Due to the limited number of compounds available in this field, there is a need to develop new compounds. In the recent works, it was shown that various thiosemicarbazone derivatives show hMAO inhibitory activity in the range of micromolar concen-tration. It is thought that benzofuran and benzothiophene structures may mimic structures such as indane and indanone, which are frequently found in the structures of such inhibitors. Based on this view, new benzofuran/benzothiophene and thiosemicarbazone hybrid compounds were synthesized, characterized and screened for their hMAO-A and hMAO-B inhibitory activity by an in vitro fluorometric method. The compounds including methoxyethyl substituent (2b and 2h) were found to be the most effective agents in the series against MAO-B enzyme with the IC50 value of 0.042 ± 0.002 μM and 0.056 ± 0.002 μM, respectively. The mechanism of hMAO-B inhibition of compounds 2b and 2h was investigated by Lineweaver–Burk graphics. Compounds 2b and 2h were reversible and non-competitive inhibitors with similar inhibition features as the substrates. The Ki values of compounds 2b and 2h were calculated as 0.035 μM and 0.046 μM, respectively, with the help of secondary plots. The docking study of compound 2b and 2h revealed that there is a strong interaction between the active sites of hMAO-B and analyzed compound.

Synthesis of novel quinoline-thiosemicarbazide hybrids and evaluation of their biological activities, molecular docking, molecular dynamics, pharmacophore model studies, and ADME-Tox properties

In the present study, a novel series of N-((substituted)carbamothioyl)-2,4-dimethylquinoline-3-carboxamide (7a-7s) was synthesized by microwave-assisted method. Structure of these derivatives was examined by spectroscopic techniques such as 1H NMR, 13C NMR, FT-IR, and ESI-MS. Further, the novel synthesized compounds were evaluated for their in-vitro biological activities against antibacterial, antifungal, antimalarial, and antituberculosis activity as well as for in-silico study. The antimalarial results demonstrated that compounds 7c and 7q (0.02 μg/mL) have notable potency against Plasmodium falciparum compared with chloroquine (0.02 μg/mL); compounds 7l (0.10 μg/mL), 7e, 7s (0.19 μg/mL), 7b, 7p (0.15 μg/mL), 7a, 7f, and 7f (0.25 μg/mL) also exhibited good activity against P. falciparum compared with quinine (0.26 μg/mL) as standard drug. Docking was performed on PFDHFR-TS, given the effect of compounds against the P. falciparum strain was excellent in comparison with standard drug. Molecular docking suggested that compounds 7b, 7i and 7c, 7e, and 7l closely bind with the active site of protein 3JSU and 4DP3, respectively, and compared with biological activity. We have also carried out molecular dynamics simulation on the best dock compound 7e complex with PDB: 3JSU to check the stability of docked complex and their molecular interaction. The calculated ADME-Tox descriptors for the synthesized compounds validated good pharmacokinetics properties, suggesting that these compounds could be used as hit for the development of the new active agents.

Synthesis, cytotoxicity, and in vivo antitumor activity study of parthenolide semicarbazones and thiosemicarbazones

Parthenolide is an important sesquiterpene lactone with potent anticancer activities. In order to further improve its biological activity, a series of parthenolide semicarbazone or thiosemicarbazone derivatives was synthesized and evaluated for their anti

An efficient synthesis of novel carbohydrate and thiosemicarbazone hybrid benzimidazole derivatives and their antimicrobial evaluation

A library of thiosemicarbazide hybrid 2-(aldo-polyhydroxyalkyl)benzimidazole derivatives have been designed and synthesized with simple and eco-friendly methodologies. The structures of the compounds have been elucidated with the aid of elemental analysis, IR, mass and 1H NMR spectral data. These novel synthesized compounds have been evaluated for their antibacterial activity against two gram-positive bacteria (S. aureus and S. pyogenus) and two gram-negative bacteria (P. aeruginosa and E. coli). The title compounds have also been studied for their antifungal activity against C. albicans, A. niger and A. clavatus using the broth dilution technique.

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 and characterization of new thiazolidin-4-one derivatives

The synthesis of some new functionalized thiazolidin-4-one derivatives has been described. The N-substituted-thiosemicarbazides 3a-3i were obtained though the reaction of alkylamines 2a-2i, carbon disulfide, and hydrazine hydrate. The condensation reaction between 3a-3i and 4-amino-2-methanesulfanylpyrimidine-5- carboxaldehyde 1 afforded the thiosemicarbazones 4a-4i. The corresponding thiazolidin-4-ones 5a-5i were prepared by cyclization of 4a-4i with ethyl bromoacetate. The structures of the final products were confirmed by IR, 1H NMR, 13C NMR, and HRMS.

Thiosemicarbazones active against Clostridium difficile

A set of closely related furylidene thiosemicarbazones was prepared and screened against various clinically important Gram-positive bacteria. One compound containing an ethylene spacer and a 5-nitrofuryl group was found to have promising activity against Clostridium difficile.

Synthesis and antitumor activity of new thiosemicarbazones of 2-acetylimidazo[4,5-b]pyridine

A number of thiosemicarbazones of 2-acetyl-imidazo[4,5-b]pyridine were prepared in order to investigate their in vitro antineoplastic activities. Three compounds: (i) 2-acetylimidazo[4,5-b]pyridin-4-tert-butyl-3-thiosemicarbazone [(A7), NSC674098], (ii) 2-acetylimidazo[4,5-e]pyridin-4-tert-butyl-3- thiosemicarbazone [(A9), NSC674099], (iii) 2-acetylimidazo[4,5-i] pyridin-4-cyclohexyl-3-thiosemicarbozone [(A11), NSC674101] showed remarkable activity against some of the cell lines tested. The Biological Evaluation Committee of N.C.I, determined that further secondary testing should be carried out (these compounds were tested against prostate cancer).

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.

Process for producing 2-amino or selected 2-(substituted)amino-5-mercapto-1,3,4-thiadiazole compounds

Disclosed is a process for producing 2-amino or 2-(lower alkyl or phenyl)amino-5-mercapto-1,3,4-thiadiazole compounds by reacting the corresponding thiosemicarbazide with an alkali metal lower alkyl xanthate salt.