2302-88-7

Basic information

• Product Name: 1-ACETYL-3-THIOSEMICARBAZIDE
• Synonyms: ACETYLTHIOSEMICARBAZIDE;1-ACETYLTHIOSEMICARBAZIDE;1-ACETYL-3-THIOSEMICARBAZIDE;Acetic acid N'-(aminothioxomethyl) hydrazide;1-Acetylthiosemicarbazide,95%;2-acetylhydrazinecarbothioaMide
• CAS NO: 2302-88-7
• Molecular Formula: C₃H₇N₃OS
• Molecular Weight: 133.17
• EINECS: 218-956-4
• Product Categories: Sulphur Derivatives
• Mol File: 2302-88-7.mol

Chemical Properties

• Melting Point: 165-170 °C
• Appearance: /solid
• Density: 1.280 (estimate)
• Refractive Index: 1.7490 (estimate)
• Storage Temp.: 2-8°C(protect from light)
• Water Solubility: Partly soluble in water.
• CAS DataBase Reference: 1-ACETYL-3-THIOSEMICARBAZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ACETYL-3-THIOSEMICARBAZIDE(2302-88-7)
• EPA Substance Registry System: 1-ACETYL-3-THIOSEMICARBAZIDE(2302-88-7)

Safety Data

• Hazard Codes: T
• Statements: 25-36/37/38
• Safety Statements: 24/25-45
• RIDADR: 2811
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 2302-88-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-Acetyl-3-thiosemicarbazide is used as an intermediate for the synthesis of various pharmaceutical compounds. Its unique chemical structure allows it to be a key component in the development of drugs with specific therapeutic applications.
As an intermediate, 1-Acetyl-3-thiosemicarbazide plays a crucial role in the production of medications that target a wide range of health conditions. Its versatility in chemical reactions enables the creation of diverse pharmaceutical products, contributing to the advancement of medical treatments and therapies.

InChI:InChI=1/C3H7N3OS/c1-2(7)5-6-3(4)8/h1H3,(H,5,7)(H3,4,6,8)

Upstream product

• 108-24-7 acetic anhydride 
• 79-19-6 thiosemicarbazide 
• 75-36-5 acetyl chloride 
• 64-19-7 acetic acid 
• 2290-65-5 trimethylsilyl isothiocyanate 
• 1068-57-1 acetic acid hydrazide 

Downstream Products

• 107776-42-1 2-(N'-acetyl-hydrazino)-4-phenyl-thiazole-5-carboxylic acid ethyl ester 
• 108-33-8 5-methyl-1,3,4-thiadiazol-2-amine 
• 20228-06-2 acetic acid N'-(4-phenyl-thiazol-2-yl)-hydrazide 
• 57772-19-7 5-methyl-[1,3,4]thiadiazol-2-ylamine; hydrochloride 
• 46802-88-4 acetic acid N'-(4-amino-5-phenyl-thiazol-2-yl)-hydrazide 
• 4872-77-9 acetic acid N'-[4-(4-methoxy-phenyl)-thiazol-2-yl]-hydrazide 
• 61407-88-3 β-D-ribofuranose 1-acetate 2,3,5-tri-O-benzoate 
• 145142-77-4 2-(2-acetylhydrazino)-4-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-thiazole hydrochloride 
• 34176-52-8 2-hydrazino-4-phenylthiazole 
• 1174757-34-6 N'-(6-benzoyl-4-phenyl-2H-1,3-thiazin-2-ylidene)-methylhydrazide 
• 52838-39-8 5-methyl-[1,3,4]oxadiazol-2-ylamine 
• 1022193-69-6 N'-(2-amino-3-cyano)spiro[pyrrol-5-ylideneacetohydrazide-4,1'-(cyclohexa-2',5'-dienylidene)]propanedinitrile 
• 1022193-73-2 C₂₄H₁₀N₈ 
• 75116-87-9 2-[(N'-Acetyl-hydrazino)-imino-methyl]-1-(2,6-dimethyl-phenyl)-isothiourea; hydrochloride 

Relevant articles and documents

Synthesis of new surfactants mono and bipolar derived from 1,2,4-triazole-5-thione

3-Phenyl-1,2,4-triazole-5-thione (PTS) and 3-methyl-1,2,4-triazole-5-thione (MTS) are prepared in two steps. The first is a condensation of the thiosemicarbazide with the benzoyl chloride and the acetyl chloride for the PTS and MTS respectively in pyridinic medium. This step leads to the formation of 1-benzoylthiosemicarbazide and 1-acetylthiosemicarbazide. The 1-acetylthiosemicarbazide is also prepared with a new method consisted of a simple solvolysis the thiosemicarbazide in acetic acid for 4 hr. The second is the intramolecular cyclization in methanol with the presence of the sodium methalate leads to the formation of the PTS and the MTS in good yields. The alkylation of MTS and PTS under the conditions of solid-liquid phase transfer catalysis (PTC) allowed us to synthesize some new mono and bipolar surfactants compounds derived from 1,2,4-triazole-5-thione in good yields.

Structure-activity relationships of triazole-benzodioxine inhibitors of cathepsin X

Cathepsin X is a cysteine carboxypeptidase that is involved in various physiological and pathological processes. In particular, highly elevated expression and activity of cathepsin X has been observed in cancers and neurodegenerative diseases. Previously, we identified compound Z9 (1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-((4-isopropyl-4H-1,2,4-triazol-3-yl)thio)ethan-1-one) as a potent and specific reversible cathepsin X inhibitor. Here, we have explored the effects of chemical variations to Z9 of either benzodioxine or triazol moieties, and the importance of the central ketomethylenethio linker. The ketomethylenethio linker was crucial for cathepsin X inhibition, whereas changes of the triazole heterocycle did not alter the inhibitory potencies to a greater extent. Replacement of benzodioxine moiety with substituted benzenes reduced cathepsin X inhibition. Overall, several synthesized compounds showed similar or improved inhibitory potencies against cathepsin X compared to Z9, with IC50 values of 7.1 μM–13.6 μM. Additionally, 25 inhibited prostate cancer cell migration by 21%, which is under the control of cathepsin X.

Novel panaxadiol triazole derivatives induce apoptosis in HepG-2 cells through the mitochondrial pathway

In this study, we introduced 1, 2, 4-triazole groups into panaxadiol (PD) to obtain 18 panaxadiol triazole derivatives. Five cancer cells and one normal cell were evaluated for cytotoxicity by MTT assay. The results showed that most of the derivatives could inhibit cancer cell proliferation, and the anti-proliferative activity of compound A1 was the most significant. For HepG-2 cells, the IC50 value was 4.21 ± 0.54 μM, which was nearly 15 times higher than the activity of PD. Further studies showed that compound A1 could induce apoptosis in HepG-2 cells, and could enhance the expression of Cl-caspase-3, Cl-caspase-9 and Cl-PARP. Moreover, Western blot analysis showed that after treating HepG-2 cells with compound A1, the expression of p53 protein was increased and the ratio of Bax/Bcl-2 was gradually increased. The cytoplasmic Bax is then translocated to the mitochondria, causing the release of Cyt c protein. Therefore, the results indicate that compound A1 induces apoptosis through the mitochondrial pathway and can be used the potential to develop new anti-proliferative agents.

1,2,4-Triazole-3-thione Compounds as Inhibitors of Dizinc Metallo-β-lactamases

Metallo-β-lactamases (MBLs) cause resistance of Gram-negative bacteria to β-lactam antibiotics and are of serious concern, because they can inactivate the last-resort carbapenems and because MBL inhibitors of clinical value are still lacking. We previously identified the original binding mode of 4-amino-2,4-dihydro-5-(2-methylphenyl)-3H-1,2,4-triazole-3-thione (compound IIIA) within the dizinc active site of the L1 MBL. Herein we present the crystallographic structure of a complex of L1 with the corresponding non-amino compound IIIB (1,2-dihydro-5-(2-methylphenyl)-3H-1,2,4-triazole-3-thione). Unexpectedly, the binding mode of IIIB was similar but reverse to that of IIIA. The 3 D structures suggested that the triazole–thione scaffold was suitable to bind to the catalytic site of dizinc metalloenzymes. On the basis of these results, we synthesized 54 analogues of IIIA or IIIB. Nineteen showed IC50 values in the micromolar range toward at least one of five representative MBLs (i.e., L1, VIM-4, VIM-2, NDM-1, and IMP-1). Five of these exhibited a significant inhibition of at least four enzymes, including NDM-1, VIM-2, and IMP-1. Active compounds mainly featured either halogen or bulky bicyclic aryl substituents. Finally, some compounds were also tested on several microbial dinuclear zinc-dependent hydrolases belonging to the MBL-fold superfamily (i.e., endonucleases and glyoxalase II) to explore their activity toward structurally similar but functionally distinct enzymes. Whereas the bacterial tRNases were not inhibited, the best IC50 values toward plasmodial glyoxalase II were in the 10 μm range.

Mild and convenient one-pot synthesis of 2-amino-1,3,4-oxadiazoles promoted by trimethylsilyl isothiocyanate (TMSNCS)

A mild, convenient, and efficient one-pot synthesis of amino-1,3,4- oxadiazoles is described. In situ preparation of various thiosemicarbazides by the reaction of different carboxylic acid hydrazides with trimethylsilyl isothiocyanate (TMSNCS), followed by cyclodesulfurization of thiosemicarbazides under basic conditions in the presence of I2/KI resulted in 2-amino-1,3,4-oxadiazoles in high yields (79-94%).

3-Mercapto-1,2,4-triazoles and N-acylated thiosemicarbazides as metallo-β-lactamase inhibitors

The production of β-lactamases is an effective strategy by which pathogenic bacteria can develop resistance against β-lactam antibiotics. While inhibitors of serine-β-lactamases are widely used in combination therapy with β-lactam antibiotics, there are no clinically available inhibitors of metallo-β-lactamases (MBLs), and so there is a need for the development of such inhibitors. This work describes the optimisation of a lead inhibitor previously identified by fragment screening of a compound library. We also report that thiosemicarbazide intermediates in the syntheses of these compounds are also moderately potent inhibitors of the IMP-1 MBL from Pseudomonas aeruginosa. The interactions of these inhibitors with the active site of IMP-1 were examined using in silico methods.

Trimethylsilyl isothiocyanate (TMSNCS): An efficient reagent for the one-pot synthesis of mercapto-1,2,4-triazoles

A mild, convenient, and efficient one-pot synthesis of mercapto-1,2,4- triazoles is described. Various hydrazides efficiently reacted with trimethylsilyl isothiocyanate (TMSNCS) under basic condition to give mercapto-1,2,4-triazoles in high yields.

The synthesis, X-ray crystal structure and optical properties of novel 1-ferrocenyl-2-(3-phenyl-1H-1,2,4-triazol-5-ylthio)ethanone derivatives

A series of novel 1-ferrocenyl-2-(3-phenyl-1H-1,2,4-triazol-5-ylthio)ethanone derivatives was synthesized by the reaction of 3-substituted-1H-1,2,4-triazole-5-thiol and chloroacetyl ferrocene in the presence of sodium hydride and potassium iodide at reflux. The structures of the new compounds were determined by IR and 1H NMR spectroscopy and HRMS. The structure of compound 5c was established by X-ray crystallography. UV-vis absorption and fluorescence spectra were recorded in ethanol and dichloromethane. The results showed that compounds 5a-g display similar absorptions ranging from 300 to 500 nm and maximal emission bands are about 566 nm. The intensity of fluorescence and maximal emission bands are dependent on the groups bonded to triazole rings.

USE OF THIAZOLOIMIDAZOLES, THIAZOLOTETRAZOLES AND THIAZOLOTRIAZOLES AS MGLUR5 ANTAGONISTS

The invention relates to the use of thiazolotriazole, thiazoloimidazole and thiazolotetrazole derivatives of formula (I) in treating diseases and conditions for which antagonism of the mGluR5 receptor is beneficial, in particular substance related disorders. The invention also relates to certain novel derivatives. In addition, the invention relates to compositions containing the derivatives and processes for their preparation.

Synthesis and structure-activity relationship of C-3 substituted triazolylthiomethyl cephems

A series of C-3 substituted triazolylthiomethyl cephems with an aminothiazolemethoxyiminoacetamido side chain at C-7 were synthesized and tested for antimicrobial activity against clinically-relevant isolates. The compound with 3-pyridyl at C-5 and methyl at N-4 of the triazole moiety exhibited good antibacterial activity against both Gram-positive and Gram-negative bacteria, with the exception of pseudomonas spp against which none of the derivatives exhibited favorable activity.