5351-66-6

Basic information

• Product Name: 2-(aminothioxomethyl)benzohydrazide
• Synonyms: 2-(aminothioxomethyl)benzohydrazide;1-Benzoylthiosemicarbazide;Benzoylthiosemicarbazide;N'-[Amino(thiocarbonyl)]benzohydrazide;1-Benzoyl-3-thio-semicarbazide;Ai3-51986;Benzoic acid 2-(aminothioxomethyl)hydrazide (9ci);Brn 2050099
• CAS NO: 5351-66-6
• Molecular Formula: C₈H₉N₃OS
• Molecular Weight: 195.24156
• EINECS: 226-328-6
• Mol File: 5351-66-6.mol
• Article Data: 45

Chemical Properties

• Melting Point: 199-200 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.325g/cm³
• Refractive Index: 1.658
• PKA: 10.09±0.70(Predicted)
• CAS DataBase Reference: 2-(aminothioxomethyl)benzohydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(aminothioxomethyl)benzohydrazide(5351-66-6)
• EPA Substance Registry System: 2-(aminothioxomethyl)benzohydrazide(5351-66-6)

Safety Data

• Hazardous Substances Data: 5351-66-6(Hazardous Substances Data)

Usage

General Description

2-(aminothioxomethyl)benzohydrazide is a chemical compound with the molecular formula C8H8N4OS. It is a derivative of benzohydrazide and contains a thioamide functional group, which consists of a carbon atom doubly bonded to a sulfur atom and singly bonded to a nitrogen atom. 2-(aminothioxomethyl)benzohydrazide has potential applications in the field of medicinal chemistry due to its pharmacological properties, including its ability to act as an intermediate in the synthesis of pharmaceuticals. Its structure and properties make it potentially useful for the development of drugs that target specific biological processes or disease pathways. Additionally, it may be used as a reagent in organic synthesis for the preparation of other bioactive compounds.

InChI:InChI=1/C8H9N3OS/c9-8(13)11-10-7(12)6-4-2-1-3-5-6/h1-5H,(H,10,12)(H3,9,11,13)

Upstream product

• 98-88-4 benzoyl chloride 
• 79-19-6 thiosemicarbazide 
• 93-89-0 benzoic acid ethyl ester 
• 100-52-7 benzaldehyde 
• 93-58-3 benzoic acid methyl ester 
• 613-94-5 benzoic acid hydrazide 
• 65-85-0 benzoic acid 
• 2290-65-5 trimethylsilyl isothiocyanate 
• 1147550-11-5 ammonium thiocyanate 
• 333-20-0 potassium thioacyanate 

Downstream Products

• 58975-55-6 N-(2-benzoylhydrazine-1-carbonothioyl)benzamide 
• 787-84-8 N'-benzoylbenzohydrazide 
• 2002-03-1 2-amino-5-phenyl-1,3,4-thiadiazole 
• 28898-88-6 N-(5-phenyl-1,3,4-thiadiazol-2-yl)acetamide 
• 56364-68-2 3-phenyl-[1,2,4]triazolo[3',4':2,3]thiazolo[4,5-b]quinoxaline 
• 56364-67-1 benzoic acid N'-thiazolo[2,3-b]quinoxalin-2-yl-hydrazide 
• 47223-30-3 benzoic acid N'-(4-amino-5-phenyl-thiazol-2-yl)-hydrazide 
• 26542-57-4 3-phenyl-5-methylthiazolo-<2,3-c>-s-triazole 
• 26542-64-3 3-phenyl-5-phenylthiazolo-<2,3-c>-s-triazole 
• 155811-65-7 C₁₈H₁₃N₅O₃S 
• 155811-73-7 C₁₉H₁₅N₅O₃S 
• 155811-89-5 C₁₈H₁₂ClN₅O₃S 
• 3414-94-6 5-phenyl-4H-1,2,4-triazol-3-thiol 
• 42484-83-3 7-methyl-2-phenyl-5H-1,3,4-thiadiazolo<3,2-a>pyrimidin-5-one 

Relevant articles and documents

Development of phenyltriazole thiol-based derivatives as highly potent inhibitors of DCN1-UBC12 interaction

Defective in cullin neddylation 1(DCN1) is a co-E3 ligase that is important for cullin neddylation. Dysregulation of DCN1 highly correlates with the development of various cancers. Herein, from the initial high-throughput screening, a novel hit compound 5a containing a phenyltriazole thiol core (IC50 value of 0.95 μM for DCN1-UBC12 interaction) was discovered. Further structure-based optimization leads to the development of SK-464 (IC50 value of 26 nM). We found that SK-464 not only directly bound to DCN1 in vitro, but also engaged cellular DCN1, suppressed the neddylation of cullin3, and hindered the migration and invasion of two DCN1-overexpressed squamous carcinoma cell lines (KYSE70 and H2170). These findings indicate that SK-464 may be a novel lead compound targeting DCN1-UBC12 interaction.

A novel approach to the synthesis of 1,3,4-thiadiazole-2-amine derivatives

The main purpose of the study was the development of a new method for synthesis of 1,3,4-thiadiazol-2-amine derivatives in a one-pot manner using the reaction between a thiosemicarbazide and carboxylic acid without toxic additives such as POCl3 or SOCl2. The reaction was investigated in the presence of polyphosphate ester (PPE). It was found that, in the presence of PPE, the reaction between the thiosemicarbazide and carboxylic acid proceeds in one-pot through three steps with the formation of corresponding 2-amino-1,3,4-thiadiazole. Using the developed approach five, 2-amino-1,3,4-thiadiazoles were synthesized. The structures of all compounds were proven by mass spectrometry, IR, and NMR spectroscopies.

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.