1079-82-9

Basic information

• Product Name: Benzoic acid, 4-methyl-, 2-(aminothioxomethyl)hydrazide
• CAS NO: 1079-82-9
• Molecular Formula: C9H11N3OS
• Molecular Weight: 209.272
• Mol File: 1079-82-9.mol
• Article Data: 21

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 4-methyl-, 2-(aminothioxomethyl)hydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 4-methyl-, 2-(aminothioxomethyl)hydrazide(1079-82-9)
• EPA Substance Registry System: Benzoic acid, 4-methyl-, 2-(aminothioxomethyl)hydrazide(1079-82-9)

Safety Data

• Hazardous Substances Data: 1079-82-9(Hazardous Substances Data)

Upstream product

• 333-20-0 potassium thioacyanate 
• 3619-22-5 p-toluic hydrazide 
• 874-60-2 4-methyl-benzoyl chloride 
• 79-19-6 thiosemicarbazide 
• 99-75-2 4-methyl-benzoic acid methyl ester 
• 99-94-5 p-Toluic acid 
• 2290-65-5 trimethylsilyl isothiocyanate 
• 1147550-11-5 ammonium thiocyanate 
• 5351-23-5 4-hydroxybenzoic acid hydrazide 
• 104-87-0 4-methyl-benzaldehyde 

Downstream Products

• 87220-03-9 4-p-Chlorophenyl-2-p-methylbenzoyl hydrazinothiazole hydrobromide 
• 1303531-61-4 C₁₉H₂₈N₄OS 
• 1303531-62-5 C₁₉H₂₈N₄OS 
• 1303531-63-6 C₁₅H₁₈N₄O₂S 
• 26907-54-0 2-amino-5-(4-methylphenyl)-1,3,4-thiadiazole 
• 111750-57-3 2-chloro-N-[5-(4-methylphenyl)-[1,3,4]-thiadiazol-2-yl]-acetamide 
• 1363773-39-0 3-[4-(3-chlorophenyl)piperazino]propyl[5-(4-methylphenyl)-4H-1,2,4-triazol-3-yl] sulfide 
• 1363773-41-4 3-(4-ethylpiperazino)propyl [5-(4-methylphenyl)-4H-1,2,4-triazol-3-yl]sulfide 
• 3414-96-8 5-p-hydroxyphenyl-4H-1,2,4-triazole-3-thiol 
• 64310-34-5 3,4-dihydro-2H-1,3,4-triazole-2-thione 
• 1620200-70-5 diethyl (3-((5-(p-tolyl)-1H-1,2,4-triazol-3-yl)thio)propyl)phosphonate 
• 1456543-21-7 1-3-[4-(3-chlorophenyl)piperazino]propyl-3-(4-methylphenyl)-4,5-dihydro-1H-1,2,4-triazole-5-thione 
• 1383783-61-6 4-(2-{[5-(4-methylphenyl)-4H-1,2,4-triazol-3-yl]thio}ethoxy)benzaldehyde 

Relevant articles and documents

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.

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.

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.

Efficient synthesis of novel conjugated 1,3,4-oxadiazole-peptides

We were interested in the design and synthesis of novel bioisosteric analogues of leuprolide acetate containing the oxadiazole moiety at the C- or N-terminal of the peptide. An efficient approach for the synthesis of 2-amino-1,3,4-oxadiazoles through the reaction of hydrazide with ammonium thiocyanate and desulfurization reaction of the thiosemicarbazides using different coupling reagents was employed. These compounds are bioisosteres of the amide bond. Furthermore, the coupling of 2-amino-1,3,4-oxadiazoles at the C-terminal of leuprolide analogues was carried out, using a coupling reagent in the solution phase. On the other hand, the addition of a 2-amino-1,3,4-oxadiazole to the N-terminal of the peptide sequence was carried out through the reaction of the 2-amino-1,3,4-oxadiazole with succinic anhydride that led to the formation of a carboxylic acid moiety. Addition of the synthesized oxadiazole containing carboxylic acid to the peptide sequence was performed using a coupling reagent and on the surface of the resin. The synthesized peptides containing the oxadiazole moiety at the C- or N-terminal of the peptide sequence are peptidomimetics of leuprolide acetate. All of the synthesized peptides were purified using preparative HPLC and their structures were confirmed using HR-MS (ESI).