836-16-8

Basic information

• Product Name: 2-[(4-nitrophenyl)carbonyl]hydrazinecarbothioamide
• Synonyms: 2-(4-nitrobenzoyl)hydrazine-1-carbothioamide
• CAS NO: 836-16-8
• Molecular Formula: C₈H₈N₄O₃S
• Molecular Weight: 240.2391
• Mol File: 836-16-8.mol
• Article Data: 17

Chemical Properties

• Density: 1.509g/cm³
• Refractive Index: 1.69
• CAS DataBase Reference: 2-[(4-nitrophenyl)carbonyl]hydrazinecarbothioamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(4-nitrophenyl)carbonyl]hydrazinecarbothioamide(836-16-8)
• EPA Substance Registry System: 2-[(4-nitrophenyl)carbonyl]hydrazinecarbothioamide(836-16-8)

Safety Data

• Hazardous Substances Data: 836-16-8(Hazardous Substances Data)

Usage

Compound type

Hydrazine derivative

Functional groups

Carbonyl group, thioamide group

Attached to

4-nitrophenyl ring

Potential applications

Pharmaceuticals, agrochemicals

Function

Potent inhibitor of enzymes and receptors

Suitability

Intermediate in the synthesis of various organic compounds

Handling precautions

Potential hazards associated with handling and use

Upstream product

• 110-86-1 pyridine 
• 122-04-3 4-nitro-benzoyl chloride 
• 79-19-6 thiosemicarbazide 
• 333-20-0 potassium thioacyanate 
• 636-97-5 N-amino-(4-nitrophenyl)carboxamide 
• 619-50-1 4-nitrobenzoic acid methyl ester 
• 2290-65-5 trimethylsilyl isothiocyanate 
• 62-23-7 4-nitro-benzoic acid 

Downstream Products

• 957768-24-0 3,4-diamino-5-(p-nitrophenyl)-1,2,4-triazole 
• 1236182-54-9 3-(4'-nitrophenyl)-5H,13aH-quinolino[3,2-f][1,2,4]triazolo[4,3-b][1,2,4]triazepine 
• 1236182-56-1 9-(3-methyl)-3-(4'-nitrophenyl)-5H,13aH-quinolino-[3,2-f][1,2,4]triazolo[4,3-b][1,2,4]triazepine 
• 1236182-61-8 9-(4-methoxy)-5-(4'-nitrophenyl)-3H,13aH-quinolino[3,2-f][1,2,4]triazolo[4,3-b][1,2,4]triazepine 
• 1236182-62-9 9-(4-methyl)-5-(4'-nitrophenyl)-3H,13aH-quinolino-[3,2-f][1,2,4]triazolo[4,3-b][1,2,4]triazepine 
• 6898-56-2 5-(4-nitrophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 
• 23455-78-9 5-(4-aminophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 
• 90920-54-0 4-nitro-benzoic acid-(4-oxo-thiazolidin-2-ylidenehydrazide) 
• 6898-56-2 3-(p-nitrophenyl)-5-mercapto-4H-1,2,4-triazole 
• 50566-90-0 4-nitro-benzoic acid N'-(4-amino-5-phenyl-thiazol-2-yl)-hydrazide 
• 855737-84-7 S-methyl-1-(4-nitro-benzoyl)-iso thiosemicarbazide 
• 833-63-6 5-(4-nitrophenyl)-1,3,4-thiadiazol-2-amine 

Relevant articles and documents

Design and development of 1,3,5-triazine-thiadiazole hybrids as potent adenosine A2A receptor (A2AR) antagonist for benefit in Parkinson's disease

Various studies showed adenosine A2A receptors (A2ARs) antagonists have profound therapeutic efficacy in Parkinsons Disease (PD) by improving dopamine transmission, thus being active in reversing motor deficits and extrapyramidal symptoms related to the disease. Therefore, in the presents study, we have showed the development of novel 1,3,5-triazine-thiadiazole derivative as potent A2ARs antagonist. In the radioligand binding assay, these molecules showed excellent binding affinity with A2AR compared to A1R, with significant selectivity. Results suggest, compound 7e as most potent antagonist of A2AR among the tested series. In docking analysis with A2AR protein model, compound 7e found to be deeply buried into the cavity of receptor lined via making numerous interatomic contacts with His264, Tyr271, His278, Glu169, Ala63, Val84, Ile274, Met270, Phe169. Collectively, our study demonstrated 1,3,5-triazine-thiadiazole hybrid as a highly effective scaffold for the design of new A2A antagonists.

Identification of 1,2,4-triazoles as new thymidine phosphorylase inhibitors: Future anti-tumor drugs

Thymidine phosphorylase (TP) is over expressed in several solid tumors and its inhibition can offer unique target suitable for drug discovery in cancer. A series of 1,2,4-triazoles 3a–3l has been synthesized in good yields and subsequently inhibitory potential of synthesized triazoles 3a–3l against thymidine phosphorylase enzyme was evaluated. Out of these twelve analogs five analogues 3b, 3c, 3f, 3l and 3l exhibited a good inhibitory potential against thymidine phosphorylase. Inhibitory potential in term of IC50 values were found in the range of 61.98 ± 0.43 to 273.43 ± 0.96 μM and 7-Deazaxanthine was taken as a standard inhibitor with IC50 = 38.68 ± 4.42 μM. Encouraged by these results, more analogues 1,2,4-triazole-3-mercaptocarboxylic acids 4a–4g were synthesized and their inhibitory potential against thymidine phosphorylase was evaluated. In this series, six analogues 4b–4g exhibited a good inhibitory potential in the range of 43.86 ± 1.11–163.43 ± 2.03 μM. Angiogenic response of 1,2,4-triazole acid 4d was estimated using the chick chorionic allantoic membrane (CAM) assay. In the light of these findings, structure activity relationship and molecular docking studies of selected triazoles to determine the key binding interactions was discussed. Docking studies demonstrate that synthesized analogues interacted with active site residues of thymidine phosphorylase enzyme through π-π stacking, thiolate and hydrogen bonding interactions.

Synthesis and biological evaluation of 1,2,4-triazole-3-thione and 1,3,4-oxadiazole-2-thione as antimycobacterial agents

Resistance among dormant mycobacteria leading to multidrug-resistant and extremely drug-resistant tuberculosis is one of the major threats. Hence, a series of 1,2,4-triazole-3-thione and 1,3,4-oxadiazole-2-thione derivatives (4a–5c) have been synthesized and screened for their antitubercular activity against Mycobacterium tuberculosis H37Ra (H37Ra). The triazolethiones 4b and 4v showed high antitubercular activity (both MIC and IC50) against the dormant H37Ra by in vitro and ex vivo. They were shown to have more specificity toward mycobacteria than other Gram-negative and Gram-positive pathogenic bacteria. The cytotoxicity was almost insignificant up to 100?μg/ml against THP-1, A549, and PANC-1 human cancer cell lines, and solubility was high in aqueous solution, indicating the potential of developing these compounds further as novel therapeutics against tuberculosis infection.