26049-70-7

Usage

Uses

Used in Organic Synthesis:
[4-(4-nitrophenyl)-1,3-thiazol-2-yl]hydrazine is used as a synthetic building block for the creation of complex organic molecules. Its unique structure allows for versatile chemical reactions, making it a valuable component in the synthesis of various compounds.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, [4-(4-nitrophenyl)-1,3-thiazol-2-yl]hydrazine is used as a key intermediate in the development of new pharmaceuticals. Its structural properties enable it to be modified and incorporated into drug candidates, potentially leading to the discovery of novel therapeutic agents.
Used in the Preparation of Bioactive Molecules:
[4-(4-nitrophenyl)-1,3-thiazol-2-yl]hydrazine is also utilized as a starting material for the preparation of bioactive molecules with potential applications in the pharmaceutical industry. Its ability to be modified and combined with other chemical entities makes it a valuable asset in the development of new bioactive compounds with specific therapeutic properties.
Used in Research and Development:
[4-(4-nitrophenyl)-1,3-thiazol-2-yl]hydrazine is employed in research and development settings to study its chemical properties, reactivity, and potential applications in various industries. Understanding its behavior in different reaction conditions can lead to the discovery of new synthetic routes and applications in the fields of chemistry and biology.
Used in Chemical Education:
[4-(4-nitrophenyl)-1,3-thiazol-2-yl]hydrazine can be used as a teaching aid in chemical education to demonstrate the principles of organic chemistry, particularly in the context of heterocyclic compounds and their synthesis. Its structure and reactivity can provide valuable insights into the behavior of similar compounds and their potential applications.

InChI:InChI=1/C9H8N4O2S/c10-12-9-11-8(5-16-9)6-1-3-7(4-2-6)13(14)15/h1-5H,10H2,(H,11,12)

Upstream product

• 371938-49-7 acetic acid-{N'-[4-(4-nitro-phenyl)-thiazol-2-yl]-hydrazide} 
• 146942-45-2 3,4,5-Trimethoxy-benzoic acid N'-[4-(4-nitro-phenyl)-thiazol-2-yl]-hydrazide 
• 2104-06-5 2-chloro-4-(4-nitro-phenyl)-thiazole 
• 99-81-0 4-Nitrophenacyl bromide 
• 79-19-6 thiosemicarbazide 
• 100-19-6 (4-nitrophenyl)ethanone 

Downstream Products

• 128228-82-0 2-(3-Methyl-5-thiophen-2-yl-pyrazol-1-yl)-4-(4-nitro-phenyl)-thiazole 
• 128228-85-3 4-(4-Nitro-phenyl)-2-(5-thiophen-2-yl-3-trifluoromethyl-pyrazol-1-yl)-thiazole 
• 117480-99-6 5-Methyl-2-[4-(4-nitro-phenyl)-thiazol-2-yl]-2H-pyrazol-3-ol 
• 84919-03-9 3-Methyl-7-(4-nitro-phenyl)-2H-thiazolo[2,3-c][1,2,4]triazepin-5-one 
• 117481-01-3 ethyl 3-[{4-(4-nitrophenyl)thiazol-2-yl}hydrazono]butanoate 
• 106691-16-1 2-(3,5-diphenyl-1H-pyrazol-1-yl)-4-(4-nitrophenyl)thiazole 
• 106691-15-0 2-(3,5-dimethyl-1H-pyrazol-1-yl)-4-(4-nitrophenyl)thiazole 
• 84919-02-8 3,5-Dimethyl-7-(4-nitro-phenyl)-thiazolo[2,3-c][1,2,4]triazepine 

Relevant academic research and scientific papers

Novel one-pot expeditious synthesis of 2,4-disubstituted thiazoles through a three-component reaction under solvent free conditions

An expeditious one pot method has been developed for the synthesis of 2,4-disubstituted thiazoles under solvent free conditions via a multicomponent approach. Substituted thiazoles were synthesized with high yields by the reaction of cyclic ketones, thios

Novel thiazole–pyrazolone hybrids as potent ACE inhibitors and their cardioprotective effect on isoproterenol-induced myocardial infarction

A facile synthesis of a group of novel thiazole–pyrazolone hybrids and their investigation for angiotensin-converting enzyme (ACE) inhibition are reported in this study. These compounds were synthesized using a well-known approach, based on the condensation of ethyl acetoacetate with thiazolylhydrazines, and characterized by various spectroscopic and analytical techniques. The entire set of compounds displayed a moderate-to-excellent inhibitory activity against ACE. In particular, compound 4i was found to be the most potent ACE inhibitor and was further studied for cardioprotective effects against isoproterenol (ISO)-induced myocardial infarction (MI) in rats. Compound 4i improved the cardiac function and prevented cardiac injury induced by ISO in Sprague Dawley rats. The levels of oxidative stress and proinflammatory cytokines were also restored to near normal by 4i as compared with the ISO group. In the Western blot analysis, compound 4i prevented mitochondrial apoptosis after MI by downregulating the expression of cleaved caspase-3 and Bax, with the upregulation of Bcl-2, as compared with the ISO group.

Discovery of potent anti-tuberculosis agents targeting leucyl-tRNA synthetase

Tuberculosis is a serious infectious disease caused by human pathogen bacteria Mycobacterium tuberculosis. Bacterial drug resistance is a very significant medical problem nowadays and development of novel antibiotics with different mechanisms of action is an important goal of modern medical science. Leucyl-tRNA synthetase (LeuRS) has been recently clinically validated as antimicrobial target. Here we report the discovery of small-molecule inhibitors of M. tuberculosis LeuRS. Using receptor-based virtual screening we have identified six inhibitors of M. tuberculosis LeuRS from two different chemical classes. The most active compound 4-{[4-(4-Bromo-phenyl)-thiazol-2-yl]hydrazonomethyl}-2-methoxy-6-nitro-phenol (1) inhibits LeuRS with IC50 of 6 μM. A series of derivatives has been synthesized and evaluated in vitro toward M. tuberculosis LeuRS. It was revealed that the most active compound 2,6-Dibromo-4-{[4-(4-nitro-phenyl)-thiazol-2-yl]-hydrazonomethyl}-phenol inhibits LeuRS with IC50 of 2.27 μM. All active compounds were tested for antimicrobial effect against M. tuberculosis H37Rv. The compound 1 seems to have the best cell permeability and inhibits growth of pathogenic bacteria with IC50 = 10.01 μM and IC90 = 13.53 μM.

Synthesis and characterisation of some novel indeno[1,2-c]pyrazoles

1-(Benzothiazol-2-yl)-4-phenylindeno[1,2-c]pyrazoles (1) and 1-(4-arylthiazol-2-yl)-4-phenylindeno[1,2-c]pyrazoles (2) have been synthesised by the reaction between 1-oxo-3-phenylindan-2-carboxaldehyde (4) and 2-hydrazinobenzothiazoles or 2-hydrazinothiazoles.

Spectrophotometric and polarographic studies on the kinetics of hydrolysis of N-(6-methyl-5-nitropyridin-2-yl methylidene)-N′-(substituted thiazol-2-yl)hydrazines

The kinetics of the hydrolysis of hydrazpne derived from nitropyridine 2-carboxaldehyde and 2-hydrazino-4-substituted thiazoles la-e in 10% (v/v) DMF-buffer mixture has been investigated by applying two independent and different techniques viz UV-spectrop

MAOI activity of some novel series of substituted thiazol-2-yl-hydrazines

Three series of 2-thiazolylhydrazines were synthetized and evaluated for their MAO inhibitory (MAOI) activity, both by in vivo tests, to assay their influence on several MAOI activity-related parameters (the variation on blood pressure induced by tyramine

Reinvestigation of the Reported Preparation of 3-(4-Nitrophenyl)thiazolotriazepines

2-(1H-Pyrazol-1-yl)-4-(4-nitrophenyl)thiazoles 2a and 2b, resulting from the condensation of 2-hydrazino-4-(4-nitrophenyl)thiazole (1) and acetylacetone and dibenzoylmethane, respectively, were previously misassigned as 3-(4-nitrophenyl)thiazolo2,3-c