4871-22-1

Usage

Uses

Used in Pharmaceutical Industry:
4-(4-BROMOPHENYL)-2(3H)-THIAZOLONE HYDRAZONE is used as a building block for the synthesis of various pharmaceutical compounds. Its unique structure and reactivity allow for further derivatization and modification, which can lead to the development of new drugs and therapeutic agents.
Used in Medicinal Chemistry Research:
4-(4-BROMOPHENYL)-2(3H)-THIAZOLONE HYDRAZONE is used as a valuable target for research and exploration in the realm of chemical and pharmaceutical sciences. Its presence of bromine and thiazolone moieties makes it an interesting subject for studying the synthesis and properties of new compounds with potential medicinal applications.

Upstream product

• 3884-33-1 2-chloro-4-(p-bromophenyl)-thiazole 
• 79-19-6 thiosemicarbazide 
• 1629144-28-0 2-phenoxy-4-(4-bromophenyl)thiazole 
• 99-73-0 para-bromophenacyl bromide 
• 146942-41-8 2-(3,4,5-trimethoxybenzylhydrazino)-4-(4-bromophenyl)thiazole 
• 4872-75-7 acetic acid N'-[4-(4-bromo-phenyl)-thiazol-2-yl]-hydrazide 

Downstream Products

• 357639-22-6 2-(2-(4-bromobenzylidene)hydrazinyl)-4-(4-bromophenyl)thiazole 
• 78559-93-0 N'-[4-(4-bromophenyl)thiazol-2-yl]-N-(4-methoxybenzylidene)hydrazine 
• 146943-04-6 N-[4-(4-bromophenyl)thiazol-2-yl]-N'-(3,4,5-trimethoxybenzylidene)hydrazine 
• 1200127-37-2 1-((3-(benzofuran-2-yl)-1-phenyl-1H-pyrazol-4-yl)methylene)-2-(4-(4-bromophenyl) thiazol-2-yl)hydrazine 
• 955976-70-2 ethyl 1-[4-(4-bromophenyl)thiazol-2-yl]-5-trifluoromethyl-1H-pyrazole-4-carboxylate 
• 307325-10-6 2-(furfurylidine-imino-amino)-4-(p-bromophenyl)thiazole 
• 61323-75-9 7-(4-bromo-phenyl)-4,5-dihydro-2H-thiazolo[2,3-c][1,2,4]triazepin-3-one 
• 61054-54-4 1-(4-bromo-phenyl)-thiazolo[2',3':3,4][1,2,4]triazino[5,6-b]indole 
• 82100-91-2 2-(4'-carboxymethyl-3',5'-dimethylpyrazol-1'-yl)-4-(p-bromophenyl)thiazole 

Relevant academic research and scientific papers

Bromine-containing compounds as antifungal agents

The invention discloses a bromine-containing compound as an antifungal drug. The invention claims to protect a compound as shown in a formula I or pharmaceutically acceptable salt, ester and solvate thereof. In the formula I, R is -NH2 or -N = C(CH3)2. Th

Unique Sulfur-Aromatic Interactions Contribute to the Binding of Potent Imidazothiazole Indoleamine 2,3-Dioxygenase Inhibitors

Indoleamine 2,3-dioxygenase (IDO1) inhibitors are speculated to be useful in cancer immunotherapy, but a phase III clinical trial of the most advanced IDO1 inhibitor, epacadostat, did not meet its primary end point and was abandoned. In previous work, we identified the novel IDO1 inhibitor N-(4-chlorophenyl)-2-((5-phenylthiazolo[2,3-c][1,2,4]triazol-3-yl)thio)acetamide 1 through high-throughput screening (HTS). Herein, we report a structure-activity relationship (SAR) study of this compound, which resulted in the potent IDO1 inhibitor 1-(4-cyanophenyl)-3-(3-(cyclopropylethynyl)imidazo[2,1-b]thiazol-5-yl)thiourea 47 (hIDO IC50 = 16.4 nM). X-ray cocrystal structural analysis revealed that the basis for this high potency is a unique sulfur-aromatic interaction network formed by the thiourea moiety of 47 with F163 and F226. This finding is expected to inspire new approaches toward the discovery of potent IDO1 inhibitors in the future.

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.

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

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.

2,4- and 2,5-disubstituted arylthiazoles: Rapid synthesis by C-H coupling and biological evaluation

Life-threatening infections caused by bacteria that have developed resistance to common antibiotics, such as methicillin-resistant Staphylococcus aureus (MRSA), have become a serious problem in hospitals and other areas all over the world. Thus, the development of an effective class of antibiotics against these bacteria is an urgent subject. Herein, we report a step-economical and diversity-oriented synthesis of a series of 2-arylidenehydrazinyl-4- arylthiazole and 2-arylidenehydrazinyl-5-arylthiazole analogues that utilizes C-H coupling methodologies. A library of 54 new congeners were synthesized and tested for their biological potential. Moreover, new knowledge regarding the structure-activity relationships (SARs) of these heterobiaryl compounds was collected. Copyright

Synthesis and characterization of some transition metal complexes with 4-(phenyl/p-bromophenyl)thiazolyl hydrazone of furfural

Complexes of the type [ML2X2], where L = 2-(furfurylidine-imino-amino)-4-phenylthiazole (FPT) or 2-(furfurylidine-imino- amino)-4-(p-bromophenyl)thiazole (FBPT), M = CoII, CuII and NiII and X = Clsup

Synthesis of some transition metal complexes with 4-(phenyl/p-bromophenyl)thiazolylhydrazone of o-anisaldehyde

Complexes of type ML2X2, where L = 2-(o-anisylidineiminoamino)-4-phenylthiazole (APT) or 2-(o-anisylidinelminoamino)-4-(p-bromophenyl)thiazole (ABPT); M = Co II, NiII, CuII) have been synthesised. The

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