208264-53-3

Usage

Uses

Used in Pharmaceutical Industry:
2-Acetyl-4-bromothiazole is used as an intermediate for the preparation of 2,4-disubstituted thiazole derivatives with biologically active properties. These derivatives have potential applications as survival motor neuron (SMN) protein modulators, which are crucial in the treatment of spinal muscular atrophy and other related neuromuscular disorders.
Used in Chemical Synthesis:
2-Acetyl-4-bromothiazole serves as a key building block in the synthesis of a variety of thiazole-based compounds with diverse applications. These compounds can be further modified to enhance their biological activities, making them valuable in the development of new drugs and therapeutic agents.

Upstream product

• 1696-20-4 4-acetylmorpholine 
• 4175-77-3 2,4-dibromo-1,3-thiazole 

Relevant academic research and scientific papers

D I H YD ROOXAZO LE AND THIOUREA DERIVATIVES MODULATING THE NLRP3 INFLAMMASOME PATHWAY

The invention relates to novel compounds of formulae (I') and (II') for the treatment, alleviation or prevention of diseases, disorders and abnormalities which are responsive to the modulation or inhibition of the activation of a component of the NLRP3 in

Miyaura borylation/Suzuki-Miyaura coupling (MBSC) sequence of 4-bromo-2,4′-bithiazoles with halides: Straightforward access to a heterocylic cluster of d-series of thiopeptide GE2270

Herein, palladium-catalyzed Miyaura borylation of 4-bromo-2,4′-bithiazoles followed by Suzuki-Miyaura cross-coupling reaction (named the MBSC process) with (hetero)aryl- and alkenyl halides is reported. This methodology offers rapid access to various 2′,4-disubstituted 2,4′-bithiazole features including naturally-occurring 4-alkenylated and 4-pyridinylated 2,4′-bithiazoles. To prove its application, a concise approach for the synthesis of a heterocyclic cluster of the thiopeptide d-series antibiotic GE2270 is reported through a late-stage MBSC strategy.

CYCLIC SULFAMIDE COMPOUNDS AND METHODS OF USING SAME

The present disclosure provides, in part, cyclic sulfamide compounds, and pharmaceutical compositions thereof, useful as modulators of Hepatitis B (HBV) core protein, and methods of treating Hepatitis B (HBV) infection.

Pyrrole inhibitors of S-nitrosoglutathione reductase as therapeutic agents

The present invention is directed to inhibitors of S-nitrosoglutathione reductase (GSNOR), pharmaceutical compositions comprising such GSNOR inhibitors, and methods of making and using the same.

Highly efficient, multigram and enantiopure synthesis of (S)-2-(2,4′-bithiazol-2-yl)pyrrolidine

(S)-2-(4-Bromo-2,4′-bithiazole)-1-(tert-butoxycarbonyl)pyrrolidine ((S)-1) was obtained as a single enantiomer and in high yield by means of a two-step modified Hantzsch thiazole synthesis reaction when bromoketone 3 and thioamide (S)-4 were used. Further conversion of (S)-1 into trimethyltin derivative (S)-2 broadens the scope for further cross-coupling reactions.

Discovery of potent and novel S-nitrosoglutathione reductase inhibitors devoid of cytochrome P450 activities

The pyrrole based N6022 was recently identified as a potent, selective, reversible, and efficacious S-nitrosoglutathione reductase (GSNOR) inhibitor and is currently undergoing clinical development for the treatment of acute asthma. GSNOR is a member of the alcohol dehydrogenase family (ADH) and regulates the levels of S-nitrosothiols (SNOs) through catabolism of S-nitrosoglutathione (GSNO). Reduced levels of GSNO, as well as other nitrosothiols (SNOs), have been implicated in the pathogenesis of many diseases including those of the respiratory, cardiovascular, and gastrointestinal systems. Preservation of endogenous SNOs through GSNOR inhibition presents a novel therapeutic approach with broad applicability. We describe here the synthesis and structure-activity relationships (SAR) of novel pyrrole based analogues of N6022 focusing on removal of cytochrome P450 inhibition activities. We identified potent and novel GSNOR inhibitors having reduced CYP inhibition activities and demonstrated efficacy in a mouse ovalbumin (OVA) model of asthma.

ALKYNYL ALCOHOLS AS KINASE INHIBITORS

Selected compounds are effective for prophylaxis and treatment of inflammation and inflammatory disorders, such as NIK-mediated disorders. The invention encompasses novel compounds, analogs, prodrugs and pharmaceutically acceptable salts thereof, pharmaceutical compositions and methods for prophylaxis and treatment of diseases and other maladies or conditions involving, inflammation and the like.

Highly efficient borylation Suzuki coupling process for 4-bromo-2-ketothiazoles: Straightforward access to micrococcinate and saramycetate esters

Image Presented The first palladium-catalyzed borylation of 4-bromo-2-ketothiazoles followed by a Suzuki cross-coupling reaction with haloheteroaromatics using Buchwald's Cy-JohnPhos and XPhos ligands is reported. The methodology has allowed the fast preparation of highly valuable 4-pyridinyl- and 4-thiazolyl-2-ketothiazoles as common subunits of thiopeptide antibiotics. As direct applications, novel concise syntheses of a sulfomycinamate thio-analogue as well as micrococcinate and saramycetate esters are described.

A concise total synthesis of melithiazole C+

A short and convergent synthesis of the myxobacterial antibiotic melithiazole C is described featuring a highly E-selective cross-metathesis as the key step.

Asymmetric synthesis of (1R,2S,3R)-2-acetyl-4-(1,2,3,4- tetrahydroxybutyl)thiazole

Two different methods for preparing the thiazole analogue 3 of the biologically active compound (1R,2S,3R)-2-acetyl-4(5)-(1,2,3,4- tetrahydroxybutyl)imidazole 1 are reported.