953-90-2

Usage

Chemical class

Thiazole

Type of compound

Heterocyclic

Key structural features

A thiazole ring with a substituted amino group

Common uses

Reagent in organic synthesis and pharmaceutical research

Potential therapeutic applications

Anti-inflammatory and antifungal agent, treatment of various medical conditions

Other studied properties

Antimicrobial and anticancer activities

Versatility

Wide range of potential applications in medicine and pharmacology

Upstream product

• 41731-23-1 2-bromo-5-methyl-1,3-thiazole 
• 63-74-1 sulfanilamide 
• 88614-86-2 N-acetyl-sulfanilic acid-(5-methyl-thiazol-2-ylamide) 
• 855230-93-2 4-nitro-N-5-methyl-thiazol-2-yl-benzenesulfonamide 
• 6325-93-5 p-nitrobenzenesulfonamide 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 121-60-8 p-acetylaminobenzenesulfonyl chloride 

Relevant academic research and scientific papers

Ultrasound accelerated sulfonylation of amines by p-acetamidobenzenesulfonyl chloride using Mg–Al hydrotalcite as an efficient green base catalyst

The sulfonylation reaction of various aliphatic, alicyclic, aromatic, and hetero-aromatic amines with p-acetamidobenzenesulfonyl chloride has been investigated using different types of base catalysis under varied reaction conditions. Mg–Al hydrotalcite, characterizable as an inexpensive, reusable, and green solid catalyst, was found to be the most efficient catalyst, when the reaction is carried out in a minimum volume of solvent (acetone). The reaction was found to be accelerated drastically with the support of ultrasound irradiation, affording the sulfonamides in yields better or equivalent to those obtained under the longer lasting conventional stirring conditions.

Synthesis and structure-activity relationship studies of 4-((2-hydroxy-3-methoxybenzyl)amino)benzenesulfonamide derivatives as potent and selective inhibitors of 12-lipoxygenase

Human lipoxygenases (LOXs) are a family of iron-containing enzymes which catalyze the oxidation of polyunsaturated fatty acids to provide the corresponding bioactive hydroxyeicosatetraenoic acid (HETE) metabolites. These eicosanoid signaling molecules are involved in a number of physiologic responses such as platelet aggregation, inflammation, and cell proliferation. Our group has taken a particular interest in platelet-type 12-(S)-LOX (12-LOX) because of its demonstrated role in skin diseases, diabetes, platelet hemostasis, thrombosis, and cancer. Herein, we report the identification and medicinal chemistry optimization of a 4-((2-hydroxy-3-methoxybenzyl)amino) benzenesulfonamide-based scaffold. Top compounds, exemplified by 35 and 36, display nM potency against 12-LOX, excellent selectivity over related lipoxygenases and cyclooxygenases, and possess favorable ADME properties. In addition, both compounds inhibit PAR-4 induced aggregation and calcium mobilization in human platelets and reduce 12-HETE in β-cells.

MODULATORS OF IMMUNOINHIBITORY RECEPTOR PD-1, AND METHODS OF USE THEREOF

Disclosed are an assay to identify modulators of the PD-1 :PD-L pathway and PD-1 :PD-L pathway modulators, e.g., compounds and pharmaceutical compositions thereof. Methods for treating diseases influenced by modulation of the PD-1 :PD-L pathway such as, for example, autoimmune diseases, inflammatory disorders, allergies, transplant rejection, cancer, immune deficiency, and other immune system-related disorders, are also disclosed.