99073-88-8

Basic information

• Product Name: 2-BROMO-6-ETHOXYCARBONYLBENZOTHIAZOLE
• Synonyms: 2-BROMO-6-ETHOXYCARBONYLBENZOTHIAZOLE;2-BROMOBENZOTHIAZOLE-6-CARBOXYLIC ACID;Ethyl 2-bromobenzothiazole-6-carboxylate;Ethyl 2-bromo-6-benzothiazolecarboxylate;6-Benzothiazolecarboxylic acid, 2-bromo-, ethyl ester;ethyl 2-bromobenzo[d]thiazole-6-carboxylate;ethyl 2-broMo-1,3-benzothiazole-6-carboxylate;2-BroMo-benzothiazole-6-carboxylic acid ethyl ester
• CAS NO: 99073-88-8
• Molecular Formula: C₁₀H₈BrNO₂S
• Molecular Weight: 286.14502
• Mol File: 99073-88-8.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 377.583 °C at 760 mmHg
• Flash Point: 182.156 °C
• Appearance: /
• Density: 1.618 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.652
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -1.37±0.10(Predicted)
• CAS DataBase Reference: 2-BROMO-6-ETHOXYCARBONYLBENZOTHIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMO-6-ETHOXYCARBONYLBENZOTHIAZOLE(99073-88-8)
• EPA Substance Registry System: 2-BROMO-6-ETHOXYCARBONYLBENZOTHIAZOLE(99073-88-8)

Safety Data

• RIDADR: UN2811
• Hazardous Substances Data: 99073-88-8(Hazardous Substances Data)

Usage

General Description

2-Bromo-6-ethoxycarbonylbenzothiazole is a relatively obscure chemical, data on its uses, toxicity, and environmental impacts are sparse. It is known that this chemical belongs to the class of organic compounds known as benzothiazoles. Benzothiazoles are essentially aromatic compounds containing a benzene fused to a thiazole ring. However, specifics about the physical and chemical properties unique to 2-Bromo-6-ethoxycarbonylbenzothiazole are not readily available. The bromo and ethoxycarbonyl groups suggest that this compound could be used in the synthesis of various other organic compounds, particularly for biologically active molecules due to its aromatic and heterocyclic nature. It is typical of chemicals in its class to be used in the development of pharmaceuticals, agrochemicals, and dyes.

InChI:InChI=1/C10H8BrNO2S/c1-2-14-9(13)6-3-4-7-8(5-6)15-10(11)12-7/h3-5H,2H2,1H3

Upstream product

• 50850-93-6 ethyl 2-aminobenzothiazole-6-carboxylate 
• 7789-45-9 copper(II)bromide 

Downstream Products

• 290363-29-0 N-[1-(3,4-dichlorobenzyl)piperidin-4-yl]-(6-ethoxycarbonyl-2-benzothiazolylthio)acetamide 
• 625080-89-9 N-[1-(3,4-dichlorobenzyl)piperidin-4-yl]-(6-carboxyl-2-benzothiazolylthio)acetamide 
• 729591-59-7 ethyl 2-(4-trifluoromethylphenyl)benzothiazole-6-carboxylate 
• 19989-64-1 ethyl 1,3-benzothiazole-6-carboxylate 
• 19989-70-9 ethyl 2-phenylbenzo[d]thiazole-6-carboxylate 
• 19989-69-6 2-phenyl-1,3-benzothiazole-6-carboxylic acid 

Relevant articles and documents

New dual ATP-competitive inhibitors of bacterial DNA gyrase and topoisomerase IV active against ESKAPE pathogens

The rise in multidrug-resistant bacteria defines the need for identification of new antibacterial agents that are less prone to resistance acquisition. Compounds that simultaneously inhibit multiple bacterial targets are more likely to suppress the evolution of target-based resistance than monotargeting compounds. The structurally similar ATP binding sites of DNA gyrase and topoisomerase Ⅳ offer an opportunity to accomplish this goal. Here we present the design and structure-activity relationship analysis of balanced, low nanomolar inhibitors of bacterial DNA gyrase and topoisomerase IV that show potent antibacterial activities against the ESKAPE pathogens. For inhibitor 31c, a crystal structure in complex with Staphylococcus aureus DNA gyrase B was obtained that confirms the mode of action of these compounds. The best inhibitor, 31h, does not show any in vitro cytotoxicity and has excellent potency against Gram-positive (MICs: range, 0.0078–0.0625 μg/mL) and Gram-negative pathogens (MICs: range, 1–2 μg/mL). Furthermore, 31h inhibits GyrB mutants that can develop resistance to other drugs. Based on these data, we expect that structural derivatives of 31h will represent a step toward clinically efficacious multitargeting antimicrobials that are not impacted by existing antimicrobial resistance.

NEW CLASS OF DNA GYRASE AND/OR TOPOISOMERASE IV INHIBITORS WITH ACTIVITY AGAINST GRAM-POSITIVE AND GRAM-NEGATIVE BACTERIA

The present invention relates to compounds having a structure of general formula (I), processes for their preparation, pharmaceutical compositions containing them as the active ingredient, to their use as medicaments and to their use in the manufacture of medicaments for use in the treatment of bacterial infections in humans and warm-blooded animals.

SUBSTITUTED BENZOTHIAZOLE AND BENZOXAZOLE DERIVATIVES USEFUL AS INHIBITORS OF DPP-1

The present invention is directed to substituted benzothiazole and benzoxazole derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by DPP-1.