93-85-6

Hazard Information

Chemical Properties

Light brown powder

Antimicrobial activity

2-Aminobenzothiazole-6-carboxylic acid is a synthetic antibacterial agent that inhibits bacterial growth by binding to the enzyme urokinase-type plasminogen (uPA) and preventing it from converting plasminogen to plasmin. This drug has been shown to have inhibitory properties against a wide range of bacteria, including Staphylococcus and Escherichia coli.

Synthesis

540-72-7

150-13-0

93-85-6

Steps for the synthesis of 2-aminobenzothiazole-6-carboxylic acid: (2) Sodium thiocyanate (NaSCN, 65 g, 0.8 mol) was added to a methanol (MeOH) suspension of 4-aminobenzoic acid (1,100 g, 0.73 mol), followed by batch addition of bromine (Br2, 38 mL, 0.73 mol). The reaction mixture was cooled to -10 °C and stirred for 2 hours while keeping the internal temperature below -5 °C. Upon completion of the reaction, the precipitate was collected by filtration and suspended in 350 ml of 1 M hydrochloric acid (HCl). The suspension was heated to reflux and maintained for 30 minutes. After rapid filtration, 150 ml of concentrated hydrochloric acid (HCl) was added to the hot filtrate to give 70 g (42% yield) of 2-aminobenzothiazole-6-carboxylic acid (white solid). The product was dried and used directly without further purification.

References

[1] Patent: US2009/123373, 2009, A1. Location in patent: Page/Page column 14-15

Questions And Answer

• Uses

  2-Aminobenzothiazole-6-carboxylic acid is a heterocyclic organic compound that can be used as an organic intermediate. 2-Aminobenzothiazoles belong to a class of heterocyclic compounds with diverse biological activities. For example, riluzole, clinically used to treat amyotrophic lateral sclerosis (ALS), belongs to the 2-aminobenzothiazole class; fulenteazole has antiviral, anthelmintic, and immunosuppressive activities; N-acyl-substituted 2-aminobenzothiazoles can inhibit HIV; and N-aryl-substituted 2-aminobenzothiazoles have strong anticancer activity. 2-Aminobenzothiazoles are also widely used in the development of antibacterial, antiviral, and anti-inflammatory drugs for the treatment of Parkinson's disease and diabetes. Therefore, 2-aminobenzothiazoles occupy a very important position in medicinal chemistry.;

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