59587-30-3

Usage

Uses

Used in Pharmaceutical Synthesis:
2-Benzothiazolecarboxylic acid, 6-hydroxy-, ethyl ester (9CI) is used as a key intermediate in the synthesis of pharmaceuticals for its potential biological activities. Its antifungal and antitumor properties make it a promising candidate for the development of new drugs targeting various diseases.
Used in Agrochemical Synthesis:
In the agrochemical industry, 2-Benzothiazolecarboxylic acid, 6-hydroxy-, ethyl ester (9CI) is utilized as a building block in the synthesis of agrochemicals. Its potential biological activities can be harnessed to develop new compounds for crop protection and pest control.
Used in Organic Compound Synthesis:
2-Benzothiazolecarboxylic acid, 6-hydroxy-, ethyl ester (9CI) is employed as a versatile building block in the synthesis of various organic compounds. Its ability to participate in different chemical reactions allows researchers and chemists to create new compounds with diverse applications in various industries.
Used in Chemical Research:
In the field of chemical research, 2-Benzothiazolecarboxylic acid, 6-hydroxy-, ethyl ester (9CI) is used as a subject of study for its potential biological activities and its role in chemical synthesis. Researchers are exploring its antifungal and antitumor properties, as well as its potential applications in the development of new compounds and materials.

Upstream product

• 59587-31-4 S-(2,5-dihydroxy-phenyl)-cysteine ethyl ester 
• 64-17-5 ethanol 
• 389135-53-9 ethyl (R)-2-amino-3-(2,5-dihydroxyphenylsulfanyl)propanoate hydrochloride 
• 67-56-1 methanol 
• 106-51-4 p-benzoquinone 
• 868-59-7 L-cysteine ethyl ester hydrochloride 
• 129340-65-4 ethyl S-(2,5-dihydroxyphenyl)cysteinate 
• 389135-55-1 Ethyl 2-ethoxy-7-hydroxy-2H-benzo[1,4]thiazine-3-carboxylate 

Downstream Products

• 129058-50-0 6-hydroxybenzo[d]thiazole-2-carboxylic acid 
• 55318-95-1 2-Carbamoyl-6-hydroxybenzothiazin 
• 313371-32-3 ethyl 6-methoxybenzothiazole-2-carboxylate 
• 13599-84-3 6-hydroxybenzothiazole 

Relevant academic research and scientific papers

Benzo thiazole carboxamides and application thereof

The invention belongs to the technical field of medicines and relates to a benzothiazole formamide compound and application thereof. The benzothiazole formamide compound comprises a derivative of the benzothiazole formamide compound and pharmaceutically applicable salt; a general molecular formula is shown in the description, wherein R1, R2 and Ar are described as claims and the description. The benzothiazole formamide compound and addition salt of the pharmaceutically applicable acid of the compound can be combined with an existing medicine or can be independently utilized as an epidermal growth factor tyrosine kinase inhibitor for treating related diseases of epidermal growth factor acceptor signal transduction disorder, such as small cell lung cancer, squamous cancer, glandular cancer, large cell lung cancer, colorectal cancer, breast cancer, ovarian cancer and renal cell carcinoma. A formula is shown in the description.

Design, synthesis and cytotoxic evaluation of a novel series of benzo[d]thiazole-2-carboxamide derivatives as potential EGFR inhibitors

A novel series of benzo[d]thiazole-2-carboxamide derivatives have been de novo designed based on virtual screening methods. The target compounds were synthesized and evaluated for the cytotoxicity against epidermal growth factor receptor high-expressed cancer cell lines (A549, HeLa, and SW480), epidermal growth factor receptor low-expressed cell line (HepG2) and human liver normal cell line (HL7702). Several target compounds have showed moderate to excellent potency against A549, HeLa, and SW480 and weak cytotoxic effects against HepG2, which implies they are probably epidermal growth factor receptor inhibitors. And scarcely did they exhibit any activities against HL7702, which signifies they are likely to overcome the nonspecific toxicity against normal cells. Especially, the compound 6-[2-(diethylamino)-2-oxoethoxy]-N-(furan-2-ylmethyl)benzo[d]thiazole-2-carboxamide (6i) was identified as a promising agent, exhibiting the most potent cytotoxic activities with IC50 values of 4.05, 12.17, 6.76 μM against the A549, HeLa, and SW480 cell lines, respectively.

A new synthesis of dehydroluciferin [2-(6′-hydroxy-2′- benzothiazolyl)-thiazole-4-carboxylic acid] from 1,4-benzoquinone

A new synthesis of dehydroluciferin [2-(6′-hydroxy-2′- benzothiazolyl)-thiazole-4-carboxylic acid], the oxidative product of luciferin, has been realized starting from 1,4-benzoquinone. Reaction of this compound with l-cysteine ethyl ester, followed by an oxidation-cyclization step afforded 2-carbethoxy-6-hydroxybenzothiazole that was in situ hydrolyzed and decarboxylated to 6-hydroxybenzothiazole. The tert-butyl(dimethyl)silyl ether of this key intermediate was subjected to α-lithiation followed by formylation with DMF, and the resulting aldehyde condensed with l-cysteine ethyl ester. Dehydrogenation of the intermediate thiazolidine followed by deprotection afforded dehydroluciferin in 35% overall yield from 1,4-benzoquinone (69% from 6-hydroxybenzothiazole).

Rapid and specific post-synthesis modification of DNA through a biocompatible condensation of 1,2-aminothiols with 2-cyanobenzothiazole

Post-synthesis modification of DNA is an important way of functionalizing DNA molecules. Herein, we describe a method that first enzymatically incorporates a cyanobenzothiazole (CBT)-modified thymidine. The side-chain handle CBT can undergo a rapid and site-specific cyclization reaction with 1,2-aminothiols to afford DNA functionalization in aqueous solution. Another key advantage of this method is the formation of a single stereo/regioisomer in the process, which allows for precise control of DNA modification to yield a single component for aptamer selection work and other applications. The first enzymatic incorporation of a cyanobenzothiazole (CBT)-modified thymidine has been developed. The side-chain handle CBT can undergo a rapid and site-specific cyclization reaction with 1,2-aminothiols to enable DNA functionalization in aqueous solution. A key advantage of this method is the formation of a single stereo/regioisomer in the process, which allows for precise control of DNA modification to yield a single component (see scheme). Copyright

Synthesis of 2-substituted-6-hydroxy and 6-methoxy benzothiazoles from 1,4-benzoquinone

A few 2-substituted-6-hydroxy and 6-methoxybenzothiazoles have been prepared from ethyl 6-hydroxybenzothiazole-2-carboxylate, obtained by oxidation of ethyl (R)-2-amino-3-(2,5-dihydroxyphenylsulfanyl)propanoate hydrochloride, in turn prepared from 1,4-benzoquinone.

A new synthesis of 2-cyano-6-hydroxybenzothiazole, the key intermediate of d-luciferin, starting from 1,4-benzoquinone

2-Cyano-6-hydroxybenzothiazole is the key intermediate for the synthesis of d-luciferin, the natural substrate of firefly luciferases. A new synthesis of 2-cyano-6-hydroxybenzothiazole has been realized starting from the reaction of 1,4-benzoquinone with l-cysteine ethyl ester, followed by oxidation-cyclization of the intermediate ethyl (R)-2-amino-3-(2,5-dihydroxyphenylsulfanyl)propan-oate hydrochloride to 2-carbethoxy-6-hydroxybenzothiazole. A suitable protection of this intermediate and a conversion to the corresponding nitrile gave, after deprotection, 2-cyano-6-hydroxybenzothiazole (32% yield from 1,4-benzoquinone). This nitrile reacts with d-cysteine to afford d-luciferin at room temperature in nearly quantitative yield (90-95%).

Synthesis of 6-Hydroxybenzothiazole-2-carboxylic Acid

The synthesis of 6-hydroxybenzothiazole-2-carboxylic acid (1) is presented. The benzothiazole ring was obtained by ring contraction of a remarkably stable 2-alkoxy-7-hydroxy-2H-benzo[1,4]thiazine intermediate that could be isolated. 6-Hydroxybenzothiazole