351520-79-1

Basic information

• Product Name: methyl 4-[(1,3-benzothiazol-2-ylamino)carbonyl]benzoate
• Synonyms: methyl 4-[(1,3-benzothiazol-2-ylamino)carbonyl]benzoate
• CAS NO: 351520-79-1
• Molecular Formula: C16H12N2O3S
• Molecular Weight: 312.34308
• Mol File: 351520-79-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: methyl 4-[(1,3-benzothiazol-2-ylamino)carbonyl]benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-[(1,3-benzothiazol-2-ylamino)carbonyl]benzoate(351520-79-1)
• EPA Substance Registry System: methyl 4-[(1,3-benzothiazol-2-ylamino)carbonyl]benzoate(351520-79-1)

Safety Data

• Hazardous Substances Data: 351520-79-1(Hazardous Substances Data)

Upstream product

• 136-95-8 2-amino-benzthiazole 
• 1571-08-0 methyl 4-formylbenzoate 
• 1679-64-7 Monomethyl terephthalate 
• 220873-58-5 4-(methoxycarbonyl)benzoyl isothiocyanate 
• 7377-26-6 4-Methoxycarbonylbenzoyl chloride 
• 201230-82-2 carbon monoxide 
• 619-44-3 methyl 4-iodobenzoate 

Relevant articles and documents

Tumor-Activated Benzothiazole Inhibitors of Stearoyl-CoA Desaturase

A series of N-acyl benzothiazoles shows selective and potent cytotoxicity against cancer cell lines expressing cytochrome P450 4F11. A prodrug form is metabolized by cancer cells into an active inhibitor of stearoyl-CoA desaturase (SCD). Substantial variation on the acyl portion of the inhibitors allowed the identification of (R)-27, which balanced potency, solubility, and lipophilicity to allow proof-of-concept studies in mice. The prodrugs were activated inside the tumor, where they can arrest tumor growth. Together, these observations offer promise that a tumor-activated prodrug strategy might exploit the essentiality of SCD for tumor growth, while avoiding toxicity associated with systemic SCD inhibition.

Copper promoted C-S and C-N cross-coupling Reactions:The synthesis of 2-(N-Aryolamino)benzothiazoles and 2-(N-Aryolamino)benzimidazoles

The synthesis of 2-(N-aryolamino)benzothiazoles and 2-(N-aryolamino)benzimidazoles has been accomplished in the presence of copper catalyst. These reactions involve C-S and C-N cross-coupling reaction. All electron donating and withdrawing substituent's readily underwent the reaction to give target products in good to excellent yield. In addition, the reaction also gave target product in high yield with bulk scale.

Synthesis of benzamide-benzothiazole conjugates via palladium-catalysed aminocarbonylation (hydrazinocarbonylation)

The palladium-catalysed aminocarbonylation of iodoarenes was investigated using 2-amino- and 2-hydrazinobenzothiazole as N-nucleophile. The reaction proved to be highly chemoselective in all cases: carboxamides and the corresponding carbohydrazides, obtained by the acylation at the nitrogen adjacent to the C-2 of the benzothiazole moiety, were obtained exclusively and isolated in moderate to high yields. Systematic investigation of the reaction conditions revealed that the reaction requires relatively high temperature (higher than 70 °C). The effect of the carbon monoxide pressure is different in the synthesis of the two types of products: while the carboxamide formation is favoured, the carbohydrazide formation is lowered by the increasing CO pressure.

Facile synthesis of N-acyl 2-aminobenzothiazoles by NHC-catalyzed direct oxidative amidation of aldehydes

A mild, general, and high yielding synthesis of N-acyl 2-aminobenzothiazoles has been demonstrated by N-heterocyclic carbene (NHC)-organocatalyzed direct amidation of aldehydes with 2-aminobenzothiazoles proceeding via acyl azolium intermediates. The carbene generated from the triazolium salt under oxidative conditions was the key for the success of this reaction. The method was subsequently applied to the synthesis of various biologically important N-acyl 2-aminobenzothiazoles.