16586-50-8

Upstream product

• 1147550-11-5 ammonium thiocyanate 
• 1137-41-3 (4-aminophenyl)(phenyl)methanone 
• 333-20-0 potassium thioacyanate 

Downstream Products

• 156246-14-9 (2-Chloro-benzothiazol-6-yl)-phenyl-methanone 
• 134949-46-5 (6-Benzoyl-benzothiazol-2-yl)-carbamic acid ethyl ester 
• 107508-38-3 2-carbomethoxyamino-6-benzoylbenzthiazole 
• 1236115-15-3 benzo[d]thiazol-6-yl(phenyl)methanone 

Relevant academic research and scientific papers

Visible-light photoredox catalytic approach for the direct synthesis of 2-aminobenzothiazoles from anilines

A novel, highly efficient and convenient approach for the visible-light-promoted direct synthesis of 2-aminobenzothiazoles from anilines and ammonium thiocyanate is presented. The reaction involves addition/cyclization cascade of SCN radical and anilines under photoredox catalysis with Ru(bpy)3Cl2. The salient features of the protocol include the utilization of atmospheric oxygen and visible light as clean, inexpensive and sustainable resources at room temperature.

AGRICULTURAL CHEMICALS

The present invention relates to picolinic acid derivatives that are useful in treating fungal diseases ofplants.

Carbon dioxide as the C1 source for direct C-H functionalization of aromatic heterocycles

(Equation Presented). A simple and straightforward method has been developed for the direct carboxylation of aromatic heterocylces such as oxazoles, thiazoles, and oxadiazoles using CO2 as the C1 source. The reactions require no metal catalyst and only Cs2CO3 as the base. A good functional group tolerance is achieved.

Substituted 2-benzothiazolamines as sodium flux inhibitors: Quantitative structure-activity relationships and anticonvulsant activity

Thirty-two aryl-substituted 2-benzothiazolamines have been tested for their ability to modulate sodium flux in rat cortical slices. A QSAR analysis, applied to these derivatives, showed a trend toward increasing potency as sodium flux inhibitors with increasing lipophilicity, decreasing size, and increasing electron withdrawal of the benzo ring substitutents. Additionally, 4- or 5-substitution of the benzo ring was found to decrease potency. The combination of increased lipophilicity, small size, and electron withdrawal severely limited which groups were tolerated on the benzo ring, thus suggesting that the optimal substitution patterns have been prepared within this series. Nine of these compounds were potent inhibitors of veratridine-induced sodium flux (NaFl). These nine compounds also proved to be anticonvulsant in the maximal electroshock (MES) assay. Fourteen additional 2-benzothiazolamines demonstrated activity in the MES screen, yet exhibited no activity in the NaFl assay. These derivatives may be interacting at the sodium channel in a manner not discernible by the flux paradigm, or they may be acting by an alternative mechanism in vivo.

QSAR study on H3-receptor affinity of benzothiazole derivatives of thioperamide

Starting from the structure of thioperamide, a known H3-antagonist, a new series of compounds with a benzothiazole nucleus instead of the cyclohexylcarbothioamide moiety was synthesized. Various substituents, selected by experimental design, were introduced in position 6 of the benzothiazole nucleus, in order to change its physico-chemical characteristics. The lipophilicity of the synthesized compounds was measured by means of RP-HPLC, and their H3-receptor affinity was evaluated by competitive binding assays on rat cortex synaptosomes, with the labelled ligand N(α)-[3H]methylhistamine. A QSAR analysis was performed on the experimental data, using also substituent constants taken from the literature. The newly synthesized compounds showed lower H3-affinities than thioperamide; quantitative structure-activity relationships, described by models obtained with PLS and MRA techniques, were observed among benzothiazole derivatives. According to these relationships, any attempt to improve the potency of these compounds should involve the substitution of the benzothiazole moiety with less bulky and/or more flexible structures, which should also be less lipophilic and allow better electronic interactions with the binding site. 1-(Benzothiazol-2-yl)-4-[(1H)-imidazol-4-yl]piperidine represents a limit structure for H3-activity, since it seems impossible to improve its affinity by means of substitution in the studied position of the benzothiazole nucleus, as shown by predictions performed by a PLS model.

Studies in antiparasitic agents: Part 17 - Synthesis of 2-acylamino-6-substituted-benzthiazoles as potential anthelmintic agents

The syntheses of a series of 2-acetamido-6-alkoxycarbonylbenzthiazoles (12-17), 2-alkoxycarbonylamino-6-alkoxycarbonylbenzthiazoles (18-27), 2-alkoxycarbonylamino-6-benzoylbenzthiazoles (29,30), and 2,2'-dicarbalkoxyamino-6,6'-dibenzthiazolyl oxides, sulphides and sulphones (38-43) have been carried out as structural congeners of tioxidazole (2) and related anthelmintics (3 and 4).All the benzthiazoles have been evaluated for their anthelmintic activity against Ancylostoma ceylanicum in hamsters, Hymenolepis nana in mice and Litomosoides carinii in cotton rats.Compound 15 showes more than 85percent clearance of hookworms (A. ceylanicum) at an oral dose of 250 mg/kg, while compound 24 eliminates nearly 90percent of the microfilariae in blood and also kills 50percent of the adult filarial worms at an intraperitonial dose of 30 mg/kg * 5 from the cotton rats infected with Litomosoides carinii.