936-46-9

Usage

Synthesis Reference(s)

Tetrahedron, 22, p. 2119, 1966 DOI: 10.1016/S0040-4020(01)82131-1

Upstream product

• 1826-13-7 5-phenylthiazole 
• 26591-66-2 2-phenyl-1,3-propanedial 
• 103-82-2 phenylacetic acid 
• 98-83-9 isopropenylbenzene 
• 83662-09-3 methyl(2-phenylprop-1-en-1-yl)sulfane 
• 4432-64-8 hydroxymethylenephenylacetaldehyde 
• 15131-89-2 α-phenyl-β-dimethylaminoacrylaldehyde 
• 53913-71-6 3-chloro-2-phenylpropenal 

Downstream Products

• 25392-24-9 1-(4-isothiazol-4-yl-phenyl)-ethanone 
• 25392-19-2 4-(4-bromophenyl)isothiazole 
• 25392-15-8 4-(2-nitro-phenyl)-isothiazole 
• 25392-14-7 4-(4-nitro-phenyl)-isothiazole 
• 25392-17-0 4-(2,4-dinitro-phenyl)-isothiazole 
• 25392-20-5 5-bromo-4-(4-bromo-phenyl)-isothiazole 
• 25392-22-7 4-isothiazol-4-yl-benzenesulfonyl chloride 
• 97164-59-5 4,6,6-Triphenyl-2-thia-1-aza-bicyclo[3.2.0]hept-3-en-7-one 
• 97148-25-9 2-(2-Oxo-2-phenyl-ethyl)-4-phenyl-isothiazol-2-ium; bromide 
• 65182-52-7 4-Phenyl-1,2-thiazol-3(2H)-on-1,1-dioxid 
• 10514-31-5 5-deuterio-4-phenyl-isothiazole 
• 1826-12-6 4-phenyl-thiazole 
• 97148-27-1 Phenyl-(5-phenyl-2H-[1,3]thiazin-2-yl)-methanone 
• 97148-35-1 2-Benzoyl-7-chloro-5-phenyl-3-thia-1-aza-bicyclo[4.2.0]oct-4-en-8-one 

Relevant academic research and scientific papers

Azole-Based Indoleamine 2,3-Dioxygenase 1 (IDO1) Inhibitors

The heme enzyme indoleamine 2,3-dioxygenase 1 (IDO1) plays an essential role in immunity, neuronal function, and aging through catalysis of the rate-limiting step in the kynurenine pathway of tryptophan metabolism. Many IDO1 inhibitors with different chemotypes have been developed, mainly targeted for use in anti-cancer immunotherapy. Lead optimization of direct heme iron-binding inhibitors has proven difficult due to the remarkable selectivity and sensitivity of the heme-ligand interactions. Here, we present experimental data for a set of closely related small azole compounds with more than 4 orders of magnitude differences in their inhibitory activities, ranging from millimolar to nanomolar levels. We investigate and rationalize their activities based on structural data, molecular dynamics simulations, and density functional theory calculations. Our results not only expand the presently known four confirmed chemotypes of sub-micromolar heme binding IDO1 inhibitors by two additional scaffolds but also provide a model to predict the activities of novel scaffolds.

Access to 4-substituted isothiazoles through three-component cascade annulation and their application in C-H activation

The use of potassium ethyl xanthate (EtOCS2k) as a sulfur atom donor enabled the transition-metal-free [3 + 1 + 1] cascade annulation of isopropene derivatives with NH4I in DMSO/H2O, affording various 4-substituted isothiazoles in moderate to good yields

Design, synthesis, and antifungal activity of inhibitors of brassilexin detoxification in the plant pathogenic fungus Leptosphaeria maculans

Potential inhibitors of Leptosphaeria maculans mediated detoxification of the phytoalexin brassilexin were designed and synthesized based on the planar heteroaromatic structure of isothiazolo[5,4-b]indole. Screening of these compounds for inhibition of br

Phototransposition chemistry of phenylisothiazoles and phenylthiazoles. 1. Interconversions in benzene solution

Phenylthiazoles 1-3 and phenylisothiazoles 4-6 undergo phototransposition in benzene solvent mainly by P5, P6, and P7 permutation pathways. Phenylisothiazoles 5 and 6 also transpose via a P4 permutation process to yield phenylthiazoles 2 and 3 in less than 1% yield. In benzene saturated with D2O, 2-phenylthiazole (1) and 5-phenylisothiazole (6) each phototranspose to yield 4-deuterio-3-phenylisothiazole (4-D-4) and 4-phenylthiazole (2) without deuterium incorporation. Irradiation of 4-phenylthiazole (2) under these conditions results in rapid photodeuteration to yield 2-deuterio-4-phenylthiazole (2-D-2), which subsequently phototransposes to 5-deuterio-3-phenylisothiazole (5-D-3). These experimental results can be rationalized by a mechanism involving initial electrocyclic ring closure and sigmatropic shift of sulfur around the four sides of the azetine ring. Rearomatization of each bicyclic intermediate thus allows sulfur to insert into each position in the carbon-nitrogen sequence. As a consequence, these compounds divide into a tetrad in which isomers 1, 2,4, and 6 interconvert mainly via P5, P6, and P7 pathways and a dyad of two compounds in which 3 phototransposes to 5 via P5 and P7 pathways. Within the tetrad, BC-6, the bicyclic intermediate derived from 5-phenylisothiazoles (6), is postulated to undergo deuteration with simultaneous sigmatropic shift of sulfur when the reaction is carried out in benzene-D2O. This mechanistic view provides one coherent interpretation for the observed phototransposition and photodeuteration reactions.

THERMOLYSIS OF 1,3-DITHIOL-2-YL AZIDES AND THERMAL PROPERTIES OF THE RESULTING 1,4,2-DITHIAZINES

2-Substituted 1,3-dithiol-2-yl azides, on thermolysis in refluxing toluene, give 3-substituted 1,4,2-dithiazines wich thermally extrude sulfur atom of the 4-position selectively to yield 3-substituted isothiazoles, while 2-unsubstituted 1,3-dithiol-2-yl azides undergo both ring expansion yielding 1,4,2-dithiazines and peculiar thermal dissociation into 1,3-dithiol-2-ylidene carbenes and hydrogen azide.