4968-41-6

Usage

Type of compound

Synthetic chemical compound, derivative of thiourea

Industries

Pharmaceutical, agricultural

Properties

Antiviral, antifungal, antibacterial

Uses

Development of drugs and agrochemicals, reagent in organic synthesis, research tool in biochemistry and pharmacology

Physical appearance

White to off-white crystalline powder

Taste

Slightly bitter

Solubility

Soluble in organic solvents

Research status

More research needed to understand potential applications and health risks

Upstream product

• 151-50-8 potassium cyanide 
• 2284-20-0 4-Methoxyphenyl isothiocyanate 
• 104-94-9 4-methoxy-aniline 
• 75318-43-3 4,5-dichloro-1,2,3-dithiazolium chloride 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 16640-68-9 cyanomethylene triphenylphosphorane 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 75318-49-9 N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-4-methoxyaniline 

Downstream Products

• 116709-03-6 3-(4-chlorophenyl)-4-imino-5-(4-methoxyphenylimino)-2-thiazolidinethione 
• 116709-02-5 3-(4-methoxyphenyl)-4-imino-5-(2-methoxy-5-chlorophenylimino)-2-thiazolidinethione 
• 291283-00-6 5-imino-3-(4-methoxy-phenyl)-1-phenyl-imidazolidine-2,4-dithione 
• 2591-17-5 D-luciferin 
• 939-69-5 2-cyano-6-hydroxybenzothiazole 
• 502173-45-7 (4-methoxyphenyl)carbamoyl cyanide 
• 1328894-68-3 1-(4-chloro-3-(trifluoromethyl)phenyl)-5-imino-3-(4-mehoxyphenyl)-4-thioxoimidazolidin-2-one 
• 1328894-60-5 3-(4-fluorophenyl)-1-(4-methoxyphenyl)-5-thioxoimidazolidine-2,4-dione 
• 1328894-51-4 1-(4-fluorophenyl)-5-imino-3-(4-methoxyphenyl)-4-thioxoimidazolidin-2-one 
• 1198619-83-8 1-(4-methoxyphenyl)-4-imino-3-(naphthalen-1-yl)-5-thioxoimidazolidin-2-one 
• 1159588-79-0 4,4'-bis(5-imino-1-(4-methoxyphenyl)-2,4-dithioxo-imidazolidin-3-yl)-1,1'-diphenylsulfone 
• 84200-19-1 1-p-Anisidyl-3-phenyl-4,5-di-p-anisidylimino-imidazolidin-2-on 

Relevant academic research and scientific papers

Synthesis and evaluation of D-thioluciferin, a bioluminescent 6'-thio analog of Dluciferin

All known light-emitting firefly-bioluminescent luciferin analogs are either derived from the 6'-hydroxy- and/or 6'-aminoluciferin. We report the synthesis of D-thioluciferin, a 6'-thio analog or isostere of D-luciferin, starting from p-aminothiophenol, using a unique thioacrylate-S-protecting-group strategy. Upon treatment of Dthioluciferin with purified Photinus pyralis (Ppy) luciferase (Luc), a bioluminescence emission with a red-shift λmax relative to D-luciferin was observed. It was also shown that disulphide and sulphide analogs of Dthioluciferin did not produce similar bioluminescences relative to D-thioluciferin when treated with Ppy Luc under standard conditions, thus, providing a foundation for the development of D-thioluciferin based probes based on disulphide reduction and S-dealkylation.

Rapid and scalable assembly of firefly luciferase substrates

Bioluminescence imaging with luciferase-luciferin pairs is a popular method for visualizing biological processes in vivo. Unfortunately, most luciferins are difficult to access and remain prohibitively expensive for some imaging applications. Here we report cost-effective and efficient syntheses of d-luciferin and 6′-aminoluciferin, two widely used bioluminescent substrates. Our approach employs inexpensive anilines and Appel's salt to generate the luciferin cores in a single pot. Additionally, the syntheses are scalable and can provide multi-gram quantities of both substrates. The streamlined production and improved accessibility of luciferin reagents will bolster in vivo imaging efforts. This journal is

Expedient synthesis of electronically modified luciferins for bioluminescence imaging

Bioluminescence imaging with luciferase enzymes requires access to light-emitting, small-molecule luciferins. Here, we describe a rapid method to synthesize d-luciferin, the substrate for firefly luciferase (Fluc), along with a novel set of electronically modified analogues. Our procedure utilizes a relatively rare, but synthetically useful dithiazolium reagent to generate heteroaromatic scaffolds in a divergent fashion. Two of the luciferin analogues produced with this approach emit light with Fluc in vitro and in live cells. Collectively, our work increases the number of substrates that can be used for bioluminescence imaging and provides a general strategy for synthesizing new collections of luciferins.

Antibacterial evaluation of novel N-arylimino-1,2,3-dithiazoles and N-arylcyanothioformamides

N-Aryl-1,2,3-dithiazoles 2 and the corresponding N-arylcyanothioformamides 3 have been synthesized via 4,5-dichloro-1,2,3-dithiazole derivatives, and their antibacterial activity measured; the dithiazoles are significantly active against Gram-positive bacteria.

Reactions of 5-Arylimino-4-chloro-5H-1,2,3-dithiazoles with Stable Phosphoranes: Novel Preparation of Dithiomethylenephosphoranes

The reactions of 5-arylimino-4-chloro-5H-1,2,3-dithiazoles with 2 equivalents of stable phosphoranes such as carboethoxymethylene-, acetylmethylene-, 4-chlorobenzoylmethylene-, and cyanomethylenetriphenylphosphoranes in the presence of pyridine in CH2Cl2 at room temperature gave a new type of the corresponding phosphoranes with aryliminocyanomethyldithiomethylene moiety as a major product.

Some chemistry of 4,5-dichloro-1,2,3-dithiazolium chloride and its derivatives

4,5-Dichloro-1,2,3-dithiazolium chloride 1 reacts with fluoroanilines (see Table 1) to give the iminodithiazoles 5 in very high yield.Thermolysis of the latter gave the corresponding 2-cyanobenzothiazoles 6 together, in some cases, with the cyanoimidoyl chlorides 7.This reaction sequence provides modest yields of 2-cyanobenzothiazoles from the corresponding aniline, in two steps.Treatment of the iminodithiazoles with m-chloroperbenzoic acid in dichloromethane at or below room temperature opened the heterocyclic ring to give the N-arylcyanothioformamides (e.g. 8 --> 10), except for the p-nitrophenyl compound which gave p-nitrophenyl isothiocyanate 14 in high yield.