2634-30-2

Upstream product

• 19602-82-5 2,2'-dithiodibenzoic acid dichloride 
• 106-49-0 p-toluidine 
• 147-93-3 Thiosalicylic acid 
• 119-80-2 2,2'-dithiobenzoic acid 

Downstream Products

• 2514-30-9 2-(4-tolyl)-1,2-benzisothiazol-3-one 
• 20054-70-0 3-p-tolyl-benzo[e][1,3]thiazine-2,4-dione 
• 20054-51-7 3-p-tolyl-benzo[e][1,3]thiazine-2,4-dithione 
• 20054-61-9 2-thioxo-3-p-tolyl-2,3-dihydro-benzo[e][1,3]thiazin-4-one 
• 20054-42-6 2-mercapto-N-(4-methylphenyl)benzamide 

Relevant academic research and scientific papers

Electron paramagnetic resonance spectroscopy as a probe of hydrogen bonding in heme-Thiolate proteins

Despite utilizing a common cofactor binding motif, hemoproteins bearing a cysteine-derived thiolate ligand (heme-Thiolate proteins) are involved in a diverse array of biological processes ranging from drug metabolism to transcriptional regulation. Though the origin of heme-Thiolate functional divergence is not well understood, growing evidence suggests that the hydrogen bonding (H-bonding) environment surrounding the Fe-coordinating thiolate influences protein function. Outside of X-ray crystallography, few methods exist to characterize these critical H-bonding interactions. Electron paramagnetic resonance (EPR) spectra of heme-Thiolate proteins bearing a six-coordinate, Fe(III) heme exhibit uniquely narrow low-spin (S = 1/2), rhombic signals, which are sensitive to changes in the heme-Thiolate H-bonding environment. To establish a well-defined relationship between the magnitude of g-value dispersion in this unique EPR signal and the strength of the heme-Thiolate H-bonding environment, we synthesized and characterized of a series of six-coordinate, aryl-Thiolate-ligated Fe(III) porphyrin complexes bearing a tunable intramolecular H-bond. Spectroscopic investigation of these complexes revealed a direct correlation between H-bond strength and g-value dispersion in the rhombic EPR signal. Using density functional theory (DFT), we elucidated the electronic origins of the narrow, rhombic EPR signal in heme-Thiolates, which arises from an Fe-S pI-dI bonding interaction. Computational analysis of the intramolecularly H-bonded heme-Thiolate models revealed that H-bond donation to the coordinating thiolate reduces thiolate donor strength and weakens this Fe-S interaction, giving rise to larger g-value dispersion. By defining the relationship between heme-Thiolate electronic structure and rhombic EPR signal, it is possible to compare thiolate donor strengths among heme-Thiolate proteins through analysis of low-spin, Fe(III) EPR spectra. Thus, this study establishes EPR spectroscopy as a valuable tool for exploring how second coordination sphere effects influence heme-Thiolate protein function.

A practical synthesis of N-substituted 1,2-benzisothiazolin-3-ones from N,N′-disubstituted 2,2′-dithiodibenzamides

A variety of N-substituted 1,2-benzisothiazolin-3-ones were easily synthesized from N,N′-disubstituted 2,2′-dithiodibenzamides in the presence of O-methylhydroxylamine hydrochloride. Derivatives with a primary, secondary, or tertiary alkyl group or an aryl group on the N-1 nitrogen of the 1,2-benzisothiazolin-3-one were obtained.

A new class of anti-HIV-1 agents targeted toward the nucleocapsid protein NCp7: The 2,2'-dithiobisbenzamides

As part of the National Cancer Institute's Drug Screening Program, a new class of antiretrovirals active against the human immunodeficiency virus HIV-1 has been identified, and the HIV-1 nucleocapsid protein NCp7 was proposed as the target of antiviral action. The 2,2'-dithiobis-[4'-(sulfamoyl)benzanilide] (3x) and the 2,2'-dithiobis(5-acetylamino)benzamide (10) represented the prototypic lead structures. A wide variety of 2,2'-dithiobisbenzamides were prepared and tested for anti-HIV-1 activity, cytotoxicity, and their ability to extrude zinc from the zinc fingers for NCp7. The structure-activity relationships demonstrated that the ability to extrude zinc from NCp7 resided in the 2,2'-dithiobisbenzamide core structure. The 3,3' and the 4,4' isomers were inactive. While many analogs based upon the core structure retained the zinc extrusion activity, the best overall anti-HIV-1 activity was only found in a narrow set of derivatives possessing carboxylic acid, carboxamide, or phenylsulfonamide functional groups. These functional groups were more important for reducing cytotoxicity than improving antiviral potency or activity vs NCp7. All of the compounds with antiviral activity also extruded zinc from NCp7. From this study several classes of low μM anti-HIV agents with simple chemical structures were identified as possible chemotherapeutic agents for the treatment of AIDS.

Antithrombotic agent

Certain 2,2'-dithiobis-N-substituted or unsubstituted benzamides or derivatives thereof are useful as antithrombotic agents because of their ability to suppress aggregation of blood platelets.

Photochemical Ring-expansion Reaction of 1,2-Benzisothiazolinones

The photochemical reaction of a series of 2-aryl-1,2-benzisothiazol-3(2H)-ones (1) under deaerated conditions was found to give dibenzothiazepin-11(10H)-ones (2).A mechanism through a biradical species is proposed for the photoreaction.When the photolysis of 1 was carried out in the presence of oxygen, 2-aryl-1,2-benzisothiazol-3(2H)-one-1-oxides (11) were formed together with compounds 2.