2527-63-1

Basic information

• Product Name: 2,2'-disulfanediylbis(N-phenylbenzamide)
• Synonyms: N,N'-Dithiobis(N-phenylbenzamide)
• CAS NO: 2527-63-1
• Molecular Formula: C₂₆H₂₀N₂O₂S₂
• Molecular Weight: 456.5792
• Mol File: 2527-63-1.mol

Chemical Properties

• Melting Point: 243 °C
• Boiling Point: 511.4°Cat760mmHg
• Flash Point: 263.1°C
• Appearance: /
• Density: 1.35g/cm³
• PKA: 12.71±0.70(Predicted)
• CAS DataBase Reference: 2,2'-disulfanediylbis(N-phenylbenzamide)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-disulfanediylbis(N-phenylbenzamide)(2527-63-1)
• EPA Substance Registry System: 2,2'-disulfanediylbis(N-phenylbenzamide)(2527-63-1)

Safety Data

• Hazardous Substances Data: 2527-63-1(Hazardous Substances Data)

Upstream product

• 1677-27-6 3H-1,2-benzodithiol-3-one 
• 62-53-3 aniline 
• 147-93-3 Thiosalicylic acid 
• 77586-83-5 2-trichloromethyl-3,1-benzoxathian-4-one 
• 19602-82-5 2,2'-dithiodibenzoic acid dichloride 
• 119-80-2 2,2'-dithiobenzoic acid 
• 18205-99-7 2-mercapto-N-phenylbenzamide 
• 6833-21-2 2-methoxy-N-phenylbenzamide 
• 93-98-1 N-phenyl benzoyl amide 
• 342631-38-3 (E)-2-[2-(3-Chlorophenyl)vinyl]-3,1-benzoxathiin-4-one 

Downstream Products

• 18205-99-7 2-mercapto-N-phenylbenzamide 
• 24434-82-0 benzo[b]thiophen-3-yl acetate 
• 2527-03-9 2-phenyl-1,2-benzisothiazolin-3-one 
• 115484-13-4 2,2-thiobis(N-phenylbenzamide) 
• 93-98-1 N-phenyl benzoyl amide 
• 1677-26-5 S-2-(phenylcarbamoyl)phenyl benzothioate 
• 10128-95-7 3-phenyl-benzo[e][1,3]thiazine-2,4-dithione 
• 7077-19-2 3-phenyl-4-thioxo-3,4-dihydro-benzo[e][1,3]thiazin-2-one 
• 7077-20-5 3-phenyl-2-thioxo-2,3-dihydrobenzo[e][1,3]thiazine-4-one 
• 20054-73-3 3-phenyl-benzo[e][1,3]thiazine-2,4-dione 
• 20051-28-9 3-phenyl-2-phenylimino-2,3-dihydro-benzo[e][1,3]thiazine-4-thione 
• 20054-79-9 S-Ethoxycarbonyl-N-phenyl-2-mercapto-benzamid 
• 20051-26-7 S-Methoxycarbonyl-dithio-salicylsaeureanilid ( S-Acetoxy-dithiosalicylsaeureanilid) 
• 20054-36-8 S-Methoxycarbonyl-N-phenyl-2-mercapto-benzamid 

Relevant articles and documents

Synthetic method 1-2 - benzisothiazol -3 -one compound (by machine translation)

The invention discloses a synthetic method of 1-2 - benzisothiazol -3 -one compound, and belongs to the field of chemical synthesis. 2 - 1-benzisothiazol 2 -one compounds are synthesized through acid chlorination, amidation and cyclization reaction by using the sulfenyl-substituted benzoic acid extracted from BIT process -3 - waste water as a starting raw material. The method disclosed by the invention has the advantages of mild reaction conditions, simple and convenient operation, strong practicability, less waste water, high product purity and the like, and is suitable for large-scale industrial production. The technical scheme provided by the invention is resource utilization and preparation 1 of wastewater extract produced in BIT production, and a feasible method is provided for the 2 -benzisothiazol -3 -one compound. (by machine translation)

Bioisosteric investigation of ebselen: Synthesis and in vitro characterization of 1,2-benzisothiazol-3(2H)-one derivatives as potent New Delhi metallo-β-lactamase inhibitors

Carbapenem-resistant Enterobacteriaceae (CRE) producing New Delhi metallo-β-lactamase (NDM-1) cause untreatable bacterial infections, posing a significant threat to human health. In the present study, by employing the concept of bioisosteric replacement of the selenium moiety of ebselen, we have designed, synthesized and characterized a small compound library of 2-substituted 1,2-benzisothiazol-3(2H)-one derivatives and related compounds for evaluating their cytotoxicity and synergistic activity in combination with meropenem against the E. coli Tg1 (NDM-1) strain. The most promising compound 3a demonstrated potent synergistic activity against a panel of clinically isolated NDM-1 positive CRE strains with FICI as low as 0.09. Moreover, its IC50 value and inhibition mechanism were also confirmed by using the enzyme inhibition assay and the ESI-MS analysis respectively. Importantly, compound 3a has acceptable toxicity and is not a PAINS. Because of its structural simplicity and potent synergistic activity in combination with meropenem, we propose that compound 3a may be a promising meropenem adjuvant and a new series of such compounds may worth further investigations.

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.

REDOX DEHYDRATION COUPLING CATALYSTS AND METHODS RELATED THERETO

This disclosure relates to synthetic coupling methods using catalytic molecules. In certain embodiments, the catalytic molecules comprise heterocyclic thiolamide, S-acylthiosalicylamide, disulfide, selenium containing heterocycle, diselenide compound, ditelluride compound or tellurium containing heterocycle. Catalytic molecules disclosed herein are useful as catalysts in the transformation of hydroxy group containing compounds to amides, esters, ketones, and other carbon to heteroatom or carbon to carbon transformations.

Potassium bromide catalyzed N[sbnd]S bond formation via oxidative dehydrogenation

N-Substituted benzo[d]isothiazol-3(2H)-ones are a family of compounds with extremely important application. Recently, we have developed a new green pathway to synthesize these compounds via potassium bromide-catalyzed intramolecular oxidative dehydrogenative cyclization. This reaction has high functional group tolerance and affords excellent yield even in gram scale.

Benzoisothiazolone organo/copper-cocatalyzed redox dehydrative construction of amides and peptides from carboxylic acids using (EtO)3P as the reductant and O2 in air as the terminal oxidant

Carboxylic acids and amine/amino acid reactants can be converted to amides and peptides at neutral pH within 5-36 h at 50 °C using catalytic quantities of a redox-active benzoisothiazolone and a copper complex. These catalytic "oxidation-reduction condensation" reactions are carried out open to dry air using O2 as the terminal oxidant and a slight excess of triethyl phosphite as the reductant. Triethyl phosphate is the easily removed byproduct. These simple-to-run catalytic reactions provide practical and economical procedures for the acylative construction of C-N bonds.

Reactions of an organoruthenium anticancer complex with 2-mercaptobenzanilide-a model for the active-site cysteine of protein tyrosine phosphatase 1B

The organometallic anticancer complex [(η6-p-cymene)Ru(en) Cl]PF6 (1, en = ethylenediamine) readily reacts with thiols and forms stable sulfenate/sulfinate adducts which may be important for its biological activity. Protein tyrosine

Crucial role of selenium in the virucidal activity of benzisoselenazol- 3(2h)-ones and related diselenides

Various N-substituted benzisoselenazol-3(2H)-ones and their non-seleniumcontaining analogues have been synthesized and tested against selected viruses (HHV-1, EMCV and VSV) to determine the extent to which selenium plays a role in antiviral activity. The data presented here show that the presence of selenium is crucial for the antiviral properties of benzisoselenazol-3(2H)-ones since their isostructural analogues having different groups but lacking selenium either did not show any antiviral activity or their activity was substantially lower. The open-chain analogues of benzisoselenazol- 3(2H)-ones-diselenides also exhibited high antiviral activity while selenides and disulfides were completely inactive towards model viruses.

Redox regulation of protein tyrosine phosphatase 1B (PTP1B): A biomimetic study on the unexpected formation of a sulfenyl amide intermediate

The effect of steric and electronic environments around the sulfur and nitrogen atoms and the role of nonbonded S...O/N interactions on the cyclization reactions of amide substituted benzene sulfenic acids are described. The reaction profiles and the role

Benzoisothiazolone compositions

A composition, suitable for topical application to the skin, containing at least one benzoisothiazolone of formula (I): Novel benzoisothiazolones of formula (I) and a method of caring for dry and/or mature skin.