19602-82-5

Basic information

• Product Name: 2,2'-dithiodibenzoyl chloride
• Synonyms: 2,2'-dithiodibenzoyl chloride;2,2'-Dithiodibenzoyl dichloride;Einecs 243-180-8;2,2'-disulfanediyldibenzoyl chloride
• CAS NO: 19602-82-5
• Molecular Formula: C₁₄H₈Cl₂O₂S₂
• Molecular Weight: 343.24812
• EINECS: 243-180-8
• Mol File: 19602-82-5.mol
• Article Data: 61

Chemical Properties

• Melting Point: 153 °C
• Boiling Point: 443.7°Cat760mmHg
• Flash Point: 222.1°C
• Appearance: /
• Density: 1.51g/cm³
• CAS DataBase Reference: 2,2'-dithiodibenzoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-dithiodibenzoyl chloride(19602-82-5)
• EPA Substance Registry System: 2,2'-dithiodibenzoyl chloride(19602-82-5)

Safety Data

• Hazardous Substances Data: 19602-82-5(Hazardous Substances Data)

Usage

Uses

2,2''-Disulfanediyldibenzoyl Chloride is an intermediate used in the synthesis of N,N’-Bis(2-mercaptobenzoyl)hydrazide (B481825), which is a selective inhibitor of HIV-1 integrase. Has no other effect on other retroviral targets, including reverse transcriptase, protease, and virus attachement, and exhibits no detectable activity against human topoisomerases I and II at concentrations that effectively inhibit integrase.

Upstream product

• 119-80-2 2,2'-dithiobenzoic acid 
• 98-07-7 Benzotrichlorid 
• 707-74-4 (trichloromethyl)mesitylene 
• 79-37-8 oxalyl dichloride 
• 79-16-3 N-methyl-acetamide 
• 147-93-3 Thiosalicylic acid 

Downstream Products

• 5459-63-2 bis[2-(methoxycarbonyl)phenyl]disulfide 
• 7765-77-7 bis[2-(N-n-propylcarbamoyl)phenyl] disulfide 
• 17927-88-7 2-(phenylsulfonyl)benzo[d]isothiazol-3(2H)-one 
• 54481-26-4 bis(2-ethoxycarbonylphenyl) disulfide 
• 91163-17-6 2,2'-disulfanediyl-di-benzoic acid dipentyl ester 
• 117025-69-1 2,2'-disulfanediyl-di-benzoic acid bis-[(phenylcarbamoyl-methyl)-amide] 
• 5556-20-7 ethyl 3-hydroxybenzothiophene-2-carboxylate 
• 2634-33-5 1,2-benzisothiazolin-3-one 
• 2527-66-4 2-methyl-1,2-benzisothiazole-3(2H)-one 
• 2527-03-9 2-phenyl-1,2-benzisothiazolin-3-one 
• 4299-23-4 2-(o-tolyl)benzo[d]isothiazol-3(2H)-one 
• 2514-36-5 2-benzylbenzo[d]isothiazol-3(2H)-one 
• 27148-07-8 2-propyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide 
• 2527-04-0 2-benzoyl-benz[d]isothiazol-3-one 

Relevant articles and documents

Synthesis of novel thiazolothiazepine based HIV-1 integrase inhibitors.

Thiazolothiazepines are among the smallest and most constrained inhibitors of human immunodeficiency virus type-1 integrase (HIV-1 IN) inhibitors (J. Med. Chem. 1999, 42, 3334). Previously, we identified two thiazolothiazepines lead IN inhibitors with antiviral activity in cell-based assays. Structural optimization of these molecules necessitated the design of easily synthesizable analogs. In order to design similar molecules with least number of substituent, herein we report the synthesis of 10 novel analogs. One of the new compounds (1) exhibited similar potency as the reference compounds, confirming that a thiazepinedione fused to a naphthalene ring system is the best combination for the molecule to accommodate into the IN active site. Thus, the replacement of sulfur in the thiazole ring with an oxygen does not seem considerably affect potency. On the other hand, the introduction of an extra methyl group at position 1 of the polycyclic system or the shift from a thiazepine to an oxazepine skeleton decreased potency. In order to understand their mode of interactions with IN active site, we docked all the compounds onto the previously reported X-ray crystal structure of IN. We observed that compounds 7-9 occupied an area close to D64 and Mg(2+) and surrounded by amino acid residues K159, K156, N155, E152, D116, H67, and T66. The oxygen atom of the oxazolo ring of 7 and 8 could chelate Mg(2+). These results indicate that the new analogs potentially interact with the highly conserved residues important for IN catalytic activities.

Comparison of classic and microwave-assisted synthesis of benzo-thio crown ethers, and investigation of their ion pair extractions

Macrocyclic benzo-thio crown ethers and benzo-oxo crown ethers were prepared using an esterification–ring closing method. These compounds were synthesised using 2,2′-dithiodibenzoyl chloride, and various glycols and dithiols, in the presence of pyridine base under a nitrogen atmosphere in chloroform. All reactions were performed under reflux condition with conventional heating and microwave (MW) irradiation. The synthesised macrocycles were characterised by FT-IR, 1H NMR, 13C NMR, LC-MS, and elemental analysis methods. Extraction studies have been performed on these original macrocycles using liquid-liquid ion-pair extraction with Li+, Na+, K+, Ni2+, Ca2+, Mg2+, Zn2+, Fe2+,Fe3+, Co3+, Pb2+, Cr3+, Ag+, and Cd2+.The KD, ext.%, ΔG and log KExt values were also calculated. While (U1-U7) ligands exhibits selectivity for Zn2+, Ag+, Ca2+, Pb2+, Fe3+, Cr3+, Co2+, Mg2+, Cd2+, and Ni2+ metal salts, they showed no selectivity for Li+, K+ and Na+ metal salts. Furthermore, Fe3+is the most selective cation for all ligands for competitive extraction. We also observed that microwave heating can have certain benefits over conventional ovens: reaction rate acceleration, milder reaction conditions, higher chemical yield, and lower energy usage. These ligands could be used as metal sensors, enzyme inhibitors, antimicrobial/antifungal agents, and in biological applications.

Axitinib intermediate compound and preparation method thereof

The invention belongs to the field of pharmaceutical chemicals, and particularly relates to an axitinib intermediate compound and a preparation method thereof. The present invention provides a novel axitinib intermediate compound S-(2-(methylcarbamoyl) phenyl) dimethylthioformate, the invention also provides a preparation method thereof. The method comprises the following steps: dissolving 2-hydroxy-N-methylbenzamide in an organic solvent, and adding dimethylaminothioformyl chloride and a catalyst to obtain the S-(2-(methylcarbamoyl) phenyl) dimethylthioformate. The new intermediate compound can be used for preparing the axitinib important intermediate 2-sulfydryl-N-methylbenzamide, and the synthesis method provided by the invention is short in route, simple to operate and high in yield and purity of the obtained 2-sulfydryl-N-methylbenzamide, and is suitable for industrial production.

Preparation method of dithiobenzamide compound

The invention provides a preparation method of a dithiobenzamide compound, and relates to the technical field of organic synthesis. The method disclosed by the invention has the advantages that applicable substrates are richer, and the method can be used for synthesizing various dithiodibenzoyl compounds; reaction conditions are mild, the synthesis reaction process is simple to operate, and practicability is achieved; the post-treatment operation is simple and convenient, and the product yield and purity are high; and the reaction process is green and environment-friendly, and the preparationmethod meets the requirements of large-scale industrial production.

Benzisothiazolinone Derivatives as Potent Allosteric Monoacylglycerol Lipase Inhibitors That Functionally Mimic Sulfenylation of Regulatory Cysteines

We describe a set of benzisothiazolinone (BTZ) derivatives that are potent inhibitors of monoacylglycerol lipase (MGL), the primary degrading enzyme for the endocannabinoid 2-arachidonoyl-sn-glycerol (2-AG). Structure-activity relationship studies evaluated various substitutions on the nitrogen atom and the benzene ring of the BTZ nucleus. Optimized derivatives with nanomolar potency allowed us to investigate the mechanism of MGL inhibition. Site-directed mutagenesis and mass spectrometry experiments showed that BTZs interact in a covalent reversible manner with regulatory cysteines, Cys201 and Cys208, causing a reversible sulfenylation known to modulate MGL activity. Metadynamics simulations revealed that BTZ adducts favor a closed conformation of MGL that occludes substrate recruitment. The BTZ derivative 13 protected neuronal cells from oxidative stimuli and increased 2-AG levels in the mouse brain. The results identify Cys201 and Cys208 as key regulators of MGL function and point to the BTZ scaffold as a useful starting point for the discovery of allosteric MGL inhibitors.