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

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

Used in Pharmaceutical Industry:
2,2'-dithiodibenzoyl chloride is used as a synthetic intermediate for the development of N,N’-Bis(2-mercaptobenzoyl)hydrazide (B481825), a selective inhibitor of HIV-1 integrase. 2,2'-dithiodibenzoyl chloride is specifically designed to target and inhibit the integrase enzyme, which plays a crucial role in the replication of the HIV virus. By inhibiting this enzyme, the compound can effectively suppress the viral replication process, making it a potential therapeutic agent for the treatment of HIV-1 infections.
The use of 2,2'-dithiodibenzoyl chloride in the synthesis of B481825 is significant because it has no other effect on other retroviral targets, such as reverse transcriptase, protease, and virus attachment. Additionally, it exhibits no detectable activity against human topoisomerases I and II at concentrations that effectively inhibit integrase. This selective targeting property makes it a valuable compound in the development of more specific and effective antiretroviral drugs.

Upstream product

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

A convenient synthesis of new macrocyclic thioether-esters and ether-esters: Extraction properties of these esters for alkali, alkaline earth, and transition metal cations

Macrocyclic thioether-esters and ether-esters have been prepared by treating 2,2′-dithiobenzoic acid dichloride and 1,2-benzendicarboxylic acid dichloride with appropriate glycols or dithiol. The complexing ability of these thioether-esters and ether-esters toward Li+, Na+, K+, Mg2+, Ca2+, Sr2+, Ba 2+, Co2+, and Ni2+ has been measured by the solvent extraction method. The extraction data indicate that compound 2 exhibits stronger selectivity toward Li+, 3 toward Ba2+, 4 toward K+, 5 toward Mg2+, 6 toward Ba2+ and Sr 2+, and 7 toward Co2+ and Ni2+ when compared with other cations. Copyright Taylor & Francis Inc.

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.

Effective Laboratory-Scale Preparation of Axitinib by Two CuI-Catalyzed Coupling Reactions

The discovery and development of an efficient synthesis route to axinitib is reported. The first-generation route researched by Pfizer implemented two Pd-catalyzed coupling reactions as key steps. In this work, the development of Heck-type and C-S coupling reactions catalyzed by CuI is briefly described, using an economial and practical protocol. Aspects of this route, such as selecting optimal ligands, solvent, and other conditions, are discussed in detail. The scale-up experiment was carried out to provide more than 300 g of active pharmaceutical ingredients of axitinib in Form XLI with 99.9% purity in 39% yield. In short, we provide a new choice of synthesis route to axitinib, through two copper-catalyzed coupling reactions with good yield.

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.

Synthesis, characterizations of aryl-substituted dithiodibenzothioate derivatives, and investigating their anti-Alzheimer's properties

The main objective of the present study was to synthesize potential inhibitor/activators of AChE and hCA I-II enzymes, which are thought to be directly related to Alzheimer's disease. Dithiodibenzothioate compounds were synthesized by thioesterification. Six different thiolate compounds produced were characterized by 1H-, 13C-NMR, FT-IR, LC-MS/MS methods. HOMO-LUMO calculations and electronic properties of all synthesized compounds were comprehensively illuminated with a semi-empirical molecular orbital (SEMO) package for organic and inorganic systems using Austin Model 1 (AM1)-Hamiltonian as implemented in the VAMP module of Materials Studio. In addition, the inhibition effects of these compounds for AChE and hCA I-II in vitro conditions were investigated. It was revealed that TE-1, TE-2, TE-3, TE-4, TE-5, and TE-6 compounds inhibited the AChE under in vitro conditions. TE-1 compound activated the enzyme hCA I while TE-2, TE-3 TE-4 compounds inhibited it. TE-5 and TE-6, on the other hand, did not exhibit a regular inhibition profile. Similarly, TE-1 activated the hCA II enzyme whereas TE-2, TE-3, TE-4, and TE-5 compounds inhibited it. TE-6 compound did not have a consistent inhibition profile for hCA II. Docking studies were performed with the compounds against AChE and hCA I-II receptors using induced-fit docking method. Molecular Dynamics (MD) simulations for best effective three protein-ligand couple were conducted to explore the binding affinity of the considered compounds in semi-real in-silico conditions. Along with the MD results, TE-1-based protein complexes were found more stable than TE-5. Based on these studies, TE-1 compound could be considered as a potential drug candidate for AD. Communicated by Ramaswamy H. Sarma.

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.

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)

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.

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.