72744-67-3

Usage

Uses

Used in Pharmaceutical Industry:
5,11-bisthio-(R,R)-1,7-diazatricyclo[7.3.0.07,11]dodecane-2,8-diketone is used as an active pharmaceutical ingredient for the development of drugs targeting oral pathogens. Its anti-biofilm activity makes it a promising candidate for treating oral infections and promoting dental health.
Used in Dental Care Products:
In the dental care industry, 5,11-bisthio-(R,R)-1,7-diazatricyclo[7.3.0.07,11]dodecane-2,8-diketone is used as an ingredient in mouthwashes, toothpastes, and other oral hygiene products. Its ability to inhibit biofilm formation helps prevent plaque buildup and supports overall oral health.
Used in Research and Development:
5,11-bisthio-(R,R)-1,7-diazatricyclo[7.3.0.07,11]dodecane-2,8-diketone is also utilized in research and development for the study of its anti-biofilm properties and potential applications in other therapeutic areas. Scientists are exploring its potential as a novel compound for the development of new drugs and therapies.
Used in Pidotimod Impurity:
5,11-bisthio-(R,R)-1,7-diazatricyclo[7.3.0.07,11]dodecane-2,8-diketone is used as an impurity in the synthesis of Pidotimod, a drug with immunomodulatory properties. Its presence in the synthesis process is monitored and controlled to ensure the quality and efficacy of the final product.

Upstream product

• 34592-47-7 L-thioproline 
• 60664-15-5 ethyl (4R)-1,3-thiazolidine-4-carboxylate 
• 67089-84-3 (R)-thiazolidine-4-carboxylic acid hydrochloride 
• 51077-16-8 N-(tert-butoxycarbonyl)-(R)-thiazolidine-4-carboxylic acid 

Relevant academic research and scientific papers

A straightforward synthesis and partial hydrolysis of cysteine-derived 2,5-diketopiperazines

A mild and straightforward preparation of cysteine-derived 2,5-diketopiperazines (DKPs) is reported, by cyclization of (R)-2,2- dimethyltetrahydrothiazole-4-carboxylic acid hydrochloride or of (R)-tetrahydrothiazole-4-carboxylic acid hydrochloride, mediated by HBTU and DIEA. One DKP has been characterized by X-ray analysis, while the other has been hydrolyzed to cyclo-Cys-Cys. The preparation of this latter compound has been previously reported to be troublesome and low yielding.

Synthesis of a chiral, polydentate ligand system setting out from L -cysteine and first nickel complexes thereof

Setting out from protected L-cysteine a 2, 5-diketopiperazine V can be synthesized, the reduction of which with NaBH4/TiCl4 leads to (6R,8aR)-7-methyl-6-(sulfanylmethyl)-thiazolidine [3,4-a] piperazine, L 1H as well as N,N′-dimethyl-(2R,5R)-bis(sulfanylmethyl) piperazine, L2H2, which were separated and characterized. L2H2 can be obtained selectively, if V is reduced by NaBH4/TiCl4 in the presence of DIEA·HCl, and it represents a precursor for a novel, chiral ligand, as after deprotonation it provides two thiolato and two amino donor functions for the coordination of a metal atom. Deprotonation of L1H and L2H2 with NaOMe followed by treatment with NiBr2(dme) led to the isolation of the dimeric complexes [L1NiBr]2 (1) and [L 2Ni]2 (2), respectively. Both were fully characterized, and cyclic voltammetry indicated the possibility of NiII → NiIII oxidations for complex 2. 2 can be regarded as a structural model for the A clusters of the acetyl coenzyme A synthase. Copyright

Synthesis and Structural Study of piperazine-2,5-diones derived from (R)-cysteine

Coupling Leuch's anhydrides obtained from (R)-thiazolidine-4-carboxylic acids 1 and 3 with one equivalent of the corresponding ethyl ester derivative of 1 or 3, leads to the formation of chiral piperazine-2,5-diones 2, 4, 5, 6, and 7, on thermal treatment of the intermediate dipeptides.The configuration of the products was established by nOe experiments.

Anti-biofilm and anti-adherence properties of novel cyclic dipeptides against oral pathogens

Microorganisms embedded in a biofilm are significantly more resistant to antimicrobial agents and the defences of the human immune system, than their planktonic counterpart. Consequently, compounds that can inhibit biofilm formation are of great interest for novel therapeutics. In this study, a screening approach was used to identify novel cyclic dipeptides that have anti-biofilm activity against oral pathogens. Five new active compounds were identified that prevent biofilm formation by the cariogenic bacterium Streptococcus mutans and the pathogenic fungus Candida albicans. These compounds also inhibit the adherence of microorganisms to a hydroxylapatite surface. Further investigations were conducted on these compounds to establish the structure–activity relationship, and it was deduced that the common cleft pattern is required for these molecules to act effectively against biofilms.

Interfacial supramolecular biomimetic epoxidation catalysed by cyclic dipeptides

We synthesised a library of cis- and trans-cyclic dipeptides and evaluated their efficacy as catalysts in the asymmetric Weitz-Scheffer epoxidation of trans-chalcone. A thorough investigation relying on structure-activity studies and computational studies provided insights into the mechanism of the process. Our results revealed some structural features required for efficient conversion and for introduction of chirality into the product. The cyclic dipeptide acts as a catalyst by templating a supramolecular arrangement at the aqueous-organic interface required for efficient transformations to occur. Among all cyclic dipeptides investigated, cyclo(Leu-Leu) was the most efficient supramolecular catalyst.