(S)-S-Benzyl 6-amino-2-(((benzyloxy)carbonyl)amino)hexanethioate hydrochloride - 69861-89-8

(S)-S-Benzyl 6-amino-2-(((benzyloxy)carbonyl)amino)hexanethioate hydrochloride

Catalog Number: EVT-247552
CAS Number: 69861-89-8
Molecular Formula: C21H27ClN2O3S
Molecular Weight: 423 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction

Description
(S)-S-Benzyl 6-amino-2-(((benzyloxy)carbonyl)amino)hexanethioate hydrochloride is a chemical compound that has gained significant attention in the field of medical research due to its potential therapeutic effects. This paper aims to provide a comprehensive overview of the synthesis, chemical structure, biological activity, and potential applications of this compound.
Applications in Various Fields
In medical research, (S)-S-Benzyl 6-amino-2-(((benzyloxy)carbonyl)amino)hexanethioate hydrochloride has been used as a lead compound in drug development. Several derivatives of this compound have been synthesized and tested for their inhibitory effects on cathepsin B and other enzymes. Clinical trials are currently underway to evaluate the safety and efficacy of these compounds in cancer patients.
In environmental research, (S)-S-Benzyl 6-amino-2-(((benzyloxy)carbonyl)amino)hexanethioate hydrochloride has been used to study its effects on ecosystems and pollution management. This compound has been shown to inhibit the growth of algae and other aquatic organisms, indicating its potential as a biopesticide. Additionally, it has been used in the treatment of wastewater to remove heavy metals and other pollutants.
In industrial research, (S)-S-Benzyl 6-amino-2-(((benzyloxy)carbonyl)amino)hexanethioate hydrochloride has been used in manufacturing processes to improve product quality and efficiency. This compound has been shown to enhance the stability and shelf life of certain products, such as cosmetics and pharmaceuticals. Health and safety considerations are crucial in the use of this compound in industrial settings, and proper handling and disposal procedures must be followed to prevent environmental contamination and worker exposure.

Properties

CAS Number

69861-89-8

Product Name

(S)-S-Benzyl 6-amino-2-(((benzyloxy)carbonyl)amino)hexanethioate hydrochloride

IUPAC Name

S-benzyl (2S)-6-amino-2-(phenylmethoxycarbonylamino)hexanethioate;hydrochloride

Molecular Formula

C21H27ClN2O3S

Molecular Weight

423 g/mol

InChI

InChI=1S/C21H26N2O3S.ClH/c22-14-8-7-13-19(20(24)27-16-18-11-5-2-6-12-18)23-21(25)26-15-17-9-3-1-4-10-17;/h1-6,9-12,19H,7-8,13-16,22H2,(H,23,25);1H/t19-;/m0./s1

InChI Key

PNDSXGXPDJRQAV-FYZYNONXSA-N

SMILES

C1=CC=C(C=C1)COC(=O)NC(CCCCN)C(=O)SCC2=CC=CC=C2.Cl

Synonyms

Z-L-Lys-SBzlhydrochloride;69861-89-8;Z-LYS-SBZLHCL;AC1L4DUS;C3647_SIGMA;N-|A-Cbz-L-lysinethiobenzylesterhydrochloride;N-alpha-Cbz-L-lysinethiobenzylesterhydrochloride;S-benzyl(2S)-6-amino-2-(phenylmethoxycarbonylamino)hexanethioatehydrochloride;Hexanethioicacid,6-amino-2-(((phenylmethoxy)carbonyl)amino)-,S-(phenylmethyl)ester,monohydrochloride,(S)-

Canonical SMILES

C1=CC=C(C=C1)COC(=O)NC(CCCCN)C(=O)SCC2=CC=CC=C2.Cl

Isomeric SMILES

C1=CC=C(C=C1)COC(=O)N[C@@H](CCCCN)C(=O)SCC2=CC=CC=C2.Cl
Method of Synthesis or Extraction
The synthesis of (S)-S-Benzyl 6-amino-2-(((benzyloxy)carbonyl)amino)hexanethioate hydrochloride can be achieved through various methods, including the use of protecting groups, coupling reactions, and deprotection. The efficiency and yield of each method depend on several factors, such as the starting materials, reaction conditions, and purification methods. However, the most commonly used method involves the coupling of N-Boc-protected amino acid with benzyl mercaptan, followed by deprotection and coupling with benzyl chloroformate. The yield of this method is typically around 50-60%, and the purity can be improved through recrystallization or chromatography.
Environmental and safety considerations are crucial in the synthesis of (S)-S-Benzyl 6-amino-2-(((benzyloxy)carbonyl)amino)hexanethioate hydrochloride. The use of toxic reagents, such as benzyl chloroformate, requires proper handling and disposal to prevent environmental contamination. Additionally, the use of protective equipment, such as gloves and goggles, is necessary to ensure the safety of the researchers.
Chemical Structure and Biological Activity
The chemical structure of (S)-S-Benzyl 6-amino-2-(((benzyloxy)carbonyl)amino)hexanethioate hydrochloride consists of a thioester group, an amino acid, and a benzyl ester group. This compound has been shown to exhibit potent inhibitory effects on several enzymes, including cathepsin B, a lysosomal cysteine protease involved in cancer progression. The mechanism of action involves the formation of a covalent bond between the thioester group and the active site of the enzyme, leading to irreversible inhibition.
Biological Effects
The biological effects of (S)-S-Benzyl 6-amino-2-(((benzyloxy)carbonyl)amino)hexanethioate hydrochloride on cell function and signal transduction have been extensively studied. This compound has been shown to induce apoptosis in cancer cells by inhibiting the activity of cathepsin B. Additionally, it has been reported to modulate the expression of several genes involved in cell cycle regulation and DNA repair.
Potential therapeutic and toxic effects of (S)-S-Benzyl 6-amino-2-(((benzyloxy)carbonyl)amino)hexanethioate hydrochloride are still under investigation. However, preliminary studies have shown promising results in the treatment of various types of cancer, including breast, lung, and prostate cancer. The toxicity of this compound is relatively low, with no significant adverse effects reported in animal studies.
Future Perspectives and Challenges
Current limitations in the use and study of (S)-S-Benzyl 6-amino-2-(((benzyloxy)carbonyl)amino)hexanethioate hydrochloride include the lack of understanding of its pharmacokinetics and toxicity in humans. Further studies are needed to evaluate the safety and efficacy of this compound in clinical settings. Possible solutions and improvements include the development of more potent and selective derivatives of this compound and the use of advanced drug delivery systems to improve its bioavailability and targeting.
Future trends and prospects in the application of (S)-S-Benzyl 6-amino-2-(((benzyloxy)carbonyl)amino)hexanethioate hydrochloride in scientific research include the identification of new biological targets and the development of novel therapeutic strategies. Additionally, the use of this compound in combination with other drugs or therapies may enhance its efficacy and reduce potential side effects.

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