1151989-04-6

Basic information

• Product Name: (4-nitrophenyl) [4-(2-pyridyldisulfanyl)phenyl]methyl carbonate
• Synonyms: (4-nitrophenyl) [4-(2-pyridyldisulfanyl)phenyl]methyl carbonate
• CAS NO: 1151989-04-6
• Molecular Weight: 414.463
• Mol File: 1151989-04-6.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (4-nitrophenyl) [4-(2-pyridyldisulfanyl)phenyl]methyl carbonate(CAS DataBase Reference)
• NIST Chemistry Reference: (4-nitrophenyl) [4-(2-pyridyldisulfanyl)phenyl]methyl carbonate(1151989-04-6)
• EPA Substance Registry System: (4-nitrophenyl) [4-(2-pyridyldisulfanyl)phenyl]methyl carbonate(1151989-04-6)

Safety Data

• Hazardous Substances Data: 1151989-04-6(Hazardous Substances Data)

Usage

Description

(4-nitrophenyl) [4-(2-pyridyldisulfanyl)phenyl]methyl carbonate is a chemical compound with the molecular formula C20H15N3O6S. It is a white to off-white powder that is insoluble in water and soluble in most organic solvents. (4-nitrophenyl) [4-(2-pyridyldisulfanyl)phenyl]methyl carbonate contains a nitrophenyl group, a pyridyldisulfanyl group, and a methyl carbonate group, which makes it useful in various chemical reactions, such as nucleophilic substitution and cross-coupling reactions. It is also used in the synthesis of pharmaceuticals and agrochemicals. (4-nitrophenyl) [4-(2-pyridyldisulfanyl)phenyl]methyl carbonate is known for its stability and selective reactivity, making it a valuable tool in chemical research and development.

Uses

Used in Organic Synthesis:
(4-nitrophenyl) [4-(2-pyridyldisulfanyl)phenyl]methyl carbonate is used as a reagent in organic synthesis for its ability to participate in nucleophilic substitution and cross-coupling reactions.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, (4-nitrophenyl) [4-(2-pyridyldisulfanyl)phenyl]methyl carbonate is used as a building block for the synthesis of various pharmaceuticals due to its unique functional groups and reactivity.
Used in Agrochemical Synthesis:
Similarly, in the agrochemical industry, this compound is used as a precursor in the synthesis of agrochemicals, contributing to the development of new pesticides and other agricultural products.
Used in Chemical Research and Development:
(4-nitrophenyl) [4-(2-pyridyldisulfanyl)phenyl]methyl carbonate is also utilized in chemical research and development due to its stability and selective reactivity, which aids in the discovery and optimization of new chemical processes and compounds.

Upstream product

• 2127-03-9 2,2'-dipyridyldisulphide 
• 53339-53-0 4-mercaptobenzyl alcohol 
• 7693-46-1 4-Nitrophenyl chloroformate 
• 5070-13-3 bis-(p-nitrophenyl) carbonate 
• 126049-37-4 (4-(pyridin-2-yldisulfanyl)phenyl)methanol 
• 1074-36-8 4-mercaptobenzoic acid 

Downstream Products

• 1151989-07-9 C₆₀H₆₀N₂O₁₆S₂ 

Relevant articles and documents

Modulated Fragmentation of Proapoptotic Peptide Nanoparticles Regulates Cytotoxicity

Peptides perform a diverse range of physiologically important functions. The formulation of nanoparticles directly from functional peptides would therefore offer a versatile and robust platform to produce highly functional therapeutics. Herein, we engineered proapoptotic peptide nanoparticles from mitochondria-disrupting KLAK peptides using a template-assisted approach. The nanoparticles were designed to disassemble into free native peptides via the traceless cleavage of disulfide-based cross-linkers. Furthermore, the cytotoxicity of the nanoparticles was tuned by controlling the kinetics of disulfide bond cleavage, and the rate of regeneration of the native peptide from the precursor species. In addition, a small molecule drug (i.e., doxorubicin hydrochloride) was loaded into the nanoparticles to confer synergistic cytotoxic activity, further highlighting the potential application of KLAK particles in therapeutic delivery.

Stabilizing p-Dithiobenzyl Urethane Linkers without Rate-Limiting Self-Immolation for Traceless Drug Release

Exploiting the redox sensitivity of disulfide bonds is a prevalent strategy in targeted prodrug designs. In contrast to aliphatic disulfides, p-thiobenzyl-based disulfides have rarely been used for prodrug designs, given their intrinsic instability caused by the low pKa of aromatic thiols. Here, we examined the interplay between steric hindrance and the low-pKa effect on thiol–disulfide exchange reactions and uncovered a new thiol–disulfide exchange process for the self-immolation of p-thiobenzyl-based disulfides. We observed a central leaving group shifting effect in the α,α-dimethyl-substituted p-dithiobenzyl urethane linkers (DMTB linkers), which leads to increased disulfide stability by more than two orders of magnitude, an extent that is significantly greater than that observed with typical aliphatic disulfides. In particular, the DMTB linkers display not only high stability, but also rapid self-immolation kinetics due to the low pKa of the aromatic thiol, which can be used as a general and robust linkage between targeting reagents and cytotoxic drugs for targeted prodrug designs. The unique and promising stability characteristics of the present DMTB linker will likely inspire the development of novel targeted prodrugs to achieve traceless release of drugs into cells.

An oral redox-sensitive self-immolating prodrug strategy

We report a novel oral prodrug approach where a solubilizing polymer conjugated to the drug is designed to be released by the action of an exogenously administered agent in the intestine. A redox-sensitive self-immolating design was implemented, and the reconversion kinetics were studied for three reducible prodrugs.