52958-74-4

Upstream product

• 2043-61-0 cyclohexanecarbaldehyde 

Downstream Products

• 212574-88-4 1-mercapto-1,1-pentamethylenethan-2-ol 
• 935676-91-8 acetic acid 1-(1-acetoxymethyl-cyclohexyldisulfanyl)-cyclohexylmethyl ester 
• 883716-66-3 5’-O-DMT-N²-isobutyryl-2’-deoxyguanosine-3’-O-(2-thio-4,4-pentamethylene-1,3,2-oxathiaphospholane) 
• 865716-19-4 5’-O-DMT-N⁶-benzoyl-2’-deoxyadenosine-3’-O-(2-thio-4,4-pentamethylene-1,3,2-oxathiaphospholane) 

Relevant academic research and scientific papers

Enantioselective organocatalytic oxidation of functionalized sterically hindered disulfides

Figure presented The first study on enantioselective oxidation of functionalized sterically hindered disulfides is reported. This study shows that the Shi organocatalytic system using carbohydrate-derived ketone with oxone is superior to the Ellman-Bolm v

Exploration of Pyrrolobenzodiazepine (PBD)-Dimers Containing Disulfide-Based Prodrugs as Payloads for Antibody-Drug Conjugates

A number of cytotoxic pyrrolobenzodiazepine (PBD) monomers containing various disulfide-based prodrugs were evaluated for their ability to undergo activation (disulfide cleavage) in vitro in the presence of either glutathione (GSH) or cysteine (Cys). A good correlation was observed between in vitro GSH stability and in vitro cytotoxicity toward tumor cell lines. The prodrug-containing compounds were typically more potent against cells with relatively high intracellular GSH levels (e.g., KPL-4 cells). Several antibody-drug conjugates (ADCs) were subsequently constructed from PBD dimers that incorporated selected disulfide-based prodrugs. Such HER2 conjugates exhibited potent antiproliferation activity against KPL-4 cells in vitro in an antigen-dependent manner. However, the disulfide prodrugs contained in the majority of such entities were surprisingly unstable toward whole blood from various species. One HER2-targeting conjugate that contained a thiophenol-derived disulfide prodrug was an exception to this stability trend. It exhibited potent activity in a KPL-4 in vivo efficacy model that was approximately three-fold weaker than that displayed by the corresponding parent ADC. The same prodrug-containing conjugate demonstrated a three-fold improvement in mouse tolerability properties in vivo relative to the parent ADC, which did not contain the prodrug.

First examples of oxidizing aldehydes to carboxylic acids in the presence of a tertiary disulfide functional group: Synthesis of novel diacid-disulfides

The disulfide functionality exists in numerous organic compounds of interest in both chemistry and biology. In view of the fact that the disulfide function is highly susceptible to further oxidation by a broad range of agents, conducting a chemoselective

Oxathiaphospholane approach to the synthesis of P-chiral, isotopomeric deoxy(ribonucleoside phosphorothioate)s and phosphates labeled with an oxygen isotope

Diastereomerically pure and isotopically labeled 5′-O-DMT-nucleoside-3′-O-(2thio- and -oxo-4,4- "spiro" -pentamethylene-1,3,2-[18O]oxathiaphospholane)s were used for stereocontrolled synthesis of P-chiral, isotopically labeled oligonucleotide phosporothioates and phosphats, as well as "chimeric" PS18O/P18O oligomers (see scheme) without loss of isotope enrichment. DBU = 1,8-diazabicyclo [5.4.0]under-7-ene, DMT = 4,4′-dimethoxytyl, ROH = 3′-O-acetylthymidine, Bz = benzoyl.

Nitrosated and nitrosylated nonsteroidal antiinflammatory compounds, compositions and methods of use

The present invention describes novel nitrosated and/or nitrosylated nonsteroidal antiinflammatory compounds, and novel compositions comprising at least one nitrosated and/or nitrosylated nonsteroidal antiinflammatory compound, and, optionally, at least o

Nitrosothiol esters of diclofenac: Synthesis and pharmacological characterization as gastrointestinal-sparing prodrugs

Despite its widespread use, diclofenac has gastrointestinal liabilities common to nonsteroidal antiinflammatory drugs (NSAIDs) that might be reduced by concomitant administration of a gastrointestinal cytoprotectant such as nitric oxide (NO). A series of novel diclofenac esters containing a nitrosothiol (-S-NO) moiety as a NO donor functionality has been synthesized and evaluated in vivo for bioavailability, pharmacological activity, and gastric irritation. All S-NO-diclofenac derivatives acted as orally bioavailable prodrugs, producing significant levels of diclofenac in plasma within 15 rain after oral administration to mice. At equimolar oral doses, S-NO-diclofenac derivatives (20a-21b) displayed rat antiinfiammatory and analgesic activities comparable to those of diclofenac in the carrageenan-induced paw edema test and the mouse phenylbenzoquinone-induced writhing test, respectively. All tested S-NO-diclofenac derivatives (20a-21b) were gastric-sparing in that they elicited markedly fewer stomach lesions as compared to the stomach lesions caused by a high equimolar dose of diclofenac in the rat. Nitrosothiol esters of diclofenac comprise a novel class of NO-donating compounds having therapeutic potential as nonsteroidal antiinflammatory agents with an enhanced gastric safety profile.

Nucleoside 3'-O-(2-oxo-'spiro'-4.4-pentamethylene-1.3.2- oxathiaphospholane)s: Monomers for stereocontrolled synthesis of oligo(nucleoside phosphorothioate/phosphate)s

Attempts at synthesis of 'chimeric' oligonucleotide constructs (PO/PS- Oligos) possessing phosphate and P-stereodefined phosphorothioate internucleotide linkages via combined phosphoramidite/oxathiaphospholane methods were unsuccessful. Therefore, novel m