6088-51-3

Usage

Uses

Used in Analytical Chemistry:
6-HYDROXY-2-NAPHTHYL DISULFIDE is used as a reagent for the determination of protein-bound sulfhydryl groups. Its chemical structure allows it to selectively react with sulfhydryl groups, making it a valuable tool in the analysis and quantification of these groups in proteins.
Used in Pharmaceutical Industry:
6-HYDROXY-2-NAPHTHYL DISULFIDE is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical properties make it a useful building block for the development of new drugs with potential therapeutic applications.
Used in Environmental Science:
6-HYDROXY-2-NAPHTHYL DISULFIDE can be used in the development of new methods for the detection and analysis of environmental contaminants, such as pesticides like DDT and its metabolite TDE. Its reactivity with sulfhydryl groups may provide a means to detect and quantify these contaminants in environmental samples.
Used in Material Science:
The unique chemical properties of 6-HYDROXY-2-NAPHTHYL DISULFIDE may also find applications in the development of new materials with specific properties, such as improved stability or reactivity. Its disulfide bond and hydroxyl group could be exploited to create novel materials with potential uses in various industries.

Purification Methods

It crystallises as leaflets from AcOH and is slightly soluble in EtOH, and AcOH, but is soluble in *C6H6 and in alkalis to give a yellow solution. [Zincke & Dereser Chem Ber 51 352 1918.] The acetoxy derivative has m 198-200o (from AcOH or dioxane/MeOH), and the diacetyl derivative has m 167-168o (from AcOH). A small amount of impure disulfide can be purified by dissolving it in a small volume of Me2CO and adding a large volume of toluene, filter rapidly and concentrate to one-third of its volume. The hot toluene solution is filtered rapidly from any tarry residue, and crystals separate on cooling. Recrystallisation from hot acetic acid gives crystals with m 220-223o [Barrett & Seligman Science 116 323 1952]. [Beilstein 6 I 481.]

Toxicity evaluation

Animal Studies. DDD is less acutely toxic than DDT (29), with an oral LD50 of 3400 to 4000 mg/kg in the rat and a dermal LD50 ca. 1200 mg/kg in the rabbit. In a 2-year chronic dietary study in the rat, a LOEL of 100 ppm (5 mg/kg/day) was quoted for tissue damage, similar to that produced by DDT.Human Studies. Most of the studies conducted in humans have used the o,p -isomer of DDD. This has been used as a drug, with medical and veterinary uses, for the treatment of Cushing’s syndrome and adrenal carcinoma, under the generic name of mitotane. After oral ingestion, o,p’-DDD binds to lung and adrenal tissue. Its toxicity to the adrenal appears to be species-dependent, however, causing gross atrophy in the dog and reducing corticosteroid production without pathological effects in other mammals, including humans.

InChI:InChI=1/C20H14O2S2/c21-17-5-1-15-11-19(7-3-13(15)9-17)23-24-20-8-4-14-10-18(22)6-2-16(14)12-20/h1-12,21-22H

Upstream product

• 6088-50-2 (6-Oxy-naphthyl-⁽²⁾)-mercaptan 
• 125518-82-3 6-<(ethoxycarbonyl)oxy>-2-mercaptonaphthalene 

Relevant academic research and scientific papers

Effects of oxygen-sulfur substitution on glycosaminoglycan-priming naphthoxylosides

Three series of sulfur-containing analogs to the selectively antiproliferative 2-(6-hydroxynaphthyl) β-d-xylopyranoside were synthesized and their biological properties investigated. A short, general route to hydroxynaphthyl disulfides from dihydroxynaphthalenes was developed to utilize the disulfide bond as a sulfur-selective protecting group to enable the orthogonal protection of hydroxyls and thiols. The results indicate that hydrophobic, uncharged oxygen-sulfur substituted naphthoxylosides are taken up by cells and initiate priming of GAG chains to a greater extent compared to the oxygen analogs. No correlation between priming ability and antiproliferative activity was observed.

COMPOSITIONS COMPRISING ENZYME-CLEAVABLE PRODRUGS OF ACTIVE AGENTS AND INHIBITORS THEREOF

The present disclosure provides pharmaceutical compositions, and their methods of use, where the pharmaceutical compositions comprise a prodrug that provides enzymatically-controlled release of a drug and an enzyme inhibitor that interacts with the enzyme(s) that mediates the enzymatically-controlled release of the drug from the prodrug so as to attenuate enzymatic cleavage of the prodrug. The disclosure provides pharmaceutical compositions which comprise an enzyme inhibitor and a prodrug that contains an enzyme-cleavable moiety that, when cleaved, facilitates release of the drug.

Compositions Comprising Enzyme-Cleavable Phenol-Modified Opioid Prodrugs and Inhibitors Thereof

Pharmaceutical compositions and their methods of use are provided, where the pharmaceutical compositions comprise a phenol-modified opioid prodrug that provides enzymatically-controlled release of a phenolic opioid, and an enzyme inhibitor that interacts with the enzyme(s) that mediates the enzymatically-controlled release of the phenolic opioid from the phenol-modified opioid prodrug so as to modify enzymatic cleavage of the phenol-modified opioid prodrug.

NOVEL MACROCYCLIC INHIBITORS OF HEPATITIS C VIRUS REPLICATION

The embodiments provide compounds of the general Formulae I, II, III, IV, V, VI, VII, and X, as well as compositions, including pharmaceutical compositions, comprising a subject compound. The embodiments further provide treatment methods, including methods of treating a hepatitis C virus infection and methods of treating liver fibrosis, the methods generally involving administering to an individual in need thereof an effective amount of a subject compound or composition.

Anti-cancer compounds

The present invention provides compounds useful to inhibit tumor growth and to induce apoptosis. In general, the anti-cancer agents (ACA) are described by the formula: [ACA]n-X??[Formula I] wherein X is a linker group having 2-5 functional groups or is absent, n=1, and ACA is selected from the group consisting of Formula II, Formula III, Formula IV, Formula V, and Formula VI, as described herein. Other compounds described herein are defined by the Formula VII, as described herein.

ANTAGONISTS OF GONADOTROPIN RELEASING HORMONE

There are disclosed compounds of formula (I) STR1 and pharmaceutically acceptable salts thereof which are useful as antagonists of GnRH and as such may be useful for the treatment of a variety of sex-hormone related and other conditions in both men and women.

Antagonists of gonadotropin releasing hormone

There are disclosed compounds of formula (I) STR1 and pharmaceutically acceptable salts thereof which are useful as antagonists of GnRH and as such may be useful for the treatment of a variety of sex-hormone related and other conditions in both men and women.

ANTAGONISTS OF GONADOTROPIN RELEASING HORMONE

There are disclosed compounds of formula (I) STR1 and pharmaceutically acceptable salts thereof which are useful as antagonists of GnRH and as such may be useful for the treatment of a variety of sex-hormone related and other conditions in both men and women.

Method for preparing mercapto propionic acid esters and polythio dipropionic acid esters

A process is provided for the preparation of mercapto propionic acid esters and/or polythio dipropionic acid esters by reaction of an acrylic acid ester with hydrogen sulfide in the presence of a weakly basic amine as a catalyst, a polythiodipropionic acid ester as a reactive solvent, and added elemental sulfur.

Method for preparing mercapto propionic acid esters and polythio dipropionic acid esters

A process is provided for the preparation of mercapto propionic acid esters and/or polythio dipropionic acid esters by reaction of an acrylic acid ester with hydrogen sulfide in the presence of a weakly basic amine base as a catalyst and a polythiodipropionic acid ester as a reactive solvent.