18274-81-2

Basic information

• Product Name: desmethylanethol trithione
• Synonyms: desmethylanethol trithione;5-(4-hydroxyphenyl)-3H-1,2-dithiole-3-thione;Adt-Oh;ACS 1
• CAS NO: 18274-81-2
• Molecular Formula: C₉H₆OS₃
• Molecular Weight: 226.33834
• Mol File: 18274-81-2.mol
• Article Data: 37

Chemical Properties

• Melting Point: 191-192 °C
• Boiling Point: 322.2°Cat760mmHg
• Flash Point: 148.6°C
• Appearance: /
• Density: 1.48g/cm³
• Vapor Pressure: 0.000284mmHg at 25°C
• Refractive Index: 1.757
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 9.78±0.30(Predicted)
• CAS DataBase Reference: desmethylanethol trithione(CAS DataBase Reference)
• NIST Chemistry Reference: desmethylanethol trithione(18274-81-2)
• EPA Substance Registry System: desmethylanethol trithione(18274-81-2)

Safety Data

• Hazardous Substances Data: 18274-81-2(Hazardous Substances Data)

Usage

Description

ADT-OH is a derivative of anethole dithiolethione (ADT) and synthetic hydrogen sulfide (H2S) donor. It can be readily esterified with other moieties. For example, it can be coupled with therapeutics like nonsteroidal anti-inflammatory drugs, as in the generation of ATB-343 . ADT-OH has also been linked with a mitochondria-targeting motif to produce AP-39 , which selectively increases mitochondrial H2S levels. ADT-OH is used both in cells and in animals for comparative studies with derived chimeras.

Uses

is used in method for preventing or treating diseases associated with administration of VEGFR and/or VEGF inhibitor.

InChI:InChI=1/C9H6OS3/c10-7-3-1-6(2-4-7)8-5-9(11)13-12-8/h1-5,11H

Upstream product

• 25679-28-1 cis-Anethole 
• 32066-29-8 methyl 3-(4-hydroxyphenyl)-3-oxo-propanoate 
• 99-93-4 4-Hydroxyacetophenone 
• 85699-00-9 1-[4-(methoxymethoxy)phenyl]-1-ethanone 
• 1237745-35-5 5-(4-(methoxymethoxy))-3H-1,2-dithiole-3-thione 
• 104-46-1 anethole 
• 4180-23-8 E-1-(4'-methoxyphenyl)prop-1-ene 
• 93-89-0 benzoic acid ethyl ester 
• 20649-39-2 (E)-1-(4-hydroxyphenyl)propene 
• 532-11-6 anethole trithione 

Downstream Products

• 1621578-16-2 4-(3-thioxo-3H-1,2-dithiol-5-yl)phenyl-2-(4-(nitrooxy)butoxy)benzoate 
• 1621578-17-3 4-(3-thioxo-3H-1,2-dithiol-5-yl)phenyl-3-(4-(nitrooxy)butoxy)benzoate 
• 1621578-18-4 4-(3-thioxo-3H-1,2-dithiol-5-yl)phenyl-2-(4-(nitrooxy)butoxy)benzoate 
• 7783-06-4 hydrogen sulfide 
• 1155414-00-8 ethyl 7-[4-(3-thioxo-3H-1,2-dithiol-5-yl)phenoxy]heptanoate 
• 1155413-88-9 4-(3-thioxo-3H-1,2-dithiol-5-yl)phenyl 8-oxo-8-(phenylamino)octanoate 
• 1155413-89-0 4-(3-thioxo-3H-1,2-dithiol-5-yl)phenyl 4-phenylbutanoate 
• 1155414-02-0 ethyl 5-[4-(3-thioxo-3H-1,2-dithiol-5-yl)phenoxy]pentanoate 
• 1134191-22-2 4-(5-thioxo-5H-1,2-dithiol-3-yl)phenyl 2-(4-(4-ethoxy-3-(5-methyl-4-oxo-7-propyl-1,4-dihydroimidazo[1,5-f][1,2,4]triazin-2-yl)phenylsulfonyl)piperazin-1-yl)acetate 
• 1134191-24-4 4-(5-thioxo-5H-1,2-dithiol-3-yl)phenyl (6R,12aR)-2,3,6,7,12,12a-hexahydro-6-(3,4-methylendioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione-2-acetate 

Relevant articles and documents

Hydrogen sulfide releasing enmein-type diterpenoid derivatives as apoptosis inducers through mitochondria-related pathways

In this study, we combined two enemin-type diterpenoid derivatives with two well-established hydrogen sulfide moieties via ester or different anhydride linkers, to search apoptosis inducing drug candidate capable of hydrogen sulfide generating. Therefore,

Synthesis and Pharmacological Evaluation of Novel Adenine-Hydrogen Sulfide Slow Release Hybrids Designed as Multitarget Cardioprotective Agents

This work deals with the design, synthesis, and evaluation of the cardioprotective properties of a number of novel hybrid compounds combining the adenine nucleus with a suitable H2S slow-releasing moiety, coupled via a stable ether bond. The H2S release rate of the hybrids and their ability to increase cGMP were estimated in vitro. The most promising derivatives 4 and 11, both containing 4-hydroxythiobenzamide moiety as H2S donor, were selected for further in vivo evaluation. Their ability to release H2S in vivo was recorded using a new fully validated UPLC-DAD method. Both compounds reduced significantly the infarct size when administered at the end of sustained ischemia. Mechanistic studies showed that they conferred enhanced cardioprotection compared to adenine or 4-hydroxythiobenzamide. They activate the PKG/PLN pathway in the ischemic myocardium, suggesting that the combination of both pharmacophores results in synergistic cardioprotective activity through the combination of both molecular pathways that trigger cardioprotection.

3-H-[1,2]Dithiole as a new anti-trypanosoma cruzi chemotype: Biological and mechanism of action studies

The current pharmacological Chagas disease treatments, using Nifurtimox or Benznidazole, show limited therapeutic results and are associated with potential side effects, like mutagenicity. Using random screening we have identified new chemotypes that were able to inhibit relevant targets of the Trypanosoma cruzi. We found 3H-[1,2]dithioles with the ability to inhibit Trypanosoma cruzi triosephosphate isomerase (TcTIM). Herein, we studied the structural modifications of this chemotype to analyze the influence of volume, lipophilicity and electronic properties in the anti-T. cruzi activity. Their selectivity to parasites vs. mammalian cells was also examined. To get insights into a possible mechanism of action, the inhibition of the enzymatic activity of TcTIM and cruzipain, using the isolated enzymes, and the inhibition of membrane sterol biosynthesis and excreted metabolites, using the whole parasite, were achieved. We found that this structural framework is interesting for the generation of innovative drugs for the treatment of Chagas disease.

Tanshinol and H2 S/NO Donor binding, preparation method thereof and application in pharmacy (by machine translation)

The invention belongs to the field of chemical pharmacy, and relates to active ingredient tanshinol and H in Chinese herbal medicine Salvia miltiorrhiza. 2 S/NO Donors and its preparation method and use in pharmacy, especially in the preparation of medicines for preventing and treating cardiovascular and cerebrovascular diseases and inflammation related diseases. To the invention, through in-vitro oxidative stress injury and inflammation model experiments, the results show that H is obviously inhibited. 2 O2 In vivo activity experiment results show that the conjugate is capable of remarkably inhibiting the release of inflammatory cytokines induced by LPS (LPS), reducing inflammation-induced mouse peritoneal macrophages, obviously inhibiting the release of inflammatory cytokines induced by LPS, and showing the result that the compound can be used for preparing drugs for preventing and treating cardiovascular and cerebrovascular diseases and inflammatory diseases. (by machine translation)