18274-81-2

Usage

Uses

Used in Pharmaceutical Industry:
Desmethylanethol trithione is used as a synthetic hydrogen sulfide (H2S) donor for enhancing the therapeutic effects of certain drugs and targeting specific cellular components, such as mitochondria.
Used in Preventive and Treatment Applications:
Desmethylanethol trithione is used as a preventive or treatment agent for diseases associated with the administration of VEGFR and/or VEGF inhibitors, potentially improving the efficacy and safety of these treatments.
Used in Comparative Studies:
Desmethylanethol trithione is used as a research compound in both cellular and animal models for comparative studies with derived chimeras, contributing to the understanding of its mechanisms of action and potential applications in medicine.

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

Upstream product

• 532-11-6 anethole trithione 
• 20649-39-2 (E)-1-(4-hydroxyphenyl)propene 
• 4180-23-8 E-1-(4'-methoxyphenyl)prop-1-ene 
• 104-46-1 anethole 
• 25679-28-1 cis-Anethole 
• 93-89-0 benzoic acid ethyl ester 
• 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 

Downstream Products

• 133430-71-4 5-(p-hydroxyphenyl)-3H-1,2-dithiole-3-one 
• 912758-00-0 2-[(2,6-dichlorophenyl)amino]benzeneacetic acid 4-(3H-1,2-dithiole-3-thione-5-yl)phenyl ester 
• 917471-48-8 (Z)-5-fluoro-2-methyl-1-[[4-(methylsulfone)phenyl]methylene]-1H-indene-3-acetic acid 4-(thioxo-5H-[1,2]dithiol-3-yl)-phenyl ester 
• 947152-78-5 C₂₆H₂₇NO₇S₃ 
• 947152-51-4 ATB-429 
• 1155414-02-0 ethyl 5-[4-(3-thioxo-3H-1,2-dithiol-5-yl)phenoxy]pentanoate 
• 1155413-89-0 4-(3-thioxo-3H-1,2-dithiol-5-yl)phenyl 4-phenylbutanoate 
• 1155413-88-9 4-(3-thioxo-3H-1,2-dithiol-5-yl)phenyl 8-oxo-8-(phenylamino)octanoate 
• 1155414-00-8 ethyl 7-[4-(3-thioxo-3H-1,2-dithiol-5-yl)phenoxy]heptanoate 
• 1234493-47-0 5-(4-(2-(dimethylamino)ethoxy)phenyl)-3H-1,2-dithiole-3-thione 
• 908288-94-8 5-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-3H-1,2-dithiole-3-thione 
• 1234493-48-1 5-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)-3H-1,2-dithiole-3-thione 
• 908288-93-7 5-(4-(2-morpholinoethoxy)phenyl)-3H-1,2-dithiole-3-thione 

Relevant academic research and scientific papers

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,

A novel H2S releasing-monastrol hybrid (MADTOH) inhibits L-type calcium channels

A new alleged monastrol-H2S releasing hybrid, named MADTOH, was designed based on the structure of monastrol (M) and 5-(4-hydroxyphenyl)-3H-1,2-dithiole-3-thione (ADTOH) and synthesized in 7.8% overall yield. MADTOH was shown to be an H2S donor under physiological conditions. In addition, the hybrid causes a decrease in global calcium transient in cardiomyocytes similar to nifedipine (NIFE), taken as a positive control. Whole-cell voltage-clamp showed that MADTOH decreases L-type Ca2+ current in isolated ventricular cardiomyocytes.

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.

Convenient method for the synthesis of 5-(4-methoxyphenyl)-3H-1,2-dithiole-3-thione (ADT-OMe) and 5-(4-hydroxyphenyl)-3H-1,2-dithiol-3-thione (ADT-OH) using microwave irradiation

A convenient method is described for the rapid synthesis of 5-(4-methoxyphenyl)-3H-1,2-dithiole-3-thione (ADT-OMe) from anethole and elemental sulfur using microwave irradiation. Various reaction conditions were applied to reduce the reaction time from several hours to 10?min, resulting in an improvement in yield and overcoming the undesired by-product formation associated with conventional methods. 5-(4-Hydroxyphenyl)-3H-1,2-dithiol-3-thione (ADT-OH) was obtained by the deprotection of ADT-OMe using pyridine hydrochloride under microwave irradiation.

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.

Gallic acid hydrogen sulfide derivative and preparation method and medical application thereof

The invention discloses a gallic acid hydrogen sulfide derivative and a preparation method and medical application thereof. The general formula of the gallic acid hydrogen sulfide derivative is A-Y-X,and A is gallic acid; Y is -C (O) O-, -C (O) NH-, -C (O) OC (O)-, -C (O) NHCH2 C (O)- or is absent, and when Y is absent, the compound is A-X; X is a moiety capable of releasing hydrogen sulfide alone or in combination with A. Compared with gallic acid and existing classic non-steroidal anti-inflammatory drugs, the gallic acid hydrogen sulfide derivative has the advantages that the anti-inflammatory activity is equivalent or enhanced, the side effects of gastrointestinal tracts and cardiovascular diseases are weakened, and the gallic acid hydrogen sulfide derivative has high anti-tumor activity and good cardiovascular and neuroprotective effects.

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)

Ligustrazine derivative and preparation method and medical application thereof

The invention discloses a ligustrazine derivative and a preparation method and medical application thereof. The invention synthesizes and prepares three ligustrazine derivatives with novel structures,and provides a preparation method of the ligustrazine derivatives. Pharmacological results show that the inhibitory activity of the three ligustrazine derivatives I-2, I-4 and I-6 on ADP-induced or AA-induced platelet aggregation is superior to that of a parent compound ligustrazine (TMP); compared with clinically common medicines with anticoagulant effects, the activity of the ligustrazine derivatives I-2, I-4 and I-6 in inhibition of ADP-induced platelet aggregation is equivalent to that of a positive drug thilopyrazine, and the inhibition activity of the ligustrazine derivatives I-2, I-4 and I-6 in inhibition of AA-induced platelet aggregation is obviously superior to that of a positive control drug aspirin.

Drug-loaded polymer micelle for treating cardiovascular diseases and preparation method and application thereof

The invention discloses a drug-loaded polymer micelle for treating cardiovascular diseases and a preparation method and application thereof, and relates to the technical field of cardiovascular therapy. In particular, the polymer micelle is encapsulated w

Metabolism of anethole dithiolethione by rat and human liver microsomes: Formation of various products deriving from its o-demethylation and s-oxidation. Involvement of cytochromes P450 and flavin monooxygenases in these pathways

A study of the metabolism of anethole dithiolethione (ADT, 5-(p-methoxyphenyl)-3H-1,2-dithiole-3-thione) by rat and human liver microsomes showed the formation of the corresponding S-oxide and the S-oxide of desmethyl-ADT (dmADT, 5-(p-hydroxyphenyl)-3H-1,