- Hydrogen sulfide releasing enmein-type diterpenoid derivatives as apoptosis inducers through mitochondria-related pathways
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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,
- Xu, Fanxing,Gao, Xiang,Li, Haonan,Xu, Shengtao,Li, Xu,Hu, Xu,Li, Zhanlin,Xu, Jinyi,Hua, Huiming,Li, Dahong
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- A novel H2S releasing-monastrol hybrid (MADTOH) inhibits L-type calcium channels
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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.
- Braga, Taniris Cafiero,De Jesus, Itamar Couto Guedes,Soares, Kathleen Viveiros,Guatimosim, Silvia,Da Silva Neto, Leonardo,Da-Silva, Cristiane Jovelina,Modolo, Luzia Valentina,Menezes Filho, José Evaldo Rodrigues,Rhana, Paula,Cruz, Jader Santos,De Fátima, ?ngelo
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- Synthesis and Pharmacological Evaluation of Novel Adenine-Hydrogen Sulfide Slow Release Hybrids Designed as Multitarget Cardioprotective Agents
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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.
- Lougiakis, Nikolaos,Papapetropoulos, Andreas,Gikas, Evangelos,Toumpas, Spyridon,Efentakis, Panagiotis,Wedmann, Rudolf,Zoga, Anastasia,Zhou, Zhongmin,Iliodromitis, Efstathios K.,Skaltsounis, Alexios-Leandros,Filipovic, Milos R.,Pouli, Nicole,Marakos, Panagiotis,Andreadou, Ioanna
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- 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
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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.
- Pournara, Dimitra,Heropoulos, Georgios A.,Koufaki, Maria
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- 3-H-[1,2]Dithiole as a new anti-trypanosoma cruzi chemotype: Biological and mechanism of action studies
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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.
- Couto, Marcos,Sánchez, Carina,Dávila, Belén,Machín, Valentina,Varela, Javier,álvarez, Guzmán,Cabrera, Mauricio,Celano, Laura,Aguirre-López, Beatriz,Cabrera, Nallely,De Gómez-Puyou, Marieta Tuena,Gómez-Puyou, Armando,Pérez-Montfort, Ruy,Cerecetto, Hugo,González, Mercedes
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- Gallic acid hydrogen sulfide derivative and preparation method and medical application thereof
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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.
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Paragraph 0063; 0067; 0068
(2021/03/31)
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- Tanshinol and H2 S/NO Donor binding, preparation method thereof and application in pharmacy (by machine translation)
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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)
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Paragraph 0137-0139
(2020/08/18)
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- Ligustrazine derivative and preparation method and medical application thereof
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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.
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Paragraph 0046-0049
(2020/11/05)
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- Drug-loaded polymer micelle for treating cardiovascular diseases and preparation method and application thereof
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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
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Paragraph 0062; 0075-0077
(2019/08/20)
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- 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
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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,
- Dulac, Martin,Sassi, Amor,Nagarathinan, Citra,Christen, Marie-Odile,Dansette, Patrick M.,Mansuy, Daniel,Boucher, Jean-Luc
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p. 1390 - 1395
(2018/09/13)
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- 5-(4-Hydroxyphenyl)-3H-1,2-dithiole-3-thione-based fibrates as potential hypolipidemic and hepatoprotective agents
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Hypolipidemic effects of the newly synthesized 5-(4-hydroxyphenyl)-3H-1,2-dithiole-3-thione-based fibrates were evaluated in Triton WR-1339 and high-fat diet (HFD)-induced hyperlipidemic mice. Preliminary screening of all the synthesized compounds was don
- Chen, Zi-Zhang,Xie, Yun-Dong,Shao, Li-Hua,Wang, Qiu-Tang,Xu, Yan-Hong,Bian, Xiao-Li
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supporting information
p. 3787 - 3792
(2018/10/20)
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- Exogenous hydrogen sulfide donor, and preparation and application thereof
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The invention provides an exogenous hydrogen sulfide donor, and discloses a therapeutic action of an anethol trithione derivative used as the exogenous hydrogen sulfide donor on cardiovascular diseases. The exogenous hydrogen sulfide donor can release hydrogen sulfide, can promote the growth of an HUVEC (human umbilical vein endothelial cell) atherosclerosis cell model, has an antiatherosclerotic effect, and hopefully becomes a new target drug researched and developed by drugs with antiatherosclerotic effects.
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Paragraph 0048; 0049
(2017/08/30)
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- Synthesis of Amino-ADT Provides Access to Hydrolytically Stable Amide-Coupled Hydrogen Sulfide Releasing Drug Targets
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As additional physiological functions of hydrogen sulfide (H2S) are discovered, developing practical methods for exogenous H2S delivery is important. In particular, nonsteroidal anti-inflammatory drugs (NSAIDs) functionalized with H2S-releasing anethole dithiolethione (ADT-OH) through ester bonds are being investigated for their combined anti-inflammatory and antioxidant potential. The chemical robustness of the connection between drug and H2S-delivery components, however, is a key and controllable linkage in these compounds. Because esters are susceptible to hydrolysis, particularly under acidic conditions such as stomach acid in oral drug delivery applications, we report here a simple synthesis of amino-ADT (ADT-NH2) and provide conditions for successful ADT-NH2 derivatization with the drugs naproxen and valproic acid. Using UV-vis spectroscopy and HPLC analysis, we demonstrate that amide-functionalized ADT derivatives are significantly more resistant to hydrolysis than ester-functionalized ADT derivatives.
- Hammers, Matthew D.,Singh, Loveprit,Montoya, Leticia A.,Moghaddam, Alan D.,Pluth, Michael D.
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supporting information
p. 1349 - 1353
(2016/06/01)
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- Synthesis and antitumor activity of ATB-429 derivatives containing a nitric oxide-releasing moiety
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A series of novel ATB-429 (an anti-inflammatory candidate) derivatives containing a nitric oxide (NO)-releasing moiety were designed, synthesized and evaluated for their in vitro activity against six human cancer cell lines. Our results reveal that phenyl
- Wang, Chunlan,Xia, Guimin,Liu, Xiujun,Zhang, Rui,Chai, Yun,Zhang, Jun,Li, Xiaoning,Yang, Yang,Wang, Juxian,Liu, Mingliang
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p. 2355 - 2359
(2016/04/20)
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- Synthesis and biological evaluation of novel hydrogen sulfide releasing nicotinic acid derivatives
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Twelve novel hybrids of slowly releasing hydrogen sulfide donor ADT-OH combined with nicotinic acid were synthesized. All of their structures had been confirmed by1H NMR,13C NMR and MS spectra. The target compounds were evaluated for their neuroprotective effects on hippocampal neuron HT22 cells against glutamate-induced injury at the concentrations of 1–100?μM with MTT assay, and their toxicity on HT22 cells untreated by glutamine at the concentration of 100?μM. The active compound was further investigated for its effect on ischemic infarct volume by intraperitoneal injection at 3?h after ischemia in mice models of permanent middle cerebral artery occlusion (pMCAO). The results showed that all the compounds significantly protected HT22 cells from glutamate-induced damage at most of the experimental concentrations, and had no or little neurotoxicity on normal HT22 cells at the high concentration. More importantly, compound A6 significantly reduced infarct volume in the pMCAO model. These results suggested that compound A6 may be promising for further evaluation for the intervention of cerebral ischemic injury.
- Sun, Yinxing,Zhang, Yusuo,Li, Yuyao,Cheng, Jian,Chen, Shiyu,Xiao, Yunqi,Ao, Guizhen
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p. 5368 - 5373
(2016/10/24)
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- 3H-1,2-DITHIOCYCLOPENTENE-3-THIOKETONE COMPOUNDS AND APPLICATION THEREOF
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The present invention relates to the field of medicaments, and in particular relates to 3H-1,2-dithiocyclopentene-3-thione compounds and application thereof. 3H-1,2-dithiocyclopentene-3-thione compounds disclosed by the invention have new structures shown in formula I or formula II. Proved by experiments, 3H-1,2-dithiocyclopentene-3-thione compounds can directly protect neurons in a cellular model, and can significantly restrain excessive inflammatory responses of brain inflammatory cells; and by using 3H-1,2-dithiocyclopentene-3-thione, focal ischemic cerebral infarct volumes of mice can be remarkably reduced in an animal model. Therefore, the invention provides the application of 3H-1,2-dithiocyclopentene-3-thione compounds and pharmaceutically acceptable salts thereof in the preparation of medicaments for preventing or treating cerebral apoplexy diseases.
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Paragraph 0029
(2015/07/15)
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- Design, synthesis and biological evaluation of hydrogen sulfide releasing derivatives of 3-n-butylphthalide as potential antiplatelet and antithrombotic agents
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In the present study, a series of hydrogen sulfide (H2S) releasing derivatives (8a-g and 9a-f) of 3-n-butylphthalide (NBP) were designed, synthesized and biologically evaluated. The most promising compound 8e significantly inhibited the adenosi
- Wang, Xiaoli,Wang, Linna,Sheng, Xiao,Huang, Zhangjian,Li, Tingting,Zhang, Ming,Xu, Jinyi,Ji, Hui,Yin, Jian,Zhang, Yihua
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p. 5995 - 6004
(2014/08/05)
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- Synthesis and biological evaluation of lipid-soluble prodrugs of anethole dithiolthione
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16 ADT carboxylate esters were prepared by means of esterification and these compounds were expected to increase the bioavailability of 4-hydroxyanehole trithione. In vivo studies showed that ADT concentration of 3a in plasma was much higher than that of ATT during 120 min. Compound 3a could reach blood peak values of ADT at 660.6 ng/mL which was about 14 times of that by ATT. Additionally, the acute toxicity assay indicated high safety of compound 3a that the maximum tolerated dose was no less than 3.25 g/kg.
- Guan, Mei,Fan, Wei,Qian, Shan,Xiao, Rui Qi,Wu, Yong
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experimental part
p. 1427 - 1429
(2011/10/09)
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- Design synthesis and biological evaluation of lipophilic analogs of anethol trithione
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16 ADT carboxylate esters were prepared and tested for their chemical characteristics, stability, bioavailability, potency and toxicity. Considering the good bioavailability, 3a was selected for the pharmacology test, and the result showed that the potency of 3a was remarkably higher than that of ATT. Additionally, 3a was also chosen for the acute toxicity test. The result indicated that the prodrug 3a was more safer than ATT. The study suggested the feasibility to improve the bioavailability of ATT by using prodrug strategy.
- Li, Xiao-Cen,Fan, Wei,Hai, Li,Qian, Shan,Xiao, Qui-Qi,Guan, Mei
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p. 747 - 753
(2013/01/09)
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- Design, synthesis, and pharmacological evaluation of the aqueous prodrugs of desmethyl anethole trithione with hepatoprotective activity
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A metabolite-based prodrug strategy to increase the solubility of anethole trithione was reported to facilitate the clinical application of this hepatoprotective agent. Water-soluble analogs of anethole trithione were synthesized via substituting the meth
- Chen, Pei,Luo, Yu,Hai, Li,Qian, Shan,Wu, Yong
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experimental part
p. 3005 - 3010
(2010/08/20)
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- PROSTAGLANDIN PHARMACEUTICAL COMPOSITIONS
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The present invention relates to new prostaglandin derivatives having improved pharmacological activity and enhanced tolerability. They can be employed for the treatment of glaucoma and ocular hypertension.
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Page/Page column 4
(2010/07/08)
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- Synthesis and preliminary pharmacological evaluation of aryl dithiolethiones with cyclooxygenase-2-selective inhibitory activity and hydrogen sulfide-releasing properties
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A series of 5-aryl-1,2-dithiolethiones and 5-aryl-1,2-dithiole-3-ones were investigated as hydrogen sulfide-releasing anti-inflammatory drugs. Generally, phenolic acetophenones were best protected by methoxymethyl groups and the dithiolethione group insta
- Zanatta, Shannon D.,Jarrott, Bevyn,Williams, Spencer J.
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p. 946 - 957
(2011/08/05)
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- NEW ANTICANCER COMPOUNDS
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The present invention relates to new polysulf urated compounds containing 2 or more sulphur atoms belonging to the class of organic thiosulf onates, or dithiole-thione derivatives cyclic or linear, or trithiocarbonates for the use alone or in combination with other anticancer treatments for the treatment and/or prevention of cancer and inflammatory diseases.
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Page/Page column 18
(2009/06/27)
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- NEW AGENTS FOR THE TREATMENT OF THE LOW URINARY TRACT DYSFUNCTIONS
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The present invention relates to novel compounds that are derivatives of 5 -phosphodiesterase inhibitors that comprise in their formula a polysulfurated group and that are useful for treating dysfunctions of low urinary tract such as incontinence, benign prostatic hyperplasia and erectile dysfunction.
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Page/Page column 20
(2009/04/25)
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- Cardiovascular agents
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The present invention relates to novel compounds that are derivatives of angiotensin receptor blocker (ARB) that comprise in their formula a polysulfurated group and that are useful for treating cardio-vascular diseases, such as hypertension, ischemic heart disease, atherosclerosis, metabolic syndrome, etc. also in combination with other cardiovascular agents.
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Page/Page column 9
(2008/12/04)
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- 5-Fluorouracil derivatives and their use for the treatment of cancer
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The present invention relates to 5-fluoropyrimidine compounds of formula I that are useful for preventing, treating or reducing tumoral diseases and pathological conditions involving various cancer forms.
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Page/Page column 6
(2008/12/06)
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- PROSTAGLANDIN PHARMACEUTICAL COMPOSITIONS
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The present invention relates to new prostaglandin derivatives having improved pharmacological activity and enhanced tolerability. They can be employed for the treatment of glaucoma and ocular hypertension.
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Page/Page column 17-18
(2009/01/20)
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- Derivaitves of 4-Or 5-Aminosalicylic Acid
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The present invention provides new derivatives of 4- or 5-aminosalicylic acid, and a pharmaceutical composition containing these derivatives of 4- or 5-aminosalicylic acid as active ingredients, useful for the treatment of intestinal diseases such as infl
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Page/Page column 11; 14-16
(2008/12/08)
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- HYDROGEN SULFIDE DERIVATIVES OF NON-STEROIDAL ANTI-INFLAMMATORY DRUGS
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The present invention relates to derivatives of non-steroidal anti-inflammatory drugs (NSAIDs) having improved anti-inflammatory properties useful in the treatment of inflammation, pain and fever. More particularly, NSAIDs are derivatized with a hydrogen
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Page/Page column 10
(2008/06/13)
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- COMPOUNDS FOR TREATING METABOLIC SYNDROME
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Compounds of general formula (I), wherein R’, R, x and z have the meaning reported in the specification, are useful for treating inflammatory diseases including metabolic syndrome, diabetes, obesity, dyslipidemia, and insulin resistance.
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Page/Page column 16-19
(2008/06/13)
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- SULINDAC DERIVATIVES FOR TREATMENT OF CANCER
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The present invention relates to novel non steroidal anti-inflammatory compounds (NSAIDs) derivatives of sulindac, for the treatment/prevention, alone or in combination, of cancer.
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Page/Page column 13-14
(2008/06/13)
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- New nuclear transcription factors regulators
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The present invention relates to novel compounds that are nuclear transcription factors (NTF) regulators. The present invention also provides methods for treating, preventing and/or reducing inflammation-associated diseases by regulating NTF in the cardiovascular, connective tissue, pulmonary, gastrointestinal, respiratory, urogenital, nervous, or cutaneous systems as well as tumoral and infective diseases employing said compounds. The present invention is based on the discovery that it is possible to link regulators of NTF to a pharmacologically active compound helpful for treating disorders in the cardiovascular, connective tissue, pulmonary, gastrointestinal, respiratory, urogenital, nervous, or cutaneous systems or tumoral and infective diseases. The resulting compounds have good bioavailability, increased activity and/or safety.
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Page/Page column 5
(2008/06/13)
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- NEW ANTI-INFLAMMATORY COMPOUNDS
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The present invention relates to novel non steroidal anti-inflammatory compounds (NSAIDs) that release hydrogen sulfide (H2S). The present invention also provides methods for treating, preventing and/or reducing inflammation-associated diseases by releasing H2S in the cardiovascular, connective tissue, pulmonary, gastrointestinal, respiratory, urogenital, nervous, or cutaneous systems as well as infective diseases employing said compounds.
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Page/Page column 9-10
(2008/06/13)
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- Derivatives of 4- or 5-aminosalicylic acid
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The present invention provides new derivatives of 4- or 5-aminosalicylic acid, and a pharmaceutical composition containing these derivatives of 4- or 5-aminosalicylic acid as active ingredients, useful for the treatment of intestinal diseases such as inflammatory bowel disease (IBD) and irritable bowel syndrome (IBS) and for the prevention/treatment of colon cancer. More particularly, these derivatives comprise a hydrogen sulfide releasing moiety linked via an azo, an ester, an anhydride, a thioester or an amide linkage to a molecule of 4- or 5-aminosalicylic acid. Furthermore, the present invention provides a process for preparing these compounds and their use for treating IBD and IBS and the prevention/treatment of colon cancer.
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Page/Page column 12; 16-17
(2008/06/13)
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- DERIVATIVES OF 4- OR 5-AMINOSALICYLIC ACID
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The present invention provides new derivatives of 4- or 5-aminosalicylic acid, and a pharmaceutical composition containing these derivatives of 4- or 5-aminosalicylic acid as active ingredients, useful for the treatment of intestinal diseases such as infl
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Page/Page column 36-37; 47
(2008/06/13)
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- DERIVATIVES OF 4-OR 5-AMINOSALICYLIC ACID
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The present invention provides new derivatives of 4-or 5-aminosalicylic acid, and a pharmaceutical composition containing these derivatives of 4-or 5-aminosalicylic acid as active ingredients, useful for the treatment of intestinal diseases such as inflam
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Page/Page column 40-41; 51
(2008/06/13)
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- 1,2-dithiol-3-thion-S-oxide compounds and pharmaceutical compositions
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The use of 5-phenyl-3H-1,2-dithiol-3-thion-S-oxides which are optionally substituted in the phenyl ring as active substances in hepato-protective medicaments and new 5-phenyl-3H-1,2-dithiol-3-thion-S-oxides which are substituted in the phenyl ring are des
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