2196-13-6

Usage

Uses

Used in Pharmaceutical Industry:
THIOISONICOTINAMIDE is used as an impurity in Ethionamide, which is a tuberculostatic agent for the treatment of tuberculosis. Its presence, despite being an impurity, contributes to the overall effectiveness of Ethionamide in combating the disease.
Used in Tuberculosis Treatment:
THIOISONICOTINAMIDE, as a component of Ethionamide, plays a role in the tuberculostatic activity that helps in the management and treatment of tuberculosis. Its contribution to the medication's efficacy is essential in the fight against this infectious disease.

InChI:InChI=1/C6H6N2S/c7-6(9)5-1-3-8-4-2-5/h1-4H,(H2,7,9)

Upstream product

• 100-48-1 pyridine-4-carbonitrile 
• 696-54-8 pyridine-4-aldoxime 
• 872-85-5 pyridine-4-carbaldehyde 
• 1453-82-3 isonicotinamide 
• 108103-05-5 dithioisonicotinic acid ; potassium-salt 

Downstream Products

• 4329-78-6 3,5-di(pyridin-4-yl)-1,2,4-triazole 
• 106950-18-9 4-phenyl-2-(pyridin-4-yl)thiazole 
• 70031-89-9 4-(4,5-diphenyl-thiazol-2-yl)-pyridine 
• 15311-09-8 2,5-bis(4-pyridyl)-1,3,4-thiadiazole 
• 89830-71-7 pyridine-4-carboxylic acid amidrazone 
• 131786-82-8 5-phenyl-2-(pyridin-4-yl)-1,3-thiazol-4-ol 
• 130735-43-2 4,5-bis(4-methoxyphenyl)-2-(4-pyridyl)thiazole 
• 138287-14-6 2-(4-Pyridyl)-4-<(phenylsulfonyl)methyl>thiazole 
• 77168-59-3 4-(4'-methylthiazol-2'-yl)pyridine hydrochloride 
• 154404-90-7 5,6-dihydro-2-(4-pyridyl)-7(4H)benzothiazolone 
• 110718-99-5 7-Phenyl-2-(4-pyridyl)hypoxanthin 
• 100-48-1 pyridine-4-carbonitrile 
• 1453-82-3 isonicotinamide 
• 177560-96-2 4-(4-Fluorophenyl)-5-(4-methylthiophenyl)-2-(pyridin-4-yl)thiazole 

Relevant academic research and scientific papers

Aerobic Visible-Light Induced Intermolecular S?N Bond Construction: Synthesis of 1,2,4-Thiadiazoles from Thioamides under Photosensitizer-Free Conditions

Aerobic visible-light induced intermolecular S?N bond construction has been achieved without the addition of photosensitizer, metal, or base. With this strategy, 1,2,4-thiadiazoles can be obtained from thioamides. Preliminary mechanistic investigation suggested that the excited state of thioamides undergoes a single-electron-transfer (SET) process to afford thioamidyl radicals, which can be further transformed into a 1,2,4-thiadiazole through desulfurization and oxidative cyclization. The reaction has good functional group tolerance and represents a green method for the construction of S?N bonds.

Potent ribonucleotide reductase inhibitors: Thiazole-containing thiosemicarbazone derivatives

The antioxidant, antimalarial, antibacterial, and antitumor activities of thiosemicarbazones have made this class of compounds important for medicinal chemists. In addition, thiosemicarbazones are among the most potent and well-known ribonucleotide reductase inhibitors. In this study, 24 new thiosemicarbazone derivatives were synthesized, and the structures and purity of the compounds were determined by IR, 1H NMR, 13C NMR, mass spectroscopy, and elemental analysis. The IC50 values of these 24 compounds were determined with an assay for ribonucleotide reductase inhibition. Compounds 19, 20, and 24 inhibited ribonucleotide reductase enzyme activity at a higher level than metisazone as standard. The cytotoxic effects of these compounds were measured on the MCF7 (human breast adenocarcinoma) and HEK293 (human embryonic kidney) cell lines. Similarly, compounds 19, 20, and 24 had a selective effect on the MCF7 and HEK293 cell lines, killing more cancer cells than cisplatin as standard. The compounds (especially 19, 20, and 24 as the most active ones) were then subjected to docking experiments to identify the probable interactions between the ligands and the enzyme active site. The complex formation was shown qualitatively. The ADME (absorption, distribution, metabolism, and excretion) properties of the compounds were analyzed using in-silico techniques.

A efficient protocol for the synthesis of thioamides in [DBUH][OAc] at room temperature

A novel, simple and eco-friendly method to synthesize thioamides from aryl nitriles and sodium sulfide (Na2S·9H2O) catalyzed by 1,8-diazabicyclo[5,4,0]undec-7-enium acetate ([DBUH][OAc]) ionic liquid (IL) at room temperature was developed in this paper. In this reaction, readily available inorganic salt (Na2S·9H2O) serves as the sulfur source, and various functional groups of aryl nitriles were well tolerated at room temperature. In addition, the products were easily separated from the IL which could be reused at least five times without considerable loss of its activity and applied in the green, concise synthesis of ethionamide.

A simple method for synthesis of thioamides and application in synthesis of 1,2,4-thiadiazoles

A novel, simple protocol is disclosed for the synthesis of 1,2,4-thiadiazoles starting from thioamides with Na2-eosin Y-sensitized titanium dioxide as catalyst through visible light irradiation (7 W blue LED light) and only 0.3 mol% catalysts were used. The raw material thioamides is prepared by aryl nitriles and sodium sulfide (Na2S9H2O) in DMF and in this reaction, readily available, inexpensive inorganic salt (Na2S9H2O) serves as the sulfur source and various functional groups of aryl nitriles were well and thioamides were synthesized successfully in gram-scale.

New promising methods of synthesis of pyridinecarbothioamides

New methods of synthesis of pyridinecarbothioamides from the corresponding cyanopyridines with the use of phosphorus pentasulfide as a thiontion agent were developed. The first method was based on the reaction of cyanopyridine with phosphorus pentasulfide in alcoholic ammonium solution followed by hydrolysis. The method provided the corresponding thioamides in 60-90% yield. The second procedure included the reaction of phosphorus pentasulfide with 4-cyanopyridine in aqueous ammonia solution, which led to the formation of pyridine-4-carbothioamides in quantitative yield.

Metal-free, one-pot oxidative conversion of aldehydes to primary thioamides in aqueous media

One-pot tandem reactions of a variety of aldehydes with aqueous ammonia, molecular iodine, and O,O-diethyl dithiophosphoric acid readily afford the corresponding primary thioamides. This is an inexpensive, practical, and metal-free way of accessing various thioamides from aldehydes in aqueous media. The pure products are obtained simply by filtration followed by successive washing with aqueous sodium thiosulfate and water. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]

Arylthioamides as H2S donors: L-cysteine-activated releasing properties and vascular effects in vitro and in vivo

A small library of arylthioamides 1-12 was easily synthesized, and their H2S-releasing properties were evaluated both in the absence or in the presence of an organic thiol such as l-cysteine. A number of arylthioamides (1-3 and 7) showed a slow and l-cysteine-dependent H2S-releasing mechanism, similar to that exhibited by the reference slow H2S- releasing agents, such as diallyl disulfide (DADS) and the phosphinodithioate derivative GYY 4137. Compound 1 strongly abolished the noradrenaline-induced vasoconstriction in isolated rat aortic rings and hyperpolarized the membranes of human vascular smooth muscle cells in a concentration-dependent fashion. Finally, a significant reduction of the systolic blood pressure of anesthetized normotensive rats was observed after its oral administration. Altogether these results highlighted the potential of arylthioamides 1-3 and 7 as H 2S-donors for basic studies, and for the rational design/development of promising pharmacotherapeutic agents to treat cardiovascular diseases.

A thiophosphoryl chloride assisted transformation of arylaldoximes to thioamides

Primary benzothioamides were accessed from benzaldoximes (benzaldehyde oximes) via benzonitriles in a sequential tandem approach utilizing thiophosphoryl chloride as a dehydrating and thionating agent. Georg Thieme Verlag Stuttgart New York.

Optimizing thiadiazole analogues of resveratrol versus three chemopreventive targets

Chemoprevention is an approach to decrease cancer morbidity and mortality through inhibition of carcinogenesis and prevention of disease progression. Although the trans stilbene derivative resveratrol has chemopreventive properties, its action is compromised by weak non-specific effects on many biological targets. Replacement of the stilbene ethylenic bridge of resveratrol with a 1,2,4-thiadiazole heterocycle and modification of the substituents on the two aromatic rings afforded potential chemopreventive agents with enhanced potencies and selectivities when evaluated as inhibitors of aromatase and NF-κB and inducers of quinone reductase 1 (QR1).

Efficient and green protocol for the synthesis of thioamides in C 6 (mim)2Cl2 as a dicationic ionic liquid

A simple, efficient, facile and eco-friendly process for the synthesis of thioamides from nitriles using 1,6-bis(3methylimidazolium-1-yl)hexane chloride [C6(mim)2Cl2] as a dicationic ionic liquid (DIL) was developed. The ionic liquid was easily separated from the reaction mixture and was recycled at least four times without any loss of its activity.