2362-62-1

Usage

Uses

Used in Pharmaceutical Industry:
4-METHYL(THIOBENZAMIDE) is used as a building block for drug discovery chemistry to facilitate the development of new pharmaceutical compounds. Its unique chemical properties make it a valuable asset in the synthesis of potential therapeutic agents.
Used in Drug Synthesis:
4-METHYL(THIOBENZAMIDE) is employed as a key component in the synthesis of various drugs, particularly those targeting specific medical conditions. Its incorporation into drug molecules can enhance their efficacy and selectivity, leading to improved treatment options for patients.
Used in Research and Development:
In the realm of research and development, 4-METHYL(THIOBENZAMIDE) serves as an essential tool for scientists and researchers working on the discovery and design of novel pharmaceutical compounds. Its versatility and chemical properties make it a popular choice for exploring new therapeutic possibilities.
Used in Drug Delivery Systems:
Similar to gallotannin, 4-METHYL(THIOBENZAMIDE) can also be utilized in the development of innovative drug delivery systems. These systems aim to improve the bioavailability, delivery, and therapeutic outcomes of drugs containing this cyclic thioamide building block, ultimately enhancing their effectiveness in treating various medical conditions.

InChI:InChI=1/C8H9NS/c1-6-2-4-7(5-3-6)8(9)10/h2-5H,1H3,(H2,9,10)

Upstream product

• 2362-63-2 3-methylthiobenzamide 
• 104-85-8 para-methylbenzonitrile 
• 2227-79-4 benzenecarbothioamide 
• 619-55-6 para-methylbenzamide 
• 104-87-0 4-methyl-benzaldehyde 
• 64-17-5 ethanol 
• 7783-06-4 hydrogen sulfide 
• 7647-01-0 hydrogenchloride 
• 60-29-7 diethyl ether 
• 45708-98-3 p-Toluylaldehyd-imin 
• 3235-02-7 p-methylbenzaldehyde oxime 
• 99-94-5 p-Toluic acid 
• 874-60-2 4-methyl-benzoyl chloride 

Downstream Products

• 505052-84-6 2-(4-methylphenyl)-4H-3,1-benzothiazine 
• 17590-34-0 3,5-di-p-tolyl-[1,2,4]thiadiazole 
• 27913-49-1 N-{thio p-toluoyl} p-tolamidine 
• 104-84-7 para-methylbenzylamine 
• 98180-43-9 bis(4-methylbenzyl)amine 
• 58765-88-1 4-methyl-2-(p-tolyl)thiazole 
• 27088-83-1 2-(4-Methylphenyl)thiazole 
• 83850-29-7 2-p-tolyl-thiazole-4,5-dione 
• 102660-63-9 N,N'-Di-p-thiotoluyl-glutarsaeure-diamid 
• 110514-12-0 4-(4-methyl-thiobenzoyl)-morpholine-3,5-dione 
• 6796-58-3 phenyl-(2-p-tolyl-thiazol-4-yl)-ethanedione 2-oxime 
• 63523-40-0 N-(methoxy-p-tolyl-methyl)-4-methyl-thiobenzamide 
• 6796-59-4 p-tolyl-(2-p-tolyl-thiazol-4-yl)-ethanedione 2-oxime 
• 6796-60-7 (4-chloro-phenyl)-(2-p-tolyl-thiazol-4-yl)-ethanedione 2-oxime 

Relevant academic research and scientific papers

Correlation of oxidation potential and toxicity in thiobenzamides

The oxidation potentials of a series of 4-substituted thiobenzamides (1) were measured by linear sweep voltammetry. When compared with the known toxicological values for these compounds it was found that there is a direct correlation between oxidation potential and toxicity.

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.

Design, synthesis, and bioactivities of novel pyridazinone derivatives containing 2-phenylthiazole or oxazole skeletons

A series of novel pyridazinone derivatives were designed and synthesized by replacing 4-(tert-butyl)phenyl moiety of pyridaben with 2-phenylthiazole or oxazole fragments via activity substructure connecting approach. The structures of all target compounds were characterized through NMR, MS, and elemental analysis. Bioassay results exhibit that most compounds showed potent bioactivities against Aphis fabae, Tetranychus urticae, Erysiphe graminis, and/or Puccinia polysora. Among the newly synthesized compounds, 2-(tert-butyl)-4-chloro-5-(((2-phenylthiazol-4-yl)methyl)thio)pyridazin-3(2H)-one (12b) displays remarkable insecticidal activity against A fabae. Its LC50 value (2.73 mg/L) is better than that of pyridaben (5.46 mg/L), although inferior to that of imidacloprid (0.51 mg/L). In addition to its extraordinary insecticidal activity, compound 12b also exerts 96.9% fungicidal activities against P polysora at 500 mg/L in vivo, significantly superior to that of pyridaben (50.0%), while slightly lower than that of tebuconazole (100%). This article discusses the synthesis, bioassay results, and structure-activity relationship of this series of novel pyridazinone derivatives.

Green preparation method for thioamide

The invention discloses a green preparation method for thioamide. According to the method, in the presence of an oxidizing agent and an iodine reagent, a cyano-containing heterocyclic ring, an aromatic hydrocarbon compound and elemental sulfur or thiuram react in a reaction solvent to prepare a thioamide compound. The method is also applicable to other compounds containing cyano groups on sp carbon. The method has the advantages of one-step reaction synthesis, simple operation, mild reaction conditions, broad spectrum, environment friendliness, usage of cheap and easily available raw materials, and good market application prospect. The method solves technical problems in direct thioamidation of cyano-containing pyridine compounds and other cyano-containing heterocyclic and aromatic compounds, and can be used for modification of various cyano-containing pesticides, such as fipronil, ethiprole and the like.

Multicomponent synthesis of diphenyl-1,3-thiazole-barbituric acid hybrids and their fluorescence property studies

A series of novel diphenyl-1,3-thiazole linked barbituric acid hybrids (4) were prepared by two catalyst-free methods from readily available starting materials. The reaction of arylglyoxal, barbituric acid and aryl thioamides in the presence of 3-4 drops of water and liquid assisted grinding (LAG) provides the corresponding trisubstituted thiazoles tethered with a barbituric acid moiety within 30 minutes. Alternatively, a sequential two-step one-pot process involving aryl nitriles, ammonium sulphide, arylglyoxal and barbituric acid in water medium was developed. In this second method, in situ thioamides were prepared at room temperature from the reaction of alkyl/aryl nitriles and ammonium sulphide in aqueous medium. Arylglyoxal and barbituric acid were added to the in situ thioamides after neutralizing the reaction medium to provide trisubstituted thiazoles linked with barbituric acid derivatives. Some of our synthesized molecules showed fluorescent properties with very good quantum yields in DMSO medium. We also observed that fluorescent quantum yields of these thiazole derivatives depend on the type of electron donating/withdrawing character of R1 and R3. R2 has a very small effect on tuning the fluorescent properties. The salient features of this work are catalyst-free reactions, wide substrate scope, green reaction conditions (liquid assisted grinding and room temperature reactions in water medium) as well as the presence of more than one pharmaceutically important heterocyclic moiety with fluorescent properties.

Design, synthesis and fungicidal activity evaluation of novel pyrimidinamine derivatives containing phenyl-thiazole/oxazole moiety

Diflumetorim is a member of pyrimidinamine fungicides that possess excellent antifungal activities. Nevertheless, as reported that the activity of diflumetorim to corn rust (Puccinia sorghi) was not ideal (EC50 = 53.26 mg/L). Herein, a series of novel pyrimidinamine derivatives containing phenyl-thiazole/oxazole moiety were designed based on our previous study and the structural characteristics of diflumetorim, synthesized and bioassayed to discover novel fungicides with excellent antifungal activities. Among these compounds, T18 gave the optimal fungicidal activity, which respectively offers control effects with EC50 values of 0.93 mg/L against P. sorghi and 1.24 mg/L against E. graminis, significantly superior to commercial fungicides diflumetorim, tebuconazole, and flusilazole. Cell cytotoxicity results suggested that compound T18 has lower toxicities than diflumetorim. Furthermore, DFT calculation indicated that the phenyl-thiazole/oxazole moiety plays an unarguable role in the improvement of activity, which will contribute to designing and developing more potent compounds in the future.

Synthesis of imidazo[1,2-: C] thiazoles through Pd-catalyzed bicyclization of tert-butyl isonitrile with thioamides

Building new biological molecules is challenging. Herein, imidazo[1,2-c]thiazoles were synthesized as a new class of heterobicyclic analogs through Pd-catalyzed cascade bicyclization from isonitriles with thioamides. The bicyclic scaffolds were constructed by inserting three molecules of isonitrile into two molecules of thioamide and then cyclizing them in a one-pot procedure. In vitro antitumor studies of these new compounds were conducted by using the MTT assay, and compound 3c showed excellent inhibitory effects against HepG2 at 7.06 ± 0.68 μM.

Regioselective C-C cross-coupling of 1,2,4-thiadiazoles with maleimides through iridium-catalyzed C-H activation

A regioselective C-C cross-coupling of 1,2,4-thiadiazoles with maleimides through iridium catalysis was developed. This transformation tactically linked the 1,2,4-thiadiazoles and succinimides together, and the novel molecules formed may have potential biological activity.

Design, synthesis, DFT study and antifungal activity of the derivatives of pyrazolecarboxamide containing thiazole or oxazole ring

Pyrazolecarboxamide fungicides are one of the most important classes of agricultural fungicides, which belong to succinodehydrogenase inhibitors (SDHIS). To discover new pyrazolecarboxamide analogues with broad spectrum and high activity, a class of new compounds of pyrazole carboxamide derivatives containing thiazole or oxazole ring were designed by scaffold hopping and bioisosterism, and 36 pyrazole carboxamide derivatives with antifungal activity were synthesized. Those compounds were evaluated against five phytopathogenic fungi, Gibberella zeae, Phytophythora capsici, Sclerotonia sclerotiorum, Erysiphe graminis and Puccinia sorghi. The results indicated that most of the compounds displayed good fungicidal activities, especially against E. graminis. Theoretical calculations were carried out at the B3LYP/6-31G (d, p) level and the full geometry optimization was carried out using the 6-31G (d, p) basis set, and the frontier orbital energy, atomic net charges, molecular docking were discussed, and the structure-activity relationships were also studied.

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.