64559-06-4

Usage

Uses

Used in Pharmaceutical Industry:
3-Methoxythio Benzamide is used as a synthetic intermediate for the development of pharmaceutical compounds. Its unique chemical structure allows it to be a valuable building block in the synthesis of various drugs.
However, it is important to note that 3-Methoxythio Benzamide and other thiobenzamides have been identified as potent hepatotoxins in vivo. Therefore, careful consideration and extensive research must be conducted to ensure the safety and efficacy of any pharmaceutical products that incorporate 3-METHOXY-THIOBENZAMIDE.

InChI:InChI=1/C8H9NOS/c1-10-7-4-2-3-6(5-7)8(9)11/h2-5H,1H3,(H2,9,11)

Upstream product

• 5813-86-5 m-methoxybenzamide 
• 1711-05-3 m-anisoyl chloride 
• 586-38-9 3-Methoxybenzoic acid 

Downstream Products

• 677355-86-1 3-methoxy-thiobenzimidic acid methyl ester 
• 940303-80-0 4-tert-butyl-2-(3-methoxyphenyl)-1,3-thiazole 
• 1424328-62-0 C₉H₇NO₂S₂ 
• 35582-13-9 2-(3-hydroxyphenyl)thiazole 
• 885280-53-5 2-(3-methoxyphenyl)-4-hydroxymethylthiazole 
• 1013554-51-2 2,4-bis(3-methoxyphenyl)-1,3-thiazole 
• 115299-08-6 ethyl 2-(3-methoxyphenyl)thiazole-4-carboxylate 

Relevant academic research and scientific papers

3H-1,2,4-Dithiazol-3-one compounds as novel potential affordable antitubercular agents

Small molecules with oxathiazol-2-one moiety were recently reported as potent inhibitors of Mycobacterium bovis var. bacilli Calmette-Guérin (BCG), among which HT1171 was the most potent and selective proteasome inhibitor. Herein we synthesized a series of novel compounds by bioisosteric replacement of the oxathiazol-2-one ring with 3H-1,2,4-dithiazol-3-one, and also fifteen 1,3,4-oxathiazol-2-one molecules in order for potency comparison and structure-activity relationship elucidation since their antibacterial effects on the virulent strains were not evaluated before. All the compounds were assessed for antitubercular activities on the virulent H37Rv strain by a serial dilution method. Among the tested compounds, 3H-1,2,4-dithiazol-3-one compound 4n was found to be the most active with a lowest MIC90 value of 1 μg/mL. Furthermore, the cytotoxicities of all the compounds against normal human liver cell line L02 were determined by an MTT method. Compound 4n displayed a lower inhibitory ratio than HT1171 at the concentration of 100 μM, indicating its better safety profile.

Single-step microwave-mediated synthesis of oxazoles and thiazoles from 3-oxetanone: A synthetic and computational study

The direct microwave-mediated condensation between 3-oxetanone and primary amides and thioamides has delivered moderate to good yields of (hydroxymethyl)oxazoles and (hydroxymethyl)thiazoles. The reactions use a sustainable solvent and only require short reaction times. These are highly competitive methods for the construction of two classes of valuable heteroarenes, which bear a useful locus for further elaboration. Electronic structure calculations have shown that the order of events involves chalcogen atom attack at sp3 carbon and alkyl-oxygen cleavage. The critical role of acid catalysis was shown clearly, and the importance of acid strength was demonstrated. The calculated barriers were also fully consistent with the observed order of thioamide and amide reactivity. Spontaneous ring opening involves a modest degree of C-O cleavage, moderating the extent of strain relief. On the acid-catalysed pathway, C-O cleavage is less extensive still, but proton transfer to the nucleofuge is well advanced with the carboxylic acid catalysts, and essentially complete with methanesulfonic acid. Open sesame: The direct microwave-mediated condensation between 3-oxetanone and primary amides and thioamides has delivered moderate to good yields of oxazoles and thiazoles. The reactions use a sustainable solvent, require only short reaction times and represent a highly competitive method for the construction of two classes of valuable heteroarenes. Electronic structure calculations have been used to probe a range of potential reaction mechanisms (see figure). Copyright

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).

Antibacterial alkoxybenzamide inhibitors of the essential bacterial cell division protein FtsZ

3-Methoxybenzamide is a weak inhibitor of the essential bacterial cell division protein FtsZ. Exploration of the structure-activity relationships of 3-methoxybenzamide analogues led to the identification of potent anti-staphylococcal compounds.