26060-30-0

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 82, p. 2656, 1960 DOI: 10.1021/ja01495a078

InChI:InChI=1/C7H6N2O2S/c8-7(12)5-1-3-6(4-2-5)9(10)11/h1-4H,(H2,8,12)

Upstream product

• 13287-49-5 4-Nitro-benzylthiocyanat 
• 298-06-6 O,O-Diethyl hydrogen phosphorodithioate 
• 619-72-7 4-nitrobenzonitrile 
• 100-14-1 4-nitrobenzyl chloride 
• 619-80-7 4-nitrobenzamide 
• 19172-47-5 Lawessons reagent 
• 1129-37-9 4-nitrobenzaldehyde oxime 
• 122-04-3 4-nitro-benzoyl chloride 
• 555-16-8 4-nitrobenzaldehdye 

Downstream Products

• 7047-14-5 5-(4-Nitrophenyl)-1,2,4-dithiazol-3-on 
• 92971-03-4 N-<4-Nitro-thiobenzoyl>-acetamidin 
• 4018-22-8 2-(4-nitro-phenyl)-thiazole-4,5-dione 
• 29942-11-8 6-[2-(4-nitro-phenyl)-thiazol-4-yl]-benzothiazole 
• 75129-22-5 4-[2-(4-nitro-phenyl)-thiazol-4-yl]-aniline 
• 83312-59-8 4-Nitro-thiobenzamid-S-oxid 
• 95642-54-9 4-hydroxy-2-p-(nitrophenyl)-6H-1,3-thiazin-6-one 
• 132361-42-3 2-(4-Nitro-phenyl)-4-thiophen-2-yl-[1,3]thiazine-6-thione 
• 96819-30-6 2-(4-Nitro-phenyl)-[1,3]thiazine-6-thione 
• 96819-34-0 5-Methyl-2-(4-nitro-phenyl)-[1,3]thiazine-6-thione 
• 96819-39-5 2-(4-Nitro-phenyl)-5-phenyl-[1,3]thiazine-6-thione 
• 132361-41-2 2-(4-Nitro-phenyl)-4-phenyl-[1,3]thiazine-6-thione 
• 26798-33-4 (p-nitrophenyl)methanethiol 
• 86814-28-0 3,5-bis(4-nitrophenyl)-1,2,4-thiadiazole 

Relevant academic research and scientific papers

Synthesis and methemoglobinemia-inducing properties of benzocaine isosteres designed as humane rodenticides

A number of isosteres (oxadiazoles, thiadiazoles, tetrazoles and diazines) of benzocaine were prepared and evaluated for their capacity to induce methemoglobinemia - with a view to their possible application as humane pest control agents. It was found that an optimal lipophilicity for the formation of methemoglobin (metHb) in vitro existed within each series, with 1,2,4-oxadiazole 3 (metHb% = 61.0 ± 3.6) and 1,3,4-oxadiazole 10 (metHb% = 52.4 ± 0.9) demonstrating the greatest activity. Of the 5 candidates (compounds 3, 10, 11, 13 and 23) evaluated in vivo, failure to induce a lethal end-point at doses of 120 mg/kg was observed in all cases. Inadequate metabolic stability, particularly towards hepatic enzymes such as the CYPs, was postulated as one reason for their failure.

Crystal landscape of primary aromatic thioamides

The crystal landscape of a series of primary aromatic thioamides is described, displaying similar characteristic intermolecular hydrogen-bonding interactions in the solid state to those observed in their widely studied amide analogues, including R22(8) dimers and C(4) chains. In a number of cases, high Z′ values were observed in the structures. On the basis of the observed solid-state features, the thioamide functional group, which is a strong hydrogen-bond donor and moderate acceptor, offers considerable potential as a key moiety for crystal engineering.

Agonists for the adenosine A1 receptor with tunable residence time. a case for nonribose 4-amino-6-aryl-5-cyano-2-thiopyrimidines

We report the synthesis and evaluation of previously unreported 4-amino-6-aryl-5-cyano-2-thiopyrimidines as selective human adenosine A 1 receptor (hA1AR) agonists with tunable binding kinetics, this without affecting their nanomolar affinity for the target receptor. They show a very diverse range of kinetic profiles (from 1 min (compound 52) to 1 h (compound 43)), and their structure-affinity relationships (SAR) and structure-kinetics relationships (SKR) were established. When put in perspective with the increasing importance of binding kinetics in drug discovery, these results bring new evidence of the consequences of affinity-only driven selection of drug candidates, that is, the potential elimination of slightly less active compounds that may display preferable binding kinetics.

Evaluation of thiazole containing biaryl analogs as diacylglycerol acyltransferase 1 (DGAT1) inhibitors

Biphenyl carboxylic acids, exemplified by compound 5, are known potent inhibitors of diacylglycerol acyltransferase, DGAT1, an enzyme involved in the final committed step of triglyceride biosynthesis. We have synthesized and evaluated 2-phenylthiazole, 4-

Sulfonic acid functionalized nano Γ-Al 2O 3: A new, efficient, and reusable catalyst for synthesis of thioamides

Sulfonic acid functionalized nano γ-Al2O3 is easily prepared by the reaction of nano γ-Al2O3 with 1,3-propane sulfone. This reagent can be used as an eficient catalyst for the synthesis of thioamides. This new method consistently has the advantages of excellent yields and short reaction times. Further, the catalyst can be recovered for several times.

Nano n -propylsulfonated magnetic γ-Fe2O3 as an efficient and reusable catalyst for the synthesis of thioamides

One-pot three-component reactions of aldehydes, amines, and sulfur are carried out in the presence of nano n-propylsulfonated magnetic γ-Fe2O3 as a catalyst for the synthesis of biologically interesting thioamide derivatives. The value of this catalytic method lies in its mild reaction catalyst and conditions, good yields, and ease of handling.

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.

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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).

O,O-Diethyl dithiophosphoric acid mediated direct synthesis of thioamides from aldehydes and ketones

A general and convenient method for a one-pot conversion of aldehydes and ketones into thioamides has been developed. The protocol involves oximation of aldehydes and ketones followed by deoxygenative thioamidation of oximes with O,O-diethyl dithiophosphoric acid which acts as an acid as well a source of sulfur. The method is operationally simple, high yielding, and also applicable to the conversion of amides and nitriles into the corresponding thioamides.