6375-65-1

Usage

Uses

Used in Organic Synthesis:
(2-NITROPHENYL)THIO]ACETIC ACID is used as a building block in organic synthesis for the creation of various organic molecules. Its unique structure allows it to be a versatile component in the formation of complex organic compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (2-NITROPHENYL)THIO]ACETIC ACID is used as a key component in research and development. Its potential role in the creation of new drugs and biologically active substances makes it a valuable asset in the pursuit of novel therapeutic agents.
Used in Anti-Cancer Research:
(2-NITROPHENYL)THIO]ACETIC ACID is being studied for its potential as an anti-cancer agent. Its unique chemical properties may contribute to the development of new cancer treatments, offering hope for more effective therapies in the future.
However, it is important to handle (2-NITROPHENYL)THIO]ACETIC ACID with caution due to its potential toxic or irritant properties, ensuring safety in research and application environments.

InChI:InChI=1/C8H7NO4S/c10-8(11)5-14-7-4-2-1-3-6(7)9(12)13/h1-4H,5H2,(H,10,11)/p-1

Upstream product

• 100559-86-2 (2-nitrophenylthio)acetonitrile 
• 68-11-1 mercaptoacetic acid 
• 88-73-3 2-Chloronitrobenzene 
• 4875-10-9 o-nitrothiophenol 
• 79-11-8 chloroacetic acid 
• 96994-48-8 3-Hydroxy-3-(4-methoxy-phenyl)-2-(2-nitro-phenylsulfanyl)-propionic acid methyl ester 
• 107922-13-4 (2-nitro-phenylsulfanyl)-acetic acid anilide 
• 861784-94-3 2,5-dichloro-benzenethiosulfonic acid S-(2-nitro-phenyl ester) 
• 141-52-6 sodium ethanolate 
• 105-53-3 diethyl malonate 
• 107922-14-5 ω-<2-Nitro-phenylmercapto>-acetophenon-syn-oxim 
• 1046124-81-5 (6S)-N-(2-amino-4,5,6,7-tetrahydrobenzothiazole-6-yl)-2-nitro-N-propylbenzenesulfonamide 
• 1694-92-4 2-Nitrobenzenesulfonyl chloride 
• 996-82-7 sodium diethylmalonate 

Downstream Products

• 21069-05-6 4-hydroxy-2H-1,4-benzothiazin-3(4H)-one 
• 50693-98-6 methyl 2-((2-nitrophenyl)thio)acetate 
• 81214-90-6 (2-Hydroxyamino-phenylsulfanyl)-acetic acid 
• 4875-10-9 o-nitrothiophenol 
• 298-12-4 Glyoxilic acid 
• 95-16-9 1,3-Benzothiazole 
• 27489-27-6 <(2-Nitro-phenyl)sulfonyl>essigsaeure 
• 117737-43-6 (2-nitro-benzenesulfinyl)-acetic acid 
• 68192-40-5 1,1-dioxo-1,4-dihydro-1λ⁶-benzo[1,4]thiazine-2,3-dione 2-phenylhydrazone 
• 93249-24-2 <(2-Nitro-phenyl)sulfonyl>essigsaeure-amid 
• 873995-07-4 2-[(2-benzothiazolylmethyl)thio]benzenamine 
• 92905-88-9 2-(2-nitro-phenylsulfanylmethyl)-benzothiazole 
• 3080-99-7 3,4-dihydro-2H-benzo[1,4]thiazine 
• 100960-61-0 bromo-(2-nitro-phenylsulfanyl)-acetic acid 

Relevant academic research and scientific papers

A novel scalable synthesis of pramipexole

Pramipexole is a dopamine D2 subfamily receptor agonist that is used for the treatment of Parkinsons disease. We report here on the successful application of the Fukuyama alkylation protocol to the development of a novel and scalable process for synthesis of pramipexole and its pharmaceutically acceptable salts. The synthesis consists of converting the crucial intermediate (S)-2,6-diamino-4,5,6,7-tetrahydrobenzothiazole to (6S)-N-(2-amino-4,5,6,7- tetrahydrobenzothiazole-6-yl)-2-nitrobenzenesulfonamide, which is in turn monoalkylated to (6S)-N-(2-amino-4,5,6,7-tetrahydrobenzothiazole-6-yl)-2-nitro- N-propylbenzenesulfonamide. Deprotection of the latter yields pramipexole base, which is finally converted to a crude pramipexole dihydrochloride monohydrate with a yield of over 50% over four steps. The process allows for the telescoping of the final three steps, has high conversion rates of intermediates, offers ease of purification, and preserves high optical purity throughout all of the stages.

Synthesis and antitumor activity of some new substituted quinolin-4- one and 1,7-naphthyridin-4-one analogs

The synthesis of some new analogs of quinolin-4-one and 1,7- naphthyridin-4-one is described. The prepared compounds were tested for their in vitro antitumor and cdc2 kinase or cdc25 phosphatase inhibitory activity. Compound ethyl 7-oxo-2,3-dihydro-7H-pyrido [1,2,3-de][2,3- b]pyrido-1,4-thiazine-6-carboxylate (6b) showed antitumor activity against CNS SNB-75, breast T-47D, and lung NCI-H522 cancer cell lines with GI50 values of 8.3, 17.6, and 22.7 μM, respectively. Meanwhile, the compounds ethyl 4-oxo-8-phenylthio-1H,4H-quinoline-3-carboxylate (11a) and 4-oxo-8- phenylthio-1H,4H-1,7-naphthyridine-3-carboxylic acid (12b) have proved to be cdc25 phosphatase inhibitors at IC50 values of 11 and 5 μM, respectively.

KINETICS AND MECHANISM OF OXIDATION OF (ARYLTHIO)ACETIC ACIDS BY PYRIDINIUM HYDROBROMIDE PERBROMIDE

Oxidation of several monosubstituted (phenylthio)acetic acids (PTAA) by pyridinium hydrobromide perbromide (PHPB) was studied in aqueous acetic acid.The reaction is first order with respect to PHPB.Michaelis-Menten type kinetics are observed with respect to (arylthio)acetic acid.The effect of solvent composition indicates that the transition state is more polar than the reactants.The formation constants of the intermediate substrate-PHPB complexes and the rates of their decomposition were determined at different temperatures.The rates of oxidation of para and meta-substituted (phenylthio)acetic acids were correlated with Hammett's substituent constants.The ρ value is -1.60 at 35 deg c.The rates of oxidation of ortho substituted compounds are correlated with Charton's triparametric equation.A mechanism involving the decomposition of the intermediate complex in the slow rate-determining step affording a sulphonium ion which hydrolyses in a subsequent fast step to the sulphoxide is proposed.

Reaction of 3-Phenylglycidic Esters. Part 2. Stereo- and Regio-selectivity in the Oxirane Ring Opening of Methyl trans-3-(4-Methoxyphenyl)glycidate with Various Thiophenols and the Effects of Solvent and Temperature

The effects of the solvent and temperature on the reaction of the trans-glycidate (1) with various substituted thiophenols (2) in the presence or absence of a catalyst have been investigated.The temperature had a surprisingly large effect on the stereochemistry of the oxirane ring-opening of (1).At room temperature, the erythro-isomer (4) (trans-opening product) was obtained as a major product in the absence of catalyst, while the cis-opening product (3) (threo-isomer) was produced predominantly at higher temperature.On the other hand, in a dipolar aprotic solvent, the regioisomer (5) was formed, the yield increasing with the electron-donating ability of the substituents on (2).The formation of compound (5) may involve single-electron transfer as a key step.