31842-01-0 Usage
Chemical Properties
ALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACID is Off-White Solid
Originator
Flosint,Carlo Erba,Italy,1976
Uses
Different sources of media describe the Uses of 31842-01-0 differently. You can refer to the following data:
1. ALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACID is a non-steroidal anti-inflammatory agent used for treatment of pain and inflammation
2. analgesic, antiinflammatory
Definition
ChEBI: A monocarboxylic acid that is propionic acid in which one of the hydrogens at position 2 is substituted by a 4-(1-oxo-1,3-dihydroisoindol-2-yl)phenyl group. Initially used as an anti-inflammatory and analgesic, it was withdrawn from the market due to causi
g severe gastrointestinal bleeding. It has been subsequently found to increase production of the survival motor neuron protein.
Manufacturing Process
The mixture of 7.9 g of ethyl α-(4-aminophenyl)propionate and 8.3 g of ethyl
2-chloromethylbenzoate is refluxed under nitrogen for one hour. The residue is
recrystallized from hexane, to yield the ethyl α-[4-(1-oxo-isoindolino)-phenyl]-
propionate of the formulamelting at 104° to 106°C. The mixture of 4.5 g thereof, 1.6 g of potassiumhydroxide, 2 ml of water and 250 ml of ethanol is refluxed under nitrogen for
2 hours and evaporated under reduced pressure. The residue is taken up in
water, the solution washed with chloroform, acidified with hydrochloric acid
and extracted with ethyl acetate. The extract is dried, evaporated and the
residue recrystallized from ethyl acetate, to yield the corresponding free acid
melting at 208° to 210°C. (Procedure reported in US Patent 3,767,805.)
Brand name
Endyne;Fenint;Flogosan;Flosine;Flosyn;K 4277;Miantor.
Therapeutic Function
Antiinflammatory
World Health Organization (WHO)
Indoprofen, a nonsteroidal anti-inflammatory agent, was
introduced in 1976 for the treatment of rheumatic disorders. By 1983 its use had
been associated with serious adverse effects, some of which were fatal. This led to
its withdrawal in the United Kingdom and Cyprus. In 1984 reports of intestinal
tumours in rats led to the drug's temporary withdrawal in Germany and Italy. This
was followed immediately by the suspension of marketing worldwide by the major
manufacturer.
Check Digit Verification of cas no
The CAS Registry Mumber 31842-01-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,1,8,4 and 2 respectively; the second part has 2 digits, 0 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 31842-01:
(7*3)+(6*1)+(5*8)+(4*4)+(3*2)+(2*0)+(1*1)=90
90 % 10 = 0
So 31842-01-0 is a valid CAS Registry Number.
InChI:InChI=1/C17H15NO3/c1-11(17(20)21)12-6-8-14(9-7-12)18-10-13-4-2-3-5-15(13)16(18)19/h2-9,11H,10H2,1H3,(H,20,21)
31842-01-0Relevant articles and documents
One-pot synthesis of pyrrolidones from levulinic acid and amines/nitroarenes/nitriles over the Ir-PVP catalyst
Chaudhari, Chandan,Nagaoka, Katsutoshi,Nishida, Yoshihide,Sato, Katsutoshi,Shiraishi, Masaya
supporting information, p. 7760 - 7764 (2020/11/27)
The synthesis of pyrrolidones via reductive amination of levulinic acid with aniline was examined over polypyrrolidone-stabilized metal nanoparticle catalysts. Among them, Ir metal was the most effective and applicable for the reductive amination of levulinic acid with nitroarenes/nitriles. Importantly, this catalyst was used for the one-pot synthesis of the anti-inflammatory drug indoprofen from 2-formylbenzoic acid and 2-(4-nitrophenyl)propanoic acid.
A g-C3N4-based heterogeneous photocatalyst for visible light mediated aerobic benzylic C-H oxygenations
Geng, Pengxin,Tang, Yurong,Pan, Guanglong,Wang, Wentao,Hu, Jinchuan,Cai, Yunfei
supporting information, p. 6116 - 6122 (2019/11/20)
A metal-free heterogeneous photocatalytic system has been developed for highly efficient benzylic C-H oxygenations using oxygen as an oxidant. This visible light mediated oxidation reaction utilizes graphitic carbon nitride (g-C3N4) as a recyclable, nontoxic and low cost photocatalyst. Mild reaction conditions allow for the generation of synthetically and biologically valued isochromannones, phthalides, isoquinolinones, isoindolinones and xanthones from readily accessible alkyl aromatic precursors in good yields. The heterogeneous nature of the g-C3N4 catalytic system enables easy recovery and recycling as well as the use in multiple runs without loss of activity. The synthetic utility of this "green" methodology was further demonstrated by applying in bioactive and drug valued target syntheses.
Transition metal free intramolecular selective oxidative C(sp3)-N coupling: Synthesis of N-aryl-isoindolinones from 2-alkylbenzamides
Verma, Ajay,Patel, Saket,Meenakshi,Kumar, Amit,Yadav, Abhimanyu,Kumar, Shailesh,Jana, Sadhan,Sharma, Shubham,Prasad, Ch. Durga,Kumar, Sangit
supporting information, p. 1371 - 1374 (2015/02/18)
A synthetic method has been developed for the preparation of biologically important isoindolinones including indoprofen and DWP205190 drugs from 2-alkylbenzamide substrates by transition metal-free intramolecular selective oxidative coupling of C(sp3)-H and N-H bonds utilizing iodine, potassium carbonate and di-tert-butyl peroxide in acetonitrile at 110-140 °C.
