1504-06-9Relevant articles and documents
Ketoprofen-induced formation of amino acid photoadducts: Possible explanation for photocontact allergy to ketoprofen
Karlsson, Isabella,Persson, Elin,Ekebergh, Andreas,M?rtensson, Jerker,B?rje, Anna
, p. 1294 - 1303 (2014)
Photocontact allergy is a well-known side effect of topical preparations of the nonsteroidal anti-inflammatory drug ketoprofen. Photocontact allergy to ketoprofen appears to induce a large number of photocross allergies to both structurally similar and structurally unrelated compounds. Contact and photocontact allergies are explained by structural modification of skin proteins by the allergen. This complex is recognized by the immune system, which initiates an immune response. We have studied ketoprofen's interaction with amino acids to better understand ketoprofen's photoallergenic ability. Irradiation of ketoprofen and amino acid analogues resulted in four different ketoprofen photodecarboxylation products (6-9) together with a fifth photoproduct (5). Dihydroquinazoline 5 was shown to be a reaction product between the indole moiety of 3-methylindole (Trp analogue) and the primary amine benzylamine (Lys analogue). In presence of air, dihydroquinazoline 5 quickly degrades into stable quinazolinone 12. The corresponding quinazolinone (17) was formed upon irradiation of ketoprofen and the amino acids N-acetyl-l-Trp ethyl ester and l-Lys ethyl ester. The formation of these models of an immunogenic complex starts with the ketoprofen-sensitized formation of singlet oxygen, which reacts with the indole moiety of Trp. The formed intermediate subsequently reacts with the primary amino functionality of Lys, or its analogue, to form a Trp-Lys adduct or a mimic thereof. The formation of a specific immunogenic complex that does not contain the allergen but that can still induce photocontact allergy would explain the large number of photocross allergies with ketoprofen. These allergens do not have to be structurally similar as long as they can generate singlet oxygen. To the best of our knowledge, there is no other suggested explanation for ketoprofen's photoallergenic properties that can account for the observed photocross allergies. The formation of a specific immunogenic complex that does not contain the allergen is a novel hypothesis in the field of contact and photocontact allergy.
Reduction of 3-acyl derivatives of oxindoles, benzo[b]furan-2-ones, and benzo[b]thiophen-2-ones to the corresponding alkyl derivatives by sodium borohydride-acetic acid
Smith, Francis X.,Williams, Brian D.,Gelsleichter, Eric,Podcasy, Judy A.,Sisko, John T.,Hrubowchak, David M.
, p. 765 - 769 (2006)
It was found that 3-acyl derivatives of oxindoles, benzo[b]furan-2-ones, and benzo[b]thiophen-2-ones could be efficiently and conveniently reduced to the corresponding alkyl derivatives by pelletized sodium borohydride in acetic acid. A typical procedure
Intramolecular Reactions Using Amide Links: Aryl Radical Cyclisation of Silylated Acryloylanilides
Jones, Keith,Wilkinson, James,Ewin, Richard
, p. 7673 - 7676 (1994)
Aryl radical cyclisations of in situ silylated o-bromoacryloylanilides are presented and shown to lead to N-unsubstituted oxindoles and dihydroquinolones in very different ratios than those previously observed for the N-alkyl o-bromoacryloylanilides.
Friedel-crafts alkylation of N-(2-chloropropionyl)aniline and the generation mechanism of byproducts
Tian, Jun,Li, Lei,Yan, Xilong,Chen, Ligong
, p. 1811 - 1813 (2014)
The cyclization of N-(2-chloropropionyl)aniline to 3-methylindolin-2-one through Friedel-Crafts alkylation was studied. It was found that N-phenylacrylamide (12.6%) and 3,4-dihydro-2(1H)-quinolinone (1.5%) as main byproducts were obtained. On the basis of the mechanism of Friedel-Crafts alkylation, the generation mechanisms of these two compounds were proposed.
Reaction of skatole with iodine in the presence of thiourea
Hino,Endo,Nakagawa
, p. 2728 - 2731 (1974)
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Rapid Oxidation Indoles into 2-Oxindoles Mediated by PIFA in Combination with n-Bu4NCl ? H2O
Liang, Peng,Zhao, Hang,Zhou, Tingting,Zeng, Kaiyun,Jiao, Wei,Pan, Yang,Liu, Yazhou,Fang, Dongmei,Ma, Xiaofeng,Shao, Huawu
supporting information, p. 3532 - 3538 (2021/06/09)
We report the development of a rapid approach for directly converting indoles into 2-oxindoles promoted by HOCl formed in situ from the combination of (bis(trifluoroacetoxy) iodo)benzene (PIFA) and n-Bu4NCl ? H2O. The procedure is widely functional group tolerant and provides 2-oxindoles in up to 95% yield within 5 min. The potential applications of the developed methodology are demonstrated by the gram-scale preparation of 3-methyl-2-oxindole (11 a), the one-pot two-step syntheses of spiro-oxindoles 26 a and 26 b, and the formal synthesis of (-)-folicanthine (2). (Figure presented.).
Green method for preparing oxindole derivative
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Paragraph 0042-0044, (2021/06/26)
The invention relates to the technical field of green organic synthesis, and provides a green method for preparing oxindole derivatives, which comprises the following steps: taking indole compounds with different functional groups as raw materials, under the conditions of room temperature, opening and neutral, adopting MBrx (M is Fe,Fe,Ce and the like) as a catalyst with X equal to 2 or 3, and adopting hydrogen peroxide as a sole oxidant to generate active bromine (RBS) in situ, and catalytically synthesizing the oxindole derivative. According to the method disclosed by the invention, MBrx (such as FeBr2, CeBr3 and the like) is used as the catalyst, so that an expensive or complex catalyst is avoided, and the method is green, environment-friendly, safe, simple, efficient, mild in reaction condition and wide in substrate application range, has a relatively good application prospect and is expected to be widely applied to organic synthesis, fine chemical engineering and pharmaceutical industry.