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.
Cyclization of N-Alkenyl-o-chloroanilides with Organonickel(0) Complexes: Conformational Analysis of 3-Substituted Oxindoles
Rodriguez, J. Gonzalo,Canoira, Laureano,Temprano, Fernando
, p. 1193 - 1196 (1986)
3-substituted oxindoles (1)-(6) have been obtained as the main products of the cyclization reaction of N-alkenyl-o-chloroanilides with the zerovalent complex tetrakis(triphenylphosphine)nickel(0). 1H N.m.r. spectra of the oxindoles (2)-(6) show an AMX pro
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
Ionic liquids as solvents of choice for electrophilic fluorination: Fluorination of indoles by F-TEDA-BF4
Baudoux, Jér?me,Salit, Anne-Frédérique,Cahard, Dominique,Plaquevent, Jean-Christophe
, p. 6573 - 6574 (2002)
Selectfluor was shown to be soluble in ionic liquid, thus allowing the 'green' electrophilic fluorination of indole compounds in high chemoselectivity and yields.
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.
A novel and efficient synthesis of 3-fluorooxindoles from indoles mediated by selectfluor
Takeuchi, Yoshio,Tarui, Takanao,Shibata, Norio
, p. 639 - 642 (2000)
(equation presented) Treatment of several 3-substituted indoles, including derivatives of tryptophan and serotonin, with commercially available Selectfluor in acetonitrile/ water furnished 3-substiuted 3-fluorooxindoles in good to high yields. Since 3-fluorooxindoles obtained are sterically similar to both oxindoles and 3-hydroxyoxindoles, they should be useful as probes for investigating the enzymatic mechanism of indole biosynthesis and metabolism.
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.
Evaluation of 3-ethyl-3-(phenylpiperazinylbutyl)oxindoles as PET ligands for the serotonin 5-HT7 receptor: Synthesis, pharmacology, radiolabeling, and in vivo brain imaging in pigs
Herth, Matthias M.,Andersen, Valdemar L.,Hansen, Hanne D.,Stroth, Nikolas,Volk, Balázs,Lehel, Szabolcs,Dyssegaard, Agnete,Ettrup, Anders,Svenningsson, Per,Knudsen, Gitte M.,Kristensen, Jesper L.
, p. 3631 - 3636 (2015)
We have investigated several oxindole derivatives in the pursuit of a 5-HT7 receptor PET ligand. Herein the synthesis, chiral separation, and pharmacological profiling of two possible PET candidates toward a wide selection of CNS-targets are de
Iron-Catalyzed Oxidative Cross-Coupling of Phenols and Tyrosine Derivatives with 3-Alkyloxindoles
Mintz, Tomer,More, Nagnath Yadav,Gaster, Eden,Pappo, Doron
supporting information, p. 18164 - 18178 (2021/12/17)
In this study, a novel iron-catalyzed oxidative cross-coupling reaction between phenols and 3-alkyloxindole derivatives is reported. The efficient method, which is based on the FeCl3 catalyst and the t-BuOOt-Bu oxidant in 1,2-dichloroethane at 70 °C, affords 3-alkyl-3-(hydroxyaryl)oxindole compounds with a high degree of selectivity. The generality of the conditions was proven by reacting various substituted phenols, naphthols, and tyrosine derivatives with 3-alkyloxindoles. To apply the chemistry for the conjugation of tyrosine-containing short peptides with oxindolylalanine (Oia) derivatives, the reaction conditions were modified [Fe(O2CCF3)3 catalyst, t-BuOOt-Bu, HFIP, 70 °C], and amino acids with acid-stable N-protecting groups were used.
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.).