18108-55-9Relevant academic research and scientific papers
3-Arylidene-N-hydroxyoxindoles: A New Class of Compounds Endowed with Antitumor Activity
Musso, Loana,Cincinelli, Raffaella,Zuco, Valentina,De Cesare, Michelandrea,Zunino, Franco,Fallacara, Anna Lucia,Botta, Maurizio,Dallavalle, Sabrina
, p. 1700 - 1704 (2016)
A series of compounds containing the N-hydroxyoxindole scaffold were synthesized and evaluated for antitumor activity. The compounds showed potent antiproliferative activity against the wild-type p53 IGROV-1 ovarian carcinoma cell line and considerably lower efficacy against the mutant IGROV-1/Pt1 subline that lacks p53 function. The differential response of ovarian carcinoma cells depending on p53 status was also reflected in the varied susceptibility to apoptosis of the treated cell lines. These results support a role for the p53 transcription factor as a determinant of cytotoxicity. The therapeutic potential of the most promising compound of the series was evaluated in the treatment of an IGROV-1 xenograft growing as ascitic tumor in mice. Using intraperitoneal administration, daily treatment with the compound for four weeks produced a significant delay in the onset of ascites.
Intermediate analogue inhibitors of mandelate racemase: N-Hydroxyformanilide and cupferron
Bourque, Jennifer R.,Burley, Rodney K.M.,Bearne, Stephen L.
, p. 105 - 108 (2007)
Mandelate racemase (MR) catalyzes the 1,1-proton transfer that interconverts the enantiomers of mandelate. The transition state/intermediate analogues N-hydroxyformanilide (Ki = 2.79 ± 0.19 μM) and cupferron (Ki = 2.67 ± 0.09 μM) are
Metal- and Oxidant-Free Modular Approach to Access N-Alkoxy Oxindoles via Aryne Annulation
Singh, Ritesh,Nagesh, Kommu,Yugandhar, Doddapaneni,Prasanthi
, p. 4848 - 4853 (2018/08/24)
An unprecedented metal- and oxidant-free (intermolecular) approach to access N-alkoxy oxindoles via [3 + 2] cycloadition of in situ generated electrophilic species viz. aryne and (putative) aza-oxyallyl cation is reported. This approach is amenable to both C3-unsubstituted as well as C3-substituted oxindoles. A one-pot manipulation further makes this reaction highly practical. The versatility of this approach was demonstrated through valuable synthetic transformations.
A safe and selective method for reduction of 2-nitrophenylacetic acid systems to N-aryl hydroxamic acids using continuous flow hydrogenation
Ichire, Ogar,Jans, Petra,Parfenov, Galina,Dounay, Amy B.
supporting information, p. 582 - 585 (2017/01/16)
The cyclic hydroxamic acid functional group is critical to the biological activity of numerous natural products and drug candidates. Efficient, reliable, and green synthetic methods to produce cyclic hydroxamic acids are needed. Herein, flow hydrogenation has been explored as a novel approach toward achieving the selective partial reduction of 2-nitrophenylacetic acid to 1-hydroxyindolin-2-one. The bidentate ligand, 1,10-phenanthroline, has been identified as a unique inhibitor for modulating product selectivity in this Pt/C-catalyzed process. Under the newly optimized reaction conditions, the targeted hydroxamic acid is produced with high selectivity (49:1) over the lactam by-product. The scope of the reaction is demonstrated for a variety of 2-nitrophenylacetic acid derivatives.
Synthesis of o-Aminophenols via a Formal Insertion Reaction of Arynes into Hydroxyindolinones
Chen, Zhilong,Wang, Qiu
supporting information, p. 6130 - 6133 (2016/01/09)
A novel approach toward the synthesis of sterically hindered o-aminophenols has been achieved by a formal aryne insertion into hydroxyindolinones. This transformation offers a rapid and efficient entry to diverse o-aminophenol scaffolds under mild transit
A nitrophenyl-based prodrug type for colorectal targeting of prednisolone, budesonide and celecoxib
Marquez Ruiz, Juan F.,Kedziora, Kinga,Pigott, Maria,Keogh, Brian,Windle, Henry,Gavin, Jason,Kelleher, Dermot P.,Gilmer, John F.
, p. 1693 - 1698 (2013/04/10)
Celecoxib is a COX-2 inhibitor drug that can be used to reduce the risk of colorectal adenocarcinoma. Glucocorticoids are used in the treatment of inflammatory bowel disease. A limitation to the use of both drug types is that they undergo absorption from the intestinal tract with serious side effects. The prodrug systems introduced here involve forming a nitro-substituted acylsulfonamide group in the case of celecoxib and a nitro-substituted 21-ester for the glucocorticoids. Drug release is triggered by the nitro reductase action of the colonic microflora, liberating a cyclization competent species. The release of the active parent drugs was evaluated in vitro using Clostridium perfringens and epithelial transport through Caco-2 monolayer evaluation was carried out to estimate the absorption properties of the prodrugs compared to the parental drugs.
Reductive cyclizations of nitroarenes to hydroxamic acids by visible light photoredox catalysis
Cismesia, Megan A.,Ischay, Michael A.,Yoon, Tehshik P.
, p. 2699 - 2705 (2013/10/21)
We have developed a photocatalytic reduction of nitroarenes as an efficient, chemoselective route to biologically important N-phenyl hydroxamic acid scaffolds. Optimal conditions call for 2.5 mol% of a ruthenium photocatalyst, visible light irradiation, and a dihydropyridine terminal reductant. Because of the mild nature of the visible light activation, functional groups that might be sensitive to other non-photochemical reduction methods are easily tolerated. Georg Thieme Verlag Stuttgart New York.
PROTON ACCEPTOR IMINIUM/CARBOCATION-TYPE COUPLING AGENTS
-
, (2010/06/19)
Novel iminium-type coupling agents containing proton acceptors in their iminium moiety, which can be used beneficially as coupling agents in various chemical polypeptide and/or polynucleotide syntheses, and are particularly useful as yield enhancing and racemization suppressing coupling agents for use in peptide syntheses, are disclosed. Further disclosed are a process of preparing such iminium-type coupling agents and their use in the preparation of polypeptides and/or polynucleotides.
Synthesis and application of N-hydroxylamine derivatives as potential replacements for HOBt
El-Faham, Ayman,Albericio, Fernando
supporting information; experimental part, p. 1499 - 1501 (2009/07/11)
Several heterocycles containing N-hydroxylamine were prepared and tested as coupling additives to replace the use of N-hydroxybenzolriazole (HOBt.) derivatives. On the basis of our results on coupling yield and racemization-suppressing properties, we propose N-hydroxyindolin-2-one and 6- cfiloro-N-hydroxy-2-phenylbenzimidazole as suitable substitutes for HOBt. Wiley-VCH Verlag GmbH & Co. KGaA.
Efficient approaches to S-alkyl-N-alkylisothioureas: Syntheses of histamine H3 antagonist clobenpropit and its analogues
Yoneyama, Hiroki,Shimoda, Ayako,Araki, Lisa,Hatano, Kouta,Sakamoto, Yasuhiko,Kurihara, Takushi,Yamatodani, Atsushi,Harusawa, Shinya
, p. 2096 - 2104 (2008/09/19)
(Chemical Equation Presented) S-Alkyl-N-alkylisothioureas were efficiently synthesized via synthetic approach (A) using 3-phenylpro-pionyl isothiocyanate (PPI). The utility of the approach was proved by the syntheses of clobenpropit, a potent histamine H3 antagonist, and its analogues. Alternatively, clobenpropit could be prepared via intramolecular amide cleavage (B) with use of 2-nitrophenylacetyl isothiocyanate (NPAI).
