- Reactivity of spiroanthraceneoxazolidines with cyclopropanes: An approach to the oxindole alkaloid scaffold
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The reaction of N-methylspiro[anthracene-oxazolidine] with spiro[cyclopropane-3,3′-indolin]-2-ones in the presence of MgI2 formed the corresponding spiro[pyrrolidine-3,3′-indolin]-2-ones in 42–65% yields. The use of N-benzylspiro[anthracene-oxazolidine] in this reaction led to the formation of a mixture of the corresponding N-methyl- and N-benzylpyrrolidines.
- Buev, Evgeny M.,Moshkin, Vladimir S.,Sosnovskikh, Vyacheslav Y.
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supporting information
p. 3409 - 3412
(2018/08/20)
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- Copper-catalyzed aerobic oxidative intramolecular amidation of 2-aminophenylacetylenes: A domino process for the synthesis of isatin
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A novel CuI-catalyzed oxidative amidation of 2-aminophenylacetylenes leading to the formation of isatins by using open air as an oxygen source has been developed. The reaction proceeded smoothly and provided a variety of isatin derivatives in good yields. The advantages of this one-pot reaction protocol include the use of a green oxidant, low-price catalyst and facile conditions, and easy handling.
- Salvanna,Ramesh, Perla,Santosh Kumar,Das, Biswanath
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p. 13754 - 13759
(2017/11/27)
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- A general and efficient method to access tetracyclic spirooxindole derivatives
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An efficient, simple, and convenient synthetic procedure for the synthesis of tetracyclic spirooxindole derivatives, starting from N-protected isatins and 2-fluoropyridine, was successfully developed. It enables the facile formation of a new class of spirooxindoles in which the oxindole core is fused with various heterocycles at the C-3 position.
- El Bouakher, Abderrahman,Massip, Stphane,Jarry, Christian,Troin, Yves,Abrunhosa-Thomas, Isabelle,Guillaumet, Grald
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p. 556 - 559
(2015/01/30)
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- Direct amidation of 2'-aminoacetophenones using I2-TBHP: A unimolecular domino approach toward isatin and iodoisatin
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Synthesis of isatin and iodoisatin from 2'-aminoacetophenone was achieved via oxidative amido cyclization of the sp3 C-H bond using I 2-TBHP as the catalytic system. The reaction proceeds through sequential iodination, Kornblum oxidation, and amidation in one pot. This method is simple, atom economic, and works under metal- and base-free conditions.
- Ilangovan, Andivelu,Satish, Gandhesiri
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p. 4984 - 4991
(2014/06/23)
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- Copper-mediated selective C-H activation and cross-dehydrogenative C-N coupling of 2′-aminoacetophenones
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Isatins were obtained by cross-dehydrogenative C-N annulation and dealkylative C-N annulation of 2′-N-aryl/alkylaminoacetophenones and 2′-N,N-dialkylaminoacetophenones respectively in the presence of Cu(OAc)2·H2O/NaOAc/air. However, on reaction with CuBr, 2′-N-benzylaminoacetophenones underwent selective oxidation of an α-methylene group of amine rather than the 2-acetyl group to provide corresponding benzamides exclusively. Base played an important role in selective oxidation by lowering the temperature and time.
- Ilangovan, Andivelu,Satish, Gandhesiri
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supporting information
p. 5726 - 5729
(2013/12/04)
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- Tetracyclic spirooxindole blockers of hNaV1.7: Activity in vitro and in CFA-induced inflammatory pain model
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The structure-activity relationship of a new series of tetracyclic spirooxindoles led to the discovery of compound 25a, a potent hNaV1.7 blocker with improved ADME properties and in vivo efficacy in the CFA-induced inflammatory pain model.
- Chowdhury, Sultan,Liu, Shifeng,Cadieux, Jay A.,Hsieh, Tom,Chafeev, Mikhail,Sun, Shaoyi,Jia, Qi,Sun, Jianyu,Wood, Mark,Langille, Jonathan,Sviridov, Serguei,Fu, Jianmin,Zhang, Zaihui,Chui, Ray,Wang, Audrey,Cheng, Xing,Zhong, Jing,Hossain, Sazzad,Khakh, Kuldip,Rajlic, Ivana,Verschoof, Henry,Kwan, Rainbow,Young, Wendy
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p. 1825 - 1836
(2013/07/26)
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- Copper-catalyzed selective oxidative acylation of secondary anilines with ethyl glyoxalate: Domino synthesis of indoline-2,3-diones
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A novel, easy and useful copper-catalyzed selective acylation of secondary anilines with ethyl glyoxalate has been developed, and the corresponding indoline-2,3-dione derivatives were prepared. The procedure comprises the sequential intermolecular copper-catalyzed selective oxidative ortho-site aromatic acylation of the NH group in secondary anilines and intramolecular nucleophilic attack of the NH group to the ester. The inexpensive, easy and efficient method should provide a new strategy for synthesis of dicarbonyl compounds. Copyright
- Liu, Tao,Yang, Haijun,Jiang, Yuyang,Fu, Hua
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supporting information
p. 1169 - 1176
(2013/05/21)
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- Discovery of XEN907, a spirooxindole blocker of NaV1.7 for the treatment of pain
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Starting from the oxindole 2a identified through a high-throughput screening campaign, a series of NaV1.7 blockers were developed. Following the elimination of undesirable structural features, preliminary optimization of the oxindole C-3 and N-1 substituents afforded the simplified analogue 9b, which demonstrated a 10-fold increase in target potency versus the original HTS hit. A scaffold rigidification strategy then led to the discovery of XEN907, a novel spirooxindole NaV1.7 blocker. This lead compound, which in turn showed a further 10-fold increase in potency, represents a promising structure for further optimization efforts.
- Chowdhury, Sultan,Chafeev, Mikhail,Liu, Shifeng,Sun, Jianyu,Raina, Vandna,Chui, Ray,Young, Wendy,Kwan, Rainbow,Fu, Jianmin,Cadieux, Jay A.
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scheme or table
p. 3676 - 3681
(2011/08/06)
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- USE OF SPIRO-OXINDOLE COMPOUNDS AS THERAPEUTIC AGENTS
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This invention is directed to methods of using spiro-oxindole compounds of formula (I): wherein k, j, Q, R1, R2a, R2b, R2c, R2d, R3a, R3b, R3c, and R3d are as defined herein, as a stereoisomer, enantiomer, tautomer thereof or mixtures thereof; or a pharmaceutically acceptable salt, solvate or prodrug thereof, for the treatment and/or prevention of hypercholesterolemia, benign prostatic hyperplasia, pruritis and cancer.
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- HYDRAZONE MODULATORS OF CANNABINOID RECEPTORS
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Hydrazone compounds which modulate cannabinoid receptors are presented. Pharmaceutical compositions containing these compounds, methods of using these compounds as modulators of cannabinoid receptors and processes for synthesizing these compounds are also described herein.
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Page/Page column 45, 47
(2009/03/07)
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- SPIRO (FURO [3, 2-C] PYRIDINE-3-3 ' -INDOL) -2' (1'H)-ONE DERIVATIVES AND RELATED COMPOUNDS FOR THE TREATMENT OF SODIUM-CHANNEL MEDIATED DISEASES, SUCH AS PAIN
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This invention is directed to methods of using spiro-oxindole compounds of formula (I): wherein j, k, m, Q, X,, R1, R2a, R2b, R2c, R2d and R3 are as defined herein, as a stereoisomer, enantiomer, tautomer thereof or mixtures thereof; or a pharmaceutically acceptable salt, N-oxide, solvate or prodrug thereof, for the treatment and/or prevention of sodium channel-mediated diseases or conditions, such as pain.
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Page/Page column 107
(2008/06/13)
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- Design and synthesis of a novel series of N-alkyl isatin acylhydrazone derivatives that act as selective cannabinoid receptor 2 agonists for the treatment of neuropathic pain
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There is growing interest in using cannabinoid receptor 2 (CB2) agonists for the treatment of neuropathic pain. We have synthesized a novel series of N-alkyl isatin acylhydrazone derivatives and have identified and characterized several of them as novel analogues with high functional activity and selectivity at human CB2 receptors using [35S]GTP-γ-S assays. Binding affinities at human CB2 and CB1 were determined for compounds 28, 33, 40, 48, and 58. Structure-activity relationship studies of this novel series led to optimization of our lead compound, compound 33 (MDA19). Compound 33 possessed potent antiallodynic effects in a rat model of neuropathic pain but did not affect rat locomotor activity. More potent and more CB2-receptor-selective compounds, including compounds 37, 40, and 48, were also discovered.
- Diaz, Philippe,Xu, Jijun,Astruc-Diaz, Fanny,Pan, Hao-Min,Brown, David L.,Naguib, Mohamed
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supporting information; experimental part
p. 4932 - 4947
(2009/07/11)
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- OXINDOLE COMPOUNDS AND THEIR USES AS THERAPEUTIC AGENTS
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This invention is directed to oxindole compounds that are useful for the treatment and/or prevention of sodium channel-mediated diseases or conditions, such as pain. Pharmaceutical compositions comprising the compounds and methods of using the compounds are also disclosed.
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Page/Page column 66
(2010/11/24)
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- SPIRO-OXINDOLE COMPOUNDS AND THEIR USES AS THERAPEUTIC AGENTS
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This invention is directed to spiro-oxindole compounds of formula (I): wherein k, j, Q, R1, R2a, R2b, R2c, R2d, R3a, R3b, R3c, and R3d are as defined herein, as a stereoisomer, enantiomer, tautomer thereof or mixtures thereof; or a pharmaceutically acceptable salt, solvate or prodrug thereof, which are useful for the treatment and/or prevention of sodium channel-mediated diseases or conditions, such as pain. Pharmaceutical compositions comprising the compounds and methods of preparing and using the compounds are also disclosed.
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Page/Page column 111
(2010/11/24)
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- 2-oxoindoline derivative
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Disclosed is a 2-oxoindoline derivative represented by the formula (I): STR1 wherein Ring A represents a benzene ring which is substituted in the 5-position or 6-position by a lower alkyl group or lower alkoxy group, R1 represents a phenyl group which is substituted by a halogen atom, a lower alkyl group or a lower alkoxy group, R2 represents a naphthyl group, indolyl group, isoquinolyl group, benzimidazolyl group or a group represented by the formula: STR2 wherein n represents 1 or 2, R3 represents a lower alkyl group which is substituted by a carboxyl group, a cyano group or a tetrazolyl group, O represents a single bonding arm, and Y represents a single bonding arm, or a pharmaceutically acceptable salt thereof.
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