- Yb(OTf)3catalyzed [1,3]-rearrangement of 3-alkenyl oxindoles
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A Yb(OTf)3catalyzed [1,3]-rearrangement of 3-alkenyl oxindoles was achieved, affording a variety of multifunctional 3-ylideneoxindoles with good yields andZ/Eselectivities (64%-89% yield, 78?:?22->99?:?1Z/E). Importantly, an operationally simple, one-pot sequential catalytic synthesis of 3-ylideneoxindoles was also developed. Additionally, a cross [1,3]-rearrangement experiment and nonracemic transformation were also carried out, which indicated a concerted rearrangement mechanism of this methodology.
- He, Lingchen,Hu, Xin-Gen,Jiang, Jun,Li, Juan,Li, Xinhua,Liu, Hongxin,Song, Chao,Wan, Junlin,Wu, Chaofei,Xiao, Hong-Ping
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supporting information
p. 122 - 126
(2021/12/29)
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- Preparation method of robecoxib
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The invention relates to a preparation method of robecoxib. The preparation method comprises the following steps: under the protection of inert gas, adding 5-ethylindole-2-ketone, 2, 3, 5, 6-tetrafluoroiodobenzene, a catalyst, alkali, a ligand and a solve
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Paragraph 0033-0035; 0043-0045; 0052-0054
(2020/11/02)
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- Discovery of a potent inhibitor of MELK that inhibits expression of the anti-apoptotic protein Mcl-1 and TNBC cell growth
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Despite recent advances in molecularly directed therapy, triple negative breast cancer (TNBC) remains one of the most aggressive forms of breast cancer, still without a suitable target for specific inhibitors. Maternal embryonic leucine zipper kinase (MELK) is highly expressed in TNBC, where level of overexpression correlates with poor prognosis and an aggressive disease course. Herein, we describe the discovery through targeted kinase inhibitor library screening, and structure-guided design of a series of ATP-competitive indolinone derivatives with subnanomolar inhibition constants towards MELK. The most potent compound, 17, inhibits the expression of the anti-apoptotic protein Mcl-1 and proliferation of TNBC cells exhibiting selectivity for cells expressing high levels of MELK. These studies suggest that further elaboration of 17 will furnish MELK-selective inhibitors with potential for development in preclinical models of TNBC and other cancers.
- Edupuganti, Ramakrishna,Taliaferro, Juliana M.,Wang, Qiantao,Xie, Xuemei,Cho, Eun Jeong,Vidhu, Fnu,Ren, Pengyu,Anslyn, Eric V.,Bartholomeusz, Chandra,Dalby, Kevin N.
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p. 2609 - 2616
(2017/04/06)
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- Umbelliferone-oxindole hybrids as novel apoptosis inducing agents
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In furtherance of our endeavour towards the synthesis of novel bioactive agents, a panel of (E)-3-((7-hydroxy-4-methyl-2-oxo-2H-chromen-8-yl)methylene)indolin-2-one derivatives were synthesized using diverse 5-substituted oxindoles and 7-hydroxy-4-methyl-
- Nagarsenkar, Atulya,Guntuku, Lalita,Prajapti, Santosh Kumar,Guggilapu, Sravanthi Devi,Sonar, Rajkiran,Vegi, Ganga Modi Naidu,Babu, Bathini Nagendra
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p. 12604 - 12610
(2017/11/06)
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- Pyrroloquinoline Derivatives And Their Use As Protein Kinases Inhibitors
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The present invention relates to inhibitors of protein kinases of formula I: which can be used in the treatment of various diseases, notably cancer, inflammation or disorders of the central nervous system. It also relates to pharmaceutical compositions containing the compounds according to the invention and their use in therapy.
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Page/Page column 25
(2009/03/07)
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- Cycloalkyl - containing 5-acylindolinones, the preparation thereof and their use as medicaments
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The present invention relates to cycloalkyl-containing 5-acylindolinones of general formula wherein R1 to R3 are defined as in claims 1 to 6, the tautomers, the enantiomers, the diastereomers, the mixtures thereof and the salts thereof, which have valuable pharmacological properties, particularly an inhibiting effect on protein kinases, particularly an inhibiting effect on the activity of glycogen synthase kinase (GSK-3).
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Page/Page column 8
(2008/06/13)
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- NOVEL ARYL-CONTAINING 5-ACYLINDOLINONES, THE PRODUCTION THEREOF AND THEIR USE AS MEDICAMENTS
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The invention relates to aryl-containing 5-acylindolinones of general formula (I) in which R1 to R3 are defined as in Claims 1 to 7, the tautomers, enantiomers, diastereomers, mixtures and salts thereof, all of which having valuable
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Page/Page column 22
(2010/02/14)
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- Aryl-containing 5-acylindolinones, the preparation thereof and their use as medicaments
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The present invention relates to aryl-containing 5-acylindolinones of general formula wherein R1 to R3 are defined herein, the tautomers, the enantiomers, the diastereomers, the mixtures thereof and the salts thereof, which have valu
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Page/Page column 7
(2010/02/14)
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- NOVEL ALKYL-CONTAINING 5-ACYLINDOLINONES, THEIR PREPARATION AND THEIR USE AS PHARMACEUTICAL PRODUCTS
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The invention relates to alkyl-containing 5-acylindolinones of the general formula (I), where R1 to R3 are as defined in claim 1, and to tautomers, enantiomers, diastereomers, mixtures and salts thereof with valuable pharmacological
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Page/Page column 22
(2008/06/13)
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- NOVEL CYCLOALKYL-CONTAINING 5-ACYLINDOLINONES, THEIR PREPARATION AND THEIR USE AS PHARMACEUTICAL PRODUCTS
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The invention relates to cycloalkyl-containing 5-acylindolinones of the general formula (I), where R1 to R3 are as defined in claims 1 to 6, and to tautomers, enantiomers, diastereomers, mixtures and salts thereof with valuable pharmacological properties, more particularly an inhibitory effect on protein kinases, more particularly an inhibitory effect on the activity of glycogen synthase kinase (GSK-3).
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Page/Page column 22
(2008/06/13)
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- Alkyl-containing 5-acylindolinones, the preparation thereof and their use as medicaments
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The present invention relates to alkyl-containing 5-acylindolinones of general formula wherein R1 to R3 are defined herein, the tautomers, the enantiomers, the diastereomers, the mixtures thereof and the salts thereof, which have val
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Page/Page column 8-9
(2008/06/13)
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- Pyrrole substituted 2-indolinone protein kinase inhibitors
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The present invention relates to novel pyrrole substituted 2-indolinone compounds and physiologically acceptable salts and prodrugs thereof which modulate the activity of protein kinases and therefore are expected to be useful in the prevention and treatment of protein kinase related cellular disorders such as cancer.
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- 3-heteroarylidene-2-indolinone protein kinase inhibitors
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The present invention relates to novel 3-heteroarylidene-2-indolinone compounds and physiologically acceptable salts thereof which modulate the activity of protein kinases and therefore are expected to be useful in the prevention and treatment of protein kinase related cellular disorders such as cancer.
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- 3-(cycloalkanoheteroarylidenyl)-2-indolinone protein tyrosine kinase inhibitors
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The present invention relates to novel 3-(cycloalkano-heteroarylidenyl)-2-indolinone compounds and physiologically acceptable salts and prodrugs thereof which are expected to modulate the activity of protein tyrosine kinases and therefore to be useful in the prevention and treatment of protein tyrosine kinase related cellular disorders such as cancer.
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Page column 29
(2010/02/05)
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- Methods of modulating protein tyrosine kinase function with substituted indolinone compounds
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The invention relates to certain indolinone compounds, their method of synthesis, and a combinatorial library consisting of the indolinone compounds. The invention also relates to methods of modulating the function of protein kinases using indolinone compounds and methods of treating diseases by modulating the function of protein kinases and related signal transduction pathways.
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- Certain 5-alkyl-2-arylaminophenylacetic acids and derivatives
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Disclosed are the compounds of formula I wherein R is methyl or ethyl; R1is chloro or fluoro; R2is hydrogen or fluoro; R3is hydrogen, fluoro, chloro, methyl, ethyl, methoxy, ethoxy or hydroxy; R4is hydrogen or fluoro; and R5is chloro, fluoro, trifluoromethyl or methyl; and pharmaceutically acceptable salts thereof, as selective COX-2 cyclooxygenase inhibitors; and pharmaceutically acceptable prodrug esters thereof.
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- 3-(cycloalkanoheteroarylidenyl)-2- indolinone protein tyrosine kinase inhibitors
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The present invention relates to novel 3-(cycloalkanoheteroarylidenyl)-2-indolinone compounds and physiologically acceptable salts and prodrugs thereof which are expected to modulate the activity of protein tyrosine kinases and therefore to be useful in the prevention and treatment of protein tyrosine kinase related cellular disorders such as cancer.
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- 1,3-disubstituted 2-oxindoles as analgesic and anti-inflammatory agents
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Certain 2-oxindole-1-carboxamide compounds having an acyl substituent at the 3-position, and also on the carboxamide nitrogen atom, are inhibitors of the cyclooxygenase (CO) and lipoxygenase (LO) enzymes, and are useful as analgesic agents and anti-inflammatory agents in mammalian subjects. These 2-oxindole-1-carboxamide compounds are of particular value for acute administration for ameliorating pain in human patients recovering from surgery or trauma, and also for chronic administration to human subjects for alleviating the symptoms of chronic diseases, such as rheumatoid arthritis and osteoarthritis. Certain 2-oxindole-1-carboxamide compounds unsubstituted at C-3, but having an acyl substituent on the carboxamide nitrogen atom, are useful as intermediates to the aforementioned analgesic and anti-inflammatory agents.
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- Process for making 2-oxindole-1-carboxamides and intermediates therefor
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Preparation of 2-oxindole-1-carboxamides by reaction of 2-oxindoles with chlorosulfonyl isocyanate to produce novel N-chlorosulfonyl-2-oxindole-1-carboxamides which are then hydrolyzed to 2-oxindole-1-carboxamides useful as intermediates for analgesic and antiinflammatory agents.
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- Intermediates for 1,3-disubstituted 2-oxindoles as analgesic and antiinflammatory agents
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Certain 2-oxindole-1-carboxamide compounds having an acyl substituent at the 3-position, and also on the carboxamide nitrogen atom, are inhibitors of the cyclooxygenase (CO) and lipoxygenase (LO) enzymes, and are useful as analgesic agents and anti-inflammatory agents in mammalian subjects. Certain 2-oxindole compounds unsubstituted at the 1-position but having an acyl substituent at C-3 of the formula STR1 and the base salts thereof, wherein X is hydrogen, 5-fluoro, 5-chloro or 5-trifluoromethyl; Y is hydrogen, 6-fluoro, 6-chloro or 6-trifluoromethyl; and R1 is benzyl, furyl, thienyl or thienylmethyl; provided that when X and Y are both hydrogen, R1 is not benzyl are useful as intermediates to the aforementioned analgesic and anti-inflammatory agents.
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- 1-acylcarbamoyloxindole-3-carboxamides as antiinflammatory agents
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1-Acylcarbamoyloxindole-3-carboxamides as antiinflammatory agents prepared by reaction of the 1-acylcarbamoyloxindole with an isocyanate in the presence of a basic reagent.
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- Analgesic and antiinflammatory 1,3-diacyl-2-oxindole compounds
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Certain novel 2-oxindole compounds, having an acyl substituent at both the 1-position and the 3-position, are inhibitors of the cyclooxygenase (CO) and lipoxygenase (LO) enzymes, and are useful as analgesic agents and antiinflammatory agents in mammalian subjects. These 1,3-diacyl-2-oxindole compounds are of particular value for acute administration for ameliorating pain in human patients recovering from surgery or trauma, and also for chronic administration to human subjects for alleviating the symptoms of chronic diseases such as rheumatoid arthritis and osteoarthritis.
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- N,3-Disubstituted 2-oxindole-1-carboxamides as analgesic and antiinflammatory agents
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Certain 2-oxindole-1-carboxamide compounds having an acyl substituent at the 3-position, and also further substituted on the carboxamide nitrogen by an alkyl, cycloalkyl, phenyl or substituted phenyl group, are inhibitors of the cyclooxygenase (CO) and lipoxygenase (LO) enzymes, and are useful as analgesic and antiinflammatory agents in mammalian subjects. These 2-oxindole-1-carboxamide compounds are of particular value for ameliorating pain in human patients recovering from surgery or trauma, and alleviating the symptoms of chronic diseases, such as rheumatoid arthritis and osteoarthritis, in human subjects. Certain 2-oxindole-1-carboxamide compounds unsubstituted at C-3, but having a substituent on the carboxamide nitrogen, are useful as intermediates to the analgesic and antiinflammatory agents of the invention.
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- 3-Substituted 2-oxindole-1-carboxamides as analgesic and anti-inflammatory agents
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Certain new 2-oxindole-1-carboxamide compounds having an acyl substituent at the 3-position are inhibitors of the cyclooxygenase (CO) and lipoxygenase (LO) enzymes, and are useful as analgesic and anti-inflammatory agents in mammalian subjects. In particular, the compounds of the invention are useful for ameliorating or eliminating pain in human subjects recovering from surgery or trauma, and in alleviating the symptoms of chronic diseases, such as rheumatoid arthritis and osteoarthritis, in human subjects.
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