- Tricyclic isoindolines by Heck cyclization
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A series of 4-formyl esters 8a-d was prepared by Michael addition of an enamine with ethyl acrylate. A subsequent condensation with 2-bromobenzylamines 3 gave rise to cyclic enamides 9aa-dd. In a Heck cyclization reaction tricyclic isoindoles 10aa-dd were formed in good yields.
- Satyanarayana, Gedu,Maier, Martin E.
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supporting information; experimental part
p. 1745 - 1749
(2012/03/10)
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- Synthesis of a unique isoindoline/tetrahydroisoquinoline-based tricyclic sultam library utilizing a Heck-aza-Michael strategy
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The synthesis of a unique isoindoline- and tetrahydroisoquinoline (THIQ)-containing tricyclic sultam library, utilizing a Heck-aza-Michael (HaM) strategy is reported. Both isoindoline and THIQ rings are installed through a Heck reaction on a vinylsulfonamide, followed by one-pot deprotection and intramolecular aza-Michael reaction. Subsequent cyclization with either paraformaldehyde condensation or 1,1′-carbonyldiimidazole coupling generates a variety of tricyclic sultams. Overall, a 160-member library of these sultams, together with their isoindolines/THIQ and secondary sulfonamides precursors, were constructed using this strategy.
- Zang, Qin,Javed, Salim,Porubsky, Patrick,Ullah, Farman,Neuenswander, Benjamin,Lushington, Gerald H.,Basha, Fatima Z.,Organ, Michael G.,Hanson, Paul R.
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body text
p. 211 - 217
(2012/05/19)
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- MACROCYCLIC COMPOUNDS AND THEIR USE AS KINASE INHIBITORS
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The present invention relates to macrocyclic compounds of Formula I: or pharmaceutically acceptable salts thereof or quaternary ammonium salts thereof wherein constituent members are provided hereinwith, as well as their compositions and methods of use, which are JAK/ALK inhibitors useful in the treatment of JAK/ALK-associated diseases including, for example, inflammatory and autoimmune disorders, as well as cancer.
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Page/Page column 75-76
(2010/08/07)
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- Intramolecular homolytic substitution of sulfinates and sulfinamides
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A general and efficient method for the synthesis of cyclic sulfi-nates and sulfinamides based on intra-molecular homolytic substitution (SHi) at the sulfur atom by aryl or alkyl radi-cals is described. Both alkyl and benzo-fused compounds can be accessed di-rectly from easily prepared acyclic pre-cursors. Enantiomerically enriched sulfur-based heterocycles were formed through an SHi process with inversion of configuration at the sulfur atom. Cyclization of prochiral radicals proceeded with varying stereochemical outcomes, depending on the size of the incoming radical. 2-Pyridyl and 2-qui-nolyl radicals led to biaryl compounds, which result from attack onto the ortho position of the arylsulfinate rather than a thiophilic substitution.
- Coulomb, Julien,Certal, Victor,Larraufie, Marie-Helene,Ollivier, Cyril,Corbet, Jean-Pierre,Mignani, Gerard,Fensterbank, Louis,Lacote, Emmanuel,Malacria, Max
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supporting information; experimental part
p. 10225 - 10232
(2010/04/05)
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- An efficient preparation of N-alkyl-2-benzazepine derivatives and investigation of their biological activity
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N-Alkyl-2-benzazepine derivatives are readily prepared through N-alkylation of secondary 2-benzazepines that are constructed via 7-endo selective cyclization of radical cyclization of N-boc-N-(2-bromo-5-methoxyphenylmethyl) methacrylamides. The structure
- Kamimura, Akio,So, Masahiro,Kuratani, Tomohiro,Matsuura, Kenji,Inui, Makoto
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scheme or table
p. 3193 - 3195
(2010/03/31)
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- Synthesis of polycyclic sultams by palladium-catalyzed intramolecular cyclization
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A practical and high-yielding method for the synthesis of new sultams from readily available sulfonamides, 1-naphthylamine, and 2-halobenzyl bromides is reported. A variety of tricyclic, tetracyclic, and pentacyclic sultams have been prepared via palladiumcatalyzed, ligand-free intramolecular cyclization. Detailed mechanistic studies of the reaction pathway are also described.
- Majumdar,Mondal, Shovan,De, Nirupam
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scheme or table
p. 3127 - 3135
(2009/12/27)
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- Synthesis of cyclic sulfonamides via Pd-catalyzed intramolecular coupling reaction: An expedient approach to polycyclic sultams
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A divergent synthetic approach to polycyclic sultams utilizing intramolecular ligand-free intramolecular coupling reaction is described. Georg Thieme Verlag Stuttgart.
- Majumdar,Mondal, Shovan,De, Nirupam
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scheme or table
p. 2851 - 2855
(2009/04/23)
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- Certain pyrazoline derivatives with kinase inhibitory activity
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The present invention provides certain pyrazoline compounds useful as inhibitors of protein kinases. The invention also provides pharmaceutical compositions and methods of using the compositions in the treatment of various diseases.
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Page/Page column 105
(2008/12/06)
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- CYCLIC COMPOUNDS CONTAINING ZINC BINDING GROUPS AS MATRIX METALLOPROTEINASE INHIBITORS
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This invention provides compounds defined by Formula I Z-L-R1-Q-D-(V1)m-R2 I or a pharmaceutically acceptable salt thereof, wherein Z, L, R1, Q, D, V1, m, and R2 are as defined in the specification. The invention also provides pharmaceutical compositions comprising a compound of Formula I, or a pharmaceutically acceptable salt thereof, as defined in the specification, together with a pharmaceutically acceptable carrier, diluent, or excipient. The invention also provides methods of inhibiting an MMP-13 enzyme in an animal, comprising administering to the animal a compound of Formula I, or a pharmaceutically acceptable salt thereof. The invention also provides methods of treating a disease mediated by an MMP-13 enzyme in a patient, comprising administering to the patient a compound of Formula I, or a pharmaceutically acceptable salt thereof, either alone or in a pharmaceutical composition. The invention also provides methods of treating diseases such as heart disease, multiple sclerosis, osteo- and rheumatoid arthritis, arthritis other than osteo- or rheumatoid arthritis, cardiac insufficiency, inflammatory bowel disease, heart failure, age-related macular degeneration, chronic obstructive pulmonary disease, asthma, periodontal diseases, psoriasis, atherosclerosis, and osteoporosis in a patient, comprising administering to the patient a compound of Formula I, or a pharmaceutically acceptable salt thereof, either alone or in a pharmaceutical composition. The invention also provides combinations, comprising a compound of Formula I, or a pharmaceutically acceptable salt thereof, together with another pharmaceutically active component as described in the specification.
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Page/Page column 235-236; 239
(2010/02/06)
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