- Synthesis of substituted t-butyl 3-alkyloxindole-3-carboxylates from di-t-butyl (2-nitrophenyl)malonates
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Using a novel tandem reduction-cyclization, we synthesized t-butyl 3-alkyloxindole-3-carboxylates from the di-t-butyl 2-alkyl-2-(2-nitrophenyl)malonate. Introduction of an α-substituent to the di-t-butyl 2-(2-nitrophenyl)-malonates and addition of acid promoted reactivity. This methodology was successfully applied to gram-scale-synthesis of the t-butyl 3-methyloxindole-3-carboxylate 1 and 3-hydroxymethyl-3-methyloxindole 2 without silica gel column chromatography.
- Yamai, Yu-Suke,Tanaka, Akio,Yajima, Tatsuo,Ishida, Kyoji,Natsutani, Itaru,Uesato, Shinichi,Nagaoka, Yasuo,Sumiyoshi, Takaaki
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p. 192 - 210
(2019/04/27)
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- MUSCARINIC RECEPTOR AGONISTS, COMPOSITIONS, METHODS OF TREATMENT THEREOF, AND PROCESSES FOR PREPARATION THEREOF-176
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Compounds of Formula 1, or pharmaceutically acceptable salts thereof: wherein X, R1, R2, R3, R4, R5, n, m, and p are as defined in the specification as well as salts and pharmaceutical compositions including the compounds are prepared. They are useful in therapy, in particular in the management of pain.
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Page/Page column 90
(2009/09/08)
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- Synthesis and pharmacological characterization of novel inverse agonists acting on the viral-encoded chemokine receptor US28
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G-protein coupled receptors encoded by viruses represent an unexplored class of potential drug targets. In this study, we describe the synthesis and pharmacological characterization of the first class of inverse agonists acting on the HCMV-encoded receptor US28. It is shown that replacement of the 4-hydroxy group of lead compound 1 with a methylamine group results in a significant 6-fold increase in affinity. Interestingly, increasing the rigidity of the spacer by the introduction of a double bond also leads to a significant increase in binding affinity compared to 1. These novel inverse agonists serve as valuable tools to elucidate the role of constitutive signaling in the pathogenesis of viral infection and may have therapeutic potential as leads for new antiviral drugs.
- Hulshof, Janneke W.,Vischer, Henry F.,Verheij, Mark H.P.,Fratantoni, Silvina A.,Smit, Martine J.,de Esch, Iwan J.P.,Leurs, Rob
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p. 7213 - 7230
(2007/10/03)
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- AGONIST AND ANTAGONIST LIGANDS OF THE NOCICEPTIN RECEPTOR
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Novel piperidyl indolinone compounds are provided that are useful as agonist and antagonist ligands of the nociceptin receptor. The compounds are useful to treat a variety of disorders, and are particularly useful as analgesics.
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- A short and efficient synthesis of N-substituted indol-2-ones (oxindoles)
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A short and high yielding process has been developed for the synthesis of N-(4-piperidinyl)-indol-2-ones. This strategy also constitutes a general route to N-substituted indol-2-ones.
- Forbes, Ian T
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p. 6943 - 6945
(2007/10/03)
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