- Catalytic Direct Cyanomethylenation of C(sp3)–H Bonds via a One-Step Double C–C Bond Formation
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An elegant and catalytic procedure for the one-step cyanomethylenation of C(sp3)–H bonds adjacent to benzazoles and ketones is described herein using DMF as a C-1 unit and TMSCN as the cyanide source. The copper-mediated reaction between DMF an
- Bhadra, Sukalyan,Kumar, Jogendra,Singh, Anupam Kumar
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supporting information
p. 1512 - 1517
(2022/01/27)
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- A convenient synthesis of 4-(2-hydroxyethyl)indolin-2-one, a useful intermediate for the preparation of both dopamine receptor agonists and protein kinase inhibitors
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This paper describes a practical approach to the preparation of 4-(2-hydroxyethyl)indolin-2-one, a key intermediate in the synthesis of dopaminergic agonists such as ropinirole - a drug used in the treatment of Parkinson's disease and restless legs syndrome - and of two sets of protein kinase inhibitors. The sequence starts from commercially available 2-(2-methyl-3-nitrophenyl)acetic acid, which is converted in five steps into the desired target compound. This procedure offers a convenient alternative route to existing methodologies, given its milder reaction conditions, ease of implementation, and its overall yield (59 %).
- Matera, Carlo,Quadri, Marta,Pelucchi, Silvia,De Amici, Marco,Dallanoce, Clelia
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p. 1139 - 1144
(2014/06/24)
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- Synthesis of 4-N,N-dialkylaminoethyl-2-indolones as potential dopamine agonists
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A set of fourteen 4-ethyl>-2-indolone analogues of dopamine were synthesized in 15 steps and evaluated for their affinities towards the D2 receptor using sulpiride or spiperone as radioligands.Six analogues displayed D2 agonist activities comparable (Ki = 450 - 650 nM) to Ropinirole or SK and F 101468.The functionalized amino side chain introduced in the 4-position can be used to modulate the lipophlicity of the analogues without significantly affecting D2 activity. - Keywords: lactam; indolone; rigid dopamine analogue; D2 receptor binding
- Namil, A.,Benoit-Guyod, M.,Leclerc, G.
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p. 973 - 982
(2007/10/03)
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- Syntheses and in Vitro Evaluation of 4-(2-Aminoethyl)-2(3H)-indolones and Related Compounds as Peripheral Prejunctional Dopamine Receptor Agonists
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A series of (β-aminoethyl)indolones and related compounds was synthesized and evaluated in vitro as peripheral prejunctional dopaminergic agonists in the field-stimulated isolated perfused rabbit ear artery. 4--7-hydroxy-2(3H)-indolone (26) was the most potent compound (ED50 = 2 +/- 0.3 nM) tested, while the related secondary amine 24 and the des-OH derivatives 28 and 34 were only slightly less potent. 4-Methoxy-benzeneethanamine and 2-methyl-3-nitrophenylacetic acid were employed as starting materials for the synthesis of the 4-(β-aminoethyl)indolones.The ring-opened 3-acylamino analogues 46 and 47 were prepared via nitration of the phenethylamine 43 derived from 4-methoxyphenylacetic acid.The inactive isomeric indolones 38, 39, and 41 were derived from 4-nitrobenzeneethanamine and from indolone-6-acetic acid (13).
- DeMarinis, Robert M.,Gallagher, Gregory,Hall, Ralph F.,Franz, Robert G.,Webster, Charles,et al.
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p. 939 - 947
(2007/10/02)
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- 4--2(3H)-indolone: A Prejunctional Dopamine Receptor Agonist
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4--2(3H)-indolone (1c) (SK and F 101468) is a potent and selective prejunctional dopamine receptor agonist.It caused a dose-related inhibition of the constrictor response to electrical stimulation in the isolated perfused rabbit ear artery (EC50 = 100 nM), and this response was antagonized by (S)-sulpiride (KB = 7 nM).Compound 1c did not stimulate or block dopamine-sensitive adenylate cyclase and did not produce stimulation of the central nervous system in rats.It was prepared from (2-methyl-3-nitrophenyl)acetic acid in a multistep sequence based on the Reissert indole synthesis.
- Gallagher, Gregory,Lavanchy, Patricia G.,Wilson, James W.,Hieble, J. Paul,DeMarinis, Robert M.
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p. 1533 - 1536
(2007/10/02)
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