50501-07-0Relevant articles and documents
Organo-Photoredox Catalyzed Oxidative Dehydrogenation of N-Heterocycles
Sahoo, Manoj K.,Jaiswal, Garima,Rana, Jagannath,Balaraman, Ekambaram
supporting information, p. 14167 - 14172 (2017/10/16)
We report here for the first time the catalytic oxidative dehydrogenation of N-heterocycles by a visible-light organo-photoredox catalyst with low catalyst loading (0.1–1 mol %). The reaction proceeds efficiently under base- and additive-free conditions with ambient air at room temperature. The utility of this benign approach is demonstrated by the synthesis of various pharmaceutically relevant N-heteroarenes such as quinoline, quinoxaline, quinazoline, acridine, and indole.
Cardioselective anti-ischemic ATP-sensitive potassium channel (KATP) openers: Benzopyranyl indoline and indole analogues
Lee, Sunkyung,Yi, Kyu Yang,Kim, Soo-Kyung,Suh, Jeehee,Kim, Nak Jeong,Yoo, Sung-Eun,Lee, Byung Ho,Seo, Ho Won,Kim, Sun-Ok,Lim, Hong
, p. 459 - 471 (2007/10/03)
This paper describes the design, syntheses, and biological evaluations of novel ATP-sensitive potassium channel (KATP) openers, benzopyranyl indoline and indole derivatives. Among those, two enantiomers of indoline-2-carboxylic ethyl esters (14, 18) showed the best cardioprotective activities both in vitro and in vivo, while their vasorelaxation potencies were very low (concentration for 50% inhibition of vasorelaxation >30 μM). The cardioprotective effect of 14 was completely reversed by 5-hydroxydecanoate, a selective mitochondrial KATP blocker, indicating its provable protective mechanism through the mitochondrial KATP opening. In addition, we performed conformational analyses using 2D-NMR, X-ray crystallography and molecular modeling to study the structure-activity relationships in this series of compounds.
Regiospecific functionalization of indole-2-carboxylates and diastereoselective preparation of the corresponding indolines
Collot, Valerie,Schmitt, Martine,Marwah, Padma,Bourguignon, Jean-Jacques
, p. 2823 - 2847 (2007/10/03)
The N-acyl derivatives of 3-substituted indole-2-carboxylates prepared through several routes were submitted to catalytic hydrogenation affording either cis- or trans-indoline diastereomers after quantitative C-2 epimerization.
Heterocyclic compounds having anti-diabetic activity and their use
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, (2008/06/13)
Compounds of formula (I): STR1 [wherein: X represents an unsubstituted or substituted indolyl, indolinyl, azaindolyl, azaindolinyl, imidazopyridyl or imidazopyrimidinyl group; Y represents an oxygen or sulfur atom; Z represents a 2,4-dioxothiazolidin-5-ylidenylmethyl, 2,4-dioxothiazolidin-5-ylmethyl, 2,4-dioxooxazolidin-5-ylmethyl, 3,5-dioxooxadiazolidin-2-ylmethyl or N-hydroxyureidomethyl group; R represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a hydroxy group, a nitro group, an aralkyl group or a unsubstituted or substituted amino group; and m is an integer of from 1 to 5] have hypoglycemic and anti-diabetic activities.
Synthesis of 3-phenylindoline-2-carboxamides as semi-rigid phenylalanine mimetics
Collot, Valerie,Schmitt, Martine,Marwah, Ashok K.,Norberg, Bernadette,Bourguignon, Jean-Jacques
, p. 8033 - 8036 (2007/10/03)
Regioselective catalytic hydrogenation of N-acyl 3-phenylindole-2-carboxylates is the key step for tile preparation of cis and trans ndoline-2-carboxamides which can be considered as phenylalanine semi-rigid derivatives.
Process for the industrial synthesis of perindopril
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, (2008/06/13)
Process for the industrial synthesis of perindopril, in which (2S,3aS,7aS)-2-carboxyperhydroindole is condensed with N-[(S)-1-carbethoxybutyl]-(S)-alanine after protection of the carboxyl group, the product resulting from the condensation being then subjected to deprotection of the carboxyl carried by the heterocyclic ring. The (2S,3aS,7aS)-2-carboxyperhydroindole and N-[(S)-1-carbethoxybutyl]-(S)-alanine are themselves obtained in excellent conditions from 2-carboxyindole and from L-alanine respectively, both available on an industrial scale.
Alpha 2-adrenergic agonists/antagonists: the synthesis and structure-activity relationships of a series of indolin-2-yl and tetrahydroquinolin-2-yl imidazolines.
Hlasta,Luttinger,Perrone,Silbernagel,Ward,Haubrich
, p. 1555 - 1562 (2007/10/02)
The synthesis and alpha 2-adrenergic activity of a series of indolin-2-yl and tetrahydroquinolin-2-yl imidazolines are described. The indolin-2-yl imidazoline 4b was found to possess potent alpha 2-adrenergic agonist and antagonist activity. The modification of the substituents on the indoline ring of 4b has led to the separation of these activities. Substitution on the aromatic ring of 4b with halogen or increasing the size of the N-alkyl substituent of 4b gave alpha 2-adrenergic antagonists without agonist activity. The N-allylindoline 4d is more potent than idazoxan in vitro and is equipotent in vivo, but is less receptor selective (alpha 2 vs. alpha 1) than idazoxan. The cis-1,3-dimethylindolin-2-yl imidazoline 6a is an alpha 2-adrenergic agonist equal in potency to clonidine in vitro, while the trans-1,3-dimethylindolin-2-yl imidazoline 6b is a moderately potent alpha 2-adrenergic antagonist.
