- Br?nsted Acid-Promoted Cyclodimerization of Indolyl Ketones: Construction of Indole Fused-Oxabicyclo[3.3.1]nonane and -Cyclooctatetraene Ring Systems
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A Br?nsted acid-promoted cyclodimerization of C(3)-, C(2)-, or N(1)-substituted indole ketone derivatives is described. A wide range of structurally diverse bisindole fused-9-oxabicyclo[3.3.1]nonane and bisindole fused-cyclooctatetraene (COT) derivatives can be prepared in good to high yields with high efficiency.
- Zhao, Lang,Yan, Zhi-Hua,Tang, Shuai,Wei, Zhong-Lin,Liao, Wei-Wei
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supporting information
p. 166 - 171
(2021/01/09)
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- Chemospecific Cyclizations of α-Carbonyl Sulfoxonium Ylides on Aryls and Heteroaryls
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The functionalization of aryl and heteroaryls using α-carbonyl sulfoxonium ylides without the help of a directing group has remained so far a neglected area, despite the advantageous safety profile of sulfoxonium ylides. Described herein are the cyclizations of α-carbonyl sulfoxonium ylides onto benzenes, benzofurans and N-p-toluenesulfonyl indoles in the presence of a base in HFIP, whereas pyrroles and N-methyl indoles undergo cyclization in the presence of an iridium catalyst. Significantly, these two sets of conditions are chemospecific for each groups of substrates.
- Clare, Daniel,Dobson, Benjamin C.,Inglesby, Phillip A.,A?ssa, Christophe
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supporting information
p. 16198 - 16202
(2019/11/03)
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- Catalytic Tandem Friedel-Crafts Alkylation/C4-C3 Ring-Contraction Reaction: An Efficient Route for the Synthesis of Indolyl Cyclopropanecarbaldehydes and Ketones
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A general strategy for the synthesis of indolyl cyclopropanecarbaldehydes and ketones via a Br?nsted acid-catalyzed indole nucleophilic addition/ring-contraction reaction sequence has been exploited. The procedure leads to a wide panel of cyclopropyl carbonyl compounds in generally high yields with a broad substrate scope.
- Turnu, Francesca,Luridiana, Alberto,Cocco, Andrea,Porcu, Stefania,Frongia, Angelo,Sarais, Giorgia,Secci, Francesco
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supporting information
p. 7329 - 7332
(2019/10/02)
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- Novel hits for acetylcholinesterase inhibition derived by docking-based screening on ZINC database
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The inhibition of the enzyme acetylcholinesterase (AChE) increases the levels of the neurotransmitter acetylcholine and symptomatically improves the affected cognitive function. In the present study, we searched for novel AChE inhibitors by docking-based virtual screening of the standard lead-like set of ZINC database containing more than 6 million small molecules using GOLD software. The top 10 best-scored hits were tested in vitro for AChE affinity, neurotoxicity, GIT and BBB permeability. The main pharmacokinetic parameters like volume of distribution, free fraction in plasma, total clearance, and half-life were predicted by previously derived models. Nine of the compounds bind to the enzyme with affinities from 0.517 to 0.735 μM, eight of them are non-toxic. All hits permeate GIT and BBB and bind extensively to plasma proteins. Most of them are low-clearance compounds. In total, seven of the 10 hits are promising for further lead optimisation. These are structures with ZINC IDs: 00220177, 44455618, 66142300, 71804814, 72065926, 96007907, and 97159977.
- Doytchinova, Irini,Atanasova, Mariyana,Valkova, Iva,Stavrakov, Georgi,Philipova, Irena,Zhivkova, Zvetanka,Zheleva-Dimitrova, Dimitrina,Konstantinov, Spiro,Dimitrov, Ivan
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p. 768 - 776
(2018/04/23)
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- HETEROCYCLIC COMPOUNDS AS INHIBITORS OF LEUKOTRIENE PRODUCTION
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The present invention relates to compound of formula (I): or pharmaceutically acceptable salts thereof, wherein R1-R7, A and HET are as defined herein. The invention also relates to pharmaceutical compositions comprising these compounds, methods of using these compounds in the treatment of various diseases and disorders, processes for preparing these compounds and intermediates useful in these processes
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Paragraph 0165; 0166; 0167
(2013/08/14)
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- Indolyl and dihydroindolyl N-glycinamides as potent and in vivo active NPY5 antagonists
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A novel series of indolyl and dihydroindolyl glycinamides were identified as potent NPY5 antagonists with in vivo activity from screen hit 1. The dihydroindolyl glycinamide 10a significantly inhibits NPY5 agonist induced feeding at a dose of 0.1 mg/kg. The indolyl glycinamide 12c also inhibits NPY5 agonist induced feeding at a dose of 1 mg/kg. Both compounds 10a and 12c represent potential tools for further investigation into the biology of the NPY5 receptor.
- Wu, Lingyun,Lu, Kai,Packiarajan, Mathivanan,Jubian, Vrej,Chandrasena, Gamini,Wolinsky, Toni C.,Walker, Mary W.
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scheme or table
p. 2167 - 2171
(2012/04/18)
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- INDOLE-DERIVATIVE MODULATORS OF STEROID HORMONE NUCLEAR RECEPTORS
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The present invention provides a compound of formula I or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising an effective amount of a compound of Formula I in combination with a suitable carrier, diluent, or excipient, and methods for treating physiological disorders, particularly congestive heart disease, comprising administering to a patient in thereof an effective amount of a compound of Formula I.
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- 4-AMINOMETHYL-1-ARYL-CYCLOHEXYLAMINE DERIVATIVES
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The invention concerns 4-aminomethyl-1-aryl-cyclohexylamine derivatives, methods for producing same, medicines containing said compounds and the use of 4-aminomethyl-1-aryl-cyclohexylamine derivatives for producing medicines.
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- Heterocyclic compounds having anti-diabetic activity and their use
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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.
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- Pharmaceutical compounds
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A compound having pharmaceutical activity, of the formula STR1 in which A is hydrogen or --(CR1 R2)x R3 where x is 0 or 1 to 4, R1 and R2 are each hydrogen or C1-4 alkyl and Rsu
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- TOTAL SYNTHESIS AND STEREOCHEMICAL REASSIGNMENT OF THE INDOLE ALKALOID VINOXINE
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The first total synthesis of the indole alkaloid vinoxine and the reassignment of the relative configuration at carbon-16 in this alkaloid is reported.
- Bosch, Joan,Bennasar, M.-Lluisa,Zulaica, Ester,Feliz, Miguel
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p. 3119 - 3122
(2007/10/02)
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- INDOLE SYNTHESES UTILIZING o-METHYLPHENYL ISOCYANIDES.
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New indole synthesis starting with o-methylphenyl isocyanides such as o-tolyl, 2,4-xylyl, and 2,6-xylyl isocyanide is described. Treatment of o-tolyl isocyanide with LDA in diglyme at minus 78 degree C generated selectively o-(lithiomethyl)phenyl isocyanide in an almost quantitative yield, which on warming up to room temperature was cyclized to indole after aqueous workup. Similarly, 2,4-xylyl and 2,6-xylyl and 2,6-xylyl isocyanides were cyclized to 5-methylindole and 7-methylindole quantitatively. The o-(lithiomethyl)phenyl isocyanides reacted with electrophiles such as alkyl halides and alkylene oxides to give o-alkylphenyl isocyanides, which were cyclized via the lithiation at the orthobenzylic carbon to afford 3-substituted indoles.
- Ito,Kobayashi,Seko,Saegusa
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- Reactivity of a tetrahedral Intermediate in Hydrolysis of N-Acetylpyrrole
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Base hydrolysis of N-acetylpyrrole (1a) involves formation of an anionic tetrahedral intermediate (2a).The equilibrium constant between these two species can be estimated by extrapolation based on the equilibrium constants for hydration of N-trichloroacetyl and N-trifluoroacetylpyrrole and the estimated pKa for deprotonation of the hydrates of these compounds.Inductive effects upon hydration and deprotonation of the hydrates were estimated by analogy with inductive effects upon the equilibrium reactions of chloral and acetaldehyde.The free energies of activation for formation and return of 2a are approximately 16 and 12.5 Kcal mole-1 respectively and for conversion of 2a to products 11 Kcal mole-1 in aqueous 1M OH-.
- Cipiciani, Antonio,Savelli, Gianfranco,Bunton, Clifford A.
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p. 975 - 976
(2007/10/02)
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- Etude spectroscopique (IR, RMN1H, masse) comparee des acides indolyl-1 acetique (AIA-1) indolyl-2 acetique (AIA-2) et indolyl-3 acetique (AIA-3) et de leurs esters methyliques (masse)
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Spectroscopic study (i.r., PMR) of 1-indolyl, 2-indolyl and 3-indolyl acetic acids points out structural differences.Conventional mass spectra of the three acids or their methyl esters are very similar.Use of the MIKE and CID-MIKE techniques on the molecular ion allows an easy discrimination of each methylic ester of the three acids.
- Vebrel, Joel,Laude, Bernard,Seguin, Alain,Dubouchet, Jacques
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p. 887 - 894
(2007/10/02)
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