Synthesis and biological activity of 1-aryl-2-oxa-5-aza-5r1-6-oxocyclooctano[6,7-b]indoles

Vlasova, M. I.; Kogan, N. A.; Lesiovskaya, E. E.; Pastushenkov, L. V.

doi:10.1007/bf00773075

Cited by 6 publications

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“…1 N-(2-Hydroxyethyl)-1H-indole-2-carboxamide (11f). 34 The title compound was synthesized according to general procedure A using ethanolamine. After stirring for two nights, the mixture was diluted with water.…”

Section: ■ Conclusionmentioning

confidence: 99%

“…13 C NMR (CDCl 3 ) δ 156. 1, 79.3, 69.7, 39.8, 37.4, 28.5, 26.5, 26.3. tert-Butyl (4-(7-Cyano-3,4-dihydroisoquinolin-2(1H)-yl)butyl)carbamate (34). To a solution of 4-((tert-butoxycarbonyl)amino)butyl methanesulfonate (33) (202 mg, 0.76 mmol) in DCM (15 mL) was added 7-cyano-1,2,3,4-tetrahydroisoquinoline (131 mg, 0.83 mmol, 1.1 equiv), followed by N,N-diisopropylethylamine (156 μL, 0.91 mmol, 1.2 equiv).…”

Section: ■ Conclusionmentioning

confidence: 99%

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Discovery of a Novel Class of Negative Allosteric Modulator of the Dopamine D₂ Receptor Through Fragmentation of a Bitopic Ligand

et al. 2015

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(2015) Discovery of a novel class of negative allosteric modulator of the dopamine D2 receptor through fragmentation of a bitopic ligand. Journal of Medicinal Chemistry, 58 (17). pp. 6819-6843. ISSN 0022-2623 Access from the University of Nottingham repository: http://eprints.nottingham.ac.uk/30315/1/jm-2015-005859.R2%20-%20JMC %2058%2817%29%202015%206819.pdf Copyright and reuse:The Nottingham ePrints service makes this work by researchers of the University of Nottingham available open access under the following conditions. This article is made available under the University of Nottingham End User licence and may be reused according to the conditions of the licence. For more details see: http://eprints.nottingham.ac.uk/end_user_agreement.pdf A note on versions:The version presented here may differ from the published version or from the version of record. If you wish to cite this item you are advised to consult the publisher's version. Please see the repository url above for details on accessing the published version and note that access may require a subscription. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 ABSTRACT Recently, we have demonstrated that N- ((trans)-4-(2-(7-cyano-3,4-dihydroisoquinolin-2(1H) 'allosteric lead', we designed and synthesised an extensive fragment library to generate novel SAR and identify N-butyl-1H-indole-2-carboxamide (11d), which displayed both increased negative cooperativity and affinity for the D 2 R. These data illustrate that fragmentation of extended compounds can expose fragments with purely allosteric pharmacology.

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Section: ■ Conclusionmentioning

confidence: 99%

Section: ■ Conclusionmentioning

confidence: 99%

Discovery of a Novel Class of Negative Allosteric Modulator of the Dopamine D₂ Receptor Through Fragmentation of a Bitopic Ligand

et al. 2015

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“…Several studies have reported that these compounds have antiproliferative capabilities in cancer cells , and moreover a crucial antiviral action . In particular, the derivatives of indole-2-carboxylic acid and indole-3-carboxylic acid are widely used in the treatment of various diseases, having these compounds anticancer, antifungal and insecticide, anti-arrhythmic properties, among others. (2 S )-2-Amino-3-(1 H -indol-3-yl)propanoic acid, known as tryptophan, is an important example of a biologically active molecule, its metabolism being associated with various physiological functions. , In addition to providing the structural backbone of proteins, tryptophan, an essential amino acid, functions as a precursor for serotonin, an important neurotransmitter widely used in psychiatry and neurology. , All these relevant practical applications of the indole derivatives lead the scientific community keeping focused in the study of their physical-chemical properties.…”

Section: Introductionmentioning

confidence: 99%

“…Several studies have reported that these compounds have antiproliferative capabilities in cancer cells 3,4 and moreover a crucial antiviral action. 5 In particular, the derivatives of indole-2-carboxylic acid and indole-3-carboxylic acid are widely used in the treatment of various diseases, having these compounds anticancer, 6 antifungal 7 and insecticide, 8 anti-arrhythmic 9 properties, among others. (2S)-2-Amino-3-(1H-indol-3-yl)propanoic acid, known as tryptophan, is an important example of a biologically active molecule, its metabolism being associated with various physiological functions.…”

Section: Introductionmentioning

confidence: 99%

Energetic Effect of the Carboxylic Acid Functional Group in Indole Derivatives

et al. 2017

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The standard molar enthalpy of formation, in the gaseous phase, at T = 298.15 K, was calculated by combining, for each compound, the standard molar enthalpy of formation, in the crystalline phase, and the standard molar enthalpy of sublimation, yielding -(222.2 ± 3.5) kJ·mol and -(234.1 ± 2.1) kJ·mol for indole-3-carboxylic acid and 1-methylindole-3-carboxylic acid, respectively. Computational studies, at the G3(MP2) composite level, were conducted for indole-3-carboxylic acid and 1-methylindole-3-carboxylic acid as a complement of the experimental work, and they were also extended to the remaining isomers, indole-2-carboxylic acid, 1-methylindole-2-carboxylic acid, 3-methylindole-2-carboxylic acid, and 2-methylindole-3-carboxylic acid, to provide reliable estimates of the corresponding thermochemical parameters. The agreement of the estimates of the standard gas-phase enthalpy of formation so obtained, indole-2-carboxylic acid -(223.6 ± 0.8) kJ·mol, 1-methylindole-2-carboxylic acid -(223.7 ± 0.8) kJ·mol, 3-methylindole-2-carboxylic acid -(251.6 ± 1.0) kJ·mol, indole-3-carboxylic acid -(227.1 ± 1.1) kJ·mol, 1-methylindole-3-carboxylic acid -(238.0 ± 1.0) kJ·mol, and 2-methylindole-3-carboxylic acid -(267.2 ± 1.0) kJ·mol, with the available experimental data gives us additional confidence for the situations not studied experimentally. The enthalpic effect resulting from the entrance of the carboxyl group into the indole ring was discussed, and an enthalpic stabilization was found for indole and pyrrole derivatives when compared with other similar systems.

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“…Mp 170-172 o C lit. 165-167 ºC(Vlasova et al 1992). 1 H NMR (400 MHz, CD 3 OD), δ: 7.63 (d, J = 8.0 Hz, H-4), 7.48 (d, J = 8.0 Hz, H-7), 7.23 (brt, J = 7.8 Hz, H-6), 7.06-7.10 (m, H-3, H-5), 3.76 (t, J = 5.8 Hz, H-2'), 3.56 (t, J = 5.8 Hz, H-1'); 13 C NMR(100 MHz, CD 3 OD), δ: 164.53 (C=O), 138.34 (C-7a), 132.23 (C-2), 129.04 (C-3a), 125.06 (C6), 122.76 (C-4), 121.18 (C-5), 113.06 (C-7), 104.50 (C--3), 61.18 (C2'), 43.17 (C-1'); ESI-MS: m/z 203.0794 ([M-H] -) (calc.…”

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Acetylcholinesterase inhibition and antimicrobial activity of hydroxyl amides synthesized from natural products derivatives

Boaventura

Xavier

Vieira

et al. 2018

An. Acad. Bras. Ciênc.

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Thirteen natural products derivatives of hydroxyl amide class, three described for the first time, were synthesized by reaction of three indole acids and 3,4,5-trimethoxybenzoic acid with six different amino alcohols in the presence of triphenylphosphine and N-bromosuccinimide. The derivatives were tested against the Gram (+) bacteria Staphylococcus aureus and Bacillus cereus, Gram (-) Pseudomonas aeruginosa and Escherichia coli, besides the yeast Candida albicans. One of the compounds (7) was selectively active against C. albicans (91.3 ± 0.49% inhibition) showing a great potential as a new drug lead, since it was more active than the positive control, miconazole (88.7 ± 2.41% inhibition). Regarding bacterial inhibition, compounds demonstrated mild activity, but inhibition of compounds 9, 10 and 13 towards E. coli is of interest since it is difficult to find drugs selectively active against Gram (-) bacteria. Most of the compounds were very active in the acetylcholinesterase inhibition assay. Compound 7 was again the most active (93.2 ± 4.47%), being more potent than the control galantamine (90.3 ± 0.45%). The most active gallic acid derivatives, compounds 3, 7 and 8 have in common, besides gallic acid skeleton, a (CH2)2OH group, which may be one of the structural requirements for AChE inhibition.

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Synthesis and biological activity of 1-aryl-2-oxa-5-aza-5r1-6-oxocyclooctano[6,7-b]indoles

Cited by 6 publications

References 0 publications

Discovery of a Novel Class of Negative Allosteric Modulator of the Dopamine D₂ Receptor Through Fragmentation of a Bitopic Ligand

Discovery of a Novel Class of Negative Allosteric Modulator of the Dopamine D₂ Receptor Through Fragmentation of a Bitopic Ligand

Energetic Effect of the Carboxylic Acid Functional Group in Indole Derivatives

Acetylcholinesterase inhibition and antimicrobial activity of hydroxyl amides synthesized from natural products derivatives

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Synthesis and biological activity of 1-aryl-2-oxa-5-aza-5r1-6-oxocyclooctano[6,7-b]indoles

Cited by 6 publications

References 0 publications

Discovery of a Novel Class of Negative Allosteric Modulator of the Dopamine D2 Receptor Through Fragmentation of a Bitopic Ligand

Discovery of a Novel Class of Negative Allosteric Modulator of the Dopamine D2 Receptor Through Fragmentation of a Bitopic Ligand

Energetic Effect of the Carboxylic Acid Functional Group in Indole Derivatives

Acetylcholinesterase inhibition and antimicrobial activity of hydroxyl amides synthesized from natural products derivatives

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Discovery of a Novel Class of Negative Allosteric Modulator of the Dopamine D₂ Receptor Through Fragmentation of a Bitopic Ligand

Discovery of a Novel Class of Negative Allosteric Modulator of the Dopamine D₂ Receptor Through Fragmentation of a Bitopic Ligand