Synthesis of 1-aryltetrahydroisoquinoline alkaloids and their analogs

Zhurakulov, Sh. N.; Виноградова, В. И.; Левкович, М. Г.

doi:10.1007/s10600-013-0507-2

Cited by 13 publications

(8 citation statements)

References 7 publications

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“…In the first synthesis of F-29, described in detail in the article by the authors [4], the starting compound was piperanal (1), which in 2 stages gave the target intermediate product homopiperanylamine (2).…”

Section: Materials and Methods Of Researchmentioning

confidence: 99%

Pharmacological Activity Of The Possessing New Atypical Neuroleptics 1-Phenyltetrahydroisoquinoline Structure

Sanoev¹,

Mirzaev²

2020

TAJMSPR

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The first synthesized derivative of (3¢,4¢-methylenedioxyphenyl)-6,7-methylenedioxy-1,2,3,4tetrahydroquinoline, conventionally designated F-29, showed neuroleptic properties-they have hypothermic, cataleptogenic, less pronounced suppression of motor activity, lack of central αadreno-and M-anticholinergic action and less toxic in severity comparable to the activity of a more close analogue of the neuroleptic haloperidol, which has motor and autonomic disorders [1], which F-29 lacks.

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Section: Materials and Methods Of Researchmentioning

confidence: 99%

Pharmacological Activity Of The Possessing New Atypical Neuroleptics 1-Phenyltetrahydroisoquinoline Structure

Sanoev¹,

Mirzaev²

2020

TAJMSPR

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“…Cylinder radii are proportional to the corresponding energy; a scale factor of 80 and a cut-off value of 10 kJ mol À1 have been used. detailed report on the synthesis of (1) and its characterization by 1 H NMR is available in Zhurakulov et al (2017). Crystals suitable for X-ray diffraction were obtained from a methanol solution by slow evaporation of the solvent at room temperature.…”

Section: Synthesis and Crystallizationmentioning

confidence: 99%

Crystal structure, Hirshfeld surface analysis and energy framework study of 6-formyl-7,8,9,11-tetrahydro-5H-pyrido[2,1-b]quinazolin-11-one

et al. 2021

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At 100 K, the title compound, C13H12N2O2, crystallizes in the orthorhombic space group Pna21 with two very similar molecules in the asymmetric unit. An intramolecular N—H...O hydrogen bond leads to an S(6) graph-set motif in each of the molecules. Intermolecular π–π stacking and C=O...π interactions involving the aldehyde O atoms link molecules into stacks parallel to [100]. A Hirshfeld surface analysis indicates that the most important contributions to the crystal packing stem from H...H (49.4%) and H...O/O...H (21.5%) interactions. Energy framework calculations reveal a significant contribution of dispersion energy. The crystal studied was refined as a two-component inversion twin.

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“…Over the years the synthetic interest in the quest for new isoquinoline derivatives has not declined (Bentley, 2006;Zhurakulov et al, 2013Zhurakulov et al, , 2014Zhurakulov et al, , 2015, because even minor changes in the molecular geometry may lead to improved therapeutic effects. Both moieties mentioned above, a quina-zoline and an isoquinoline, have been successfully connected by a methylidene bridge (Elmuradov et al, 1998(Elmuradov et al, , 2008Turdibayev et al, 2011;Zhurakulov et al, 2015).…”

Section: Chemical Contextmentioning

confidence: 99%

Stereochemistry of the methylidene-bridged quinazoline-isoquinoline alkaloid 3-{[6,7-dimethoxy-1-(4-nitrophenyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]methylidene}-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-one methanol monosolvate

et al. 2020

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Two potentially bioactive fragments, namely a tricyclic quinazoline derivative with an exocyclic alkene moiety and a substituted isoquinoline, are coupled to give 3-{[6,7-dimethoxy-1-(4-nitrophenyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]methylidene}-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-one. The target product crystallizes as a methanol solvate, C29H26N4O5·CH4O, and is E configured. The alternative Z isomer would necessarily imply either considerable twist about the central double bond or very unfavourable intramolecular contacts between sterically more demanding substituents. The main residue and the co-crystallized solvent molecule aggregate to discrete pairs via a classical O—H...O hydrogen bond with a distance of 2.8581 (7) Å between the methanol OH donor and the quinazolinone O=C acceptor.

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Synthesis of 1-aryltetrahydroisoquinoline alkaloids and their analogs

Cited by 13 publications

References 7 publications

Pharmacological Activity Of The Possessing New Atypical Neuroleptics 1-Phenyltetrahydroisoquinoline Structure

Pharmacological Activity Of The Possessing New Atypical Neuroleptics 1-Phenyltetrahydroisoquinoline Structure

Crystal structure, Hirshfeld surface analysis and energy framework study of 6-formyl-7,8,9,11-tetrahydro-5H-pyrido[2,1-b]quinazolin-11-one

Stereochemistry of the methylidene-bridged quinazoline-isoquinoline alkaloid 3-{[6,7-dimethoxy-1-(4-nitrophenyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]methylidene}-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-one methanol monosolvate

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