Cubane derivatives

Erëmenko, L. T.; Романова, Л. Б.; Ivanova, M. E.; Malygina, V. S.; Barinova, L. S.; Lagodzinskaya, G. V.; Лодыгина, В. П.; Еременко, И. Л.; Александров, Г. Г.

doi:10.1007/s11172-007-0215-9

Cited by 7 publications

(9 citation statements)

References 6 publications

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“…Previously, 5, 6 it has been shown that the reduction of dimethyl cubane 1,4 dicarboxylate (1a) and methyl 4 bromocubane 1 carboxylate (2) afforded 1,4 bis (hydroxymethyl)cubane (3) and 4 bromo 1 hydroxy methylcubane (4). In the present work, 1,4 bis(nitroxy methyl)cubane (5) and 4 bromo 1 nitroxymethylcubane (6) (Scheme 1) were synthesized for the first time and characterized.…”

Section: Methodsmentioning

confidence: 69%

“…It is known that cubane derivatives also show rather high anti ischemic activity. 3, 4 With the aim of search for new anti ischemic drugs, we performed the synthesis of nitroesters of the cubane series.…”

Section: Methodsmentioning

confidence: 99%

“…The anti ischemic activity of the nitroxy ethylamide group has been demonstrated by us previ ously. 3, 4 The reduction of 4 methoxycarbonylcubane 1 car boxylic acid (1b) with sodium borohydride led to 4 hydroxy methylcubane 1 carboxylic acid (7) in 88-90% yield, the nitration of that resulted in 4 nitroxymethylcubane 1 carboxylic acid (8) (Scheme 2). The choice of a nitra tion system and reaction conditions was problematic due to intermolecular hydrogen bonds in compound 7 caused by the presence of the carboxylic groups.…”

Section: Methodsmentioning

confidence: 99%

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Cubane derivatives 10. Synthesis and molecular structures of nitroxymethylcubanes

et al. 2010

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The reactions of hydroxymethylcubanes with nitric acid result in the respective nitroxy methylcubanes.The search for the drugs to treat cardiovascular and oncological diseases is currently highly topical. The prepa ration of new polyfunctional compounds, study of their structures and properties will allow expansion of the spec trum of exogenous NO donors as potential drugs.Nitrates (or nitroesters) are a well known class of or ganic substances the pharmacological activity of which is determined by their metabolism with NO liberation (see Ref. 2). They include such compounds as Nitroglycerin, Nitrosorbide, Erinite, and others, which are commonly * For Part 9, see Ref. 1. † Deceased. Scheme 1used to treat ischemic cardiovascular diseases, for ex ample, stenocardia. It is known that cubane derivatives also show rather high anti ischemic activity. 3,4With the aim of search for new anti ischemic drugs, we performed the synthesis of nitroesters of the cubane series.Previously, 5,6 it has been shown that the reduction of dimethyl cubane 1,4 dicarboxylate (1a) and methyl 4 bromocubane 1 carboxylate (2) afforded 1,4 bis (hydroxymethyl)cubane (3) and 4 bromo 1 hydroxy methylcubane (4). In the present work, 1,4 bis(nitroxy methyl)cubane (5) and 4 bromo 1 nitroxymethylcubane

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Section: Methodsmentioning

confidence: 69%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Cubane derivatives 10. Synthesis and molecular structures of nitroxymethylcubanes

et al. 2010

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“…Further, it was also found that 1(9)-homocubenes (153) rearrange to 9-homocubylidenes (156). This type of rearrangement of an olefin to a carbene is extraordinarily rare.…”

Section: Iodocubanesmentioning

confidence: 99%

“…The study found that structure 195 was most active in aorta relaxation and calcium channel blocking, even more active than nicorandil. 156 Nicorandil is used as an antiangina medication which is comprised of a linked nitrate and K+ATP channel agonist, and it is approved for use in Europe, Australia, and the United Kingdom.…”

Section: Cubane In Medicinementioning

confidence: 99%

Cubane: 50 Years Later

et al. 2015

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Not Your Usual Bioisostere: Solid State Study of 3D Interactions in Cubanes

Flanagan

Bernhard

Plunkett

2019

Chemistry A European J

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Previous studies by Desiraju and co‐workers have implicated the acidic hydrogen atoms of cubane as a support network for hydrogen bonding groups. Herein we report a detailed structural analysis of all currently available 1,4‐disubstituted cubane structures with an emphasis on how the cubane scaffold interacts in its solid‐state environment. In this regard, the interactions between the cubane hydrogen atoms and acids, ester, halogens, ethynyl, nitrogenous groups, and other cubane scaffolds were cataloged. The goal of this study was to investigate the potential of cubane as a substitute for phenyl. This could be achieved by analyzing all contacts that are directed by the cubane hydrogen atoms in the X‐ray crystal structures. As a result, we have established several new cubane interaction profiles, such as the catemer formation seen in esters, the preferences of halogen–hydrogen contacts over direct halogen bonding, and the stabilizing effects caused by the cubane hydrogen atoms interacting with ethynyl groups. These interaction profiles can then be used as a guide for designing cubane bioisosteres of known materials and drugs containing phenyl moieties.

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Cubane derivatives

Cited by 7 publications

References 6 publications

Cubane derivatives 10. Synthesis and molecular structures of nitroxymethylcubanes

Cubane derivatives 10. Synthesis and molecular structures of nitroxymethylcubanes

Cubane: 50 Years Later

Not Your Usual Bioisostere: Solid State Study of 3D Interactions in Cubanes

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