Molecular and crystal structure of indole derivatives fused with substituted bicyclo[3.3.1]nonane

Zefirova, O. N.; Potekhin, K. A.; Touchin, A. I.; Averina, N. V.; Baranova, T. Yu.; Зык, Н. В.; Зефиров, Н. С.

doi:10.1007/s11224-007-9174-x

Cited by 8 publications

(3 citation statements)

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“…He was one of pioneers in the application graphs for describing hydrogen bonded aggregates [41,45] (Fig. 3) and analysing crystal structure in that way [47]; some examples of this approach may be found in this issue [108,113]. The detailed classification of benzene...benzene contacts proposed in his works [74,77] (Fig.…”

Section: Organic Crystal Chemistrymentioning

confidence: 99%

Petr Markovich Zorky. Scientific life

Grineva

2007

Struct Chem

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Section: Organic Crystal Chemistrymentioning

confidence: 99%

Petr Markovich Zorky. Scientific life

Grineva

2007

Struct Chem

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“…Zefirova et al [208] report in the next article about molecular and crystal structure of 6-oxo-indolo[2,3-b]-bicyclo[3.3.1]non-2-ene oxime and 6-oxo-(5-methoxyindolo[2,3-b])-bicyclo[3.3.1]non-2-ene. The presence of the methoxy group in the second compound was found to lead to the changes in molecular packing in comparison with the structure of the second.…”

Section: Issuementioning

confidence: 99%

Interplay of thermochemistry and Structural Chemistry, the journal (volume 18, 2007) and the discipline

Ponikvar

Liebman

2008

Struct Chem

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In this study, we relate the contents of the journal Structural Chemistry for the calendar year 2007 and thermochemistry. The year's articles were briefly summarized and a thermochemical comment written to supplement them. Frequently questions were asked and future research was suggested.Keywords Structural Chemistry Á Thermochemistry Á Thermodynamics Á Enthalpy of formation Á Enthalpy of phase change Á Enthalpy of reaction As practiced disciplines, structural chemistry and thermochemistry are very often unrelated. In this study, these disciplines are linked as relations are explicitly made using the contents of the journal Structural Chemistry (Vol. 18) for the calendar year 2007 as a scaffold for our analysis, for our selected articles in the discipline of structural chemistry. These studies have been reviewed by us, where we give them a thermochemical flavor. While this commentary is most generally written in terms of brief summaries of literature papers involving enthalpies of formation and/or reaction, not uncommonly we raise questions and even suggest possible future research. We are not, however, going to give a thermochemical slant on book reviews, honorary dedications, and obituaries although these works will be cited in our text.As such, this article is a sequel to our earlier related reviews of Structural Chemistry for the calendar years 2000 through 2004 [1-5]. Reviews for 2005 and 2006 are currently being prepared. Issue 1In the first article in the first issue of Structural Chemistry for 2007, Hargittai [6] asserted that while research is currently usually carried out in big groups, the most important ideas, observations and discoveries still belong to individuals who have to bring down dogmas or open entirely new areas in science. This may bring solace to the thermochemical community in which research groups are generally small, and the number of new practitioners sadly few.In the past decade, the crystal engineering of multidimensional arrays and networks containing metal ions has achieved considerable progress because of the increased interest in the potential utility of these compounds as zeolite-like materials [7-11], catalysts [12], or magnetic materials [13][14][15]. The thermochemistry of these species is complicated by their inherent complexity: however, estimation approaches of their key thermochemical quantities are increasingly reliable [16]. In the second article of this issue, by Wang et al. [17], the versatility of malonate dianion as a ligand for the construction of extended networks with different topologies dependent on the coordination geometry of the metal ion was discussed. The synthesis and structure of a novel malonate-bridged copper(II) compound in which copper(II) ions have two different coordination environments in a novel three-dimensional (3D) network was described. Metal malonates have been studied from a

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“…Some compounds, including amide I [2], were studied by X-ray analysis [4]. In the present work we made an attempt to perform X-ray analysis of an analog of I containing a methoxy group in the indole fragment.…”

mentioning

confidence: 99%

Crystallographic study and molecular modeling on the oxidation product of N-[(8R)-2-methoxy-5,6,7,8,9,10-hexahydro-6,9-methanocyclohepta[b]indol-8-yl]acetamide

et al. 2012

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Crystallization of N- [(8R)-2-methoxy-5,6,7,8,9,10-hexahydro-6,9-methanocyclohepta[b]indol-8-yl]acetamide was accompanied by oxidation at the C 5a -C 10a bond with formation of N- [(5S)-10-methoxy-2,8-dioxo-1,2,3,4,5,6,7,8-octahydro-3,6-methano-1-benzazecin-5-yl]acetamide whose structure was determined by X-ray analysis. Docking of this compound into melatonin-binding pocket of MT 1A receptor was simulated by computer-assisted molecular modeling.While performing studies on conformationally rigid melatonin analogs, we synthesized a series of indole derivatives fused to bicyclic structures [1-3]. Some compounds, including amide I [2], were studied by X-ray analysis [4]. In the present work we made an attempt to perform X-ray analysis of an analog of I containing a methoxy group in the indole fragment. The structure of methoxy derivative II was unambiguously confirmed by NMR, IR, and mass spectra and elemental analysis [2]. However, during preparation of a single crystal of II for X-ray analysis by slow crystallization from a colorless solution in anhydrous CH 2 Cl 2 pale rose crystals separated. The X-ray diffraction data (Fig. 1) allowed us to identify this compound as N- [(5S)-10-methoxy-2,8-dioxo-1,2,3,4,5,6,7,8-octa-hydro-3,6-methano-1-benzazecin-5-yl]acetamide (III) which was formed as a result of oxidative cleavage of the double C 5a -C 10a bond in II (Scheme 1).

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Molecular and crystal structure of indole derivatives fused with substituted bicyclo[3.3.1]nonane

Cited by 8 publications

References 6 publications

Petr Markovich Zorky. Scientific life

Petr Markovich Zorky. Scientific life

Interplay of thermochemistry and Structural Chemistry, the journal (volume 18, 2007) and the discipline

Crystallographic study and molecular modeling on the oxidation product of N-[(8R)-2-methoxy-5,6,7,8,9,10-hexahydro-6,9-methanocyclohepta[b]indol-8-yl]acetamide

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