Extension and revision of the von Baeyer system for naming polycyclic compounds (including bicyclic compounds)

Moss, G. P.

doi:10.1351/pac199971030513

Cited by 31 publications

(27 citation statements)

References 5 publications

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“…For compounds 38 – 41 , the integral of the H3’-signal of the least predominant isomer was set to 1.0. Systematic compound names for bicyclic nucleosides are given according to the von Baeyer nomenclature 21. High resolution mass spectroscopic (HRMS) measurements were performed on a proteomics optimized Q-TOF-2 (Micromass-Waters) using external calibration with polyalanine.…”

Section: Methodsmentioning

confidence: 99%

Structure−Activity Relationship of (N)-Methanocarba Phosphonate Analogues of 5′-AMP as Cardioprotective Agents Acting Through a Cardiac P2X Receptor

et al. 2010

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P2X receptor activation protects in heart failure models. MRS2339 3, a 2-chloro-AMP derivative containing a (N)-methanocarba (bicyclo[3.1.0]hexane) system, activates this cardioprotective channel. Michaelis-Arbuzov and Wittig reactions provided phosphonate analogues of 3, expected to be stable in vivo due to the C-P bond. After chronic administration via a mini-osmotic pump (Alzet), some analogues significantly increased intact heart contractile function in calsequestrinoverexpressing mice (genetic model of heart failure) compared to vehicle-infused mice (all inactive at the vasodilatory P2Y 1 receptor). Two phosphonates, (1'S,2'R,3'S,4'R,5'S)-4'-(6-amino-2-chloropurin-9-yl)-2',3'-(dihydroxy)-1'-(phosphonomethylene)-bicyclo[3.1.0]hexane 4 and its homologue 9, both 5'-saturated, containing a 2-Cl substitution, improved echocardiography-derived fractional shortening (20.25% and 19.26%, respectively, versus 13.78% in controls), while unsaturated 5'-extended phosphonates, all 2-H analogues, and a CH 3 -phosphonate were inactive. Thus, chronic administration of nucleotidase-resistant phosphonates conferred a beneficial effect, likely via cardiac P2X receptor activation. Thus, we have greatly expanded the range of carbocyclic nucleotide analogues that represent potential candidates for the treatment of heart failure.

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Section: Methodsmentioning

confidence: 99%

Structure−Activity Relationship of (N)-Methanocarba Phosphonate Analogues of 5′-AMP as Cardioprotective Agents Acting Through a Cardiac P2X Receptor

et al. 2010

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“…1) is based on the International Union of Pure and Applied Chemistry (IUPAC) von Baeyer convention, a tremendously complicated method when applied to higher diamondoids and other complex polycyclic hydrocarbons (usually performed with the aid of computers). [54,55] [56,57] A valuable feature of the IUPAC von Baeyer naming/carbon numbering convention is that it represents instructions for constructing the carbon network of a molecule and is therefore also a representation of its 13 C-…”

Section: Introductionmentioning

confidence: 99%

“…[46] c IUPAC name. [54] Figure 3. Schlegel diagrams: (A) [123]tetramantane (underlined numbers explained in groups in triamantane ( Fig.…”

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confidence: 99%

NMR spectral properties of the tetramantanes – nanometer‐sized diamondoids

Balaban

Young

Plavec

et al. 2015

Magnetic Reson in Chemistry

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Tetramantanes, and all diamondoid hydrocarbons, possess carbon frameworks that are superimposable upon the cubic diamond lattice. This characteristic is invaluable in assigning their (1)H and (13)C NMR spectra because it translates into repeating structural features, such as diamond-cage isobutyl moieties with distinctively complex methine to methylene signatures in COSY and HMBC data, connected to variable, but systematic linkages of methine and quaternary carbons. In all tetramantane C22H28 isomers, diamond-lattice structures result in long-range (4)JHH, W-coupling in COSY data, except where negated by symmetry; there are two highly symmetrical and one chiral tetramantane (showing seven (4)JHH). Isobutyl-cage methines of lower diamondoids and tetramantanes are the most shielded resonances in their (13)C spectra (<29.5 ppm). The isobutyl methylenes are bonded to additional methines and at least one quaternary carbon in the tetramantanes. W-couplings between these methines and methylenes clarify spin-network interconnections and detailed surface hydrogen stereochemistry. Vicinal couplings of the isobutyl methylenes reveal positions of the quaternary carbons: HMBC data then tie the more remote spin systems together. Diamondoid (13) C NMR chemical shifts are largely determined by α and β effects, however γ-shielding effects are important in [123]tetramantane. (1)H NMR chemical shifts generally correlate with numbers of 1,3-diaxial H-H interactions. Tight van der Waals contacts within [123]tetramantane's molecular groove, however, form improper hydrogen bonds, deshielding hydrogen nuclei inside the groove, while shielding those outside, indicated by Δδ of 1.47 ppm for geminal hydrogens bonded to C-3,21. These findings should be valuable in future NMR studies of diamondoids/nanodiamonds of increasing size.

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“…However, for specifying the structures of substituted diamondoids, the more general von Baeyer nomenclature system adopted by IUPAC provides a general and unambiguous solution. 8,9 C. and G. Rücker devised the computer program POLCYC for naming polycyclic compounds and numbering carbon atoms therein according to the IUPAC Nomenclature Rules. 10 This program was instrumental to the present paper.…”

Section: Introductionmentioning

confidence: 99%

“…15 15 This name, however, though correctly describing the structure, was not correct in the sense of IUPAC rule VB-6-4, which states "The superscript locants of the secondary bridges shall be as small as possible when considered as a set in ascending numerical order, a decision being made at the first point of difference". 8 In 2009 a different numbering scheme for cyclohexamantane was used, 16 The second member of this class has as dualist the graph corresponding to trans-decalin, see Figure 7, second structure. Its IUPAC name is nonadecacyclo [20.16. In Table 2 we present data for the first perimantanes with all-trans-perhydroacene graphs as dualists.…”

Section: Introductionmentioning

confidence: 99%

Helical [n]catamantanes and all-trans-perhydroacenic [n]perimantanes: structures and von Baeyer IUPAC numbering of carbon atoms

Balaban¹,

Rücker²

2013

Arkivoc

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Abstract[n]Diamondoids are hydrocarbons whose carbon skeleton is a portion of the diamond lattice, and contains n adamantane cells (or units) sharing chair-shaped hexagons of carbon atoms. When centers of these adamantane units are connected by lines, the resulting construction is called the dualist of the diamondoid, and it also is similar to a portion of the diamond lattice. While these hydrocarbons can be distinguished by the Balaban-Schleyer nomenclature system, substituted derivatives are to be described by the IUPAC von Baeyer nomenclature that attributes a unique number (locant) to each carbon atom within a molecule. In this paper, von Baeyer names and corresponding atom numberings were obtained by the computer program POLCYC for members of two classes of diamondoids: [n]catamantanes whose dualists are tight helices, and [n]perimantanes whose dualists are all-trans-perhydroacenes; general numbering schemes were derived for these compound classes. The structures and some regularities in their structural properties are discussed.

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Extension and revision of the von Baeyer system for naming polycyclic compounds (including bicyclic compounds)

Cited by 31 publications

References 5 publications

Structure−Activity Relationship of (N)-Methanocarba Phosphonate Analogues of 5′-AMP as Cardioprotective Agents Acting Through a Cardiac P2X Receptor

Structure−Activity Relationship of (N)-Methanocarba Phosphonate Analogues of 5′-AMP as Cardioprotective Agents Acting Through a Cardiac P2X Receptor

NMR spectral properties of the tetramantanes – nanometer‐sized diamondoids

Helical [n]catamantanes and all-trans-perhydroacenic [n]perimantanes: structures and von Baeyer IUPAC numbering of carbon atoms

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