Relevant bibliographies by topics / Carbocyclic rings bound

Academic literature on the topic 'Carbocyclic rings bound'

Author: Grafiati
Published: 6 September 2023

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Journal articles on the topic "Carbocyclic rings bound"

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Searle, M. S., J. G. Hall, W. A. Denny, and L. P. Wakelin. "Interaction of the antitumour antibiotic luzopeptin with the hexanucleotide duplex d(5′-GCATGC)2. One-dimensional and two-dimensional n.m.r. studies." Biochemical Journal 259, no. 2 (April 15, 1989): 433–41. http://dx.doi.org/10.1042/bj2590433.

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1H- and 31P-n.m.r. spectroscopy were used to characterize the solution structure of the 1:1 complex formed between the antitumour antibiotic luzopeptin and the self-complementary hexanucleotide d(5'-GCATGC)2. Eighteen nuclear Overhauser effects between antibiotic and nucleotide protons, together with ring-current-induced perturbations to base-pair and quinoline 1H resonances, define the position and orientation of the bound drug molecule. Luzopeptin binds in the minor groove of the DNA with full retention of dyad symmetry, its quinoline chromophores intercalating at the 5'-CpA and 5'-TpG steps and its depsipeptide ring spanning the central two A.T base-pairs. The chromophores stack principally on the adenine base with their carbocyclic rings pointing towards the deoxyribose of the cytosine. There is no evidence for Hoogsteen base-pairing in the complex, all glycosidic bond angles and sugar puckers being typical of B-DNA as found for the free hexanucleotide. The ‘breathing’ motions of the A.T and internal G.C base-pairs are substantially slowed in the complex compared with the free DNA, and the observation that two phosphate resonances are shifted downfield by at least 0.5 p.p.m. in the 31P-n.m.r. spectrum of the complex suggests pronounced local helix unwinding at the intercalation sites. The data are consistent with a model of the complex in which luzopeptin bisintercalates with its depsipeptide essentially in the conformation found in the crystal of the free antibiotic [Arnold & Clardy (1981) J. Am. Chem. Soc. 103, 1243-1244]. We postulate only one conformational change within the peptide ring, which involves rotation of the pyridazine-glycine amide group linkage by 90 degrees towards the DNA surface. This manoeuvre breaks the glycine-to-glycine transannular hydrogen bonds and enables the glycine NH groups to bond to the thymine O-2 atoms of the sandwiched A.T base-pairs. It also shortens the major axis of the depsipeptide so that the interchromophore distance is more suitable for spanning two base-pairs. The model further implies that the carboxy and hydroxy groups of the L-beta-hydroxyvaline residue are appropriately positioned for hydrogen-bonding to the 2-amino group of guanine and the O-2 atom of cytosine of the adjacent G.C base-pair.
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Boyd, Derek R., Narain D. Sharma, Ludmila V. Modyanova, Jonathan G. Carroll, John F. Malone, Christopher CR Allen, John TG Hamilton, David T. Gibson, Rebecca E. Parales, and Howard Dalton. "Dioxygenase-catalyzed cis-dihydroxylation of pyridine-ring systems." Canadian Journal of Chemistry 80, no. 6 (June 1, 2002): 589–600. http://dx.doi.org/10.1139/v02-062.

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Toluene dioxygenase-catalyzed dihydroxylation, in the carbocyclic rings of quinoline, 2-chloroquinoline, 2-methoxyquinoline, and 3-bromoquinoline, was found to yield the corresponding enantiopure cis-5,6- and -7,8-dihy dro diol metabolites using whole cells of Pseudomonas putida UV4. cis-Dihydroxylation at the 3,4-bond of 2-chloroquino line, 2-methoxyquinoline, and 2-quinolone was also found to yield the heterocyclic cis-dihydrodiol metabolite, (+)-cis-(3S,4S)-3,4-dihydroxy-3,4-dihydro-2-quinolone. Heterocyclic cis-dihydrodiol metabolites, resulting from dihydroxylation at the 5,6- and 3,4-bonds of 1-methyl 2-pyridone, were isolated from bacteria containing toluene, naphthalene, and biphenyl dioxygenases. The enantiomeric excess (ee) values (>98%) and the absolute configurations of the carbocyclic cis-dihydrodiol metabolites of quinoline substrates (benzylic R) and of the heterocyclic cis-diols from quinoline, 2-quinolone, and 2-pyridone substrates (allylic S) were found to be in accord with earlier models for dioxygenase-catalyzed cis-dihydroxylation of carbocyclic arenes. Evidence favouring the dioxygenase-catalyzed cis-dihydroxylation of pyridine-ring systems is presented.Key words: dioxygenases; cis-dihydroxylation, pyridines, 2-pyridones, absolute configurations.
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Sowmya, Haliwana B. V., Tholappanavara H. Suresha Kumara, Jerry P. Jasinski, Sean P. Millikan, Hemmige S. Yathirajan, and Christopher Glidewell. "The crystal structure of 3-chloro-2-(4-methylphenyl)-2H-pyrazolo[3,4-b]quinoline." Acta Crystallographica Section E Crystallographic Communications 71, no. 5 (April 30, 2015): 567–70. http://dx.doi.org/10.1107/s205698901500818x.

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In the molecule of 3-chloro-2-(4-methylphenyl)-2H-pyrazolo[3,4-b]quinoline, C17H12ClN3, (I), the dihedral angle between the planes of the pyrazole ring and the methylated phenyl ring is 54.25 (9)°. The bond distances in the fused tricyclic system provide evidence for 10-π delocalization in the pyrazolopyridine portion of the molecule, with diene character in the fused carbocyclic ring. In the crystal, molecules of (I) are linked by two independent C—H...N hydrogen bonds, forming sheets containing centrosymmetricR22(16) andR64(28) rings, and these sheets are all linked together by π–π stacking interactions with a ring-centroid separation of 3.5891 (9) Å.
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Girisha, Marisiddaiah, Hemmige S. Yathirajan, Jerry P. Jasinski, and Christopher Glidewell. "Different acid–base behaviour of a pyrazole and an isoxazole with organic acids: crystal and molecular structures of the salt 3-(4-fluorophenyl)-1H-pyrazolium 2,4,6-trinitrophenolate and of the cocrystal 4-amino-N-(3,4-dimethyl-1,2-oxazol-5-yl)benzenesulfonamide–3,5-dinitrobenzoic acid (1/1)." Acta Crystallographica Section C Structural Chemistry 72, no. 8 (July 12, 2016): 612–18. http://dx.doi.org/10.1107/s2053229616010494.

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Pyrazole and isoxazole rings differ only in the notional replacement of a potential hydrogen-bond-donor NH unit in pyrazole by a potential hydrogen-bond-acceptor O atom in isoxazole. It is thus of interest to compare the hydrogen-bonding characteristics of these rings. (4-Fluorophenyl)pyrazole undergoes protonation in the presence of 2,4,6-trinitrophenol to yield the salt 3-(4-fluorophenyl)-1H-pyrazolium 2,4,6-trinitrophenolate, C9H8FN2+·C6H2N3O7−, (I), whereas there is no proton transfer between 4-amino-N-(3,4-dimethyl-1,2-oxazol-5-yl)benzenesulfonamide and 3,5-dinitrobenzoic acid, whose reaction gives the 1:1 cocrystal, C11H13N3O3S·C7H4N2O6, (II). The bond lengths in salt (I) provide evidence for aromatic-type delocalization in the pyrazolium ring and for extensive delocalization of the negative charge into the ring of the trinitrophenolate anion. The O atoms of one of the nitro groups in the trinitrophenolate anion are disordered over two sets of atomic sites having occupancies of 0.571 (6) and 0.429 (6), but all of the other substituents on the carbocyclic rings are fully ordered. The ions in salt (I) are linked by an extensive series of N—H...O hydrogen bonds to form a three-dimensional framework structure, and in cocrystal (II), the molecular components are linked by a combination of O—H...N and N—H...O hydrogen bonds to form complex bilayers. Comparisons are made with some related compounds.
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Ghosh, Subrata, and Shyamapada Banerjee. "Carbon-carbon bond cleavage in norbornane derivatives. Convenient route to novel carbocyclic rings." Arkivoc 2002, no. 7 (May 26, 2002): 8–20. http://dx.doi.org/10.3998/ark.5550190.0003.702.

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Inglebert, S. Antony, Jayabal Kamalraja, K. Sethusankar, and Gnanasambandam Vasuki. "4-(4-Bromophenyl)-7,7-dimethyl-2-methylamino-3-nitro-7,8-dihydro-4H-chromen-5(6H)-one including an unknown solvate." Acta Crystallographica Section E Structure Reports Online 70, no. 5 (April 18, 2014): o579—o580. http://dx.doi.org/10.1107/s1600536814007983.

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In the title compound, C18H19BrN2O4, the chromene unit is not quite planar (r.m.s. deviation = 0.199 Å), with the methyl C atoms lying 0.027 (4) and 1.929 (4) Å from the mean plane of the chromene unit. The six-membered carbocyclic ring of the chromene moiety adopts an envelope conformation, with the dimethyl-substituted C atom as the flap. The methylamine and nitro groups are slightly twisted from the chromene moiety, with C—N—C—O and O—N—C—C torsion angles of 2.7 (4) and −0.4 (4)°, respectively. The dihedral angle between the mean plane of the chromene unit and the benzene ring is 85.61 (13)°. An intramolecular N—H...O hydrogen bond generates anS(6) ring motif, which stabilizes the molecular conformation. In the crystal, molecules are linkedviaN—H...O hydrogen bonds, forming hexagonal rings lying parallel to theabplane. A region of disordered electron density, most probably disordered ethanol solvent molecules, occupying voids ofca432 Å3for an electron count of 158, was treated using the SQUEEZE routine inPLATON[Spek (2009).Acta Cryst. D65, 148–155]. Their formula mass and unit-cell characteristics were not taken into account during refinement.
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Shi, Xinzhe, Arpan Sasmal, Jean-François Soulé, and Henri Doucet. "Metal-Catalyzed C−H Bond Activation of 5-Membered Carbocyclic Rings: A Powerful Access to Azulene, Acenaphthylene and Fulvene Derivatives." Chemistry - An Asian Journal 13, no. 2 (December 11, 2017): 143–57. http://dx.doi.org/10.1002/asia.201701455.

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Shi, Xinzhe, Arpan Sasmal, Jean-François Soulé, and Henri Doucet. "Front Cover: Metal-Catalyzed C−H Bond Activation of 5-Membered Carbocyclic Rings: A Powerful Access to Azulene, Acenaphthylene and Fulvene Derivatives (Chem. Asian J. 2/2018)." Chemistry - An Asian Journal 13, no. 2 (January 5, 2018): 126. http://dx.doi.org/10.1002/asia.201701813.

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Dissertations / Theses on the topic "Carbocyclic rings bound"

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Watson, Timothy James. "Through-bond conjugation via cyclobutane relay orbitals. Multiple functionalization of medium-sized carbocyclic rings /." The Ohio State University, 1994. http://rave.ohiolink.edu/etdc/view?acc_num=osu1487858417981521.

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Book chapters on the topic "Carbocyclic rings bound"

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Taber, Douglass F. "The Tan/Chen/Yang Synthesis of Schindilactone A." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0088.

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Schindilactone A 3 is one of a closely related family of polycyclic lactones that have been used in China for the treatment of rheumatic disease. The synthesis of 3 reported (Angew. Chem. Int. Ed. 2011, 50, 7373) by Ye-Feng Tang of Tsinghua University and Jia-Hua Chen and Zhen Yang of Peking University is an elegant tour of metal-mediated bond construction, as exemplified by the cyclization of 1 to 2. The preparation of 1 began with the Diels-Alder reaction of 4 with the butadiene 5. Addition of methyl magnesium chloride converted 6 to the crystalline lactone 7. Angular hydroxylation followed by ring expansion gave the bromo enone 8, which was homologated to the lactone 11. Apparently, the bulky silyloxy group directed the addition of the butenyl Grignard reagent 10 to the top face of the ketone carbonyl. Hydroxylation of the lactone followed by the addition of 12 then gave 1 as a mixture of diastereomers. Only one of the two diastereomers of 1 could undergo ring-closing metathesis to form the second of the three carbocyclic rings of 3. The two lactol diastereomers were in equilibrium with each other by way of the open-chain enone. When MgBr2 was added to encourage equilibration, the metathesis proceeded to completion to give 2. The tertiary alcohol of 2 was esterified with 2-butynoic acid to give 13. Intramolecular Pauson-Khand cyclization, using the optimized protocol developed by the authors, then delivered the enone 13, completing the last carbocyclic ring of 3. The last remarkable metal-mediated reaction in the synthesis was the oxidative carbonylation of 14 to 15. It is not clear if the postcarbonylation event is direct Pd-mediated C–O bond formation or the intramolecular addition of alkoxide to a transient butenolide. To complete the synthesis, 15 was methylated, then deprotonated and kinetically quenched to set the proper relative configuration of the last methyl group. Remarkably, despite the presence in the molecule of three other acidic protons, including the one that had just been removed and kinetically reset, exposure of the acetate 16 to a large excess of base, followed by oxidation, gave clean conversion to schindilactone A 3.
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"3. Reactions at the Cyclopropane σ-Bond." In Carbocyclic Three- and Four Membered Ring Compounds, edited by Armin de Meijere. Stuttgart: Georg Thieme Verlag, 1997. http://dx.doi.org/10.1055/b-0035-112527.

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"5.1. With Cleavage of a Cyclopropyl–Carbon Bond." In Carbocyclic Three- and Four Membered Ring Compounds, edited by Armin de Meijere. Stuttgart: Georg Thieme Verlag, 1997. http://dx.doi.org/10.1055/b-0035-112729.

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"5.1. With Cleavage of a Cyclobutenyl to Carbon Bond." In Carbocyclic Three- and Four-Membered Ring Compounds, edited by Armin de Meijere. Stuttgart: Georg Thieme Verlag, 1997. http://dx.doi.org/10.1055/b-0035-112567.

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"5.2. Without Cleavage of a Cyclopropyl–Carbon Bond (I)." In Carbocyclic Three- and Four Membered Ring Compounds, edited by Armin de Meijere. Stuttgart: Georg Thieme Verlag, 1997. http://dx.doi.org/10.1055/b-0035-112730.

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"5.2. Without Cleavage of a Cyclopropyl–Carbon Bond (II)." In Carbocyclic Three- and Four Membered Ring Compounds, edited by Armin de Meijere. Stuttgart: Georg Thieme Verlag, 1997. http://dx.doi.org/10.1055/b-0035-112731.

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"5.2. Without Cleavage of a Cyclopropyl–Carbon Bond (III)." In Carbocyclic Three- and Four Membered Ring Compounds, edited by Armin de Meijere. Stuttgart: Georg Thieme Verlag, 1997. http://dx.doi.org/10.1055/b-0035-112732.

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"5.2. Without Cleavage of a Cyclopropyl–Carbon Bond (IV)." In Carbocyclic Three- and Four Membered Ring Compounds, edited by Armin de Meijere. Stuttgart: Georg Thieme Verlag, 1997. http://dx.doi.org/10.1055/b-0035-112733.

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"5.2. Without Cleavage of a Cyclopropyl–Carbon Bond (V)." In Carbocyclic Three- and Four Membered Ring Compounds, edited by Armin de Meijere. Stuttgart: Georg Thieme Verlag, 1997. http://dx.doi.org/10.1055/b-0035-112734.

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"5.2. Without Cleavage of a Cyclopropyl–Carbon Bond (VI)." In Carbocyclic Three- and Four Membered Ring Compounds, edited by Armin de Meijere. Stuttgart: Georg Thieme Verlag, 1997. http://dx.doi.org/10.1055/b-0035-112735.

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