Porphyrin Synthesis in Water Provides New Expanded Porphyrins with Direct Bipyrrole Linkages:  Isolation and Characterization of Two Heptaphyrins

Hiroto, Satoru; Shinokubo, Hiroshi; Osuka, Atsuhiro

doi:10.1021/ja061621g

Cited by 36 publications

(57 citation statements)

References 22 publications

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“…[51] In this reaction, the compound was accompanied by another heptaphyrin 65c-H 3 , and an octaphyrin (78e-H 5 , Section 8.2). While the selectivity of this reaction remains to be explained, it provides a potentially general route to expanded macrocycles with unsymmetrical meso patterns.…”

Section: Heptaphyrinsmentioning

confidence: 99%

“…[51] Compound 65c-H 3 , to which a [30]annulenoid formulation was assigned on the basis of mass spectrometric and X-ray structural data, is of interest because it exhibits distinct paratropicity in the free base form, in spite of the 4n + 2 conjugation pathway. In the original report, a T2 conformation was proposed for 65c-H 3 , which is not consistent with the observed ring current.…”

Section: Heptaphyrinsmentioning

confidence: 99%

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Figure Eights, Möbius Bands, and More: Conformation and Aromaticity of Porphyrinoids

2011

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The aromatic character of porphyrins, which has significant chemical and biological consequences, can be substantially altered by judicious modifications of the parent ring system. Expansion of the macrocycle, which is achieved by introducing additional subunits, usually increases the so-called free curvature of the ring, leading to larger angular strain. This strain is reduced by a variety of conformational changes, most notably by subunit inversion and p surface twisting. The latter effect creates a particularly convenient access to Möbius aromatic molecules, whose properties, predicted over 40 years ago, are of considerable theoretical importance. The conformational processes occurring in porphyrin analogues are often coupled to other chemical phenomena, and can thus be exploited as a means of constructing functional molecular devices. In this Review, the structural chemistry of porphyrinoids is discussed in the context of their conformational dynamics and p-electron conjugation.

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Section: Heptaphyrinsmentioning

confidence: 99%

Section: Heptaphyrinsmentioning

confidence: 99%

Figure Eights, Möbius Bands, and More: Conformation and Aromaticity of Porphyrinoids

2011

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“…[51] Nebenprodukte der Reaktion [51] Die Verbindung 65c-H 3 , der anhand von massenspektrometrischen und röntgen-kristallographischen Daten ein [30]Annulensystem zugeordnet wurde, ist deshalb interessant, weil sie trotz ihres 4n + 2-Konjugationsweges deutliche diatrope Eigenschaften der freien Base aufweist. In der Originalveröffentlichung wurde 65c-H 3 noch eine T2-Konformation zugeordnet, die aber nicht zum beobachteten Ringstrom passte.…”

Section: Heptaphyrineunclassified

Figure‐Eight‐Strukturen, Möbius‐Bänder und mehr: Konformation und Aromatizität von Porphyrinoiden

2011

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Der aromatische Charakter von Porphyrinen, der signifikante chemische und biologische Auswirkungen hat, kann durch gezielte Modifikationen des Stammringsystems beträchtlich verändert werden. Zusätzliche Untereinheiten expandieren den Makrocyclus und erhöhen seine Ringkrümmung, was zu einer höheren Winkelspannung führt. Diese Winkelspannung kann der Ring durch eine Reihe von Konformationsänderungen wieder abbauen, insbesondere durch Invertieren von Untereinheiten und Verdrillen (twisting) der π‐Oberfläche. Letzterer Effekt bietet einen Zugang zu Möbius‐aromatischen Molekülen, deren Eigenschaften, gleichwohl vor über 40 Jahren vorausgesagt, unter theoretischen Aspekten von großer Bedeutung sind. Häufig gehen Konformationsprozesse in den Porphyrinanaloga mit anderen chemischen Phänomenen einher, sodass sie für den Aufbau von molekularen Funktionseinheiten verwendet werden können. In diesem Aufsatz wird die Strukturchemie der Porphyrinoide im Zusammenhang mit ihrer Konformationsdynamik und elektronischen π‐Konjugation diskutiert.

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“…These reactions include dehydrative esterification, etherification, thioesterification, and dithiol acetalization. In these reactions, DBSA and substrates form emulsion droplets where the interior side is hydrophobic enough to repel water molecules generated during the reactions [34,35,36]. Previous studies on the esterification-mediated surfactant catalyst showed that the yields of esters and ether quinine derivatives were affected by temperature, amounts of DBSA, and the substrates.…”

Section: Resultsmentioning

confidence: 99%

In Silico Screening and Designing Synthesis of Cinchona Alkaloids Derivatives as Potential Anticancer

Hanafi

Rosmalena

Prasasty

et al. 2017

JTLS

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P-glycoprotein (P-gp) resistance in cancer cells decreases the intracellular accumulation of various anticancer drugs. This multidrug resistance (MDR) protein can be modulated by number of non-cytotoxic drugs. We have screened 30 cinchona alkaloids derivatives as a potent P-gp inhibitor agent in silico. Hereby, we report the highest potential inhibitions of P-gp is Cinchonidine isobutanoate through molecular docking approach with affinity energy -8.6 kcal/mol and inhibition constant, Ki is 4.89 × 10 -7 M. Cinchonidine isobutanoate is also known has molecular weight below 500, Log P value 3.5, which is indicated violation free of Lipinski`s rule of five. Thus, Cinchonidine isobutanoate is the most potent compound as anticancer compare to other Cinchona alkaloids. Ultimately, we design Cinchonidine isobutanoate for further lead synthesis by using DBSA, act as a combined Brønsted acid-surfactantcatalyst (BASC) to obtain a high concentration of organic product by forming micellar aggregates which are very powerful catalytic application in a water environment.

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Porphyrin Synthesis in Water Provides New Expanded Porphyrins with Direct Bipyrrole Linkages: Isolation and Characterization of Two Heptaphyrins

Cited by 36 publications

References 22 publications

Figure Eights, Möbius Bands, and More: Conformation and Aromaticity of Porphyrinoids

Figure Eights, Möbius Bands, and More: Conformation and Aromaticity of Porphyrinoids

Figure‐Eight‐Strukturen, Möbius‐Bänder und mehr: Konformation und Aromatizität von Porphyrinoiden

In Silico Screening and Designing Synthesis of Cinchona Alkaloids Derivatives as Potential Anticancer

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