THE SYNTHESIS OF 1,2,3,7,8,9-HEXAHYDRODIBENZO[<i>def, mno</i>]CHRYSENE AND THE USE OF HYDRIODIC ACID-RED PHOSPHORUS IN THE DEOXYGENATION OF KETONES

Ansell, L. L.; Rangarajan, T. M.; Burgess, Wayland M.; Eisenbraun, E. J.; Keen, G. W.; Hamming, M. C.

doi:10.1080/00304947609355606

Cited by 14 publications

(11 citation statements)

References 6 publications

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“…The syntheses of DB[ a,l ]P was carried out following our recently reported Suzuki cross-coupling reaction approach. 19 Briefly, 5,6-dihydrobenz[ d,e ]anthracene, prepared from benzanthrone, 20 was brominated using Br 2 /AcOH to afford 7-bromobenzanthracene derivative which was subjected to palladium-catalyzed Suzuki coupling reaction with 2-formylphenylboronic acid. Refluxing of the resulting aldehyde derivative with aniline followed by t -BuOK assisted cyclization yielded the DB[ a,l ]P.…”

Section: Methodsmentioning

confidence: 99%

Mutagenesis and carcinogenesis induced by dibenzo[a,l]pyrene in the mouse oral cavity: a potential new model for oral cancer

Guttenplan

Kosinska

Zhao

et al. 2011

Intl Journal of Cancer

123

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Cancer of the oral cavity is a serious disease, affecting about 30,000 individuals in US annually. There are several animal models of oral cancer, but each has certain disadvantages. As a new model, we investigated whether topical application of the tobacco smoke carcinogen, dibenzo[a,l]pyrene (DB[a,l]P) is mutagenic and carcinogenic in the oral cavity of the B6C3F1 lacI and B6C3F1 mouse, respectively. B6C3F1 lacI mice received DB[a,l]P (0, 3, 6, 12 nmol) 3× per week. B6C3F1 mice received the same doses and also 24 nmol. At 38 weeks mutagenesis was measured in oral tissues in lacI mice. For the high dose group, the mutant fraction (MF) in upper mucosa and tongue increased about twofold relative to that in vehicle-alone. The increases were statistically significant. The mutational profile in the DB[a,l]P-induced mutants was compared with that induced by benzo[a]pyrene (BaP) in oral tissue. BaP is mutagenic in many tissues when administered by gavage. The mutational profile for DB[a,l]P was more similar to that reported for p53 mutations in head and neck cancers than was that of BaP. At 47 weeks, oral squamous cell carcinomas (OSCC) were found in 31% of the high-dose B6C3F1 group. Elevations of p53 and COX-2 protein were observed in tumor and dysplastic tissue. As DB[a,l]P induces mutations and tumors in the oral cavity, and has a mutational profile in oral tissue similar to that found in p53 in human OSCC, the treatment protocol described here may represent a new and relevant model for cancer of the oral cavity.

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Section: Methodsmentioning

confidence: 99%

Mutagenesis and carcinogenesis induced by dibenzo[a,l]pyrene in the mouse oral cavity: a potential new model for oral cancer

Guttenplan

Kosinska

Zhao

et al. 2011

Intl Journal of Cancer

123

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“…Water, (Fisher, HPLC grade, submicron filtered, pH 7), lithium iodide (LiI, Aldrich, 99.8%), lithium chloride (Aldrich, >99.0%), sodium hydroxide (Aldrich, pellets, >99%) sodium iodide (NaI, Aldrich, >99.5%), sodium chloride (Aldrich, 99%), potassium iodide (KI, Aldrich, 99%), potassium chloride (Aldrich, >99.0%), cesium iodide (CsI, Aldrich, 99.9%), and cesium chloride (Aldrich, 99%) were used as received. Tetramethylammonium iodide (TMAI, Aldrich, 99%), tetramethylammonium chloride (Alfa, >98%), tetraethylammonium iodide (TEAI, Aldrich, 98%), tetraethylammonium chloride (Alfa, >98%), and PyBu (mp 187.1–188.0 °C (Lit: 187–188 °C); Alfa, 97%) were recrystallized twice from absolute ethanol. 1,3,6,8-Tetrakis(2,6-dimethyl-4-(α-carboxy)methoxyphenyl)pyrene (Py4C) was available from other studies and was >99% pure according to HPLC analyses …”

Section: Methodsmentioning

confidence: 99%

Influence of Cations on the Fluorescence Quenching of an Ionic, Sterically Congested Pyrenyl Moiety by Iodide in Water

Bertocchi¹,

Lupicki²,

Bajpai

et al. 2017

J. Phys. Chem. A

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Quenching of the excited singlet states of a water-soluble, sterically congested tetraarylpyrene, 1,3,6,8-tetrakis(2,6-dimethyl-4-(α-carboxy)methoxyphenyl)pyrene (Py4C), by a series of iodide salts has been investigated by steady-state and time-resolved fluorescence measurements. Access to the pyrenyl group of Py4C is restricted sterically as a result of the four flanking (2,6-dimethylphenoxy)acetic acid groups and the energy costs associated with their rotation. Deprotonation of the carboxylic acid groups of Py4C permits examination of ion-ion electrostatic interactions on the rates of quenching by iodide salts in which different steric and electrostatic factors are introduced by varying the cationic portions. At the same concentrations and with the same cations, chloride anions are ineffective quenchers. The quenching rate constants of Py4C by iodide are found to correlate linearly with the ionic radii of the cations and their enthalpies of hydration. These correlations are discussed in terms of the Hofmeister series. Furthermore, the results indicate that the cations that flank Py4C decrease the quenching efficiency of iodide through polarization and shielding effects (i.e., lowering the effective charge), which isolate to varying degrees the π-system. The effects of the different cations on quenching the fluorescence of a simpler and sterically unencumbered pyrenyl derivative, 1-pyrenylbutyric acid (PyBu), by iodide are much smaller. Overall, the results with Py4C indicate that the fluorescence quenching efficiency by iodide is influenced by direct interactions with the cations associated with the carboxylate groups of Py4C and not the solvation of water molecules. This observation is germane to a topic of current debate: Are the effects of the cations more closely related to bulk water properties or to direct ion-ion interactions? The conclusions obtained from these studies are applicable clearly to a wide variety of other systems in which ion pairing influences cooperative or inhibitory interactions.

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“…Moreover, it also demonstrated the good tolerance of chloroalkyl and carboxylic groups, especially the former, which was intolerable in many reductive conditions for deoxygenations. [1][2][3][4][5][6][7][8][9][10][11][12][13][15][16][17]…”

Section: Gram-scale Synthesis Product Derivations and Synthetic Appmentioning

confidence: 99%

“…The complementary two step carbonyl thioketalization with thiols and thioketal desulfurization with Raney-nickel (Mozingo reaction) under neutral conditions show good functional group tolerance but less satisfactory step-and atom economy. [3] Other stoichiometric reagents [1d,e] that directly convert aromatic ketones or aldehydes to the corresponding hydrocarbons include boranes, [4] borohydrides, [5] LiAlH 4 À AlCl 3 , [6] HI-red P, [7] NiÀ Al alloy, [8] P(OiPr) 3 , [9] SeÀ COÀ H 2 O, [10] Raney Ni, [11] and (i-BuClAl) 2 O. [12] To preclude hazardous reductants and reduce organic by-products, homogeneously or heterogeneously catalytic hydrogenations with high-pressure hydrogen gas (up to 60 bar) are developed.…”

Section: Introductionmentioning

confidence: 99%

Iridium‐Catalysed Reductive Deoxygenation of Ketones with Formic Acid as Traceless Hydride Donor

et al. 2020

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An iridium-catalysed deoxygenation of ketones and aldehydes is achieved, with formic acid as hydride donor and water as co-solvent. At low catalyst loading, a number of 4-(N,N-disubstituted amino) aryl ketones are readily deoxygenated in excellent yields and chemoselectivity. Numerous functional groups, especially phenolic and alcoholic hydroxyls, secondary amine, carboxylic acid, and alkyl chloride, are well tolerable. Geminally dideuterated alkanes are obtained with up to 90% D incorporation, when DCO 2 D and D 2 O are used in place of their hydrogenative counterparts. The activating 4-(N,N-disubstituted amino)aryl groups have been demonstrated to undergo a variety of useful transformations. The deoxygenative deuterations have been used to prepare a deuterated drug molecule Chlorambucil-4,4-d 2 .

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THE SYNTHESIS OF 1,2,3,7,8,9-HEXAHYDRODIBENZO[def, mno]CHRYSENE AND THE USE OF HYDRIODIC ACID-RED PHOSPHORUS IN THE DEOXYGENATION OF KETONES

Cited by 14 publications

References 6 publications

Mutagenesis and carcinogenesis induced by dibenzo[a,l]pyrene in the mouse oral cavity: a potential new model for oral cancer

Mutagenesis and carcinogenesis induced by dibenzo[a,l]pyrene in the mouse oral cavity: a potential new model for oral cancer

Influence of Cations on the Fluorescence Quenching of an Ionic, Sterically Congested Pyrenyl Moiety by Iodide in Water

Iridium‐Catalysed Reductive Deoxygenation of Ketones with Formic Acid as Traceless Hydride Donor

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