FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2059409127> ?p ?o ?g. }

• W2059409127 endingPage "7633" @default.
• W2059409127 startingPage "7625" @default.
• W2059409127 abstract "1,4-Difluorobenzo[c]phenanthrene (1,4-DFBcPh) and its putative metabolites, the dihydrodiol and diol epoxides, have been synthesized and structurally characterized, and the extent of DNA binding by the metabolites has been assessed. 1,4-DFBcPh and 1,4-difluoro-10-methoxybenzo[c]phenanthrene were prepared by photochemical cyclization of appropriate naphthylphenylethylenes. The dihydrodiol was synthesized from 1,4-difluoro-10-methoxybenzo[c]phenanthrene, and the diol epoxides were diastereoselectively synthesized from the dihydrodiol. Interesting differences were noted in 1H NMR spectra of the series 1 (syn) diol epoxides of benzo[c]phenanthrene (BcPh) and 1,4-DFBcPh; the BcPh diol epoxide displays a quasi-diequatorial orientation of the hydroxyl groups, but in the 1,4-DFBcPh case these are diaxially disposed. This difference probably stems from the presence of the fjord-region fluorine atom in 1,4-DFBcPh. A through-space, fjord-region H−F coupling has also been observed for 1,4-DFBcPh and its derivatives. Comparative X-ray crystallographic analyses of BcPh and 1,4-DFBcPh and their dihydrodiols show that introduction of fluorine increases the molecular distortion by about 6−7°. As a guide to estimating the molecular distortion and its effects, and for comparison with the X-ray structures in known cases, optimized structures of BcPh, 1,4-DFBcPh, and 1,4-DMBcPh (the dimethyl analogue) as well as their dihydrodiols and diol epoxides were computed. Relative aromaticities of these compounds were assessed by nucleus-independent chemical shift calculations, and 13C NMR chemical shifts were computed by gauge-inducing atomic orbital calculations. 1,4-DFBcPh and its dihydrodiol were subjected to metabolism, and the amount of DNA binding in human breast cancer MCF-7 cells was assessed. The extent of DNA binding was then compared with that for BcPh and its dihydrodiol and the potent carcinogen benzo[a]pyrene. The 1,4-DFBcPh series 2 (anti) diol epoxide-derived DNA adducts were also compared with those arising from intracellular oxidation of the dihydrodiol with subsequent DNA binding. These experiments showed that increased molecular distortion decreased metabolic activation to the terminal metabolites but that diol epoxide metabolites that are formed are the DNA-damaging species." @default.
• W2059409127 created "2016-06-24" @default.
• W2059409127 creator A5001619872 @default.
• W2059409127 creator A5010134206 @default.
• W2059409127 creator A5017397348 @default.
• W2059409127 creator A5026277311 @default.
• W2059409127 creator A5040503085 @default.
• W2059409127 creator A5045970730 @default.
• W2059409127 creator A5046167902 @default.
• W2059409127 creator A5048714188 @default.
• W2059409127 creator A5065626281 @default.
• W2059409127 creator A5078529091 @default.
• W2059409127 creator A5091487383 @default.
• W2059409127 creator A5078191084 @default.
• W2059409127 date "2007-09-01" @default.
• W2059409127 modified "2023-09-24" @default.
• W2059409127 title "Synthetic, Crystallographic, Computational, and Biological Studies of 1,4-Difluorobenzo[<i>c</i>]phenanthrene and Its Metabolites" @default.
• W2059409127 cites W189344779 @default.
• W2059409127 cites W1967602990 @default.
• W2059409127 cites W1975695965 @default.
• W2059409127 cites W1981873063 @default.
• W2059409127 cites W1993581511 @default.
• W2059409127 cites W1994934978 @default.
• W2059409127 cites W2000319560 @default.
• W2059409127 cites W2005083487 @default.
• W2059409127 cites W2009972378 @default.
• W2059409127 cites W2037263129 @default.
• W2059409127 cites W2041440686 @default.
• W2059409127 cites W2052899527 @default.
• W2059409127 cites W2054164390 @default.
• W2059409127 cites W2057329486 @default.
• W2059409127 cites W2065091408 @default.
• W2059409127 cites W2069175708 @default.
• W2059409127 cites W2079361001 @default.
• W2059409127 cites W2156115804 @default.
• W2059409127 cites W2314362610 @default.
• W2059409127 cites W2314666052 @default.
• W2059409127 cites W2318468106 @default.
• W2059409127 cites W2346161654 @default.
• W2059409127 cites W2952560030 @default.
• W2059409127 cites W3004773992 @default.
• W2059409127 cites W307860133 @default.
• W2059409127 doi "https://doi.org/10.1021/jo071145s" @default.
• W2059409127 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/17764198" @default.
• W2059409127 hasPublicationYear "2007" @default.
• W2059409127 type Work @default.
• W2059409127 sameAs 2059409127 @default.
• W2059409127 citedByCount "20" @default.
• W2059409127 countsByYear W20594091272012 @default.
• W2059409127 countsByYear W20594091272013 @default.
• W2059409127 countsByYear W20594091272015 @default.
• W2059409127 countsByYear W20594091272016 @default.
• W2059409127 countsByYear W20594091272017 @default.
• W2059409127 countsByYear W20594091272018 @default.
• W2059409127 countsByYear W20594091272020 @default.
• W2059409127 crossrefType "journal-article" @default.
• W2059409127 hasAuthorship W2059409127A5001619872 @default.
• W2059409127 hasAuthorship W2059409127A5010134206 @default.
• W2059409127 hasAuthorship W2059409127A5017397348 @default.
• W2059409127 hasAuthorship W2059409127A5026277311 @default.
• W2059409127 hasAuthorship W2059409127A5040503085 @default.
• W2059409127 hasAuthorship W2059409127A5045970730 @default.
• W2059409127 hasAuthorship W2059409127A5046167902 @default.
• W2059409127 hasAuthorship W2059409127A5048714188 @default.
• W2059409127 hasAuthorship W2059409127A5065626281 @default.
• W2059409127 hasAuthorship W2059409127A5078191084 @default.
• W2059409127 hasAuthorship W2059409127A5078529091 @default.
• W2059409127 hasAuthorship W2059409127A5091487383 @default.
• W2059409127 hasConcept C111429119 @default.
• W2059409127 hasConcept C147789679 @default.
• W2059409127 hasConcept C161790260 @default.
• W2059409127 hasConcept C178790620 @default.
• W2059409127 hasConcept C185592680 @default.
• W2059409127 hasConcept C2776891815 @default.
• W2059409127 hasConcept C2776920199 @default.
• W2059409127 hasConcept C2779515768 @default.
• W2059409127 hasConcept C71240020 @default.
• W2059409127 hasConcept C8010536 @default.
• W2059409127 hasConceptScore W2059409127C111429119 @default.
• W2059409127 hasConceptScore W2059409127C147789679 @default.
• W2059409127 hasConceptScore W2059409127C161790260 @default.
• W2059409127 hasConceptScore W2059409127C178790620 @default.
• W2059409127 hasConceptScore W2059409127C185592680 @default.
• W2059409127 hasConceptScore W2059409127C2776891815 @default.
• W2059409127 hasConceptScore W2059409127C2776920199 @default.
• W2059409127 hasConceptScore W2059409127C2779515768 @default.
• W2059409127 hasConceptScore W2059409127C71240020 @default.
• W2059409127 hasConceptScore W2059409127C8010536 @default.
• W2059409127 hasIssue "20" @default.
• W2059409127 hasLocation W20594091271 @default.
• W2059409127 hasLocation W20594091272 @default.
• W2059409127 hasOpenAccess W2059409127 @default.
• W2059409127 hasPrimaryLocation W20594091271 @default.
• W2059409127 hasRelatedWork W1693521579 @default.
• W2059409127 hasRelatedWork W1967603262 @default.
• W2059409127 hasRelatedWork W1996659121 @default.
• W2059409127 hasRelatedWork W2033393251 @default.
• W2059409127 hasRelatedWork W2043036149 @default.

• next