Synthesis and electrochemical properties of a series of ferrocene-containing alcohols

Davis, Wade L.; Shago, Rebotsamang F.; Langner, Ernst H.G.; Swarts, Jannie C.

doi:10.1016/j.poly.2005.04.022

Cited by 56 publications

(45 citation statements)

References 17 publications

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“…The observed shift of E 1/2 to a lower potential reflects replacement of an electron-withdrawing carbonyl group in 11c by the CH(OH)-moiety in 11d. The E 1/2 of alcohol 11d is 13 mV more positive than that of its simpler analog 1-hydroxyethylferrocene [51]. This (11) 1.473 (5) 1.468(6) C(11)eC (12) 1.516 (5) 1.491(6) C(11)eO (1) 1.223(4) 1.221(5) C(12)eC (13) 1.500 (5) 1.309(7) C(13)eC(l1) 1.781(4) e C(2)eN(1)eC (5) 106.5(3) 106.1(3) W(1)eN(1)eC (2) 68.8(2) 68.9(2) W(1)eN(1)eC (5) 69.5(2) 69.4(2) O(1)eC(11)eC (10) 121.0(3) 120.4(4) O(1)eC(11)eC (12) 121.6(3) 120.7(4) C(10)eC(11)eC (12) 117.3 (3) 118.9(4) C(11)eC(12)eC (13) 114.6(3) 122.6(4) C(11)eC(13)eC (12) 112.8(3) e C(10)eC(11)eC(12)eC (13) 173.9(5) 179.8(4) O(1)eC(11)eC(12)eC (13) À5.4(5) À0.4 (7) reflects a weak but still measurable electron-withdrawing effect of the thymine end-chain group.…”

Section: Cyclic Voltammetrical Study Of 11c 11d 12a and 12bmentioning

confidence: 92%

The synthesis, structure, electrochemistry and in vitro anticancer activity studies of ferrocenyl-thymine conjugates

Kowalski

Koceva‐Chyła

Pieniążek

et al. 2012

Journal of Organometallic Chemistry

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Section: Cyclic Voltammetrical Study Of 11c 11d 12a and 12bmentioning

confidence: 92%

The synthesis, structure, electrochemistry and in vitro anticancer activity studies of ferrocenyl-thymine conjugates

Kowalski

Koceva‐Chyła

Pieniążek

et al. 2012

Journal of Organometallic Chemistry

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“…Materials: By using the same protocol as that previously reported, [22][23][24] the phosphoramidite of (2-hydroxyethyl)ferrocene [44] for IqA C H T U N G T R E N N U N G (free)1 was prepared in 96 % yield as a yellow oil. 1 Immobilization of the DNA probe onto a gold electrode: Commercially available gold electrodes (Tanaka Kikinzoku, Tokyo, Japan) were cleaned as previously reported [22][23][24] and dried under an argon stream before use.…”

Section: Methodsmentioning

confidence: 99%

Detection of Mismatched Duplexes by Synchronizing the Pulse Potential Frequency with the Dynamics of Ferrocene/Isoquinoline Conjugate‐Connected DNA Probes Immobilized onto Electrodes

Ikeda

Kobayashi

Chiba

et al. 2009

Chemistry A European J

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Cyclic voltammetry was performed at various scan rates for the duplexes from ferrocene/isoquinoline conjugate-connected DNA probes on gold electrodes. The relationship between the observed currents and the scan rates disclosed the enhanced bending elasticity of the mismatched duplexes compared with the fully matched duplexes. The difference of the dynamics was easily detected through the currents from the conjugate by adjusting the pulse potential frequency in square-wave voltammetry. By using the present strategy, we succeeded in accurately detecting various naturally occurring single-nucleotide polymorphisms.

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“…Compounds 6 a, 7 a, and 7 c were purchased from Acros and used as received. The syntheses of compounds Fc-diOH, [20] 5, [38] 7, [42] 7b, [43] 8c, [25] 8d, [42] 9, 10, 11, and 12 [44] have been previously described.…”

Section: Discussionmentioning

confidence: 99%

Synthesis and Structure–Activity Relationships of Ferrocenyl Tamoxifen Derivatives with Modified Side Chains

Nguyen

Top

Pigeon

et al. 2008

Chemistry A European J

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We report here the synthesis and cell-proliferation properties of derivatives of the breast cancer drug tamoxifen, in which the -O(CH(2))(2)N(CH(3))(2) side chain, responsible for the drug's antiestrogenic properties, has been modified by a ferrocenyl moiety. We recently reported the diphenol compound 5, in which this amino chain had been replaced with an acyl-ferrocenyl (-O(CH(2))(2)C(O)[(eta(5)-C(5)H(4))FeCp]) group, and which showed antiproliferative effects against both the hormone-dependent MCF-7 and -independent MDA-MB-231 breast cancer cell lines. We now report the results of a structure-activity relationship (SAR) study, in which the lateral chain length has been varied, the ketone group has been omitted, and the number of phenol groups has been varied. Compounds 1-4, with a side chain lacking the carbonyl function (-O(CH(2))(n)[(eta(5)-C(5)H(4))FeCp], n = 1-4) and which show a decreasing affinity for ERalpha (ER = estrogen receptor) with increasing chain length, act as estrogens on MCF-7 cells, and mild cytotoxics on PC-3 prostate cancer cells, with IC(50) values around 10 microM. The two monophenolic derivatives of 2, 2 a and 2 b, which show a reduced affinity for ERalpha compared to 2, are also estrogenic, but are only slightly cytotoxic. Finally, we have reexamined compound 5 and discovered that its antiproliferative effect against the MCF-7 cell line does not arise from antiestrogenicity as we had originally suspected, but by means of a cytotoxic pathway. This compound is also sensitive to the number of phenol groups as cell death is diminished when one of the hydroxyl groups is omitted (5 a and 5 b). Molecular modeling studies of the ligand-ERalpha binding stability are broadly consistent with the experimental binding affinity results for compounds 2, 2 a, 2 b, 5, 5 a, and 5 b. Electrochemical experiments show that 1-4, 2 a, and 2 b are stable to oxidation on the electrochemical timescale, unlike 5, 5 a, and 5 b, and that cytotoxicity is related to less positive phenol oxidation potentials. The SAR study shows that the presence of a ketone group and two phenol groups is necessary for strong receptor binding and cytotoxic effects, and that all compounds are estrogenic, despite the presence of a bulky side chain.

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Synthesis and electrochemical properties of a series of ferrocene-containing alcohols

Cited by 56 publications

References 17 publications

The synthesis, structure, electrochemistry and in vitro anticancer activity studies of ferrocenyl-thymine conjugates

The synthesis, structure, electrochemistry and in vitro anticancer activity studies of ferrocenyl-thymine conjugates

Detection of Mismatched Duplexes by Synchronizing the Pulse Potential Frequency with the Dynamics of Ferrocene/Isoquinoline Conjugate‐Connected DNA Probes Immobilized onto Electrodes

Synthesis and Structure–Activity Relationships of Ferrocenyl Tamoxifen Derivatives with Modified Side Chains

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