Enantioselective Synthesis of Planar Chiral Ferrocifens that Show Chiral Discrimination in Antiproliferative Activity on Breast Cancer Cells.
Antineoplastic Agents
/ chemical synthesis
Breast Neoplasms
/ drug therapy
Catalysis
Cell Proliferation
/ drug effects
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Female
Ferrous Compounds
/ chemical synthesis
Humans
Molecular Structure
Palladium
/ chemistry
Stereoisomerism
Structure-Activity Relationship
Tumor Cells, Cultured
anti-tumor agents
bio-organometallics
chirality
enantioselective synthesis
ferrocifen
Journal
Chembiochem : a European journal of chemical biology
ISSN: 1439-7633
Titre abrégé: Chembiochem
Pays: Germany
ID NLM: 100937360
Informations de publication
Date de publication:
15 10 2020
15 10 2020
Historique:
received:
14
05
2020
revised:
25
05
2020
pubmed:
27
5
2020
medline:
7
7
2021
entrez:
27
5
2020
Statut:
ppublish
Résumé
The design and first enantioselective synthesis of a series of chiral ferrocifens and ferrociphenols was realised by enantioselective palladium-catalysed intramolecular direct C-H bond activation followed by McMurry coupling. Biological evaluation revealed moderate anticancer activities on breast cancer cells and evidence of chiral discrimination between enantiomers. Treatment of the novel ferrocifens with Ag
Identifiants
pubmed: 32453493
doi: 10.1002/cbic.202000311
doi:
Substances chimiques
Antineoplastic Agents
0
Ferrous Compounds
0
ferrocifen
0
ferrociphenol
0
Palladium
5TWQ1V240M
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
2974-2981Informations de copyright
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Références
G. Jaouen, S. Top, A. Vessières, G. Leclercq, M. J. McGlinchey, Curr. Med. Chem. 2004, 2505-2517.
G. Jaouen, A. Vessières, S. Top, Chem. Soc. Rev. 2015, 44, 8802-8817.
G. Jaouen, W. Beck, M. J. McGlinchey in Bioorganometallics: Biomolecules, Labelling, Medicine (Ed: G, Jaouen), Wiley-VCH, Weinheim, 2006, pp. 1-37.
C. G. Hartinger, P. J. Dyson, Chem. Soc. Rev. 2009, 391-401.
G. Jaouen, N. Metzler-Notle, Medicinal Organometallic Chemistry, Springer-Verlag, Berlin, 2010.
G. Jaouen, S. Top, M. J. McGlinchey in Bioorganometallic Chem. Appl. Drug Discov. Biocatal. Imaging, Wiley-VCH, Weinheim, 2015, 43-83.
T. Hirao, T. Moriuchi, Advances in Bioorganometallic Chemistry, Elsevier, Amsterdam, 2018.
W. Weigand, U.-P. Apfel, Bioorganometallic Chemistry, De Gruyter, Berlin, 2020.
F. Ali, L. Aamer, S. Tanzeela, A. Fattah, U. Muqadar, Appl. Organomet. Chem. 2016, 31, 1-22.
W. A. Wani, U. Baig, S. Shreaz, R. Sjiekh, P. F. Iqbal, E. Jameel, A. Ahmad, S. H. Mohd-Setapar, M. Mushtaque, L. T. Huna, New J. Chem. 2016, 40, 1063-1090.
I. Montes-González, A. M. Alsina-Sánchez, J. C. Aponte-Santini, S. M. Delgado-Rivera, G. L. Durán-Camacho, Pure Appl. Chem. 2019, 9, 3239-3278.
M. Zaki, RSC Adv. 2019, 9, 3239-3278.
K. Kowalski, Coord. Chem. Rev. 2018, 366, 91-108.
S. S. Braga, A. M. S. Silva, Organometallics 2013, 32, 5626-5639.
S. Peter, B. A. Aderibigbe, Molecules 2019, 24, 3604.
D. Nieto, A. M. González-Vadillo, S. Bruña, C. J. Pastor, C. Ríos-Luci, L. G. León, J. M. Padrón, C. Navarro-Ranninger, I. Cuadrado, Dalton Trans. 2012, 41, 432-441.
E. A. Hillard, P. Pigeon, A. Vessières, C. Amatore, G. Jaouen, Dalton Trans. 2007, 5073-5081.
P. Pigeon, M. Görmen, K. Kowalski, H. Müller-Bunz, M. J. McGlinchey, S. Top, G. Jaouen, Molecules 2014, 19, 10350-10369.
S. Top, J. Tang, A. Vessières, D. Carrez, C. Provot, G. Jaouen, Chem. Commun. 1996, 48, 955-956.
G. Jaouen, S. Top, A. Vessières, G. Leclercq, J. Quivy, L. Jin, A. Croisy, C. R. Acad. Sci., Ser. IIc: Chim. 2000, 3, 89-93.
D. Hamels, P. M. Dansette, E. A. Hillard, S. Top, A. Vessières, P. Herson, G. Jaouen, D. Mansuy, Angew. Chem. Int. Ed. 2009, 48, 9124-9126.
Y. Wang, P. Pigeon, S. Top, M. J. McGlinchey, G. Jaouen, Angew. Chem. Int. Ed. 2015, 54, 10230-10233.
Y. Wang, P. Pigeon, M. J. McGlinchey, S. Top, G. Jaouen, J. Organomet. Chem. 2017, 829, 108-115.
Y. Wang, P. M. Dansette, P. Pigeon, S. Top, M. J. McGlinchey, D. Mansuy, G. Jaouen, Chem. Sci. 2018, 9, 70-78.
Y. Wang, M.-A. Richard, S. Top, P. M. Dansette, P. Pigeon, A. Vessières, D. Mansuy, G. Jaouen, Angew. Chem. Int. Ed. 2016, 55, 10431-10434.
P. Pigeon, Y. Wang, S. Top, F. Najlaoui, M. C. Garcia Alvarez, J. Bignon, M. J. McGlinchey, G. Jaouen, J. Med. Chem. 2017, 60, 8358-8368.
Y. Wang, P. Pigeon, S. Top, J. Sanz García, C. Troufflard, I. Ciofini, M. J. McGlinchey, G. Jaouen, Angew. Chem. Int. Ed. 2019, 58, 8421-8425.
D. Plazuk, S. Top, A. Vessières, M. A. Plamont, M. Huché, J. Zakrzewski, A. Makal, K. Woźniak, G. Jaouen, Dalton Trans. 2010, 39, 7444-7450.
D. Plazuk, A. Vessières, E. A. Hillard, O. Buriez, E. Labbé, P. Pigeon, M. A. Plamont, C. Amatore, J. Zakrzewski, G. Jaouen, J. Med. Chem. 2009, 52, 4964-4967.
M. Görmen, P. Pigeon, Y. Wang, A. Vessières, S. Top, F. Martial, C. Gros, M. J. McGlinchey, G. Jaouen, Eur. J. Inorg. Chem. 2017, 2017, 454-465.
M. Görmen, P. Pigeon, S. Top, E. A. Hillard, M. Huché, C. G. Hartinger, F. de Montigny, M.-A. Plamont, A. Vessières, G. Jaouen, ChemMedChem 2010, 5, 2039-2050.
M. Görmen, P. Pigeon, E. A. Hillard, A. Vessières, M. Huché, M.-A. Richard, M. J. McGlinchey, S. Top, G. Jaouen, Organometallics 2012, 31, 5856-5866.
S. Top, G. Jaouen, A. Vessières, J.-P. Abjean, D. Davoust, C. A. Rodger, B. G. Sayer, M. J. McGlinchey, Organometallics 1985, 12, 12, 2143-2150.
B. Ferber, S. Top, A. Vessières, R. Welter, G. Jaouen, Organometallics 2006, 25, 5730-5739.
L. Delhaes, C. Biot, L. Berry, P. Delcourt, L. A. Maciejewski, D. Camus, J. S. Brocard, D. Dive, ChemBioChem 2002, 3, 418-423.
M. Patra, G. Gasser, M. Wenzel, K. Merz, J. E. Bandow, N. Metzler-Nolte, Eur. J. Inorg. Chem. 2011, 22, 3295-3302.
C. Nottingham, H. Müller-Bunz, P. J. Guiry, Angew. Chem. Int. Ed. 2016, 55, 11115-11119.
D. W. Gao, Q. Yin, Q. Gu, S. L. You, J. Am. Chem. Soc. 2014, 136, 4841-4844.
R. Deng, Y. Huang, X. Ma, G. Li, R. Zhu, B. Wang, Y. B. Kang, Z. Gu, J. Am. Chem. Soc. 2014, 136, 4472-4475.
M. Patra, G. Gasser, Nat. Rev. Chem. 2017, 1, 0066.
S. Top, A. Vessières, C. Cabestaing, I. Laios, G. Leclercq, C. Provot, G. Jaouen, J. Organomet. Chem. 2001, 637-639, 500-506.
F. Tonolo, M. Salmain, V. Scalcon, S. Top, P. Pigeon, A. Folda, B. Caron, M. J. McGlinchey, R. Toillon, A. Bindoli, et al., ChemMedChem 2019, 14, 1717-1726.
P. Messina, E. Labbé, O. Buriez, E. A. Hillard, A. Vessières, D. Hamels, S. Top, G. Jaouen, Y. M. Frapart, D. Mansuy, et al., Chem. Eur. J. 2012, 18, 6581-6587.
E. Hillard, A. Vessières, L. Thouin, G. Jaouen, C. Amatore, Angew. Chem. Int. Ed. 2006, 45, 285-290.
Y. L. K. Tan, P. Pigeon, S. Top, E. Labbé, O. Buriez, E. A. Hillard, A. Vessières, C. Amatore, W. K. Leong, G. Jaouen, Dalton Trans. 2012, 41, 7537-7549.
J. Prousek, Pure Appl. Chem. 2007, 2325-2338.
M. J. Meegan, R. B. Hughes, D. G. Lloyd, D. C. Williams, D. M. Zisterer, J. Med. Chem. 2001, 44, 1072-1084.
H. A. M. Hejaz, L. W. L. Woo, A. Purohit, M. J. Reed, B. V. L. Potter, Bioorg. Med. Chem. 2004, 12, 2759-2772.
E. S. Tan, J. C. Naylor, E. S. Groban, J. R. Bunzow, M. P. Jacobson, D. K. Grandy, T. S. Scanlan, ACS Chem. Biol. 2009, 4, 209-220.