The Palladium-Catalyzed Cross-Coupling Reaction of Phenylboronic Acid with Haloarenes in the Presence of Bases

Miyaura, Norio; Yanagi, Teiji; Suzuki, Akira

doi:10.1080/00397918108063618

Cited by 1,829 publications

(817 citation statements)

References 11 publications

Supporting

Mentioning

799

Contrasting

Unclassified

Order By: Relevance

“…III was reacted with 4-aminophenylboronic acid pinacol ester in a Suzuki cross coupling reaction [43] to afford the final compound 1. Compounds 2 and 30 were prepared from I and II, respectively, using the same methods as for 1 but in reversed order because the intermediates 2a and 30a were needed as starting materials in the syntheses according to scheme 2, vide infra.…”

Section: Chemistrymentioning

confidence: 99%

Towards the evaluation in an animal disease model: Fluorinated 17β-HSD1 inhibitors showing strong activity towards both the human and the rat enzyme

Abdelsamie

Bey²,

Gargano

et al. 2015

European Journal of Medicinal Chemistry

View full text Add to dashboard Cite

CitationTowards the evaluation in an animal disease model: Fluorinated 17-HSD1 inhibitors showing strong activity towards both the human and the rat enzyme. Abstract 17β-Estradiol (E2), the most potent human estrogen, is known to be involved in the etiology of estrogen-dependent diseases (EDD) like breast cancer and endometriosis. 17β-Hydroxysteroid dehydrogenase type 1 (17β-HSD1) catalyses the last step of E2 biosynthesis and is thus a promising target for the treatment of EDD. The previously described bicyclic substituted hydroxyphenyl methanones (BSHs) display high inhibitory potency towards human 17β-HSD1, but marginal activity towards rodent 17β-HSD1, precluding a proof of principle study in an animal endometriosis model. The aim of this work was to perform structural optimizations in the BSHs class to enhance inhibitory activity against rodent (mouse and rat) 17β-HSD1 while maintaining activity against the human enzyme. The introduction of fluorine atoms on the benzoyl moiety resulted in compounds with the desired properties. Molecular docking and homology modelling were applied to elucidate the binding mode and interspecies differences in activity. Compound 33 is the most potent inhibitor of both human and rat 17β-HSD1 up to date (IC 50 = 2 nM and 97 nM, respectively).Keywords: 17β-Hydroxysteroid dehydrogenase type 1, Interspecies differences, Estrogendependent diseases, Estrogen mimetics, Non-steroidal inhibitors

show abstract

Section: Chemistrymentioning

confidence: 99%

Towards the evaluation in an animal disease model: Fluorinated 17β-HSD1 inhibitors showing strong activity towards both the human and the rat enzyme

Abdelsamie

Bey²,

Gargano

et al. 2015

European Journal of Medicinal Chemistry

View full text Add to dashboard Cite

show abstract

“…[33] FriedelCrafts acylation of the resulting intermediate 1a [34] with the appropriate benzoic acid chloride gave access to compounds 1-4.…”

Section: Chemistrymentioning

confidence: 99%

Inhibition of 17β-HSD1: SAR of bicyclic substituted hydroxyphenylmethanones and discovery of new potent inhibitors with thioether linker

Abdelsamie

Bey²,

Hanke³

et al. 2014

European Journal of Medicinal Chemistry

View full text Add to dashboard Cite

“…Palladium-catalyzed reactions of organic boron compounds with arylclorides are one of common synthetic methods for forming new carbon-carbon bonds [3]. Organic boron reagents are readily available, stable to air and non-reactive to various active fragments for which usually the protective groups introduction requires.…”

Section: Reactions With the Formation Of C-c Bondsmentioning

confidence: 99%

Chlorophenols in organic synthesis

et al. 2016

View full text Add to dashboard Cite

show abstract

The Palladium-Catalyzed Cross-Coupling Reaction of Phenylboronic Acid with Haloarenes in the Presence of Bases

Cited by 1,829 publications

References 11 publications

Towards the evaluation in an animal disease model: Fluorinated 17β-HSD1 inhibitors showing strong activity towards both the human and the rat enzyme

Towards the evaluation in an animal disease model: Fluorinated 17β-HSD1 inhibitors showing strong activity towards both the human and the rat enzyme

Inhibition of 17β-HSD1: SAR of bicyclic substituted hydroxyphenylmethanones and discovery of new potent inhibitors with thioether linker

Chlorophenols in organic synthesis

Contact Info

Product

Resources

About