Synthesis and antiproliferative activity of α-branched α,β-unsaturated ketones

Karpaviciene, Ieva; Čikotienė, Inga; Padrón, José M.

doi:10.1016/j.ejmech.2013.10.041

Cited by 15 publications

(7 citation statements)

References 27 publications

(17 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The coupling of the alkenylzinc reagents with sp 2 ‐hybridized carbon halides was stereospecific and only single stereoisomers were formed. As a result, compound 3 l , which exhibits an anti ‐proliferative activity toward a number of tumor cell lines,20 was readily prepared by using this protocol, without the problem of separation from a mixture of isomeric products as previously described.…”

Section: Resultsmentioning

confidence: 99%

Stereoselective Synthesis of Trisubstituted Alkenes through Sequential Iron‐Catalyzed Reductive anti‐Carbozincation of Terminal Alkynes and Base‐Metal‐Catalyzed Negishi Cross‐Coupling

Cheung

2015

Chemistry A European J

View full text Add to dashboard Cite

The stereoselective synthesis of trisubstituted alkenes is challenging. Here, we show that an iron‐catalyzed anti‐selective carbozincation of terminal alkynes can be combined with a base‐metal‐catalyzed cross‐coupling to prepare trisubstituted alkenes in a one‐pot reaction and with high regio‐ and stereocontrol. Cu‐, Ni‐, and Co‐based catalytic systems are developed for the coupling of sp‐, sp2‐, and sp3‐hybridized carbon electrophiles, respectively. The method encompasses a large substrate scope, as various alkynyl, aryl, alkenyl, acyl, and alkyl halides are suitable coupling partners. Compared with conventional carbometalation reactions of alkynes, the current method avoids pre‐made organometallic reagents and has a distinct stereoselectivity.

show abstract

Section: Resultsmentioning

confidence: 99%

Stereoselective Synthesis of Trisubstituted Alkenes through Sequential Iron‐Catalyzed Reductive anti‐Carbozincation of Terminal Alkynes and Base‐Metal‐Catalyzed Negishi Cross‐Coupling

Cheung

2015

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…Furthermore, Tin(II) chloride was also used to promote such a coupling, and has been used to prepare α‐Me‐ and α‐Pr‐chalcone [39] . α‐CH 2 Cl, α‐CH 2 OAc, and α‐CH 2 OBz‐chalcones were prepared through acid (BF 3 .Et 2 O) catalyzed coupling between arylalkynes and benzaldehydes [40] . These chalcones were evaluated for their antiproliferative activity in various human solid tumor cell lines.…”

Section: Different α‐Substituted Chalconesmentioning

confidence: 99%

α‐Substituted Chalcones: A Key Review

Al-Rifai

Mubarak

2021

ChemistrySelect

View full text Add to dashboard Cite

Chalcones are attractive chemical motifs with various biological activities. Aryl substituted chalcones have been extensively studied and reviewed through the years. However, α‐substituted chalcones have rarely been investigated. Hence, this review highlights the α‐substituted chalcones: their synthetic routes, reported biological activities, and transformations to other organic compounds. To the best of our knowledge, this would be the first comprehensive review about α‐substituted chalcones. α‐Substitution of chalcones represents a promising approach to tune their reactivity since it has a direct influence on their activity as Michael acceptors. Additionally, α‐substitution has its effect on the structure and conformation of chalcones. Altering the reactivity of chalcones by α‐substitution has a great impact on their biological activity.

show abstract

“…The unique molecular structures and low toxic biological activities of chalcones have attracted a great deal of attention in organic chemistry, and there are many reports on the synthesis of their derivatives for pharmaceutical and food applications. [8][9][10][11][12][13][14][15][16][17][18][19] With this background, however, little attention has been paid to water-soluble chalcones, which have the potential to exhibit novel biological activities. In this study, we focused on a chalcone diol, in which its two OH groups are directly attached to the phenyl ring A and B, with the expectation that an anionic charge generated due to deprotonation delocalizes over its p-conjugated structure.…”

Section: Introductionmentioning

confidence: 99%