Synthesis and Resolution of a Multifunctional Inherently Chiral Calix[4]arene with an ABCD Substitution Pattern at the Wide Rim: The Effect of a Multifunctional Structure in the Organocatalyst on Enantioselectivity in Asymmetric Reactions

2009 ◽  
Vol 74 (3) ◽  
pp. 1288-1296 ◽  
Author(s):  
Seiji Shirakawa ◽  
Tomohiro Kimura ◽  
Shun-ichi Murata ◽  
Shoichi Shimizu
Keyword(s):  
Asymmetric Reactions ◽  
Substitution Pattern ◽  
Inherently Chiral

Recent advances on the synthesis of the antidepressant Paroxetine

2020 ◽  
Vol 27 ◽  
Author(s):  
Joana Santos ◽  
M. Fernanda Proença ◽  
Ana Joao Rodrigues ◽  
Patricia Patrício ◽  
H. Sofia Domingues
Keyword(s):  
Total Synthesis ◽  
Neurological Disorders ◽  
Serotonin Reuptake ◽  
Potent Inhibitor ◽  
Starting Material ◽  
Substitution Pattern ◽  
Biological Probes ◽  
Recent Advances ◽  
Treatment Of Depression ◽  
Made In

: Paroxetine is a potent inhibitor of serotonin reuptake and is widely prescribed for the treatment of depression and other neurological disorders. The synthesis of paroxetine and the possibility to prepare derivatives with a specific substitution pattern that may allow their use as biological probes, is an attractive topic especially for medicinal chemists engaged in neurosciences research. Considering the extensive work that was developed in the last decade on the total synthesis of paroxetine, this review summarizes the most important contributions in this field, organized according to the reagent that was used as starting material. Most of the methods allowed to prepare paroxetine in 4-9 steps with an overall yield of 9-66%. Despite the progress made in this area, there is still room for improvement, searching for new eco-friendly and sustainable synthetic alternatives.

D-Glucosamine-derived Chiral Catalysts For Asymmetric Reactions

2013 ◽  
Vol 17 (14) ◽  
pp. 1507-1524 ◽  
Author(s):  
Chao Shen ◽  
Peng-Fei Zhang
Keyword(s):  
Asymmetric Reactions ◽  
Chiral Catalysts

Anticancer Activity and Topoisomerase II Inhibition of Naphthalimides with ω-Hydroxylalkylamine Side-Chains of Different Lengths

2019 ◽  
Vol 15 (5) ◽  
pp. 550-560
Author(s):  
Mateusz D. Tomczyk ◽  
Anna Byczek-Wyrostek ◽  
Klaudia Strama ◽  
Martyna Wawszków ◽  
Przemysław Kasprzycki ◽  
...  
Keyword(s):  
Anticancer Activity ◽  
Cancer Cells ◽  
Cell Lines ◽  
Inhibitory Activity ◽  
Topoisomerase Ii ◽  
Significant Activity ◽  
Anticancer Activities ◽  
Human Colon Cancer ◽  
Substitution Pattern ◽  
Topo Ii

Background: The substituted 1,8-Naphthalimides (1H-benzo[de]isoquinoline-1,3(2H)- diones) are known as DNA intercalators stabilizing DNA-Topoisomerase II complexes. This interaction disrupts the cleavage-relegation equilibrium of Topo II, resulting in formation of broken strands of DNA. Objective: To investigate the influence of type of substituents and substitution positions in 1,8- naphthalimde skeleton on the inhibition of Topoisomerase II activity. Methods: The starting 1,8-naphthalimide were prepared from acenaphthene by introduction of appropriate substituents followed by condensation with ω-hydroxylakylamines of different chain length. The substituents were introduced to 1,8-naphthalimide molecule by nucleophilic substitution of leaving groups like nitro or bromo present in 4 or 4,5- positions using the ω- hydroxylalkylamines. The bioactivity of obtained compounds was examined in model cell lines. Results: Antiproliferative activity of selected compounds against HCT 116 human colon cancer cells, human non-small cell lung cells A549 and non-tumorigenic BEAS-2B human bronchial epithelium cells was examined. Several of investigated compounds exhibit a significant activity (IC50 µM to 7 µM) against model cancer cell lines. It was demonstrated that upon treatment with concentration of 200 µM, all derivatives display Topo II inhibitory activity, which may be compared with activity of Amonafide. Conclusion: The replacement of the nitro groups in the chromophore slightly reduces its anticancer activities, whereas the presence of both nitro group and ω-hydroxylalkylamine chain resulted in seriously increased anticancer activity. Obtained compounds showed Topo II inhibitory activity, moreover, influence of the substitution pattern on the ability to inhibit Topo II activity and cancer cells proliferation was observed.

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