Primary aminomethyl derivatives of kaempferol: hydrogen bond-assisted synthesis, anticancer activity and spectral properties

Organic & Biomolecular Chemistry
Shuanglian CaiQiu-An Wang

Abstract

A series of primary aminomethyl derivatives of kaempferol were synthesized by a combination strategy involving two steps of the Mannich reaction and SN2 nucleophilic substitution. The structures of the products show that the preferential aminomethylations are in the position C-6 or C-8 of the A-ring of kaempferol, especially the latter. Interestingly, the experimental data indicate that the intermolecular hydrogen bonding plays a key role in the formation of primary aminomethyl products of kaempferol. The formation of appropriate hydrogen bonds between strong nucleophilic amino acids and phenol is essential for the smooth reaction of the SN2 nucleophilic substitution. The SN2 mechanism hypothesis involving a hydrogen bond-assisted process was also supported by the density functional theory (DFT) analysis. An antiproliferative test of synthetic compounds shows the moderate to potent cytotoxic activity against three human cancer cell lines (HeLa, HCC1954, and SK-OV-3) by the CCK-8 assay. Compound 4e shows selective antiproliferative activity against HeLa cells with a low IC50 value (4.27 μm) and is worthy of further development. Another interesting result is that the maximum emission bands for most metal complexes are located at ...Continue Reading

References

Jul 23, 2004·The Journal of Chemical Physics·Hrant P Hratchian, H Bernhard Schlegel
Oct 24, 2007·The Journal of Physical Chemistry. a·Jeffrey P MerrickLeo Radom
Dec 17, 2008·The Journal of Physical Chemistry. a·Chyi-Lin ChenPi-Tai Chou
Mar 11, 2011·Organic & Biomolecular Chemistry·P Ricardo GirlingAndrew Whiting
Dec 14, 2011·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Nawal Al-MusayeibAjaz Hussain
Apr 4, 2012·Organic & Biomolecular Chemistry·Fanbo SongZhen Xi
Oct 26, 2012·The Journal of Organic Chemistry·Chun WuPatrick S Mariano
Mar 7, 2013·Chemical Reviews·Adam Noble, James C Anderson
Dec 10, 2014·Bioorganic & Medicinal Chemistry Letters·Travis R HelgrenTimothy J Hagen
Dec 31, 2014·Current Topics in Medicinal Chemistry·Marcelo D CatarinoSusana M Cardoso
Dec 15, 2015·Journal of the American Chemical Society·Lennart BrewitzMasakatsu Shibasaki
Mar 24, 2016·Cellular Physiology and Biochemistry : International Journal of Experimental Cellular Physiology, Biochemistry, and Pharmacology·Jie JianRenbin Huang
Oct 6, 2016·Journal of Molecular Modeling·Rogério V A JúniorNathalia B D Lima
May 4, 1998·Angewandte Chemie·Michael ArendNikolaus Risch

❮ Previous
Next ❯

Methods Mentioned

BETA
fluorescence spectroscopy
NMR

Software Mentioned

GaussView
Gaussian
Spss

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.