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Synthesis and DNA methyltransferase inhibitory activity of N,N'-(alkanediyl)bis(phenylacetamide) derivatives
Yakhak Hoeji 2019;63(2):113-119
Published online April 30, 2019
© 2019 The Pharmaceutical Society of Korea.

Sohyun Lee and Eunsook Ma#

College of Pharmacy, Daegu Catholic University
Correspondence to: #Eunsook Ma, College of Pharmacy, Daegu Catholic University, 13-13 Hayang-ro Gyeongsan-si, 38430, Korea, Tel: +82-53-850-3621, Fax: +82-53-850-3602, E-mail:
Received March 26, 2019; Revised April 18, 2019; Accepted April 20, 2019.
DNA methyltransferases (DNMTs) are epigenetic enzymes responsible for gene expression in cancer, therefore their inhibitors have been considered as target for the treatment and prevention of cancer. Psammaplin A (PsA) with dimeric disulfide structure exhibits excellent DNMT inhibitory activity, but there are synthetic limitations in the development of various derivatives. To develop various DNMT inhibitors that are easy to synthesize, N,N'-(alkanediyl) bis(phenylacetamide) derivatives 1-16 were synthesized from 3- or 4-substituted phenylacetic acids and α,ω-diaminoalkanes (NH2(CH2)nNH2, n=2-5) and evaluated for the preliminary screening of DNMT inhibitory activity using PsA as an positive control. The DNMT inhibitory activities (21-91%) of all synthesized compounds were lower than that of PsA (>100%) at 200 μM concentration. Among them, N,N'-(pentane-1,5-diyl)bis(2-(3-bromophenyl)acetamide) (12) was found to be most active compound with DNMT inhibition of 91%.
Keywords : DNA methyltransferase, N,N'-(alkanediyl)bis(phenylacetamide), epigenetics

August 2019, 63 (4)
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