A facile synthetic route to diazepinone derivatives via ring closing metathesis and its application for human cytidine deaminase inhibitors

Minkyoung Kim; Kondaji Gajulapati; Chorong Kim; Hwa Young Jung; Jail Goo; Kyeong Lee; Navneet Kaur; Hyo Jin Kang; Sang J. Chung; Yongseok Choi

doi:10.1039/C2CC35484E

A facile synthetic route to diazepinone derivatives viaring closing metathesis and its application for human cytidine deaminase inhibitors†

Minkyoung Kim,‡^a Kondaji Gajulapati,‡^a Chorong Kim,^a Hwa Young Jung,^a Jail Goo,^a Kyeong Lee,^b Navneet Kaur,^c Hyo Jin Kang,^d Sang J. Chung*^d and Yongseok Choi*^a

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* Corresponding authors

^a College of Life Sciences and Biotechnology, Korea University, Seoul 136-701, Korea
E-mail: ychoi@korea.ac.kr
Fax: +82-2-3290-3650
Tel: +82-2-3290-3650

^b College of Pharmacy, Dongguk University-Seoul, Seoul 100-715, Korea

^c Centre for Nanoscience and Nanotechnology, Panjab University, Chandigarh 160014, India

^d BioNanotechnology Research Center, KRIBB and NanoBio Major, UST, Yuseong, Daejeon 305-333, Korea
E-mail: sjchung@kribb.re.kr
Tel: +82-42-860-4362

Abstract

A variety of diazepinone derivatives were prepared from α-amino acids and amino alcohols by a new synthetic methodology based on ring closing metathesis as a key step. The diazepinones were coupled with ribose derivatives to afford novel diazepinone nucleosides. Among them, (4R)-1-ribosyl-4-methyl-3,4-dihydro-1H-1,3-diazepin-2(7H)-one (3) showed a potent inhibitory effect (K_i = 145.97 ± 4.87 nM) against human cytidine deaminase.

Chemical Communications

A facile synthetic route to diazepinone derivatives viaring closing metathesis and its application for human cytidine deaminase inhibitors†

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A facile synthetic route to diazepinone derivatives via ring closing metathesis and its application for human cytidine deaminase inhibitors

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