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

College of Life Sciences and Biotechnology, Korea University, Seoul, Korea.

Chemical communications (Cambridge, England) 2012 Dec 4

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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.

Citation

Minkyoung Kim, Kondaji Gajulapati, Chorong Kim, Hwa Young Jung, Jail Goo, Kyeong Lee, Navneet Kaur, Hyo Jin Kang, Sang J Chung, Yongseok Choi. A facile synthetic route to diazepinone derivatives via ring closing metathesis and its application for human cytidine deaminase inhibitors. Chemical communications (Cambridge, England). 2012 Dec 4;48(93):11443-5