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 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

Department of Pharmacy

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

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.

Original language	English
Pages (from-to)	11443-11445
Number of pages	3
Journal	Chemical Communications
Volume	48
Issue number	93
DOIs	https://doi.org/10.1039/c2cc35484e
State	Published - 29 Oct 2012

Access to Document

10.1039/c2cc35484e

Cite this

@article{ab05d9329199401b832130a954c68157,

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

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.",

author = "Minkyoung Kim and Kondaji Gajulapati and Chorong Kim and Jung, {Hwa Young} and Jail Goo and Kyeong Lee and Navneet Kaur and Kang, {Hyo Jin} and Chung, {Sang J.} and Yongseok Choi",

year = "2012",

month = oct,

day = "29",

doi = "10.1039/c2cc35484e",

language = "English",

volume = "48",

pages = "11443--11445",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "93",

}

TY - JOUR

T1 - A facile synthetic route to diazepinone derivatives via ring closing metathesis and its application for human cytidine deaminase inhibitors

AU - Kim, Minkyoung

AU - Gajulapati, Kondaji

AU - Kim, Chorong

AU - Jung, Hwa Young

AU - Goo, Jail

AU - Lee, Kyeong

AU - Kaur, Navneet

AU - Kang, Hyo Jin

AU - Chung, Sang J.

AU - Choi, Yongseok

PY - 2012/10/29

Y1 - 2012/10/29

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=84869057668&partnerID=8YFLogxK

U2 - 10.1039/c2cc35484e

DO - 10.1039/c2cc35484e

M3 - Article

C2 - 23086289

AN - SCOPUS:84869057668

SN - 1359-7345

VL - 48

SP - 11443

EP - 11445

JO - Chemical Communications

JF - Chemical Communications

IS - 93

ER -

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

Abstract

Access to Document

Other files and links

Fingerprint

Cite this