2-Substitiuted thio- and amino-5,8-dimethoxy-1,4-naphthoquinones as a novel class of acyl-CoA: Cholestrol acyltransferase inhibitors

Gui Nan Shen; Jung Ho Choi; Kondaji Gajulapati; Jee Hyun Lee; Young Kook Kim; Mun Chal Rho; Sang Hun Jung; Kyeong Lee; Sung Sik Han; Gyu Yong Song; Yongseok Choi

doi:10.5012/bkcs.2009.30.5.1088

2-Substitiuted thio- and amino-5,8-dimethoxy-1,4-naphthoquinones as a novel class of acyl-CoA: Cholestrol acyltransferase inhibitors

Gui Nan Shen, Jung Ho Choi, Kondaji Gajulapati, Jee Hyun Lee, Young Kook Kim, Mun Chal Rho, Sang Hun Jung, Kyeong Lee, Sung Sik Han, Gyu Yong Song, Yongseok Choi

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

6 Citations (Scopus)

Abstract

A series of 2-alkyl or 2-arylthio-5,8-dimethoxy-1,4-naphthoquinones (2-Thio-DMNQ, 5a-s) and 2-alkylamino-5,8-dimethoxy-1,4-naphthoquinones (2-Amino-DMNQ, 6a-k) was synthesized and evaluated for their ACAT inhibitory activities. Among them, the 2-dodecylthio-DMNQ 5l and 2-isobutylamidoundodecylthio-DMNQ 5r showed the most potent ACAT inhibitory activities with IC₅₀ value of 22.8 and 24.4 μM, respectively. In a structure-activity relationship study, 2-thio-DMNQs with side chains of carbon number 11 ~ 15 exhibited significant ACAT inhibitory activities.

Original language	English
Pages (from-to)	1088-1092
Number of pages	5
Journal	Bulletin of the Korean Chemical Society
Volume	30
Issue number	5
DOIs	https://doi.org/10.5012/bkcs.2009.30.5.1088
Publication status	Published - 2009

Keywords

Acyl CoA: Cholestrol acyl transferase (ACAT)
Mast cells
Naphthoquinones
Structure-activity relationship

ASJC Scopus subject areas

Chemistry(all)

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10.5012/bkcs.2009.30.5.1088

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Shen, G. N., Choi, J. H., Gajulapati, K., Lee, J. H., Kim, Y. K., Rho, M. C., Jung, S. H., Lee, K., Han, S. S., Song, G. Y., & Choi, Y. (2009). 2-Substitiuted thio- and amino-5,8-dimethoxy-1,4-naphthoquinones as a novel class of acyl-CoA: Cholestrol acyltransferase inhibitors. Bulletin of the Korean Chemical Society, 30(5), 1088-1092. https://doi.org/10.5012/bkcs.2009.30.5.1088

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title = "2-Substitiuted thio- and amino-5,8-dimethoxy-1,4-naphthoquinones as a novel class of acyl-CoA: Cholestrol acyltransferase inhibitors",

abstract = "A series of 2-alkyl or 2-arylthio-5,8-dimethoxy-1,4-naphthoquinones (2-Thio-DMNQ, 5a-s) and 2-alkylamino-5,8-dimethoxy-1,4-naphthoquinones (2-Amino-DMNQ, 6a-k) was synthesized and evaluated for their ACAT inhibitory activities. Among them, the 2-dodecylthio-DMNQ 5l and 2-isobutylamidoundodecylthio-DMNQ 5r showed the most potent ACAT inhibitory activities with IC50 value of 22.8 and 24.4 μM, respectively. In a structure-activity relationship study, 2-thio-DMNQs with side chains of carbon number 11 ~ 15 exhibited significant ACAT inhibitory activities.",

keywords = "Acyl CoA: Cholestrol acyl transferase (ACAT), Mast cells, Naphthoquinones, Structure-activity relationship",

author = "Shen, {Gui Nan} and Choi, {Jung Ho} and Kondaji Gajulapati and Lee, {Jee Hyun} and Kim, {Young Kook} and Rho, {Mun Chal} and Jung, {Sang Hun} and Kyeong Lee and Han, {Sung Sik} and Song, {Gyu Yong} and Yongseok Choi",

year = "2009",

doi = "10.5012/bkcs.2009.30.5.1088",

language = "English",

volume = "30",

pages = "1088--1092",

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T1 - 2-Substitiuted thio- and amino-5,8-dimethoxy-1,4-naphthoquinones as a novel class of acyl-CoA

T2 - Cholestrol acyltransferase inhibitors

AU - Shen, Gui Nan

AU - Choi, Jung Ho

AU - Gajulapati, Kondaji

AU - Lee, Jee Hyun

AU - Kim, Young Kook

AU - Rho, Mun Chal

AU - Jung, Sang Hun

AU - Lee, Kyeong

AU - Han, Sung Sik

AU - Song, Gyu Yong

AU - Choi, Yongseok

PY - 2009

Y1 - 2009

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AB - A series of 2-alkyl or 2-arylthio-5,8-dimethoxy-1,4-naphthoquinones (2-Thio-DMNQ, 5a-s) and 2-alkylamino-5,8-dimethoxy-1,4-naphthoquinones (2-Amino-DMNQ, 6a-k) was synthesized and evaluated for their ACAT inhibitory activities. Among them, the 2-dodecylthio-DMNQ 5l and 2-isobutylamidoundodecylthio-DMNQ 5r showed the most potent ACAT inhibitory activities with IC50 value of 22.8 and 24.4 μM, respectively. In a structure-activity relationship study, 2-thio-DMNQs with side chains of carbon number 11 ~ 15 exhibited significant ACAT inhibitory activities.

KW - Acyl CoA: Cholestrol acyl transferase (ACAT)

KW - Mast cells

KW - Naphthoquinones

KW - Structure-activity relationship

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SN - 0253-2964

VL - 30

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JO - Bulletin of the Korean Chemical Society

JF - Bulletin of the Korean Chemical Society

IS - 5

ER -

2-Substitiuted thio- and amino-5,8-dimethoxy-1,4-naphthoquinones as a novel class of acyl-CoA: Cholestrol acyltransferase inhibitors

Abstract

Keywords

ASJC Scopus subject areas

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