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

Department of Pharmacy

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

6 Scopus citations

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
State	Published - 2009

Keywords

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

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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

@article{06670622bb4044959322fbc4de6bc36a,

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 \textasciitilde{} 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",

journal = "Bulletin of the Korean Chemical Society",

issn = "0253-2964",

publisher = "Wiley-Blackwell",

number = "5",

}

TY - JOUR

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

N2 - 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.

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

UR - https://www.scopus.com/pages/publications/70349730363

U2 - 10.5012/bkcs.2009.30.5.1088

DO - 10.5012/bkcs.2009.30.5.1088

M3 - Article

AN - SCOPUS:70349730363

SN - 0253-2964

VL - 30

SP - 1088

EP - 1092

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

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