Design, synthesis and anticancer activity of novel dihydrobenzofuro[4,5-b] [1,8]naphthyridin-6-one derivatives

Jin Ah Kang; Zunhua Yang; Ji Yeon Lee; Umasankal De; Tae Hyung Kim; Ji Young Park; Hye Jin Lee; Yun Jung Park; Pusoon Chun; Hyung Sik Kim; Lak Shin Jeong; Hyung Ryong Moon

doi:10.1016/j.bmcl.2011.08.016

Design, synthesis and anticancer activity of novel dihydrobenzofuro[4,5-b] [1,8]naphthyridin-6-one derivatives

Jin Ah Kang, Zunhua Yang, Ji Yeon Lee, Umasankal De, Tae Hyung Kim, Ji Young Park, Hye Jin Lee, Yun Jung Park, Pusoon Chun, Hyung Sik Kim, Lak Shin Jeong, Hyung Ryong Moon

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

9 Scopus citations

Abstract

On the basis of the chemical structures of psorospermin with a xanthone template and acronycine derivatives with an acridone template, rac-1 and rac-2 constructed on an 1,2-dihydrobenzofuro[4,5-b][1,8]naphthyridin-6(11H)-one scaffold were designed and synthesized as potential anticancer agents. Their anticancer activities were evaluated against five human cancer cell lines. Rac-2 showed similar anticancer activity to doxorubicin and rac-1 exhibited even higher anticancer activity against LNCaP (IC ₅₀ = 0.14 μM), DU145 (IC ₅₀ = 0.15 μM), PC3 (IC ₅₀ = 0.30 μM) and MCF-7 (IC ₅₀ = 0.26 μM) cancer lines than doxorubicin and rac-2. Also, rac-1 revealed very potent anticancer activity (IC ₅₀ = 0.15 μM) against MCF-7/ADR cell (doxorubicin-resistant breast cancer cell) lines and induced G2/M phase arrest of the cell cycle in MCF-7/ADR cells.

Original language	English
Pages (from-to)	5730-5734
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	21
Issue number	19
DOIs	https://doi.org/10.1016/j.bmcl.2011.08.016
State	Published - 1 Oct 2011
Externally published	Yes

Keywords

Anticancer activity
Dihydrobenzofuro[4,5-b][1,8]naphthyridin-6-one
Epoxide
G2/M phase arrest

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.bmcl.2011.08.016

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title = "Design, synthesis and anticancer activity of novel dihydrobenzofuro[4,5-b] [1,8]naphthyridin-6-one derivatives",

abstract = "On the basis of the chemical structures of psorospermin with a xanthone template and acronycine derivatives with an acridone template, rac-1 and rac-2 constructed on an 1,2-dihydrobenzofuro[4,5-b][1,8]naphthyridin-6(11H)-one scaffold were designed and synthesized as potential anticancer agents. Their anticancer activities were evaluated against five human cancer cell lines. Rac-2 showed similar anticancer activity to doxorubicin and rac-1 exhibited even higher anticancer activity against LNCaP (IC 50 = 0.14 μM), DU145 (IC 50 = 0.15 μM), PC3 (IC 50 = 0.30 μM) and MCF-7 (IC 50 = 0.26 μM) cancer lines than doxorubicin and rac-2. Also, rac-1 revealed very potent anticancer activity (IC 50 = 0.15 μM) against MCF-7/ADR cell (doxorubicin-resistant breast cancer cell) lines and induced G2/M phase arrest of the cell cycle in MCF-7/ADR cells.",

keywords = "Anticancer activity, Dihydrobenzofuro[4,5-b][1,8]naphthyridin-6-one, Epoxide, G2/M phase arrest",

author = "Kang, \{Jin Ah\} and Zunhua Yang and Lee, \{Ji Yeon\} and Umasankal De and Kim, \{Tae Hyung\} and Park, \{Ji Young\} and Lee, \{Hye Jin\} and Park, \{Yun Jung\} and Pusoon Chun and Kim, \{Hyung Sik\} and Jeong, \{Lak Shin\} and Moon, \{Hyung Ryong\}",

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doi = "10.1016/j.bmcl.2011.08.016",

language = "English",

volume = "21",

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number = "19",

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T1 - Design, synthesis and anticancer activity of novel dihydrobenzofuro[4,5-b] [1,8]naphthyridin-6-one derivatives

AU - Kang, Jin Ah

AU - Yang, Zunhua

AU - Lee, Ji Yeon

AU - De, Umasankal

AU - Kim, Tae Hyung

AU - Park, Ji Young

AU - Lee, Hye Jin

AU - Park, Yun Jung

AU - Chun, Pusoon

AU - Kim, Hyung Sik

AU - Jeong, Lak Shin

AU - Moon, Hyung Ryong

PY - 2011/10/1

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N2 - On the basis of the chemical structures of psorospermin with a xanthone template and acronycine derivatives with an acridone template, rac-1 and rac-2 constructed on an 1,2-dihydrobenzofuro[4,5-b][1,8]naphthyridin-6(11H)-one scaffold were designed and synthesized as potential anticancer agents. Their anticancer activities were evaluated against five human cancer cell lines. Rac-2 showed similar anticancer activity to doxorubicin and rac-1 exhibited even higher anticancer activity against LNCaP (IC 50 = 0.14 μM), DU145 (IC 50 = 0.15 μM), PC3 (IC 50 = 0.30 μM) and MCF-7 (IC 50 = 0.26 μM) cancer lines than doxorubicin and rac-2. Also, rac-1 revealed very potent anticancer activity (IC 50 = 0.15 μM) against MCF-7/ADR cell (doxorubicin-resistant breast cancer cell) lines and induced G2/M phase arrest of the cell cycle in MCF-7/ADR cells.

AB - On the basis of the chemical structures of psorospermin with a xanthone template and acronycine derivatives with an acridone template, rac-1 and rac-2 constructed on an 1,2-dihydrobenzofuro[4,5-b][1,8]naphthyridin-6(11H)-one scaffold were designed and synthesized as potential anticancer agents. Their anticancer activities were evaluated against five human cancer cell lines. Rac-2 showed similar anticancer activity to doxorubicin and rac-1 exhibited even higher anticancer activity against LNCaP (IC 50 = 0.14 μM), DU145 (IC 50 = 0.15 μM), PC3 (IC 50 = 0.30 μM) and MCF-7 (IC 50 = 0.26 μM) cancer lines than doxorubicin and rac-2. Also, rac-1 revealed very potent anticancer activity (IC 50 = 0.15 μM) against MCF-7/ADR cell (doxorubicin-resistant breast cancer cell) lines and induced G2/M phase arrest of the cell cycle in MCF-7/ADR cells.

KW - Anticancer activity

KW - Dihydrobenzofuro[4,5-b][1,8]naphthyridin-6-one

KW - Epoxide

KW - G2/M phase arrest

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DO - 10.1016/j.bmcl.2011.08.016

M3 - Article

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SN - 0960-894X

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EP - 5734

JO - Bioorganic and Medicinal Chemistry Letters

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ER -

Design, synthesis and anticancer activity of novel dihydrobenzofuro[4,5-b] [1,8]naphthyridin-6-one derivatives

Abstract

Keywords

UN SDGs

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