Synthesis and Biological Properties of Luotonin a Derivatives

A. F.M.Motiur Rahman; Hyeon Kim Dong; Lu Liang Jing; Eung Seok Lee; Younghwa Na; Kyu Yeon Jun; Youngjoo Kwon; Yurngdong Jahng

doi:10.5012/bkcs.2008.29.10.1988

Synthesis and Biological Properties of Luotonin a Derivatives

A. F.M.Motiur Rahman, Hyeon Kim Dong, Lu Liang Jing, Eung Seok Lee, Younghwa Na, Kyu Yeon Jun, Youngjoo Kwon, Yurngdong Jahng

Department of Pharmaceutical Sciences

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

21 Scopus citations

Abstract

A series of new derivatives on the ring A of luotonin A were prepared by Friedländer condensation of 6,7,8,10-tetrahydropyrrolo[2,1-b]quinazoline-6, 10-dione and suitably substituted 2-aminobenzaldehydes and 2-aminoacetophenones. Their inhibitory activities on topoisomerases and cytotoxicities against selected human cancer cell lines were evaluated. Among the compounds tested, 8-fluoroluotonin A showed similar inhibitory activity on topoisomerase I comparable to camptothecin while luotonin A and 9-hydroxyluotonin A showed 1.37 and 0.94 times stronger inhibitory activity, respectively, on topoisomerase II compared to etoposide. Some derivatives of luotonin A showed moderate cytotoxicity. The possible relationship between the inhibitory activity on Topo II and the cytotoxicity of luotonin A and its analogues, thus, cannot be ruled out.

Original language	English
Pages (from-to)	1988-1992
Number of pages	5
Journal	Bulletin of the Korean Chemical Society
Volume	29
Issue number	10
DOIs	https://doi.org/10.5012/bkcs.2008.29.10.1988
State	Published - 20 Oct 2008

Keywords

Cytotoxicity
Friedländer reaction
Luotonin A
Topoisomerase I
Topoisomerase II

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

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10.5012/bkcs.2008.29.10.1988

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title = "Synthesis and Biological Properties of Luotonin a Derivatives",

abstract = "A series of new derivatives on the ring A of luotonin A were prepared by Friedl{\"a}nder condensation of 6,7,8,10-tetrahydropyrrolo[2,1-b]quinazoline-6, 10-dione and suitably substituted 2-aminobenzaldehydes and 2-aminoacetophenones. Their inhibitory activities on topoisomerases and cytotoxicities against selected human cancer cell lines were evaluated. Among the compounds tested, 8-fluoroluotonin A showed similar inhibitory activity on topoisomerase I comparable to camptothecin while luotonin A and 9-hydroxyluotonin A showed 1.37 and 0.94 times stronger inhibitory activity, respectively, on topoisomerase II compared to etoposide. Some derivatives of luotonin A showed moderate cytotoxicity. The possible relationship between the inhibitory activity on Topo II and the cytotoxicity of luotonin A and its analogues, thus, cannot be ruled out.",

keywords = "Cytotoxicity, Friedl{\"a}nder reaction, Luotonin A, Topoisomerase I, Topoisomerase II",

author = "Rahman, {A. F.M.Motiur} and Dong, {Hyeon Kim} and Jing, {Lu Liang} and Lee, {Eung Seok} and Younghwa Na and Jun, {Kyu Yeon} and Youngjoo Kwon and Yurngdong Jahng",

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doi = "10.5012/bkcs.2008.29.10.1988",

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T1 - Synthesis and Biological Properties of Luotonin a Derivatives

AU - Rahman, A. F.M.Motiur

AU - Dong, Hyeon Kim

AU - Jing, Lu Liang

AU - Lee, Eung Seok

AU - Na, Younghwa

AU - Jun, Kyu Yeon

AU - Kwon, Youngjoo

AU - Jahng, Yurngdong

PY - 2008/10/20

Y1 - 2008/10/20

N2 - A series of new derivatives on the ring A of luotonin A were prepared by Friedländer condensation of 6,7,8,10-tetrahydropyrrolo[2,1-b]quinazoline-6, 10-dione and suitably substituted 2-aminobenzaldehydes and 2-aminoacetophenones. Their inhibitory activities on topoisomerases and cytotoxicities against selected human cancer cell lines were evaluated. Among the compounds tested, 8-fluoroluotonin A showed similar inhibitory activity on topoisomerase I comparable to camptothecin while luotonin A and 9-hydroxyluotonin A showed 1.37 and 0.94 times stronger inhibitory activity, respectively, on topoisomerase II compared to etoposide. Some derivatives of luotonin A showed moderate cytotoxicity. The possible relationship between the inhibitory activity on Topo II and the cytotoxicity of luotonin A and its analogues, thus, cannot be ruled out.

AB - A series of new derivatives on the ring A of luotonin A were prepared by Friedländer condensation of 6,7,8,10-tetrahydropyrrolo[2,1-b]quinazoline-6, 10-dione and suitably substituted 2-aminobenzaldehydes and 2-aminoacetophenones. Their inhibitory activities on topoisomerases and cytotoxicities against selected human cancer cell lines were evaluated. Among the compounds tested, 8-fluoroluotonin A showed similar inhibitory activity on topoisomerase I comparable to camptothecin while luotonin A and 9-hydroxyluotonin A showed 1.37 and 0.94 times stronger inhibitory activity, respectively, on topoisomerase II compared to etoposide. Some derivatives of luotonin A showed moderate cytotoxicity. The possible relationship between the inhibitory activity on Topo II and the cytotoxicity of luotonin A and its analogues, thus, cannot be ruled out.

KW - Cytotoxicity

KW - Friedländer reaction

KW - Luotonin A

KW - Topoisomerase I

KW - Topoisomerase II

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U2 - 10.5012/bkcs.2008.29.10.1988

DO - 10.5012/bkcs.2008.29.10.1988

M3 - Article

AN - SCOPUS:55249090178

SN - 0253-2964

VL - 29

SP - 1988

EP - 1992

JO - Bulletin of the Korean Chemical Society

JF - Bulletin of the Korean Chemical Society

IS - 10

ER -

Synthesis and Biological Properties of Luotonin a Derivatives

Abstract

Keywords

UN SDGs

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