2,2-Dimethyl-2H-pyran-derived alkaloids I. Practical synthesis of acronycine and benzo[b]acronycine and their biological properties

A. F.M. Motiur Rahman; Jing Lu Liang; Seung Ho Lee; Jong Keun Son; Mi Ja Jung; Youngjoo Kwon; Yurngdong Jahng

doi:10.1007/s12272-001-1273-7

2,2-Dimethyl-2H-pyran-derived alkaloids I. Practical synthesis of acronycine and benzo[b]acronycine and their biological properties

A. F.M. Motiur Rahman, Jing Lu Liang, Seung Ho Lee, Jong Keun Son, Mi Ja Jung, Youngjoo Kwon, Yurngdong Jahng

Department of Pharmaceutical Sciences

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

9 Scopus citations

Abstract

The 2,2-dimethyl-2H-pyran-derived alkaloids acronycine and its demethylated congeners were prepared in three steps from anthranilic acid and phloroglucinol. The phenylboronic acid-mediated interamolecular cyclization reaction of 1,3-dihydroxyacridone and 3-methylbut-2-enal was employed as a key step, which was also applied to the synthesis of related cytotoxic benzo[b]acronycine. Inhibitory activities of the compounds prepared on topoisomerase I and II as well as their cytotoxicities were evaluated. Cytotoxicity of 2 is closely related to the strong inhibitory activity against topo II at 20 μM level.

Original language	English
Pages (from-to)	1087-1093
Number of pages	7
Journal	Archives of Pharmacal Research
Volume	31
Issue number	9
DOIs	https://doi.org/10.1007/s12272-001-1273-7
State	Published - Sep 2008

Keywords

2,2-Dimethyl-2H-pyran-derived alkaloid
Acronycine
Benzo[b]acronycine
Cytotoxicity
Phenylboronic acid
Topoisomerase inhibitor

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10.1007/s12272-001-1273-7

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title = "2,2-Dimethyl-2H-pyran-derived alkaloids I. Practical synthesis of acronycine and benzo[b]acronycine and their biological properties",

abstract = "The 2,2-dimethyl-2H-pyran-derived alkaloids acronycine and its demethylated congeners were prepared in three steps from anthranilic acid and phloroglucinol. The phenylboronic acid-mediated interamolecular cyclization reaction of 1,3-dihydroxyacridone and 3-methylbut-2-enal was employed as a key step, which was also applied to the synthesis of related cytotoxic benzo[b]acronycine. Inhibitory activities of the compounds prepared on topoisomerase I and II as well as their cytotoxicities were evaluated. Cytotoxicity of 2 is closely related to the strong inhibitory activity against topo II at 20 μM level.",

keywords = "2,2-Dimethyl-2H-pyran-derived alkaloid, Acronycine, Benzo[b]acronycine, Cytotoxicity, Phenylboronic acid, Topoisomerase inhibitor",

author = "{Motiur Rahman}, {A. F.M.} and Liang, {Jing Lu} and Lee, {Seung Ho} and Son, {Jong Keun} and Jung, {Mi Ja} and Youngjoo Kwon and Yurngdong Jahng",

year = "2008",

month = sep,

doi = "10.1007/s12272-001-1273-7",

language = "English",

volume = "31",

pages = "1087--1093",

journal = "Archives of Pharmacal Research",

issn = "0253-6269",

publisher = "Pharmaceutical Society of Korea",

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T1 - 2,2-Dimethyl-2H-pyran-derived alkaloids I. Practical synthesis of acronycine and benzo[b]acronycine and their biological properties

AU - Motiur Rahman, A. F.M.

AU - Liang, Jing Lu

AU - Lee, Seung Ho

AU - Son, Jong Keun

AU - Jung, Mi Ja

AU - Kwon, Youngjoo

AU - Jahng, Yurngdong

PY - 2008/9

Y1 - 2008/9

N2 - The 2,2-dimethyl-2H-pyran-derived alkaloids acronycine and its demethylated congeners were prepared in three steps from anthranilic acid and phloroglucinol. The phenylboronic acid-mediated interamolecular cyclization reaction of 1,3-dihydroxyacridone and 3-methylbut-2-enal was employed as a key step, which was also applied to the synthesis of related cytotoxic benzo[b]acronycine. Inhibitory activities of the compounds prepared on topoisomerase I and II as well as their cytotoxicities were evaluated. Cytotoxicity of 2 is closely related to the strong inhibitory activity against topo II at 20 μM level.

AB - The 2,2-dimethyl-2H-pyran-derived alkaloids acronycine and its demethylated congeners were prepared in three steps from anthranilic acid and phloroglucinol. The phenylboronic acid-mediated interamolecular cyclization reaction of 1,3-dihydroxyacridone and 3-methylbut-2-enal was employed as a key step, which was also applied to the synthesis of related cytotoxic benzo[b]acronycine. Inhibitory activities of the compounds prepared on topoisomerase I and II as well as their cytotoxicities were evaluated. Cytotoxicity of 2 is closely related to the strong inhibitory activity against topo II at 20 μM level.

KW - 2,2-Dimethyl-2H-pyran-derived alkaloid

KW - Acronycine

KW - Benzo[b]acronycine

KW - Cytotoxicity

KW - Phenylboronic acid

KW - Topoisomerase inhibitor

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U2 - 10.1007/s12272-001-1273-7

DO - 10.1007/s12272-001-1273-7

M3 - Article

C2 - 18806949

AN - SCOPUS:52649092382

SN - 0253-6269

VL - 31

SP - 1087

EP - 1093

JO - Archives of Pharmacal Research

JF - Archives of Pharmacal Research

IS - 9

ER -

2,2-Dimethyl-2H-pyran-derived alkaloids I. Practical synthesis of acronycine and benzo[b]acronycine and their biological properties

Abstract

Keywords

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