Facile formation of hydrophilic derivatives of 5H-8,9-dimethoxy-5-[2-(N,N-dimethylamino)ethyl]-2,3-methylenedioxydibenzo[c,h] [1,6]naphthyridin-6-one (ARC-111) and its 12-aza analog via quaternary ammonium intermediates

Wei Feng; Mavurapu Satyanarayana; Yuan chin Tsai; Angela A. Liu; Leroy F. Liu; Edmond J. LaVoie

doi:10.1016/j.bmcl.2008.05.005

Facile formation of hydrophilic derivatives of 5H-8,9-dimethoxy-5-[2-(N,N-dimethylamino)ethyl]-2,3-methylenedioxydibenzo[c,h] [1,6]naphthyridin-6-one (ARC-111) and its 12-aza analog via quaternary ammonium intermediates

Wei Feng, Mavurapu Satyanarayana, Yuan chin Tsai, Angela A. Liu, Leroy F. Liu, Edmond J. LaVoie

Ernest Mario School of Pharmacy, Medicinal Chemistry

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

12 Scopus citations

Abstract

Several new TOP1-targeting agents were prepared using as intermediates the N,N,N-trimethyl quaternary ammonium salts of either ARC-111 or its 12-aza analog (ARC-31), 3 and 4, respectively. Direct displacement of the quaternary ammonium group with water, imidazole, alkylethylenediamines, or polyhydroxylated alkylamines provides a convenient means for furthering the structure-activity relationships associated with these non-camptothecin TOP1-targeting agents.

Original language	English (US)
Pages (from-to)	3570-3572
Number of pages	3
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	18
Issue number	12
DOIs	https://doi.org/10.1016/j.bmcl.2008.05.005
State	Published - Jun 15 2008

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

Keywords

ARC-111
ARC-31
Antitumor
Cytotoxicity
Dibenzo[c,h][1,6]naphthyridin-6-ones
Isoquino[4,3-c]cinnoline-12-ones
Quaternary ammonium salts
Topoisomerase I

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Feng, W., Satyanarayana, M., Tsai, Y. C., Liu, A. A., Liu, L. F., & LaVoie, E. J. (2008). Facile formation of hydrophilic derivatives of 5H-8,9-dimethoxy-5-[2-(N,N-dimethylamino)ethyl]-2,3-methylenedioxydibenzo[c,h] [1,6]naphthyridin-6-one (ARC-111) and its 12-aza analog via quaternary ammonium intermediates. Bioorganic and Medicinal Chemistry Letters, 18(12), 3570-3572. https://doi.org/10.1016/j.bmcl.2008.05.005

Feng, Wei ; Satyanarayana, Mavurapu ; Tsai, Yuan chin et al. / Facile formation of hydrophilic derivatives of 5H-8,9-dimethoxy-5-[2-(N,N-dimethylamino)ethyl]-2,3-methylenedioxydibenzo[c,h] [1,6]naphthyridin-6-one (ARC-111) and its 12-aza analog via quaternary ammonium intermediates. In: Bioorganic and Medicinal Chemistry Letters. 2008 ; Vol. 18, No. 12. pp. 3570-3572.

@article{ab73fe0c145446bc987dfbf04b497ec0,

title = "Facile formation of hydrophilic derivatives of 5H-8,9-dimethoxy-5-[2-(N,N-dimethylamino)ethyl]-2,3-methylenedioxydibenzo[c,h] [1,6]naphthyridin-6-one (ARC-111) and its 12-aza analog via quaternary ammonium intermediates",

abstract = "Several new TOP1-targeting agents were prepared using as intermediates the N,N,N-trimethyl quaternary ammonium salts of either ARC-111 or its 12-aza analog (ARC-31), 3 and 4, respectively. Direct displacement of the quaternary ammonium group with water, imidazole, alkylethylenediamines, or polyhydroxylated alkylamines provides a convenient means for furthering the structure-activity relationships associated with these non-camptothecin TOP1-targeting agents.",

keywords = "ARC-111, ARC-31, Antitumor, Cytotoxicity, Dibenzo[c,h][1,6]naphthyridin-6-ones, Isoquino[4,3-c]cinnoline-12-ones, Quaternary ammonium salts, Topoisomerase I",

author = "Wei Feng and Mavurapu Satyanarayana and Tsai, {Yuan chin} and Liu, {Angela A.} and Liu, {Leroy F.} and LaVoie, {Edmond J.}",

note = "Funding Information: This study was supported by NIH Grant CA098127 (E.J.L.) and Genzyme Corporation. Mass spectrometry was provided by the Washington University Mass Spectrometry Resource with support from the NIH National Center for Research Resources (Grant No. P41RR0954). ",

year = "2008",

month = jun,

day = "15",

doi = "10.1016/j.bmcl.2008.05.005",

language = "English (US)",

volume = "18",

pages = "3570--3572",

journal = "Bioorganic and Medicinal Chemistry Letters",

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Feng, W, Satyanarayana, M, Tsai, YC, Liu, AA, Liu, LF & LaVoie, EJ 2008, 'Facile formation of hydrophilic derivatives of 5H-8,9-dimethoxy-5-[2-(N,N-dimethylamino)ethyl]-2,3-methylenedioxydibenzo[c,h] [1,6]naphthyridin-6-one (ARC-111) and its 12-aza analog via quaternary ammonium intermediates', Bioorganic and Medicinal Chemistry Letters, vol. 18, no. 12, pp. 3570-3572. https://doi.org/10.1016/j.bmcl.2008.05.005

Facile formation of hydrophilic derivatives of 5H-8,9-dimethoxy-5-[2-(N,N-dimethylamino)ethyl]-2,3-methylenedioxydibenzo[c,h] [1,6]naphthyridin-6-one (ARC-111) and its 12-aza analog via quaternary ammonium intermediates. / Feng, Wei; Satyanarayana, Mavurapu; Tsai, Yuan chin et al.
In: Bioorganic and Medicinal Chemistry Letters, Vol. 18, No. 12, 15.06.2008, p. 3570-3572.

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

TY - JOUR

T1 - Facile formation of hydrophilic derivatives of 5H-8,9-dimethoxy-5-[2-(N,N-dimethylamino)ethyl]-2,3-methylenedioxydibenzo[c,h] [1,6]naphthyridin-6-one (ARC-111) and its 12-aza analog via quaternary ammonium intermediates

AU - Feng, Wei

AU - Satyanarayana, Mavurapu

AU - Tsai, Yuan chin

AU - Liu, Angela A.

AU - Liu, Leroy F.

AU - LaVoie, Edmond J.

N1 - Funding Information: This study was supported by NIH Grant CA098127 (E.J.L.) and Genzyme Corporation. Mass spectrometry was provided by the Washington University Mass Spectrometry Resource with support from the NIH National Center for Research Resources (Grant No. P41RR0954).

PY - 2008/6/15

Y1 - 2008/6/15

N2 - Several new TOP1-targeting agents were prepared using as intermediates the N,N,N-trimethyl quaternary ammonium salts of either ARC-111 or its 12-aza analog (ARC-31), 3 and 4, respectively. Direct displacement of the quaternary ammonium group with water, imidazole, alkylethylenediamines, or polyhydroxylated alkylamines provides a convenient means for furthering the structure-activity relationships associated with these non-camptothecin TOP1-targeting agents.

AB - Several new TOP1-targeting agents were prepared using as intermediates the N,N,N-trimethyl quaternary ammonium salts of either ARC-111 or its 12-aza analog (ARC-31), 3 and 4, respectively. Direct displacement of the quaternary ammonium group with water, imidazole, alkylethylenediamines, or polyhydroxylated alkylamines provides a convenient means for furthering the structure-activity relationships associated with these non-camptothecin TOP1-targeting agents.

KW - ARC-111

KW - ARC-31

KW - Antitumor

KW - Cytotoxicity

KW - Dibenzo[c,h][1,6]naphthyridin-6-ones

KW - Isoquino[4,3-c]cinnoline-12-ones

KW - Quaternary ammonium salts

KW - Topoisomerase I

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U2 - 10.1016/j.bmcl.2008.05.005

DO - 10.1016/j.bmcl.2008.05.005

M3 - Article

C2 - 18511275

AN - SCOPUS:44649191682

SN - 0960-894X

VL - 18

SP - 3570

EP - 3572

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 12

ER -

Feng W, Satyanarayana M, Tsai YC, Liu AA, Liu LF, LaVoie EJ. Facile formation of hydrophilic derivatives of 5H-8,9-dimethoxy-5-[2-(N,N-dimethylamino)ethyl]-2,3-methylenedioxydibenzo[c,h] [1,6]naphthyridin-6-one (ARC-111) and its 12-aza analog via quaternary ammonium intermediates. Bioorganic and Medicinal Chemistry Letters. 2008 Jun 15;18(12):3570-3572. doi: 10.1016/j.bmcl.2008.05.005

Facile formation of hydrophilic derivatives of 5H-8,9-dimethoxy-5-[2-(N,N-dimethylamino)ethyl]-2,3-methylenedioxydibenzo[c,h] [1,6]naphthyridin-6-one (ARC-111) and its 12-aza analog via quaternary ammonium intermediates

Abstract

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Keywords

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