Efficient Synthesis of 1,9-Substituted Benzo[h][1,6]naphthyridin-2(1H)-ones and Evaluation of their Plasmodium falciparum Gametocytocidal Activities

Hao Li; Wei Sun; Xiuli Huang; Xiao Lu; Paresma R. Patel; Myunghoon Kim; Meghan J. Orr; Richard M. Fisher; Takeshi Q. Tanaka; John C. McKew; Anton Simeonov; Philip E. Sanderson; Wei Zheng; Kim C. Williamson; Wenwei Huang

doi:10.1021/acscombsci.7b00119

Efficient Synthesis of 1,9-Substituted Benzo[h][1,6]naphthyridin-2(1H)-ones and Evaluation of their Plasmodium falciparum Gametocytocidal Activities

Hao Li, Wei Sun, Xiuli Huang, Xiao Lu, Paresma R. Patel, Myunghoon Kim, Meghan J. Orr, Richard M. Fisher, Takeshi Q. Tanaka, John C. McKew, Anton Simeonov, Philip E. Sanderson, Wei Zheng, Kim C. Williamson, Wenwei Huang^*

^*Corresponding author for this work

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

10 Scopus citations

Abstract

A novel three-component, two-step, one-pot nucleophilic aromatic substitution (S_NAr)-intramolecular cyclization-Suzuki coupling reaction was developed for the synthesis of benzo[h][1,6]naphthyridin-2(1H)-ones (Torins). On the basis of the new efficiently convergent synthetic route, a library of Torin analogs was synthesized. The antimalarial activities of these compounds were evaluated against asexual parasites using a growth inhibition assay and gametocytes using a viability assay.

Original language	English
Pages (from-to)	748-754
Number of pages	7
Journal	ACS Combinatorial Science
Volume	19
Issue number	12
DOIs	https://doi.org/10.1021/acscombsci.7b00119
State	Published - 11 Dec 2017
Externally published	Yes

Keywords

benzo[h][1,6]naphthyridin-2(1H)-ones
gametocytocidal activity
malaria
one-pot reaction
quinoline
Torin

Access to Document

10.1021/acscombsci.7b00119

Cite this

Li, H., Sun, W., Huang, X., Lu, X., Patel, P. R., Kim, M., Orr, M. J., Fisher, R. M., Tanaka, T. Q., McKew, J. C., Simeonov, A., Sanderson, P. E., Zheng, W., Williamson, K. C., & Huang, W. (2017). Efficient Synthesis of 1,9-Substituted Benzo[h][1,6]naphthyridin-2(1H)-ones and Evaluation of their Plasmodium falciparum Gametocytocidal Activities. ACS Combinatorial Science, 19(12), 748-754. https://doi.org/10.1021/acscombsci.7b00119

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title = "Efficient Synthesis of 1,9-Substituted Benzo[h][1,6]naphthyridin-2(1H)-ones and Evaluation of their Plasmodium falciparum Gametocytocidal Activities",

abstract = "A novel three-component, two-step, one-pot nucleophilic aromatic substitution (SNAr)-intramolecular cyclization-Suzuki coupling reaction was developed for the synthesis of benzo[h][1,6]naphthyridin-2(1H)-ones (Torins). On the basis of the new efficiently convergent synthetic route, a library of Torin analogs was synthesized. The antimalarial activities of these compounds were evaluated against asexual parasites using a growth inhibition assay and gametocytes using a viability assay.",

keywords = "benzo[h][1,6]naphthyridin-2(1H)-ones, gametocytocidal activity, malaria, one-pot reaction, quinoline, Torin",

author = "Hao Li and Wei Sun and Xiuli Huang and Xiao Lu and Patel, {Paresma R.} and Myunghoon Kim and Orr, {Meghan J.} and Fisher, {Richard M.} and Tanaka, {Takeshi Q.} and McKew, {John C.} and Anton Simeonov and Sanderson, {Philip E.} and Wei Zheng and Williamson, {Kim C.} and Wenwei Huang",

note = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2017",

month = dec,

day = "11",

doi = "10.1021/acscombsci.7b00119",

language = "English",

volume = "19",

pages = "748--754",

journal = "ACS Combinatorial Science",

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Li, H, Sun, W, Huang, X, Lu, X, Patel, PR, Kim, M, Orr, MJ, Fisher, RM, Tanaka, TQ, McKew, JC, Simeonov, A, Sanderson, PE, Zheng, W, Williamson, KC & Huang, W 2017, 'Efficient Synthesis of 1,9-Substituted Benzo[h][1,6]naphthyridin-2(1H)-ones and Evaluation of their Plasmodium falciparum Gametocytocidal Activities', ACS Combinatorial Science, vol. 19, no. 12, pp. 748-754. https://doi.org/10.1021/acscombsci.7b00119

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AU - Li, Hao

AU - Sun, Wei

AU - Huang, Xiuli

AU - Lu, Xiao

AU - Patel, Paresma R.

AU - Kim, Myunghoon

AU - Orr, Meghan J.

AU - Fisher, Richard M.

AU - Tanaka, Takeshi Q.

AU - McKew, John C.

AU - Simeonov, Anton

AU - Sanderson, Philip E.

AU - Zheng, Wei

AU - Williamson, Kim C.

AU - Huang, Wenwei

PY - 2017/12/11

Y1 - 2017/12/11

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