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

11 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

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

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10.1021/acscombsci.7b00119

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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

@article{83485942fe45493fbc4be19b8bb673d5,

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

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",

issn = "2156-8952",

publisher = "American Chemical Society",

number = "12",

}

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

TY - JOUR

T1 - Efficient Synthesis of 1,9-Substituted Benzo[h][1,6]naphthyridin-2(1H)-ones and Evaluation of their Plasmodium falciparum Gametocytocidal Activities

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

N2 - 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.

AB - 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.

KW - Torin

KW - benzo[h][1,6]naphthyridin-2(1H)-ones

KW - gametocytocidal activity

KW - malaria

KW - one-pot reaction

KW - quinoline

UR - https://www.scopus.com/pages/publications/85037831371

U2 - 10.1021/acscombsci.7b00119

DO - 10.1021/acscombsci.7b00119

M3 - Article

C2 - 29024590

AN - SCOPUS:85037831371

SN - 2156-8952

VL - 19

SP - 748

EP - 754

JO - ACS Combinatorial Science

JF - ACS Combinatorial Science

IS - 12

ER -

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

Abstract

Keywords

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