Journal of Medicinal Chemistry

, volume 56 , issue 13 , pages 5473-5494

Synthesis and Antiprotozoal Activity of Dicationic m-Terphenyl and 1,3-Dipyridylbenzene Derivatives

Donald A Patrick ¹

Mohamed Ismail ^{2, 3}

Reem K. Arafa ^{2, 4}

Tanja Wenzler ^{5, 6}

Xiaohua Zhu ⁷

Trupti Pandharkar ⁷

Susan Kilgore Jones ¹

Karl A. Werbovetz ⁷

Reto Brun ^{5, 6}

D. W. Boykin ²

Richard R Tidwell ¹

Hide authors affiliations Show authors affiliations: 7 affiliations

Department of Pathology and Laboratory Medicine, School of Medicine, University of North Carolina, Chapel Hill, North Carolina 27599-7525, United States |

Department of Chemistry and Center for Biotechnology and Drug Design, Georgia State University, Atlanta, Georgia 30303-3083, United States |

Department of Chemistry, College of Science, King Faisal University, Hofuf 31982, Saudi Arabia |

⁴

Department of Medicinal and Pharmaceutical Chemistry, Faculty of Pharmacy, Cairo University, Cairo, Egypt |

⁵

Department of Medical Parasitology and Infection Biology, Swiss Tropical and Public Health Institute, Basel, Switzerland |

⁶

University of Basel, Basel, Switzerland |

⁷

Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, Ohio 43210, United States |

Publication type: Journal Article

Publication date: 2013-06-24

American Chemical Society (ACS)

Journal of Medicinal Chemistry

scimago Q1

wos Q1

SJR: 1.801

CiteScore: 11.5

Impact factor: 6.8

ISSN: 00222623, 15204804

DOI: 10.1021/jm400508e

Copy DOI

PubMed ID: 23795673

Drug Discovery

Molecular Medicine

Abstract

4,4″-Diamidino-m-terphenyl (1) and 36 analogues were prepared and assayed in vitro against T rypanosoma brucei rhodesiense , Trypanosoma cruzi , Plasmodium falciparum , and Leishmania amazonensis . Twenty-three compounds were highly active against T. b. rhodesiense or P. falciparum. Most noteworthy were amidines 1, 10, and 11 with IC50 of 4 nM against T. b. rhodesiense, and dimethyltetrahydropyrimidinyl analogues 4 and 9 with IC50 values of ≤ 3 nM against P. falciparum. Bis-pyridylimidamide derivative 31 was 25 times more potent than benznidazole against T. cruzi and slightly more potent than amphotericin B against L. amazonensis. Terphenyldiamidine 1 and dipyridylbenzene analogues 23 and 25 each cured 4/4 mice infected with T. b. rhodesiense STIB900 with four daily 5 mg/kg intraperitoneal doses, as well as with single doses of ≤ 10 mg/kg. Derivatives 5 and 28 (prodrugs of 1 and 25) each cured 3/4 mice with four daily 25 mg/kg oral doses.

Found

2 citations

Kaiser Marcel

489 publications, 13 881 citations

h-index: 58

University of Basel

Swiss Tropical and Public Health Institute

1 citation

Maslivets Andrey

🥼 🤝

DSc in Chemistry, professor

347 publications, 1 766 citations, 1 review

h-index: 14

Perm State National Research University

Research interests

Organic Chemistry

1 citation

Galeev Andrew

🤝

10 publications, 30 citations

h-index: 3

Perm State National Research University

1 citation

Novikov Alexander

🥼 🤝

PhD in Chemistry

414 publications, 8 235 citations, 261 reviews

h-index: 54

Saint Petersburg State University

Lomonosov Moscow State University

ITMO University

Peoples' Friendship University of Russia

Research interests

Computational chemistry

Machine learning

Non-covalent Interactions

Quantum Chemistry

Reaction mechanisms

Supramolecular chemistry

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GOST |

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GOST Copy

Patrick D. A. et al. Synthesis and Antiprotozoal Activity of Dicationic m-Terphenyl and 1,3-Dipyridylbenzene Derivatives // Journal of Medicinal Chemistry. 2013. Vol. 56. No. 13. pp. 5473-5494.

GOST all authors (up to 50) Copy

Patrick D. A., Ismail M., K. Arafa R., Wenzler T., Zhu X., Pandharkar T., Jones S. K., Werbovetz K. A., Brun R., Boykin D. W., Tidwell R. R. Synthesis and Antiprotozoal Activity of Dicationic m-Terphenyl and 1,3-Dipyridylbenzene Derivatives // Journal of Medicinal Chemistry. 2013. Vol. 56. No. 13. pp. 5473-5494.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/jm400508e

UR - https://doi.org/10.1021/jm400508e

TI - Synthesis and Antiprotozoal Activity of Dicationic m-Terphenyl and 1,3-Dipyridylbenzene Derivatives

T2 - Journal of Medicinal Chemistry

AU - Patrick, Donald A

AU - Ismail, Mohamed

AU - K. Arafa, Reem

AU - Wenzler, Tanja

AU - Zhu, Xiaohua

AU - Pandharkar, Trupti

AU - Jones, Susan Kilgore

AU - Werbovetz, Karl A.

AU - Brun, Reto

AU - Boykin, D. W.

AU - Tidwell, Richard R

PY - 2013

DA - 2013/06/24

PB - American Chemical Society (ACS)

SP - 5473-5494

IS - 13

VL - 56

PMID - 23795673

SN - 0022-2623

SN - 1520-4804

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2013_Patrick,

author = {Donald A Patrick and Mohamed Ismail and Reem K. Arafa and Tanja Wenzler and Xiaohua Zhu and Trupti Pandharkar and Susan Kilgore Jones and Karl A. Werbovetz and Reto Brun and D. W. Boykin and Richard R Tidwell},

title = {Synthesis and Antiprotozoal Activity of Dicationic m-Terphenyl and 1,3-Dipyridylbenzene Derivatives},

journal = {Journal of Medicinal Chemistry},

year = {2013},

volume = {56},

publisher = {American Chemical Society (ACS)},

month = {jun},

url = {https://doi.org/10.1021/jm400508e},

number = {13},

pages = {5473--5494},

doi = {10.1021/jm400508e}

}

MLA

Cite this

MLA Copy

Patrick, Donald A., et al. “Synthesis and Antiprotozoal Activity of Dicationic m-Terphenyl and 1,3-Dipyridylbenzene Derivatives.” Journal of Medicinal Chemistry, vol. 56, no. 13, Jun. 2013, pp. 5473-5494. https://doi.org/10.1021/jm400508e.

Publisher

American Chemical Society (ACS)

Journal

Journal of Medicinal Chemistry

scimago Q1

wos Q1

SJR

1.801

CiteScore

11.5

Impact factor

6.8

ISSN

00222623 (Print)

15204804 (Electronic)