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Synthesis and Antichlamydial Activity of Novel Phenazines

[ Vol. 16 , Issue. 2 ]

Author(s):

Xiaofeng Bao, Xiaowei Yu, Chao Xia, Ningjing Yang, Shengju Yang* and Yu Zhao*   Pages 174 - 181 ( 8 )

Abstract:


Abstract: Background: Chlamydiae are widespread Gram-negative bacteria that cause a number of human diseases. Chlamydia trachomatis is the most prevalent sexually transmitted bacterial pathogen.

Methods: Fourteen novel phenazine derivatives were efficiently synthesized via Buchwald-Hartwig cross coupling reaction and Suzuki reaction from 4-bromo-1-methoxyphenazine. All the derivatives displayed antichlamydial activity with IC50 values from 1.01-19.77 µM against Chlamydia trachomatis D and L2 for inhibiting progeny formation.

Results: C-4 morpholinyl 8a and C-4 phenyl phenazine 9c exhibited stronger antichlamydial activity with no apparent cytotoxicity. Both phenazine derivatives inhibited chlamydial inclusions formation and growth in a dose-dependent manner. They inhibited Chlamydia infection by reducing elementary body infectivity and disturbing Chlamydia growth at the mid-stage of the chlamydial developmental cycle.

Conclusion: Our findings suggest C-4 aryl and C-4 amino phenazine derivatives as promising lead molecules for antichlamydials development.

Keywords:

Phenazine, synthesis, antichlamydial activity, Buchwald-Hartwig, chlamydia, elementary body.

Affiliation:

School of Pharmacy, Nantong University, Nantong 226001, School of Pharmacy, Nantong University, Nantong 226001, School of Pharmacy, Nantong University, Nantong 226001, School of Pharmacy, Nantong University, Nantong 226001, Department of Dermatology and Venereology, Affiliated Hospital of Nantong University, Nantong, School of Pharmacy, Nantong University, Nantong 226001

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