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. 2023 Oct 14;22(1):e137969.
doi: 10.5812/ijpr-137969. eCollection 2023 Jan-Dec.

Synthesis and Biological Evaluation of New Nitroimidazole Derivatives as Anti- Helicobacter pylori Agents Against Metronidazole-Resistant Strains

Zahra Bayati  1 , Salimeh Amidi  1 , Mahnaz Shahabimehr  2 , Masoud Alebouyeh  3 , Arash Mahboubi  4 , Sayyed Abbas Tabatabai  1   5
Affiliations

Synthesis and Biological Evaluation of New Nitroimidazole Derivatives as Anti- Helicobacter pylori Agents Against Metronidazole-Resistant Strains

Zahra Bayati et al. Iran J Pharm Res. .

Abstract

Since several Helicobacter pylori strains have become resistant to metronidazole, new nitroimidazole derivatives based on metronidazole were designed and synthesized with different substituents on imidazole nitrogen. The activity of the synthesized compounds was evaluated against 20 clinically isolated metronidazole-resistant H. pylori strains. Some synthesized compounds were effective against those metronidazole-resistant H. pylori strains. Three compounds exhibited the most potent inhibitory activities (MIC50 = 8 µg/mL and MIC90 = 16 µg/mL).

Keywords: Helicobacter pylori; Metronidazole Resistance; Nitroimidazole Derivatives; Synthesis.

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Conflict of interest statement

The authors have no conflict of interest.

Figures

Figure 1.
Figure 1.. Structure of designed compounds
Figure 2.
Figure 2.. Reagents and conditions: A, Phthalimide, PPh3, DIAD, dry THF, Stir at rt; B, Hydroxyphthalimide, PPh3, DIAD, dry THF, Stir at rt; C, Succinimide, PPh3, DIAD, dry THF, Stir at 0ºC; D, Benzenesulfonyl chloride, dry pyridine, stir at rt; E, HBr, Reflux 16 h; F, Benzoyl chloride derivatives, dry THF, Et3N, stir 5 h; G, NaN3, Xylene, crown ether, water, Et3N, reflux 48 h; H, Piperazine, NaHCO3, reflux 24 h; I, Oxalyl chloride, DMSO, Et3N, stir at -50ºC; J, N-aminophthalimide, dioxane, acetic acid, reflux.
See this image and copyright information in PMC

References

    1. Vaziri F, Najar Peerayeh S, Alebouyeh M, Mirzaei T, Yamaoka Y, Molaei M, et al. Diversity of Helicobacter pylori genotypes in Iranian patients with different gastroduodenal disorders. World J Gastroenterol. 2013;19(34):5685–92. doi: 10.3748/wjg.v19.i34.5685. - DOI - PMC - PubMed
    1. Ebrahimi Daryani N, Taher M, Shirzad S. Helicobacter Pylori Infection: A Review. Arch Clin Infect Dis. 2011;6(1):56–64.
    1. Farzi N, Malekian T, Alebouyeh M, Vaziri F, Zali MR. Genotype Diversity and Quasispecies Development of Helicobacter pylori in a Single Host. Jpn J Infect Dis. 2015;68(3):176–80. doi: 10.7883/yoken.JJID.2014.165. - DOI - PubMed
    1. Rokkas T, Karameris A, Mavrogeorgis A, Rallis E, Giannikos N. Eradication of Helicobacter pylori reduces the possibility of rebleeding in peptic ulcer disease. Gastrointest Endosc. 1995;41(1):1–4. doi: 10.1016/s0016-5107(95)70266-0. - DOI - PubMed
    1. Chan FK, To KF, Wu JC, Yung MY, Leung WK, Kwok T, et al. Eradication of Helicobacter pylori and risk of peptic ulcers in patients starting long-term treatment with non-steroidal anti-inflammatory drugs: A randomised trial. Lancet. 2002;359(9300):9–13. doi: 10.1016/s0140-6736(02)07272-0. - DOI - PubMed

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