Evidences for adduct formation between intracellular non-protein thiols and nitroazoles possessing an α,β-unsaturated carbonyl side chain and the effects on radiosensitization of hypoxic cells

Zhou, Ling; Ino, Akira; Dai, Wei‐Min; Nishimoto, Sei‐ichi

doi:10.1016/s0968-0896(99)00187-x

Cited by 5 publications

(3 citation statements)

References 38 publications

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“…Imidazole and its derivatives, including nitroimidazole, are the compounds that raise continuous interest as biologically active substances [1][2][3][4]. The simplest derivative, 2-nitroimidazole (azomycin), is a natural antibiotic with antitrichomonal activity [5].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and prediction of bioactivity of new nitroimidazole derivatives

Kowalski

Nowak

Szpakiewicz

2005

Journal of Heterocyclic Chem

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Syntheses of 1-propyl derivatives of 2-methyl-5-nitroimidazole (11-17), containing various azanaphthalene systems attached at 3-position of the propyl group have been described. Due to structural similarity of the derivatives 11-17 with metronidazole, an antibacterial and antiprotozoal drug, pharmacological properties of the target compounds were predicted using the PASS program. Polar surface area (PSA) parameter was also applied for estimation of the physical properties of 11-17 as drug-like candidates.

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Section: Introductionmentioning

confidence: 99%

Synthesis and prediction of bioactivity of new nitroimidazole derivatives

Kowalski

Nowak

Szpakiewicz

2005

Journal of Heterocyclic Chem

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show abstract

“…Imidazole and its derivatives, including nitroimidazole, are the compounds that raise continuous interest as biologically active substances [1][2][3][4]. The simplest derivative, 2nitroimidazole (azomycin), is a natural antibiotic with antitrichomonal activity [5].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Prediction of Bioactivity of New Nitroimidazole Derivatives.

2005

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“…7 Previously, we reported a series of nitroazole derivatives containing an a,bunsaturated carbonyl group in the side chains that are able to deplete GSH in tumor cells, thereby resulting in more enhanced hypoxic-cell radiosensitization in vitro relative to a well-documented nitroimidazole radiosensitizers, such as misonidazole. [12][13][14] On the other hand, propargylic sulfones have been identified as prodrugs that undergo isomerization to allenic sulfones with alkylating reactivity for a variety of nucleophiles including DNA bases and thiols. [15][16][17][18] In view of such an alkylating mechanism, propargylic sulfones may be applicable to a family of NPSHdepleting agents.…”

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confidence: 99%