Correlation of Antitumor Activity and Electron Deficiency of Nitrofuranylhydrazone Compounds

Newman, Robert A.; Strauss, Michael J.; Renfrow, Richard

doi:10.1002/jps.2600710731

Cited by 3 publications

(1 citation statement)

References 13 publications

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“…Calculations at a low level of theory of some derivatives (3‐NH2, 5‐CH3, 5‐F, 5‐NO2, 6‐CH3; see Table 1) and NMR studies (3‐CH3, 3‐NH2, 4‐CH3, 6‐NH2, 6‐F) have been previously published 6, 15–25. In particular, 5‐CH3 and 5‐NO2 have been widely studied due to environmental implications and their pharmacological applications 26–35…”

Section: Introductionmentioning

confidence: 99%

Theoretical model of internal rotation in monosubstituted derivatives of furfural

et al. 2003

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The present work explores the effect of substitution in all free positions of furfural on conformational preferences of formyl group by using ab-initio calculations at the MP2/6-31G(p,d) level of theory. Theoretical modeling was made in vacuo. The selected substituents were -CH(3), NH(2), NO(2) and F groups in 3, 4, 5 and ipso carbonyl positions. Geometries of all derivatives were analyzed and it is ascertained that substitution has not important consequences on furan ring geometry. Differences of energy between OO-cis and trans conformers and energy barriers between them are described and extreme cases are explained. Interesting features appear in the cases of -NH(2) and -NO(2) groups, and particularly when the 3 and ipso carbonyl positions are substituted. Variations in energy barriers are correlated with variations in C2-C6 distances for the transition states and planar forms. Substitution effect on Mülliken charges are analyzed and related with internal rotation energy barriers and differences between conformers.

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Section: Introductionmentioning

confidence: 99%

Theoretical model of internal rotation in monosubstituted derivatives of furfural

et al. 2003

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Nitrofurazone repurposing towards design and synthesis of novel apoptotic-dependent anticancer and antimicrobial agents: Biological evaluation, kinetic studies and molecular modeling

El-Wakil

Meheissen

Abu‐Serie

2021

Bioorganic Chemistry

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The Effect of Nitrofurantoin on Bladder Tumor Cell Lines: In Vitro Growth and Implantation in the Cauterized Mouse Bladder

et al. 1985

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Nitrofurans compounds and derivatives demonstrate antineoplastic activity in vitro as well as in vivo. Nitrofurantoin caused in vitro growth inhibition of a FANFT-induced murine bladder tumor (MBT2) and a human transitional cell carcinoma cell line (GIBB) in concentrations of 125 microM, 250 microM and 500 microM. The implantation and growth of MBT2 in the cauterized mouse bladder was inhibited by 250 microM nitrofurantoin. The bladder mucosa of two groups of C3Hf/HeHa female mice was electrically cauterized. In group I, 1 X 10(6) MBT2 cells were injected into the bladders of 42 mice, while in group II 1 X 10(6) MBT2 cells in 250 microM nitrofurantoin solution were injected into the bladders of 51 mice. Positive tumor implantation was seen in 25 bladders (59.5 per cent) of group I as compared to 15 bladders (29.5 per cent) of group II. All tumors in group I were large, occupying more than 50 per cent of bladder cross sectional area with 24 per cent showing extravesical extention. Sixty-six per cent of tumors in groups II were less than 25 per cent of bladder cross sectional area and 13.4 per cent had extravesical extention.

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Correlation of Antitumor Activity and Electron Deficiency of Nitrofuranylhydrazone Compounds

Cited by 3 publications

References 13 publications

Theoretical model of internal rotation in monosubstituted derivatives of furfural

Theoretical model of internal rotation in monosubstituted derivatives of furfural

Nitrofurazone repurposing towards design and synthesis of novel apoptotic-dependent anticancer and antimicrobial agents: Biological evaluation, kinetic studies and molecular modeling

The Effect of Nitrofurantoin on Bladder Tumor Cell Lines: In Vitro Growth and Implantation in the Cauterized Mouse Bladder

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