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Quantitative Structure–Cytotoxicity Relationship of Bioactive Heterocycles by the Semi-empirical Molecular Orbital Method with the Concept of Absolute Hardness

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Bioactive Heterocycles VII

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 16))

Abstract

The relationship between the cytotoxicity of N-heterocycles (13 4-trifluoromethylimidazole, 15 phenoxazine and 12 5-trifluoromethyloxazole derivatives), O-heterocycles (11 3-formylchromone and 20 coumarin derivatives) and seven vitamin K2 derivatives against eight tumor cell lines (HSC-2, HSC-3, HSC-4, T98G, HSG, HepG2, HL-60, MT-4) and a maximum of 15 chemical descriptors was investigated using CAChe Worksystem 4.9 project reader. After determination of the conformation of these compounds and approximation to the molecular form present in vivo (biomimetic) by CONFLEX5, the most stable structure was determined by CAChe Worksystem 4.9 MOPAC (PM3). The present study demonstrates the best relationship between the cytotoxic activity and molecular shape or molecular weight of these compounds. Their biological activities can be estimated by hardness and softness, and by using η–χ activity diagrams.

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Author information

Authors and Affiliations

  1. Division of Basic Chemistry, Department of Oral Biology and Tissue Engineering, Meikai University School of Dentistry, Sakado, 350-0283, Saitama, Japan

    Mariko Ishihara

  2. Division of Pharmacology, Meikai University School of Dentistry, Sakado, 350-0283, Saitama, Japan

    Hiroshi Sakagami

  3. Faculty of Pharmaceutical Sciences, Matsuyama University, Matsuyama, 790-8578, Ehime, Japan

    Masami Kawase

  4. Meiji Pharmaceutical University, Kiyose, 204-8588, Tokyo, Japan

    Noboru Motohashi

Authors
  1. Mariko Ishihara
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  2. Hiroshi Sakagami
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  3. Masami Kawase
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  4. Noboru Motohashi
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Corresponding author

Correspondence to Mariko Ishihara .

Editor information

Noboru Motohashi

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Ishihara, M., Sakagami, H., Kawase, M., Motohashi, N. (2008). Quantitative Structure–Cytotoxicity Relationship of Bioactive Heterocycles by the Semi-empirical Molecular Orbital Method with the Concept of Absolute Hardness. In: Motohashi, N. (eds) Bioactive Heterocycles VII. Topics in Heterocyclic Chemistry, vol 16. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2007_100

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