Relationship between electronic structure and cytotoxic activity of tropolones.

A structure-activity relationship of the cytotoxic activity of tropolone derivatives was discussed, using theoretical calculations. In order to clearly divide the tropolones into two structurally analogous groups, four different dipole moments (muG, muESP-G, muW and muESP-W) and heats of formation (deltaHf) of the tropolones [1-21] were calculated in the gas-phase and in water-solution by the conductor-like screening model/parametric method 3 (COSMO/PM3). The cytotoxic activities of the tropolones and 2-methoxytropones seem to be related to the three QSAR parameters deltadeltaHf, HOMO energy (EH) and muw. The cytotoxic activity of the five tropone derivatives [17-21] might depend on the QSAR parameters deltadeltaHf, LUMO energy (EL) and muESP-G. The results of the present study suggest the applicability of theoretical calculations such as frontier molecular orbital, dipole moments and deltadeltaHf in the prediction of the cytotoxic activity of tropolone derivatives.

• Publication year

  2006

• Venue

  In Vivo

• Publication date

  Unknown publication date

• Fields of study

  Medicine, Chemistry

• Identifiers
  PMID 16724677
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Relationship between electronic structure and cytotoxic activity of azulenes.

  2006cited by this paper
• Relationship between electronic structure and cytotoxic activity of dopamine and 3-benzazepine derivatives.

  2004cited by this paper
• Cytotoxic activity of tropolones against human oral tumor cell lines.

  2003cited by this paper
• Cytotoxicity of the hinokitiol-related compounds, gamma-thujaplicin and beta-dolabrin.

  2001cited by this paper
• Cytotoxicity of the Hinokitiol-Related Compounds, γ-Thujaplicin and β-Dolabrin

  2001cited by this paper
• Antifungal activity of Hinokitiol-related compounds on wood-rotting fungi and their insecticidal activities.

  2000cited by this paper
• Phytogrowth-Inhibitory activities of beta-dolabrin and gamma-thujaplicin, hinokitiol-related compounds and constituents of Thujopsis dolabrata Sieb. et Zucc. var hondai Makino.

  2000cited by this paper
• Phytogrowth-inhibitory activities of β-dolabrin and γ-thujaplicin, hinokitiol-related compounds and constituents of Thujopsis dolabrata Sieb. et Zucc. var hondai MAKINO.

  2000cited by this paper
• Antimicrobial activity and metalloprotease inhibition of hinokitiol-related compounds, the constituents of Thujopsis dolabrata S. and Z. hondai MAK.

  1999cited by this paper
• Analysis of structure-permeability correlation of nitrophenol analogues in newborn rat abdominal skin using semiempirical molecular orbital calculation.

  1999cited by this paper
• Cytotoxic effect of hinokitiol and tropolone on the growth of mammalian cells and on blastogenesis of mouse splenic T cells.

  1993cited by this paper
• Phytogrowth-Inhibitory Activities of Tropolone and Hinokitiol

  1991cited by this paper
• Catechol O-methyltransferase. 1. Kinetics of tropolone inhibition.

  1973cited by this paper

• Discovery of New Hits as Antitrypanosomal Agents by In Silico and In Vitro Assays Using Neolignan-Inspired Natural Products from Nectandra leucantha

  2021cites this paper
• Tumor-specific cytotoxicity and type of cell death induced by naphtho[2,3-b]furan-4,9-diones and related compounds in human tumor cell lines: relationship to electronic structure.

  2009cites this paper
• Relationship between electronic structure and cytotoxic activity of azulenequinones and trihaloacetylazulenes.

  2007cites this paper
• Metal chelators as antiviral agents.

  2007cites this paper
• Plant troponoids: chemistry, biological activity, and biosynthesis.

  2007cites this paper