Synthesis and cytotoxic evaluation of eremophilane sesquiterpene 07H239-A derivatives

Chem Pharm Bull (Tokyo). 2011;59(9):1186-9. doi: 10.1248/cpb.59.1186.

Abstract

Nine new derivatives (6-14) of the eremophilane sesquiterpene 07H239-A (5) were designed and semisynthesized with two types of R-groups by amidation. Most of them were active against five human tumor cell lines, and compounds 6-10 were more potent than the natural product 5. In particular, compounds 6 and 9 exhibited the strongest cytotoxic activity against MDA-MB-435 with IC₅₀ values of 0.91 and 0.96 μM, respectively. Preliminary structure-activity relationships (SARs) analysis indicated that the 14-carboxyl in 5 was an ideal target for chemical modification, and the side chain of 5 might play a necessary role in facilitating their cytotoxic potencies.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / toxicity
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Humans
  • Naphthalenes / chemical synthesis
  • Naphthalenes / chemistry*
  • Naphthalenes / toxicity
  • Polycyclic Sesquiterpenes
  • Sesquiterpenes / chemical synthesis
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / toxicity
  • Structure-Activity Relationship

Substances

  • 07H239-A
  • Antineoplastic Agents
  • Naphthalenes
  • Polycyclic Sesquiterpenes
  • Sesquiterpenes
  • eremophilane compounds