Regioselective synthesis of phenanthrenes and evaluation of their anti-oxidant based anti-inflammatory potential

Eur J Med Chem. 2013 Sep:67:454-63. doi: 10.1016/j.ejmech.2013.06.016. Epub 2013 Jun 18.

Abstract

Regioselective synthesis of 9,10-dihydro-2,5-dimethoxyphenanthrene-1,7-diol (1) and 9,10-dihydro-2,7-dimethoxyphenanthrene-1,5-diol (2) was achieved using regioselective methylation, Wittig reaction, intramolecular cyclization and hydrogenation as key steps. The synthesis was successfully completed in total of 15 steps with 3.3% overall yield in case of 1 and in total of 13 steps with 9.0% overall yield in case of 2. All compounds (1-4) showed good antioxidant and anti-inflammatory activity in in vitro assays and these activities were found to be due the presence of phenolic hydroxyl groups.

Keywords: AKQZCVGNQPNGCN-UHFFFAOYSA-N; AYNKAXMSZZZOKZ-UHFFFAOYSA-N; Anti-inflammatory; Anti-oxidant; BONZUBOOGNLLPJ-UHFFFAOYSA-N; CBGNWUINIDQCCM-UHFFFAOYSA-N; CDJDSQVTRDRYNP-UHFFFAOYSA-N; GBESWDWAYNNSLH-UHFFFAOYSA-N; GLJLCZSVSWEONA-UHFFFAOYSA-N; GWRPDZYHRFTJHI-UHFFFAOYSA-N; HDBBNMLLPKIKGK-UHFFFAOYSA-N; IOKUVQZOQGQLJX-UHFFFAOYSA-N; IUEQPFFUSKONCU-UHFFFAOYSA-N; JLYSWVJOEWQBMD-UHFFFAOYSA-N; JXHACMBYZZWSEG-UHFFFAOYSA-N; KCNZQSQLCOWRRP-UHFFFAOYSA-N; KHBXSVKLBOMJAD-UHFFFAOYSA-N; KRIPXDLNXPJDKZ-UHFFFAOYSA-N; KXBGOVZWCRLLOR-UHFFFAOYSA-N; LVUPFFBOVAMKQT-UHFFFAOYSA-N; LXOUJONCKZPDKA-UHFFFAOYSA-N; MKLFXDXNXORURG-MSUUIHNZSA-N; NRQGIQXMGQQHFZ-MSUUIHNZSA-N; ODJKEUWVBSQHIZ-UHFFFAOYSA-N; OKMISEPAUVGQMZ-UHFFFAOYSA-N; OQIGXCSBMYVDOZ-UHFFFAOYSA-N; PVWBMFLLBACRJL-UHFFFAOYSA-N; Regioselective synthesis; SOHTUOALNFQEMJ-UHFFFAOYSA-N; TNF-alpha; TZDOXAQDBDJUMB-UHFFFAOYSA-N; UUUWTNIEFNNIAF-UHFFFAOYSA-N; VHHUBNSVHIMJSD-UHFFFAOYSA-N; VUNWBEIDIFFPMG-UHFFFAOYSA-N; WPNXLBKYYDXMCX-UHFFFAOYSA-N; XCGSVZJXMLVULN-UHFFFAOYSA-N; XLLSFBFZOFIRBQ-UHFFFAOYSA-N; YSSFIGREEVEYNI-UHFFFAOYSA-N; ZUQDIPSVEZOOJE-UHFFFAOYSA-N.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis*
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
  • Antioxidants / chemical synthesis*
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Cell Survival / drug effects
  • Humans
  • Lipopolysaccharides / antagonists & inhibitors
  • Lipopolysaccharides / pharmacology
  • Molecular Structure
  • Phenanthrenes / chemical synthesis*
  • Phenanthrenes / chemistry
  • Phenanthrenes / pharmacology*
  • Stereoisomerism
  • Tumor Cells, Cultured
  • Tumor Necrosis Factor-alpha / antagonists & inhibitors
  • Tumor Necrosis Factor-alpha / biosynthesis

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Antioxidants
  • Lipopolysaccharides
  • Phenanthrenes
  • Tumor Necrosis Factor-alpha