Catalysis by molecular iodine: A rapid synthesis of 1,8-dioxo- octahydroxanthenes and their evaluation as potential anticancer agents

Naveen Mulakayala, P. V.N.S. Murthy, D. Rambabu, Madhu Aeluri, Raju Adepu, G. R. Krishna, C. Malla Reddy, K. R.S. Prasad, M. Chaitanya, Chitta S. Kumar, M. V. Basaveswara Rao, Manojit Pal

Research output: Contribution to journalArticlepeer-review

113 Scopus citations

Abstract

Molecular iodine facilitated the reaction of 5,5-dimethyl-1,3- cyclohexanedione with aromatic aldehydes in iso-propanol affording a variety of 1,8-dioxo-octahydroxanthenes in high yields. Most of the compounds synthesized showed good anti-proliferative properties in vitro against three cancer cell lines and 9-(2-hydroxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H- xanthene-1,8(2H)-dione possessing a 2-hydroxy phenyl group at C-9 position was found to be promising. Further structure elaboration of the same compound and the crystal structure analysis and hydrogen bonding patterns of another compound that is, 9-(4-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H- xanthene-1,8(2H)-dione prepared by using this methodology is presented.

Original languageEnglish
Pages (from-to)2186-2191
Number of pages6
JournalBioorganic and Medicinal Chemistry Letters
Volume22
Issue number6
DOIs
StatePublished - 15 Mar 2012
Externally publishedYes

Keywords

  • 1,8-Dioxo-octahydroxanthene
  • 5,5-Dimethyl-1,3-cyclohexanedione
  • Iodine

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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