Isostere-based design of 8-azacoumarin-type photolabile protecting groups: a hydrophilicity-increasing strategy for coumarin-4-ylmethyls

Org Lett. 2014 Feb 21;16(4):1184-7. doi: 10.1021/ol5000583. Epub 2014 Feb 4.

Abstract

Described is the development of 8-azacoumarin-4-ylmethyl groups as aqueous photolabile protecting groups. A key feature of the strategy is the isosteric replacement of the C7-C8 enol double bond of the Bhc derivative with an amide bond, resulting in conversion of the chromophore from coumarin to 8-azacoumarin. This strategy makes dramatically enhanced water solubility and facile photocleavage possible.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry
  • Aza Compounds / chemical synthesis*
  • Aza Compounds / chemistry*
  • Coumarins / chemical synthesis*
  • Coumarins / chemistry*
  • Hydrophobic and Hydrophilic Interactions
  • Molecular Structure
  • Photochemistry

Substances

  • Amides
  • Aza Compounds
  • Coumarins