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Dihydroporphyrin Synthesis: New Methodology.

Kalyn M. Shea1, Laurent Jaquinod, Kevin M. Smith

  • 1Department of Chemistry, University of California, Davis, California 95616.

The Journal of Organic Chemistry
|October 24, 2001
PubMed
Summary

Researchers selectively synthesized nitrochlorins, cyclopropylchlorins, and functionalized trans-chlorins from tetraphenylporphyrin. Reaction conditions control product formation through Michael additions and nitro group displacement, offering new routes to reduced porphyrins for photodynamic therapy.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry

Background:

  • Porphyrins are crucial macrocyclic compounds with diverse applications, including in photodynamic therapy (PDT).
  • Developing efficient synthetic routes to functionalized porphyrins and their reduced forms is essential for expanding their therapeutic potential.

Purpose of the Study:

  • To achieve selective synthesis of various reduced porphyrin derivatives, including nitrochlorins, cyclopropylchlorins, and trans-chlorins.
  • To investigate the reaction mechanisms and control factors governing the selective formation of these porphyrin products.
  • To explore the potential of these novel reduced porphyrins in applications like cancer treatment via PDT.

Main Methods:

  • Reaction of 2-nitro-5,10,15,20-tetraphenylporphyrin with active methylene compounds (malonates, malononitrile) in the presence of a base.

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  • Utilizing sequential Michael additions followed by intramolecular nucleophilic displacement of a nitro group for reaction control.
  • Employing varying reaction temperatures and sterically hindered/unhindered carbanion substituents to influence product selectivity.

    • Main Results:

    • Selective formation of trans-nitrochlorins, cyclopropylchlorins, and functionalized trans-chlorins was achieved.
    • Reaction outcomes were governed by steric and thermodynamic effects, with temperature and carbanion bulk influencing product distribution.
    • Nucleophilic ring-opening of cyclopropyl-derivatives provided further mechanistic insights and access to disubstituted trans-chlorins.

    Conclusions:

    • A versatile methodology for the synthesis of reduced porphyrins has been established, controlled by reaction conditions.
    • The developed method allows for the preparation of a wide array of functionalized porphyrins.
    • These novel reduced porphyrins show promise for applications in photodynamic therapy (PDT) of cancer.