Studies in chlorin chemistry. 3. A practical synthesis of c,d-ring symmetric chlorins of potential utility in photodynamic therapy.
[reaction: see text] C,D-ring symmetric chlorins 8 were prepared in 47-85% yield, on scales up to several hundred milligrams, by condensation of appropriately substituted bis-formyldihydrodipyrrins 6 and dipyrromethane bis-carboxylic acids 7 in 5% TFA/CH2Cl2 (25 examples). Target chlorins were chosen to systematically probe the effect of lipophilic and hydrophilic substituents on tissue partitioning and cellular membrane penetration in photodynamic therapy (PDT).
O'Neal
William G
WG
Burke Chemical Laboratory, Dartmouth College, Hanover, New Hampshire 03755, USA.
Roberts
William P
WP
Ghosh
Indranath
I
Wang
Hui
H
Jacobi
Peter A
PA
D010084:Oxidation-Reduction; D010778:Photochemotherapy; D011166:Porphyrins / Q000138:chemical synthesis*
D011166:Porphyrins; C006969:chlorin