title: Studies in chlorin chemistry. 3. A practical synthesis of c,d-ring symmetric chlorins of potential utility in photodynamic therapy.
abstract: [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).
authors.affiliation: Burke Chemical Laboratory, Dartmouth College, Hanover, New Hampshire 03755, USA.
authors.forename: William G
authors.initials: WG
authors.lastname: O'Neal
authors.forename: William P
authors.initials: WP
authors.lastname: Roberts
authors.forename: Indranath
authors.initials: I
authors.lastname: Ghosh
authors.forename: Hui
authors.initials: H
authors.lastname: Wang
authors.forename: Peter A
authors.initials: PA
authors.lastname: Jacobi
mesh_terms: D010084:Oxidation-Reduction; D010778:Photochemotherapy; D011166:Porphyrins / Q000138:chemical synthesis*
chemical_list: D011166:Porphyrins; C006969:chlorin