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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).

SUBMITTER: O'Neal WG

PROVIDER: S-EPMC2587451 | biostudies-literature | 2006 Apr

REPOSITORIES: biostudies-literature

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Studies in chlorin chemistry. 3. A practical synthesis of c,d-ring symmetric chlorins of potential utility in photodynamic therapy.

O'Neal William G WG Roberts William P WP Ghosh Indranath I Wang Hui H Jacobi Peter A PA

The Journal of organic chemistry 20060401 9

[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). ...[more]

PMID: 16626128

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