Synthesis of glycoporphyrin derivatives and their antiviral activity against herpes simplex virus types 1 and 2

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

“…The substitution of the glycosyl group on the ortho position of the meso phenyl caused steric hindrance to metallation by zinc [160] . In extension of this work Maillard et al synthesized a range of tetraglycosylated TPP's containing glucopyranosyl, galactopyranosyl, maltosyl, and glucosaminosyl residues Olinked at the para position under Lindsey condensation conditions (29)(30)(31)(32)(33)(34)(35)(36) [162] . Similar compounds were prepared to determine the effect the glycosyl unit had on the singlet oxygen production for possible application in asymmetric photooxygenation.…”

“…Similar concepts can also be employed to prepare unsymmetrical cationic glycoporphyrins. In an extension of previous work on the synthesis of neutral glycoporphyrins which displayed good inactivation of herpes simplex virus (HSV-1 and HSV-2) [30] Tomé et al synthesized glycosylated neutral and cationic tripyridylporphyrins and evaluated their antiviral activity [229] . The porphyrin starting material 412 was synthesized via crossed Rothemund reaction which underwent a one-pot conversion to the activated ester 413 by reaction with thionyl chloride and addition of N-hydroxysuccinimide.…”

“…Various methods of linking carbohydrates to porphyrin scaffolds, for example by direct glycosylation to the porphyrin [30] , amide [31] , or triazole linkages [32] are available. The number and regiochemical arrangement of the sugar units gives scope for fine-tuning the hydrophobicity and hydrophilicity.…”

“…The simple spectra identified the molecular weight and showed the groups appended at the meso positions unlike DCI-CID (desorption chemical ioizationcollision-induced dissociation) which does not yield mass spectra of higher mass compounds [225] . Similarly, four series of meso-tetraaryl-glycoporphyrins were synthesized with protected and de-protected hydroxyl groups to evaluate their photo-inactivation of HSV-1 and HSV-2 herpes simplex virus [30] . Three different classes of porphyrins (83,190,197) were prepared by Rothemund or cross-Rothemund reactions and porphyrin 190 was reacted with hexafluorobenzene affording 198 in addition to the series.…”

“…Three different classes of porphyrins (83,190,197) were prepared by Rothemund or cross-Rothemund reactions and porphyrin 190 was reacted with hexafluorobenzene affording 198 in addition to the series. The first two series of glycoporphyrins were synthesized via the coupling of tetraphenylporphyrins with a hydroxyl group (190) [30] . All porphyrin derivatives were tested against HSV-1 and HSV-2 in Vero cells.…”