The chemistry of pyrrolic compounds. LIII. Polyhydroxy and polyacetoxy derivatives of porphyrins

Abstract

Several polyhydroxy- and polyacetoxy-porphyrins have been prepared and their properties studied as part of an investigation to find suitable porphyrins for use in the detection and/or treatment of malignant tumours. Low solubility in aqueous media has so far prevented a clear assessment of their biological properties.

Intramolecular hydrogen bonding and linear pentapyrrole conformation

“…: 155–160 °C (0.27 mbar) (Ref. [56] m.p. : 40–41 °C); 1 H NMR (CDCl 3 ): δ = 1.18 (3H, t, J = 7 Hz), 1.20 (3H, t, J = 7 Hz), 1.29 (3H, t, J = 7 Hz), 2.17 (3H, s), 2.36 (2H, t, J = 7.5 Hz, 8.0 Hz), 2.48 (2H, t, J = 7.6 Hz, 8.6 Hz), 2.67 (2H, t, J = 7.5 Hz, 8.0 Hz), 2.94 (2H, t, J = 7.6 Hz, 8.6 Hz), 4.06 (2H, q, J = 7 Hz), 4.08 (2H, q, J = 7 Hz), 4.24 (2H, q, J = 7 Hz), 9.37 (1H, broad s) ppm; 13 C NMR (CDCl 3 ): δ = 11.2 (q), 13.95 (q), 13.99 (q), 14.2 (q), 19.1 (t), 20.6 (t), 35.4 (t), 35.5 (t), 59.7 (t), 60.0 (t), 60.1 (t), 116.5 (s), 119.4 (s), 129.5 (s), 130.3 (s), 161.2 (s), 172.8 (s), 173.0 (s) ppm; GC-MSC: m / z = 353 [M + 17 ], 308, 279, 234, 192, 146, 91.…”