Triazoleporphyrazines: A New Class of Intrinsically Unsymmetrical Azaporphyrins

Abstract

Triazoleporphyrazine 5 has been prepared by means of a ''3+1'' crossover condensation of the pyrroline derivative 6 with 3,5-diamino-1,2,4-triazole. Metallation of 5 under standard conditions afforded the metallotriazoleporphyrazines 7.In contrast with the porphyrinic nature observed for its triazoleporphyrin counterpart 3, the free base triazoleporphyrazine 5 possessed a cross-conjugated, hemiporphyrazine-like

Structural analogs of tetrapyrrole macrocycles and their biological properties

“…63 The use of substituted maleonitriles and pyrrolines led to the discovery of a new class of non centrosymmetric ABBB type macroheterocycles, viz., porphyrazine deriva tives, called triazoleporphyrazines. 18 For example, the reactions of 3,4 bis(4 tert butylphenyl) 2,5 diimino pyrroline with 3,5 diamino 1,2,4 triazole or 1 dodecyl 3,5 diamino 1,2,4 triazole in a molar ratio of 3 : 1 pro duced hexakis(4 tert butylphenyl)triazoleporphyrazine 38a and its N dodecyl substituted analog 38b, respec tively, in good yields (Scheme 9). The reactions of triazoleporphyrazine 38a with nickel, copper, and cobalt acetates in DMF at 100 °C afforded 18 the corresponding complexes 39a-c (Scheme 10).…”

Novel Porphyrazine Derivatives show Promise for Photodynamic Therapy despite Restrictions in Hydrophilicity

“…Of the novel Ni–Pz complexes that have been developed, their analyses have been limited to chemical characterization with no photophysical/photoactive properties documented . The inability to determine photophysical parameters of Ni(II)Pz derivatives herein due to solvation issues, prompted an alternative means of detecting possible phototoxicity generated through PDT.…”

Synthesis, Structure Peculiarities and Acid-Basic Behaviour of Triazoleporphyrazines

“…The metal complexes ( 3-5) were prepared [22] by treatment of metal free triazoleporphyrazine (1) with an appropriate metal acetate in DMF at 100 ºC in 78-90% yields (Scheme 2).…”

“…Recently the first representatives of a new class of noncentrosymmetric tetrapyrrole macrocycles -triazoleporphyrazines, have been synthesized. [22] These compounds should be considered as analogues of porphyrazine in which one pyrrole subunit is replaced by 1,2,4-triazole.…”