Synthesis of the first N-hydroxycycloimide in the bacteriochlorophyll a series

Abstract

The first N-hydroxycycloimide of bacteriochlorin p6has been synthesized and chemical modification at the hydroxyl group demonstrated. The relative reactivities of the acetyl substituent and the anhydride ring in reaction with hydroxylamine were studied.

New efficient near-IR photosensitizer based on bacteriochlorin p N-methoxycycloimide oxyme methyl ester

“…In this work we have performed an in vivo investigation of bacteriochlorin p N-methoxycycloimide oxyme methyl ester (BchlpOx-NOMe), synthesized by chemical modification of bacteriochlorophyll а, obtained from purpuric bacteria Rhodobacter capsulatus, as was described earlier in [9][10][11]. Structure of photosensitizer is shown on Fig.…”

De novo synthesis and photophysical characterization of annulated bacteriochlorins. Mimicking and extending the properties of bacteriochlorophylls

“…The Q y (0,0) band of bacteriochlorin-imides derived from bacteriochlorophyll a occurs in the same spectral range (800-830 nm). 32,33,36 The spectra of MeOBOP, MeOBC-I and HBC-I in toluene are shown in Fig. 1.…”

“…Synthetic manipulation of bacteriochlorophylls has afforded a number of derivatives including (i) bacteriopyropheophorbides, which lack the 13 2 -methoxycarbonyl substituent, the phytyl-like chain, and the central magnesium; [2][3][4]29,30 and (ii) bacteriopurpurinimides (hereafter referred to as bacteriochlorin-imides), which bear a six-membered imide ring (Chart 1, panel B). 6,12,16,17,[31][32][33][34][35][36][37] The presence of the imide ring in bacteriochlorin-imides provides a number of attractions including (1) a hyperchromic and bathochromic shift of the long-wavelength absorption band; (2) the ability to introduce diverse groups at the nitrogen of the imide ring; 38 and (3) increased stability of the macrocycle toward routine handling due to the presence of the second carbonyl group at the 15-position. So far, bacteriochlorins bearing the five membered oxopentano or six-membered imide ring have only been available from the natural compounds or upon semisynthesis therefrom, respectively, although synthetic porphyrins and chlorins with a wide variety of annulated rings have been prepared.…”

Efficient Synthesis and in vitro PDT Effect of Purpurin-18-N-Aminoimides

“…Converting the six-membered anhydride ring of purpurin-18 into a six-membered cyclic imide structure was found to greatly increased wavelength absorption and good stability for the requirement of an improved photodynamic therapeutic agent. [10][11][12][13][14][15][16][17][18][19] Although previous report has described the synthesis of purpurin-18-N-(N,N-dimethyl)ethylimide from the chlorin p 6 . 14 However, the yield of the purpurinimide formed in this reaction was low.…”