Synthesis of cationic bacteriochlorins

Expansion of a Pyrrole in meso‐Tetra­phenylporphyrin to a Pyrazine Imide Moiety­ Using a Beckmann Rearrangement

“…The purpurinimides are one class of derivatives that are distinguished by the presence of a six‐membered imide annulated to a hydroporphyrin framework. Many chlorin‐ and bacteriochlorin‐like derivatives that contain this imide have been reported, some of them with proven efficacy as photochemotherapeutics 31,32. A representative example is the semisynthetic bacteriopurpurin‐18‐ N ‐hexylimide 12 .…”

Synthesis and evaluation of cationic bacteriochlorin amphiphiles with effective in vitro photodynamic activity against cancer cells at low nanomolar concentration

“…Each compound is amphiphilic given the location of the charged groups with respect to the hydrophobic bacteriochlorin macrocycle. A naturally derived bacteriochlorin-imide containing a single positive charge ( I ) has been prepared [28], but to our knowledge has not yet been examined for PDT activity, and a number of non-cationic analogs also have been prepared [31]. A family of tetraanionic bacteriochlorins, of which II is the parent member, and aryl sulfonamide analogs, have been designed and subjected to extensive PDT studies [32–34].…”

“…21–27). On the other hand, to our knowledge only one example of an analogous cationic derivative of bacteriochlorophyll has been reported [28]. …”

Novel Dicationic Chlorin e6 Derivatives

“…4 General procedure for alkylation of chlorins dimethylamino groups by methyl iodide. 0.1 ml of iodomethane was added to a solution of 5-50 mg of starting chlorin (18)(19)(20)(21)(22)(23)(24)(25)(26)(27)(28) СH 3 ], -1.964 br.s (I-NH), -2.20/-2.24* br.s (III-NH). …”

“…This approach was used in the case of synthetic porphyrins [19][20][21][22][23][24][25] as well as in the case of natural porphyrins. [26][27][28][29] We have previously developed the method of aminomethylation of chlorin e 6 derivatives vinyl group by action of bis(N,N-dimethylamino)methane. [30] This method allows to obtain chlorin e 6 derivatives with two dimethylamino substituents in vinyl group.…”