Design, Synthesis and Evaluation of Novel Carbazole-Derived Photocages.
Chemistry
; 28(18): e202200311, 2022 Mar 28.
Article
em En
| MEDLINE
| ID: mdl-35218096
ABSTRACT
We report the design, synthesis and evaluation of two novel photocages, NCARB and isoNCARB, belonging to the o-nitrobenzyl chemotype and based on the carbazole ring system. The synthesis of each of these isomeric caging molecules was achieved in five steps and in 29 % overall yield, and their photochemical properties were evaluated using benzoic acid as a model for caging. In the event, upon irradiation at 400â
nm for 60â
min, 82 % and 42 % of benzoic acid was freed from the NCARB and isoNCARB photocages, respectively, whereas only 22 % was released from the nitrodibenzofuran (NDBF) cage. Moreover, the photochemical decaging efficiencies, ϵΦ, of the benzoates photocaged with NCARB and isoNCARB are about 150- and 20-fold better, respectively, at 400â
nm than the corresponding caged benzoate derived from NDBF. The water solubility of molecules caged with nitrocarbazole analogs was improved by N-alkylation of NCARB, the better of the two new photocages, with an aminodicarboxylate group. This modified cage, NCARB-DA, was exploited in the design of a caged fluoroquinolone antibiotic, the efficacy of which was illustrated in a bacterial growth inhibition assay, and a phenol-caged tyrosine derivative.
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MEDLINE
Assunto principal:
Carbazóis
Idioma:
En
Ano de publicação:
2022
Tipo de documento:
Article