2005
DOI: 10.1007/s00706-004-0275-6
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Syntheses and Properties of Two Heterocyclically Substituted Hypericin Derivatives: 10,11-Dibenzothiazolyl-10,11-didemethylhypericin and 10,11-Dibenzoxazolyl-10,11-didemethylhypericin

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Cited by 9 publications
(6 citation statements)
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“…Falk and co-workers, renowned for their research in hypericin synthesis and the elucidation of the physicochemical properties of this molecule, developed a new class of modified hypericin derivatives, which contained extra heterocyclic rings such as benzothiazolyl, benzoxazolyl [ 60 ] and benzothiazole [ 61 ]. Basic concept of these syntheses was that the methyl groups of the hypericin moiety served as “anchors” for the substitution by the extra chromophore units.…”
Section: Extraction Isolation and Synthesis Of Hypericin And Pseudohmentioning
confidence: 99%
“…Falk and co-workers, renowned for their research in hypericin synthesis and the elucidation of the physicochemical properties of this molecule, developed a new class of modified hypericin derivatives, which contained extra heterocyclic rings such as benzothiazolyl, benzoxazolyl [ 60 ] and benzothiazole [ 61 ]. Basic concept of these syntheses was that the methyl groups of the hypericin moiety served as “anchors” for the substitution by the extra chromophore units.…”
Section: Extraction Isolation and Synthesis Of Hypericin And Pseudohmentioning
confidence: 99%
“…To avoid a cycloaddition between the two adjacent double bonds in the corresponding hypericin derivatives, the products 3 and 4 thus available in modest yields could be easily and nearly quantitatively hydrogenated using palladium on charcoal as catalyst and methanol as solvent under ambient conditions to 5 and 6. The latter were deprotected and reduced in acceptable yields to the anthrone derivatives 7 and 8 in the common way (12)(13)(14)(15)(16)(17) using SnCl 2 ⁄ HBr in glacial acetic acid. Dimerization by means of Fe(SO 4 ) 2 ⁄ pyridine-N-oxide in pyridine and piperidine as the catalyst (12)(13)(14)(15)(16)(17) provided the protohypericin derivatives 9 and 10, which were immediately photocyclized to the hypericin derivatives 11 and 12.…”
Section: Synthesismentioning
confidence: 99%
“…During the last decade its fundamental chromophore has been derivatized in order to generate second-generation agents (11). These efforts resulted in analogs with redshifted absorption spectra to provide compounds excitable at wavelengths with enhanced penetration depth on the one hand (12)(13)(14)(15)(16)(17), and better physicochemical properties, e.g. higher solubility under physiological conditions or targeting of specific cellular sites, on the other hand (18)(19)(20)(21)(22)(23)(24)(25).…”
Section: Introductionmentioning
confidence: 99%
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“…Hypericin and seven derivatives were prepared as described earlier. [12][13][14][15][16][17] Stock solutions of 10 mM were made in dimethyl sulfoxide (DMSO) and stored at -20 • C under dark circumstances. All compounds were manipulated under subdued light conditions (<1 mW cm -2 ).…”
Section: Experimental Photosensitizersmentioning
confidence: 99%