1930-56-9Relevant articles and documents
Electronic Finetuning of 8-Methoxy Psoralens by Palladium-Catalyzed Coupling: Acidochromicity and Solvatochromicity
Geenen, Sarah R.,Presser, Lysander,H?lzel, Torsten,Ganter, Christian,Müller, Thomas J. J.
supporting information, p. 8064 - 8075 (2020/06/02)
Differently 5-substituted 8-methoxypsoralens can be synthesized by an efficient synthetic route with various cross-coupling methodologies, such as Suzuki, Sonogashira and Heck reaction. Compared to previously synthesized psoralens, thereby promising daylight absorbing compounds as potentially active agents against certain skin diseases can be readily accessed. Extensive investigations of all synthesized psoralen derivatives reveal fluorescence in the solid state as well as several distinctly emissive derivatives in solution. Donor-substituted psoralens exhibit remarkable photophysical properties, such as high fluorescence quantum yields and pronounced emission solvatochromicity and acidochromicity, which were scrutinized by Lippert–Mataga and Stern–Volmer plots. The results indicate that the compounds exceed the limit of visible light, a significant factor for potential applications as an active agent. In addition, (TD)DFT calculations were performed to elucidate the underlying electronic structure and to assign experimentally obtained data.
Synthesis and evaluation of linear furanocoumarins as potential anti-breast and anti-prostate cancer agents
Chauthe, Siddheshwar K.,Mahajan, Shivani,Rachamalla, Mahesh,Tikoo, Kulbhushan,Singh, Inder P.
, p. 2476 - 2484 (2015/02/19)
A series of 22 furanocoumarin derivatives were synthesized and evaluated for cytotoxicity against breast cancer (MCF-7 and MDA-MB-231) and prostate cancer (PC-3) cell lines along with normal cell line. Several analogs were synthesized by replacing prenyl moiety with alkyl, aromatic, and heteroaromatic functionality to study the structure-activity relationship. Compounds 20 and 22 with adamantoylamino, diprenylamino and substituted benzene sulfonamide substituents showed potent antiproliferative activity in MCF-7 cell line with IC50 values of 0.48 and 0.53 μM, respectively. Both the compounds showed higher IC50 value in MCF-10A cell lines indicating nontoxicity in normal cell lines.
Alkoxypsoralens, novel nonpeptide blockers of Shaker-type K+ channels: Synthesis and photoreactivity
Wulff, Heike,Rauer, Heiko,Düring, Tim,Hanselmann, Christine,Ruff, Katharina,Wrisch, Anja,Grissmer, Stephan,H?nsel, Wolfram
, p. 4542 - 4549 (2007/10/03)
A series of psoralens and structurally related 5,7-disubstituted coumarins was synthesized and investigated for their K+ channel blocking activity as well as for their phototoxicity to Artemia salina and their ability to generate singlet oxygen and to photomodify DNA. After screening the compounds on Ranvier nodes of the toad Xenopus laevis, the affinities of the most promising compounds, which proved to be psoralens bearing alkoxy substituents in the 5-position or alkoxymethyl substituents in the neighboring 4- or 4'-position, to a number of homomeric K+ channels were characterized. All compounds exhibited the highest affinity to Kv1.2. 5,8- Diethoxypsoralen (10d) was found to be an equally potent inhibitor of Kv1.2 and Kv1.3, while lacking the phototoxicity normally inherent in psoralens. The reported compounds represent a novel series of nonpeptide blockers of Shaker-type K+ channels that could be further developed into selective inhibitors of Kv1.2 or Kv1.3.
