15183-96-7Relevant academic research and scientific papers
Improved synthesis, X-ray structure, and antifungal activity of a sugar-psoralen conjugate: 4,4′-Dimethylxanthotoxol 2,3,4,6-tetra-O-Acetyl-β-D-glucoside
Chen, Chao-Yue,Yang, Ting-Hai,Pan, Chang-Duo,Wang, Xin
, p. 179 - 191 (2019)
An improved synthesis for 4,4′-dimethylxanthotoxol 2,3,4,6-tetra-O-acetyl-β-D-glucoside (1) starting from resorcinol was developed. Crystallographic analysis of glucoside 1 indicated that the dihedral angles between the mean planes of the tricyclic ring system of adjacent molecules was 54.820(22)° probably due to the steric hindrance caused by the bulky O-glucoside moiety, which prevents the molecules from packing via π···π stacking between the tricyclic cores. The antifungal screening data revealed that glucoside 1 had higher inhibition than its parent compound 4,4′-dimethylxanthotoxol and azoxystrobin against Rhizoctonia solani, Pyricularia grisea, and Alternaria alternate Japanese pear pathotype, with the inhibitory rates of 75.4, 65.7 and 70.1%, respectively, at the 50 μg/mL concentration.
Synthesis of Novel Anti-inflammatory Psoralen Derivatives?-?Structures?with?Distinct?Anti-Inflammatory?Activities
Timonen, Juri M.,Vuolteenaho, Katriina,Lepp?nen, Tiina,Nieminen, Riina M.,Aulaskari, Paula,J?nis, Janne,Vainiotalo, Pirjo,Moilanen, Eeva
, p. 2590 - 2597 (2018/09/25)
As a continuum to our work with coumarins, 12 psoralens were synthesized and evaluated for their anti-inflammatory activity. Psoralens were prepared in three steps; at first, 7-hydroxycoumarins were synthesized by von Pechmann condensation and then converted to 7-(2-oxopropoxy)coumarins. In the final step, a fused furan ring was introduced in an intramolecular ring-formation reaction. Based on a SciFinder search, two out of the 12 synthesized psoralen derivatives (compounds 9 and 12) were found to be novel. The derivatives displayed anti-inflammatory activity by suppressing iNOS and IL-6 expression, but their mechanism of action seemed to be dependent on the substitution. Compound 6 with propyl side chain inhibited NF-κB mediated transcription, while compound 10 with a phenyl substituent down-regulated iNOS expression in a posttranscriptional manner. The results introduce psoralen derivatives as promising anti-inflammatory compounds with potential for treatment of conditions involving iNOS and/or IL-6-mediated adverse responses.
Studies in synthesis of new psoralenamines
Patel, Jagdish M.,Soman, Shubhangi S.
experimental part, p. 379 - 383 (2010/06/16)
(Chemical Equation Presented) New amino psoralen derivatives have been synthesized via bromination. Bromination of 3,5-substituted psoralens has been studied. The second position of the furan ring is more susceptible to bromination than the α-position of
Synthesis and biological evaluation of functionalized coumarins as acetylcholinesterase inhibitors
Shen, Qiong,Peng, Quan,Shao, Jialiang,Liu, Xufeng,Huang, Zhishu,Pu, Xianzhang,Ma, Lin,Li, Yue-Ming,Chan, Albert S.C.,Gu, Lianquan
, p. 1307 - 1315 (2007/10/03)
Three series of functionalized coumarin compounds were designed and prepared as cholinesterase (AChE and BuChE) inhibitors. The biological profile against AChE and BuChE of the prepared compounds was determined. Compound 7b exhibited a mixed-type of AChE
An efficient and convenient synthesis of furocoumarins via Pechmann reaction on ZnCl2/Al2O3 under microwave irradiation
Shockravi, Abbas,Heravi, Majid M.,Valizadeh, Hassan
, p. 143 - 147 (2007/10/03)
Furocoumarins were rapidly synthesized via Pechmann condensation of 6-hydroxybenzofurans with ethylacetoacetate catalyzed by ZnCl2/Al2O3 under solvent-free condition.
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.
5'-Aminoalkyl-4',4-dialkylpsoralens
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, (2008/06/13)
The invention relates to 5'-aminoalkyl-4',4-dialkylpsoralens having enhanced photosensitizing activity, especially oral activity, including early onset, increased maximum, and rapid decline, as well as low toxicity, when compared with psoralens of different structure.
