10080-43-0Relevant articles and documents
Design, synthesis, and antifungal evaluation of novel coumarin-pyrrole hybrids
Zhang, Shuguang,Tan, Xin,Liang, Chaogen,Zhang, Weihua
, p. 450 - 458 (2021)
A series of coumarin derivatives bearing a pyrrole scaffold were designed, prepared, and assessed for their in vitro antifungal activities against six phytopathogenic fungi. The antifungal activity screening results suggest that some synthesized hybrids exhibited potential fungicidal activities against the tested fungi. In particular, compounds 6j, 6k, 6o, 6p, and 6r displayed significant antifungal effects against Rhizoctorzia solani, and possessed EC50 values of 3.94, 7.75, 6.38, 6.25, and 7.67 μg/ mL, respectively. The above activities are more potent than the commercialized fungicide Boscalid (11.52 μg/mL) and Osthole (9.79 μg/mL). These results provide a significant reference for further rational design of coumarin-based fungicides.
Phototoxicity of 7-oxycoumarins with keratinocytes in culture
Guillon, Christophe,Jan, Yi-Hua,Heck, Diane E.,Mariano, Thomas M.,Rapp, Robert D.,Jetter, Michele,Kardos, Keith,Whittemore, Marilyn,Akyea, Eric,Jabin, Ivan,Laskin, Jeffrey D.,Heindel, Ned D.
, (2019/06/06)
Seventy-one 7-oxycoumarins, 66 synthesized and 5 commercially sourced, were tested for their ability to inhibit growth in murine PAM212 keratinocytes. Forty-nine compounds from the library demonstrated light-induced lethality. None was toxic in the absence of UVA light. Structure-activity correlations indicate that the ability of the compounds to inhibit cell growth was dependent not only on their physiochemical characteristics, but also on their ability to absorb UVA light. Relative lipophilicity was an important factor as was electron density in the pyrone ring. Coumarins with electron withdrawing moieties – cyano and fluoro at C3 – were considerably less active while those with bromines or iodine at that location displayed enhanced activity. Coumarins that were found to inhibit keratinocyte growth were also tested for photo-induced DNA plasmid nicking. A concentration-dependent alteration in migration on neutral gels caused by nicking was observed.
Regioselective mononitration of coumarins using claycop reagent
Kanodia, Saraswati,Thapliyal, Prakash Chander
experimental part, p. 241 - 244 (2012/03/11)
Coumarins are nitrated by claycop (cupric nitrate impregnated on the K10 montmorillonite) in acetic anhydride at room temperature to give corresponding regioselective mononitro coumarins in good to excellent yields. Among the products three nitrocoumarins are new.
Synthetic approaches to 4,8-dimethyl-4′- (N-pyridiniummethyl)-4′,5′-dihydropsoralens and their activity against PAM 212 keratinocytes
Whittemore, Marilyn,Heindel, Ned,Guillon, Christophe,McNeel, Thomas,Rapp, Robert,Mariano, Thomas,Heck, Diane,Laskin, Jeffrey
, p. 1081 - 1093 (2007/10/03)
Synthetic approaches to novel 4,8-dimethyl-4′-halomethyl-4′,5′-dihydropsoralens as synthetic precursors to 4,8-dimethyl-4′-(N-pyridiniummethyl)-4′,5′-dihydropsoralens are described. The compounds are potential therapeutic agents for improved psoralen ultraviolet radiation therapy with reduced mutagenicity.
4′-Substituted-4′,5′-dihydropsoralens and therapeutical uses thereof
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, (2008/06/13)
The invention relates to 4′-substituted-4′,5′-dihydropsoralen compounds of formula(V): In the formula R is hydrogen, a halogen, CN or an acyl group; T is a halogen, CN, a carboalkoxy group NR1R2, or (N+R1R2R3)X?, R1and R2are independently a C1-C6alkyl, or R1and R2together with the nitrogen form a 5-8 member heterocyclic ring, or when T is (N+R1R2R3)X?, R1and R2together with the nitrogen form a 5-8 member heterocyclic ring or heterocyclic aromatic ring; R3is hydrogen, a C1-C12alkyl, or, when R1and R2together with the nitrogen form a heterocyclic aromatic ring, R3is a double bond within the heterocyclic aromatic ring; X?is a halide. In another embodiment, the invention relates to processes for preparing 4′-substituted-4′,5′-dihydropsoralen compounds described above. The compounds of the invention have beneficial pharmaceutical properties and can be used alone or in pharmaceutical compositions used to treat a proliferative skin disorder and to treat microbial infections in a mammal by administering to the mammal an effective amount of a compound of the invention and then irradiating the mammal with ultraviolet light.
