25220-07-9Relevant academic research and scientific papers
Synthesis and free radical scavenging activity of some new spiropyranocoumarins
Panteleon, Vassiliki,Kostakis, Ioannis K.,Marakos, Panagiotis,Pouli, Nicole,Andreadou, Ioanna
scheme or table, p. 5781 - 5784 (2009/06/18)
A series of novel spiro-substituted 4-hydroxypyranocoumarins and their corresponding dihydropyrano cis-diols has been synthesized. Among them the spiroadamantylpyranocoumarin and the diols can interact with the stable free radical 1,1-diphenyl-2-picrylhydrazyl and scavenge superoxide anions generated in the xanthine-xanthine oxidase system.
6-(2-Adamantan-2-ylidene-hydroxybenzoxazole)-O-sulfamate: A potent non-steroidal irreversible inhibitor of human steroid sulfatase
Schreiner, Erwin P.,Wolff, Barbara,Winiski, Anthony P.,Billich, Andreas
, p. 4313 - 4316 (2007/10/03)
We report the synthesis and results from the in vitro evaluation of 6-(adamantan-2-ylidene-hydroxybenzoxazole)-O-sulfamate 1 as an irreversible inhibitor of human steroid sulfatase (STS). Highly straightforward, condensation of 2-methyl-6-hydroxybenzoxazole with 2-adamantanone, subsequent elimination of water and sulfamoylation provide the title compound in 45% overall yield from the inexpensive 2,4-dihydroxyacetophenone. 1 was found to be a potent irreversible inhibitor of purified human steroid sulfatase (STS) and specific for this enzyme relative to human arylsulfatases A and B. In cellular assays with human keratinocytes, sebocytes and fibroblasts, 1 blocked STS activity with IC50 values in the range of 0.15-0.8 nM, and in MCF-7 breast cancer cells with IC50=2.3 nM, while it did not bind to estrogen receptors α and β. Thus, 1 is a candidate for further investigation of its potential as a drug to be used in androgen- and estrogen-dependent diseases.
A new procedure for the in situ generation of methylene ketenes
Masters, Andrew P.,Sorensen, Ted S.,Tran, Phu Mahn
, p. 1499 - 1502 (2007/10/02)
The reaction of pentacarbonylmanganate anion 3 and 2-bromopropenoyl chlorides 2 leads to 2,4-alkylidenecyclobutane-1,3-diones 5.The latter are formed from dimerization of the corresponding methylene ketenes 1 so that the reaction of 2 and 3 constitutes a
