18523-76-7Relevant articles and documents
A Mixed-Ligand Chiral Rhodium(II) Catalyst Enables the Enantioselective Total Synthesis of Piperarborenine B
Panish, Robert A.,Chintala, Srinivasa R.,Fox, Joseph M.
, p. 4983 - 4987 (2016)
A novel, mixed-ligand chiral rhodium(II) catalyst, Rh2(S-NTTL)3(dCPA), has enabled the first enantioselective total synthesis of the natural product piperarborenine B. A crystal structure of Rh2(S-NTTL)3(dCPA) r
NEW PHENOLIC ETHERS FROM ESSENTIAL OILS OF SOME RUTACEAE
Campbell, William E.,George, Peter
, p. 1455 - 1456 (1982)
Two phenolic ethers were isolated from the essential oils of some Agathosma species.Structures elucidated by spectral analysis and synthesis were trans-1,2-methylenedioxy-4-(3'-methoxy-1'-propenyl)benzene and trans-1,2-dimethoxy-4-(3'-methoxy-1'-propenyl)
Acquisition of female-attracting fragrance by males of oriental fruit fly from a Hawaiian lei flower, Fagraea berteriana
Nishida, Ritsuo
, p. 2275 - 2285 (1997)
Males of the Oriental fruit fly, Bactrocera dorsalis, are strongly attracted to and compulsively feed on a fragrant let flower, Fagraea berteriana. A series of phenylpropanoid components, trans-3,4-dimethoxycinnamyl alcohol, its acetate, and trans-3,4-dim
Laccase-catalyzed oxidation of allylbenzene derivatives: Towards a green equivalent of ozonolysis
Antoniotti, Sylvain,Blerot, Bernard,Chietera, Giorgiana,Lecourt, Mathilde
supporting information, (2021/10/19)
Laccase-based biocatalytic reactions have been tested with and without mediators and optimized in the oxidation of allylbenzene derivatives, such as methyl eugenol taken as a model substrate. The reaction primarily consisted in the hydroxylation of the propenyl side chain, either upon isomerization of the double bond or not. Two pathways were then observed; oxidation of both allylic alcohol intermediates could either lead to the corresponding α,β-unsaturated carbonyl com-pound, or the corresponding benzaldehyde derivative by oxidative cleavage. Such a process consti-tutes a green equivalent of ozonolysis or other dangerous or waste-generating oxidation reactions. The conversion rate was sensitive to the substitution patterns of the benzenic ring and subsequent electronic effects.
(±)-trans-2-phenyl-2,3-dihydrobenzofurans as leishmanicidal agents: Synthesis, in vitro evaluation and SAR analysis
Bernal, Freddy A.,Gerhards, Marcel,Kaiser, Marcel,Wünsch, Bernhard,Schmidt, Thomas J.
, (2020/08/06)
Leishmaniasis, a neglected tropical disease caused by parasites of the genus Leishmania, causes a serious burden of disease around the world, represents a threat to the life of millions of people, and therefore is a major public health problem. More effective and non-toxic new treatments are required, especially for visceral leishmaniasis, the most severe form of the disease. On the backdrop that dihydrobenzofurans have previously shown antileishmanial activity, we present here the synthesis of a set of seventy trans-2-phenyl-2,3-dihydrobenzofurans and evaluation of their in vitro activity against Leishmania donovani as well as a discussion of structure-activity relationships. Compounds 8m-o and 8r displayed the highest potency (IC50 4.6). Nonetheless, structural optimization as further requirement was inferred from the high clearance of the most potent compound (8m) observed during determination in vitro of its metabolic stability. On the other hand, chiral separation of 8m and subsequent biological evaluation of its enantiomers demonstrated no effect of chirality on activity and cytotoxicity. Holistic analysis of in silico ADME-like properties and ligand efficiency metrics by a simple scoring function estimating druglikeness highlighted compounds 16c, 18 and 23 as promising candidates for further development. Overall, the potential of trans-2-phenyl-2,3-dihydrobenzofurans as leishmanicidal agents was confirmed.
