106543-50-4Relevant academic research and scientific papers
(±)-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.
Antileishmanial activity, cytotoxicity and QSAR analysis of synthetic dihydrobenzofuran lignans and related benzofurans
Miert, Sabine Van,Dyck, Stefaan Van,Schmidt, Thomas J.,Brun, Reto,Vlietinck, Arnold,Lemière, Guy,Pieters, Luc
, p. 661 - 669 (2007/10/03)
A series of synthetic dihydrobenzofuran lignans and related benzofurans were evaluated for their cytotoxicity in a screening panel consisting of various human tumour cell lines, and for their antiprotozoal activity against L. donovani (axenic amastigotes)
Regioselective Synthesis of 2- and 3-Aryl-1,4-benzodioxanes
Antus, Sandor,Baitz-Gacs, Eszter,Bauer, Rudolf,Gottsegen, Agnes,Seligmann, Otto,Wagner, Hildebert
, p. 1147 - 1152 (2007/10/02)
3-Aryl- and 2-aryl-1,4-benzodioxane derivatives of type 4d and 5d are excellent starting compounds for the synthesis of natural flavano- and neolignans.The syntheses of 4d and 5d were achieved with high regioselectivity by oxidative coupling of caffeic ac
Synthesis of Americanin-D
Antus, Sandor,Bauer, Rudolf,Gottsegen, Agnes,Seligmann, Otto,Wagner, Hildebert
, p. 357 - 360 (2007/10/02)
By regioselective self-coupling with silver oxide as oxidant the 2,3-trans-2-phenylbenzofuran 8 was synthesized in good yield.Reduction of 8 led in an unambiguous way to americanin-D (rac-1).Synthetic and natural product were identical in every respect.
