Dittrich, Torsten published the artcileSynthesis of 5-oxyquinoline derivatives for reversal of multidrug resistance, Application In Synthesis of 115314-17-5, the publication is Beilstein Journal of Organic Chemistry (2012), 1700-1704, database is CAplus and MEDLINE.
The inhibition of ABC (ATP binding cassette) transporters is considered a powerful tool to reverse multidrug resistance. (αR)-4-[(1Aα,6α,10bα)-1,1-Difluoro-1,1a,6,10b-tetrahydrodibenzo[a,e]cyclopropa[c]cyclohepten-6-yl]-α-[(5-quinolinyloxy)methyl]-1-piperazineethanol (Zosuquidar) featuring a difluorocyclopropyl-annulated dibenzosuberyl moiety has been found to be an inhibitor of the P-glycoprotein, one of the best-studied multidrug efflux pumps. Twelve 5-oxyisoquinoline derivatives, which are analogs of Zosuquidar wherein the dibenzosuberyl-piperazine moiety is replaced by either a diarylaminopiperidine or a piperidone-derived acetal or thioacetal group, have been synthesized as pure enantiomers. Their inhibitory power has been evaluated for the bacterial multidrug-resistance ABC transporter LmrCD and fungal Pdr5. Four of the newly synthesized compounds reduced the transport activity to a higher degree than Zosuquidar, being up to fourfold more efficient than the lead compound in the case of LmrCD and about two times better for Pdr5. The title compounds thus formed included a quinoline piperidineethanol derivative (I) and related substances. The synthesis of the target compounds was achieved using 5-[(2R)-2-oxiranylmethoxy]quinoline as a key intermediate.
Beilstein Journal of Organic Chemistry published new progress about 115314-17-5. 115314-17-5 belongs to esters-buliding-blocks, auxiliary class Epoxides,Chiral,Nitro Compound,Sulfonate,Benzene, name is (R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate, and the molecular formula is C9H9NO6S, Application In Synthesis of 115314-17-5.
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