On June 19, 1990, Kuehne, Martin published a patent.Safety of Isochroman-3-ol The title of the patent was Preparation of cycloalkyl and aromatic moieties-containing vinblastines and vincristines as antitumors. And the patent contained the following:
The title compounds [I; R1R2 = alkylene, benzo; R10 = HCO, Me; R11 = alkoxy, trialkylammoniumyl; R12 = alkanoyloxy, OH; R13 = alkyl] were prepared Vindoline-HCl was condensed with Me (3aRS,4RS,11bSR)]-3-benzyl-4-[2-(tert-butyldimethylsilyloxymethyl)phenyl]-1,2,3,3a,4,5-hexahydro-7H-pyrrolo[2,3-d]carbazole-6-carboxylate to give, after desilylation, a 1:1 mixture of (5R,7S)-3-benzyl-5-[2-(hydroxymethyl)phenyl]-1,2,3,4,5,6,7,8-octahydroazonino[5,4-b]indole-7-(15-vindolinyl)-7-carboxylate (II) and its 5R,7R-diastereomer. II was then cyclized in CH2Cl2 containing Et3N and p-toluenesulfonic anhydride to give, after hydrogenolysis, (9R,11S)-15-[1,2,4,9,10,11,12,17-octahydro-11-(methoxycarbonyl)indolo[2′,3′:6,7]azonino[1,2,3:bc]isoquinolin-11-yl]vindoline (III). III had an ED50 comparable to that of vinblastine against P388 leukemia cells resistant to adriamycin. The experimental process involved the reaction of Isochroman-3-ol(cas: 42900-89-0).Safety of Isochroman-3-ol
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