[(1-Pyrenylmethyl) amino] alcohols, a new class of antitumor DNA intercalators. Discovery and initial amine side chain structure-activity studies

…, RL Tuttle, VC Knick, M Cory, DD McKee

Index: Bair, Kenneth W.; Tuttle, Richard L.; Knick, Vincent C.; Cory, Michael; McKee, David D. Journal of Medicinal Chemistry, 1990 , vol. 33, # 9 p. 2385 - 2393

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Citation Number: 75

Abstract

2 6 R= CH, OCOCH, converted to 205 (HNEt,/PhH/A)(Scheme 11). The acetoxy derivatives 24, 25, and 26 were prepared by reaction of the HCl salts 21, 22, and 23, respectively, with AcCl in THF at reflux (Scheme 111). The oxime 276 was also prepared from aldehyde 6 and reduced (Hz/PtOz/glacial HOAc) to give l-pyrenylmethylamine (28). s Further reaction of 28 with the epoxide 29 (prepared by the procedure of Elliot and Fried)'gave 30, which in turn ...