کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
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5217926 | 1383311 | 2013 | 12 صفحه PDF | دانلود رایگان |
Several analogues of the fungal natural product aigialomycin D (AmD) have been synthesised. These include the stereoisomer 5â²R,6â²S-AmD, 2,4-di-deoxyAmD, 1â²,2â²,7â²,8â²-tetrahydroAmD and a 15-membered macrocyclic sulfone. Growth inhibitory activities of these compounds against the HL-60 leukaemic cell line were measured. The ring-expanded sulfone and tetrahydro-analogue were found to have similar IC50 values to the natural product, whereas the 5â²R,6â²S-stereoisomer was inactive. Energy minimisation of AmD and the synthesised analogues resulted in a range of lowest energy conformers, from planar, open arrangements of the macrocycle in AmD and tetrahydroAmD to bent, L-shaped structures for the sulfone. The synthesis of methyl orsellinate was investigated and optimised as part of this work. A stereodivergent route to both enantiomers of the diol fragment from d-ribose was also achieved.
Journal: Tetrahedron - Volume 69, Issue 49, 9 December 2013, Pages 10581-10592