One-pot synthesis and SAR study of cis-2,6-dialkyl-4-chloro-tetrahydropyrans.
A series of cis-2,6-dialkyl-4-chloro-tetrahydropyrans were prepared by means of an iron(III)-catalyzed process. The in vitro antiproliferative activities were examined in the human solid tumor cell lines A2780, SW1573, and WiDr. The results show that the presence of bulky substituents favors the Prins cyclization leading to new products with better activity profile against all cell lines tested.
Miranda
Pedro O
PO
Instituto Universitario de Bio-Orgánica Antonio González, Universidad de La Laguna, C/ Astrofísico Francisco Sánchez 2, 38206 La Laguna, Spain.
León
Leticia G
LG
Martín
Víctor S
VS
Padrón
Juan I
JI
Padrón
José M
JM
D000447:Aldehydes / Q000737:chemistry; D000478:Alkylation; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002713:Chlorine / Q000737:chemistry*; D003500:Cyclization; D006801:Humans; D006859:Hydrogen / Q000737:chemistry; D057927:Hydrophobic and Hydrophilic Interactions; D006900:Hydroxylation; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D000447:Aldehydes; D020005:Propanols; D011714:Pyrans; C006463:allyl alcohol; D002713:Chlorine; D006859:Hydrogen