首页 | 本学科首页   官方微博 | 高级检索  
     检索      


Vinyl sulfones
Authors:Jessica H Wong  Marilyn M Olmstead  James C Fettinger  Jacquelyn Gervay‐Hague
Abstract:Four neutral vinyl sulfones, two of which are paired with phosphonate groups, are described. The compounds are diisopropyl (2‐phenylethenylsulfonylmethyl)phosphonate, C15H23O5PS, (I), diisopropyl {2‐(7‐methoxy‐1,3‐benzodioxol‐5‐yl)ethenylsulfonyl]methylsulfonylmethyl}phosphonate, C18H27O10PS2, (II), bis(trans‐2‐phenylethenyl) sulfone, C16H14O2S, (III), and bis(trans‐2‐phenylethenylsulfonyl)methane, C17H16O4S2, (IV). Their structures can be considered as highly functionalized mimics of mono‐, di‐ and triphosphates. These phosphate isosteres are currently of interest as agents for enzyme inhibition in both cancer and HIV therapy. All except one of the compounds has Z′ > 1. The lone exception is (IV), a disulfone with twofold crystallographic symmetry. Geometrically, the sulfone functionality is found to be a good mimic for phosphate. The principal effect of the vinyl group is to shorten the S—C(vinyl) distance relative to the S—CH2 distance by ca 0.05 Å. The S—C—S and S—C—P backbones resemble the P—O—P backbone but are not identical because the S—C and P—C distances are longer than the P—O distance and the S—C—S and S—C—P angles are more acute than the P—O—P angle. No prior crystal structures of comparable compounds have been published.
Keywords:
设为首页 | 免责声明 | 关于勤云 | 加入收藏

Copyright©北京勤云科技发展有限公司  京ICP备09084417号