The spiroketals containing a benzyloxymethyl moiety at C8 position showed the most potent apoptosis-inducing activity

S Mitsuhashi; H Shima; T Kawamura; K Kikuchi; M Oikawa; A Ichihara; H Oikawa

doi:10.1016/s0960-894x(99)00309-1

The spiroketals containing a benzyloxymethyl moiety at C8 position showed the most potent apoptosis-inducing activity

Bioorg Med Chem Lett. 1999 Jul 19;9(14):2007-12. doi: 10.1016/s0960-894x(99)00309-1.

Authors

S Mitsuhashi¹, H Shima, T Kawamura, K Kikuchi, M Oikawa, A Ichihara, H Oikawa

Affiliation

¹ Institute of Immunological Science, Hokkaido University, Sapporo, Japan.

PMID: 10450971
DOI: 10.1016/s0960-894x(99)00309-1

Abstract

The spiroketals containing a benzyloxymethyl moiety at the C8 position showed the most potent apoptosis-inducing activity, whereas its analogous compounds lacking any substituent at C8 or possessing ones other than the benzyloxymethyl moiety at C8 were all much less active. These results strongly suggest an important role of the benzyloxymethyl moiety linked to the C8 oxygen atom.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Apoptosis / drug effects*
DNA Fragmentation
Humans
Jurkat Cells / drug effects
Jurkat Cells / pathology
Lethal Dose 50
Okadaic Acid / chemistry
Phosphoprotein Phosphatases / antagonists & inhibitors
Pyrans / chemistry*
Pyrans / pharmacology*
Spiro Compounds / chemistry*
Spiro Compounds / pharmacology*
Structure-Activity Relationship

Substances

Pyrans
Spiro Compounds
Okadaic Acid
Phosphoprotein Phosphatases