Oxy-and amino-substituted tetrahydrofuryl derivatives with antitumour activity

Abstract

Compounds of formula (I) wherein Ris selected from H, C(═O)R', P(═O)R′R″, S(═O)R′R″, substituted or unsubstituted C-Calkyl, substituted or unsubstituted C-Calkenyl, substituted or unsubstituted C-Calkynyl, or substituted or unsubstituted aryl; or Rtogether with Rforms a saturated or unsaturated heterocyclic ring; Rand Rare each, independently, selected from H, C(═O)R′, P(═O)R′R″, S(═O)R′R″, substituted or unsubstituted C-Calkyl, substituted or unsubstituted C-Calkenyl, substituted or unsubstituted C-Calkynyl, or substituted or unsubstituted aryl; or one of Ror Rtogether with Rforms a saturated or unsaturated heterocyclic ring; or Rand Rtogether form a saturated or unsaturated heterocyclic ring; Ris selected from H, C(═O)R′, P(═O)R′R″, S(═O)R′R″, substituted or unsubstituted C-Calkyl, substituted or unsubstituted C-Calkenyl, substituted or unsubstituted C-C, alkynyl, or substituted or unsubstituted aryl, wherein R′ is selected from the group consisting of H, OH, NO, NH, SH, CN, halogen, C(═O)H, C(═O)CH, COH, COCH, substituted or unsubstituted C-Calkyl, substituted or unsubstituted C-Calkenyl, substituted or unsubstituted C-Calkynyl, substituted and unsubstituted aryl; R″ is selected from the group consisting of H, OH, NO, NH, SH, CN, halogen, ═O, C(═O)H, C(═O)CH, COH, COCH, substituted or unsubstituted C-Calkyl, substituted or unsubstituted C-Calkenyl, substituted or unsubstituted C-Calkynyl, substituted and unsubstituted aryl; wherein X, XXon formula I are independently placed in any particular position of the chain and independently selected from H, OH, OR′, SH, SR′, SOR′, SOR′, NO, NH, NHR′, N(R′), NHC(O)R′, CN, halogen, ═O, C(═O)H, C(═O)CH, COH, COCH, substituted or unsubstituted C-Calkyl, substituted or unsubstituted C-Calkenyl, substituted or unsubstituted C-Calkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaromatic, wherein substituent groups defined by R′ are each independently selected from the group consisting of H, OH, OR′, SH, SR′, SOR′, SOR′, NO, NH, NHR′, N(R′), NHC(O)R′, CN, halogen, ═O, C(═O)H, C(═O)CH, COH, COCH, substituted or unsubstituted C-Calkyl, substituted or unsubstituted C-Calkenyl, substituted or unsubstituted C-Calkynyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaromatic; wherein x is 6 to 20; and wherein the dotted lined is one or several optional double bonds placed in any particular position of the side chain; or pharmaceutically acceptable salts thereof are useful as antitumor compounds and include compound IK-8-73-4 of structure (a) which was isolated from a spongesp.