156205-14-0Relevant academic research and scientific papers
Antiulcer agents. III. Synthesis and antiulcer activity of N-[3-(3- piperidinomethylphenoxy)propyl]pentacyclo[4.2.0.02,5.03,8.04,7]- octane carboxamides and related compounds
Hasegawa,Nigo,Kakita,Toyoda,Toya,Ueda
, p. 1760 - 1768 (1993)
The synthesis and antiulcer activity of highly strained cage compounds such as pentacyclo[4.2.0.02,5.03,8.04,7]-octane (cubane), pentacyclo[4.3.0.02,5.03,8.04,7]nonane (homocubane) and pentacyclo[5.3.0.02,4.03,6.05,8]decane are described. Of the compounds obtained, N-[3-(3-piperidinomethylphenoxy)propyl]-4- piperidinocarbonylpentacyclo[4.2.0.02,5.03,8.04,7]octane carboxamide (26a) and N-[3'-(3'-piperidinomethylphenoxy)propyl]-1-bromo-9,9- ethylenedioxypentacyclo[4.3.0.02,5.03,8.04,7]nonane]-4-carboxamide (26q) showed more potent antiulcer activity with very good cytoprotective ability in the HCl·ethanol-treated rat model. Compounds 26a and 26q exhibited H2-receptor antagonist potency (in vitro) comparable to that of ranitidine, but did not inhibit histamine-stimulated acid secretion (in vivo) in the gastric fistula rat model, when orally administered in the dose range at which antiulcer and cytoprotective activities were seen. The structure- activity relationships are discussed.
Cage Enlargement of 1,4-Bis(hydroxymethyl)pentacyclo2,5.03,8.04,7>octane to a Tetracyclo3,9.04,7>nonane System in Formic Acid
Hasegawa, Takeshi,Kimura, Yoshihide,Kuwatani, Yoshiyuki,Higuchi, Hiroyuki,Hatanaka, Minoru,Ueda, Ikuo
, p. 462 - 472 (2007/10/02)
Cationic rearrangement of 1,4-bis(diarylhydroxymethyl)pentacyclooctanes (1) in formic acid gave new cage compounds, 8,8-diaryl-2-diarylmethylene-exo-5-(formyloxy)tetracyclononan-7-ols (3) and new cage-degradation products, 5,5-diaryl-4--2-cyclopenten-1-ones (4) along with Wagner-Meerwein rearrangement products, pentacyclodecanes (5; C 2 -bishomocubanes) and pentacyclodecanes (6; D 2h -bishomocubanes). 9,9-Diaryl-4-(diarylhydroxymethyl) pentacyclononan-1-ols (2) gave 4, 5, and 6 without the formation of 3.A Wagner-Meerwein 1,2-bond shift of 1 gave key intermediates 2 which were converted into 3 via homoallylic rearrangement, into 4 via pinacol-pinacolone-like rearrangement, or into 5 and 6 via Wagner-Meerwein rearrangement.
