5 research outputs found

    Kleinhospitine E and Cycloartane Triterpenoids from <i>Kleinhovia hospita</i>

    No full text
    A novel cycloartane triterpenoid alkaloid, kleinhospitine E (<b>1</b>), six new cycloartane triterpenoids (<b>2</b>–<b>7</b>), three known cycloartane triterpenoids (<b>8</b>–<b>10</b>), and taraxerone (<b>11</b>) were isolated from a methanol extract of <i>Kleinhovia hospita</i>. Their structures were elucidated by 1D- and 2D-NMR spectroscopy as well as HRMS analysis. The absolute configurations of all isolated compounds were determined from their ECD spectra by comparison with theoretical values. Kleinhospitine E (<b>1</b>) is the first cycloartane alkaloid possessing an unusual γ-lactam with an oxopropylidene side chain. Compounds <b>2</b>, <b>3</b>, and <b>6</b> were assigned as cycloartane triterpenoids with a 9α,10α-cyclopropyl ring, which is found rarely among naturally occurring compounds, while <b>4</b> and <b>5</b> were established as isomers of compound <b>3</b> containing a 21,23-diacetal side chain. Biological evaluation revealed that compounds <b>4</b> and <b>9</b> exhibited more potent antiproliferative activities against a multidrug-resistant tumor cell line compared with its parent chemosensitive cell line. Furthermore, compound <b>6</b> exhibited submicromolar anti-HIV activity

    Synthesis and Cytotoxicity of 1,2-Disubstituted Naphth[2,3-<i>d</i>]imidazole-4,9-diones and Related Compounds

    No full text
    As part of our continuing search for potential anticancer drug candidates that are selective against slowly growing solid tumors, we have synthesized several series of 1- and 2-substituted derivatives of the lead structure, 1-ethyl-2-methylnaphth[2,3-d]imidazole-4,9-dione (5). Their cytotoxic activity in the National Cancer Institute's in vitro cancer cell line panel is reported. In general, substitution of various alkyl, phenyl, or benzyl moieties did not improve activity, and compound 5 remains the most active naphth[2,3-d]imidazole-4,9-dione derivative. However, high levels of activity and selectivity were found with several related 2-(acylamino)-3-chloro-1,4-naphthoquinones (2f−j). Compound 2i, 2-[(2-fluorophenyl)acetamido]-3-chloro-1,4-naphthoquinone, has been selected for further in vivo testing and as an additional lead compound for further structural modification
    corecore