(‐)‐β‐Narcotine: A Facile Synthesis and the Degradation with Ethyl Chloroformate.

Abstract

Alkaloids Alkaloids U 0600(-)-β-Narcotine: A Facile Synthesis and the Degradation with Ethyl Chloroformate. -A facile synthesis of the synthetic title alkaloid (VII) based on the direct condensation of iodomeconine (IV) with cotarnine (V) is developed. This synthetic alkaloid is degraded with ethyl chloroformate to form the chlorocarbamate (IX) as a crystalline intermediate, which is converted into the carbinol (X) and the ethoxycarbamate (XI) during the purification by column chromatography. -(LEE, D.-U.; Bull.

Synthesis of microtubule-interfering halogenated noscapine analogs that perturb mitosis in cancer cells followed by cell death

“…Some of these reported procedures involved harsh conditions such as nitric acid-sulfuric acid system (HNO 3 ] are also routinely employed for iodination. Nonetheless, iodination of noscapine even under the most gentle conditions gave only the hydrolysis products, meconine and cotarnine [37]. In addition, direct aromatic iodination of noscapine using thallium trifluoroacetate or iodine monochloride also resulted in bond fission between C-5 and C-3 0 under acidic conditions.…”

Development of a Novel Nitro-Derivative of Noscapine for the Potential Treatment of Drug-Resistant Ovarian Cancer and T-Cell Lymphoma

“…Thus, achieving selective nitration at C-9 position without disruption and cleavage of these labile groups and C-C bonds was challenging. Treatment of noscapine with other nitrating agents like acetyl nitrate or benzoyl nitrate also resulted in epimerization or diastereoisomers (Lee, 2002). Next, we tried inorganic nitrate salts like ammonium nitrate or silver nitrate in the presence of acidic media to achieve aromatic nitration (Crivello, 1981).…”