Medicinal-Pharmaceutical Chemistry Commons^™

Progress Toward The Development Of A "Catch/Release" Strategy For Isolating Salvinorin A, From Plant Materails Including Microwave Promotion, Douglas Armstrong, Logan Smith

Faculty Scholarship – Chemistry

We are investigating using the Diels-Alder and retro-Diels-Alder reactions as a potential “catch/release” strategy for isolating Salvinorin A from plant samples (Salvia divinorum), hopefully to improve the current method, which is very long and laborious. Salvinorin A has analgesic activity by activating the kappa opioid receptor, not the mu receptor, and thus it has potential for being developed into a non-addicting analgesic.

Anti-Tb And Antibacterial Activities Of Natural Products Extracts, Douglas Armstrong, Nathan Krause, Drew Frey

Faculty Scholarship – Chemistry

Samples of numerous plant species were received from the southwestern part of the USA from Richard Spjut, and plant samples were collected here in Illinois. All were extracted with typical solvents, giving crude residues, some of which were subjected to counter-current or flash chromatographic methods. Some of the crude extracts and chromatographic fractions had anti-tuberculosis and/or antibacterial activity.

In a general way, bioactive natural products are dealt with very well by Liang & Fang, 2006. More specifically, the southwestern part of the United States has a large variety of indigenous plants, many of which have not been investigated for their …

Anti-Tb And Antibacterial Activities Of Natural Products Extracts, Douglas Armstrong, Nathan Krause

Faculty Scholarship – Chemistry

Further progress has been made upon the research reported in last year’s (2012) Gordon Research Conference poster. This includes applying counter-current chromatography (CCC) to selected crude plant extracts. Two CCC fractions (DA-19 and DA-3), from different plant species, had about the same or higher anti-TB activity as their respective crude extracts, suggesting that each fraction has achieved a separation of one or more active compound(s), from other (possibly inactive) compounds. Also included was the result from the crude extract (DA-12) of still another plant species, not reported last year, which also showed significant anti-TB activity. Further work is expected to …

Small Ring Analogs Of Acetylcholine. Synthesis And Absolute Configurations Of Cyclopropane Derivatives., Douglas Armstrong, Joseph G. Cannon

Faculty Scholarship – Chemistry

Conformational rigidity has been conferred upon the OCCN portion of acetylcholine by incorporation of the C atoms into a cyclopropane ring. trans-2-Acetoxycyclopropyltrimethylammonium iodide has been prepared from an olefinic starting material, 2-vinyloxytetrahydropyran; assignment of the trans configuration to the 1,2-disubstituted cyclopropane systems was based upon literature precedent and upon nmr data, and was confirmed by X-ray crystallographic analysis. Resolution of one of the racemic intermediates in the reaction sequence was achieved, which permitted preparation of both enantiomers of the final product. X-Ray crystallographic analysis has demonstrated that the muscarinically active (+)-trans-2-acetoxycyclopropyltrimethylammonium iodide possesses the same absolute configuration …