4 The Chemistry and Pharmacology of the Rauwolfia Alkaloids

Natural Product‐Like Combinatorial Libraries

“…174 These compounds have been shown to have activity as antihypertensive agents, anti-arrythmics, and as adrenoreceptor antagonists, 175 making them attractive targets for library synthesis. The alkaloid templates were attached to Tentagel resin-bound α-amino acids via the Ering carboxyl group, to yield intermediates 156, which were then acylated with a range of carboxylic acids to afford a 792-member library (157) (Figure 42).…”

Solution- and Solid-Phase Strategies for the Design, Synthesis, and Screening of Libraries Based on Natural Product Templates: A Comprehensive Survey

“…An early demonstration of combinatorial modifications to an existing natural product template was illustrated in the derivatization of the Rauwolfia alkaloids yohimbine (86) and rauwolscine (87) (Figure 18). 72 These alkaloids have known activity as antihypertensive agents, antiarrythmics, and as adrenoceptor antagonists, 73 making them attractive targets for library synthesis. These particular alkaloids were good candidates for combinatorial derivatization by satisfying the following criteria: (1) being commercially available in large quantities, allowing for the optimization of reactions prior to library synthesis; (2) containing a point of attachment onto the solid support, which can be accomplished via the E-ring ester after conversion to the acid; (3) containing functionality within the core skeleton which can be modified combinatorially; and (4) being stable to the reaction conditions that will be employed during library synthesis.…”

Synthesis and DPPH scavenging assay of reserpine analogues, computational studies and in silico docking studies in AChE and BChE responsible for Alzheimer's disease

“…Among alkaloids, indole alkaloids represent one of the most interesting class of compounds, especially pentacyclic natural indole alkaloids such as reserpine (Figure 3). Reserpine was isolated from Rauwolfia serpentina and is regarded an important pharmacological agent due to its extensive use in the treatment of hypertension and mental disorders (Chatterjee, Pakrashi, Werner, 1956;Woodson et al, 1957;Lucas et al, 1963;Monachino, 1954).…”