Strychnos 1990 - 2004 - Crops for the Future

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Author Title Year Source title Reference Abstract Yu, S., O. M. Berner and J. M. Cook General approach for the synthesis of indole alkaloids via the asymmetric pictet-s 2000 Journal of the American Chemical Society 122(32): 7827-7828 - Author Title Year Source title Reference Zlotos, D. P. Stereochemistry of caracurine v 2000 Journal of Natural Products 63(6): 864-865 Abstract The 3D structure of the Strychnos alkaloid caracurine V was determined by means of NMR spectroscopy and semiempirical calculations. The previously unknown absolute configuration in the central eight-membered ring was assigned as (16R, 16'R, 17R, and 17'R). Author Title Year Source title Reference Zlotos, D. P., S. Buller, C. Trankle and K. Mohr Bisquaternary caracurine v derivatives as allosteric modulators of ligand binding t 2000 Bioorganic and Medicinal Chemistry Letters 10(22): 2529-2532 Abstract The allosteric effect on muscarinic acetylcholine M-2 receptors of 11 bisquaternary salts of the Strychnos alkaloid caracurine V was determined. The effect was indicated by the concentration which retarded the rate of dissociation of the antagonist [H-3]-N-methylscopolamine from porcine cardiac cholinoceptors by a factor of 2 (EC50). The most potent compounds carry allyl and propargyl substituents, respectively. Introduction of more bulky substituents (e.g., benzyl groups) resulted in a considerably reduced allosteric potency. The wide range of EC50 Values (3 nM for R = allyl, 1750 nM for R = 2-naphthyl) suggests a sterically restricted binding pocket. Molecular modeling studies indicated that the caracurine V ring system satisfies the pharmacophore model for the allosteric interaction. (C) 2000 Elsevier Science Ltd. All rights reserved.
Author Title Year Source title Reference Bennasar, M. L., J. M. Jimenez, B. Vidal, B. A. Sufi and J. Bosch Nucleophilic addition of 1-acetylindole enolates to pyridinium salts. Stereoselecti 1999 Journal of Organic Chemistry 64(26): 9605-9612 Abstract Addition of the enolate derived from 1-acetylindole (3) to pyridinium salt 4b followed by acidinduced cyclization of the resulting 1,4-dihydropyridine 5b in the presence of lithium iodide gives tetracyclic 3,7-methano[1,4]diazonino[1,2-alpha]indole 6b, which has subsequently been elaborated into the (E)-ethylidene derivative 7b. From this compound is reported a stereocontrolled route to (+/- )-geissoschizine, involving closure of C ring by Pummerer reaction, methanolysis of the resulting pentacyclic lactam 12, and desulfurization. A similar synthetic sequence starting from the enolate of 3 and 2-fluoropyridinium salt 15b gives access to the pentacyclic dilactam 2, which had previously b een converted to (+/-)-akagerine through opening of the piperidone (D) ring. Author Title Year Source title Reference Brandt, V., M. Tits, A. Geerlings, M. Frederich, J. Penelle, C. Delaude, R. Verpoo Beta-carboline glucoalkaloids from Strychnos mellodora 1999 Phytochemistry 51(8): 1171-1176 Abstract Two new N-b-methylated beta-carbolinium glucoalkaloids, 3,4,5,6-tetradehydropalicoside and 3,4,5,6-tetradehydrodolichantoside, together with the known beta-carboline compounds desoxycordifoline (beta-carboline 3-carboxylate glucoalkaloid) and melinonine F (N-b-methylated harmanium cation), were isolated from Strychnos mellodora stembark. The structures of the compounds were elucidated on the basis of spectroscopic studies. (C) 1999 Elsevier Science Ltd. All r i g h t s r e s e r v e d .
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