Chemical synthesis of galantamine, an acetylcholinesterase inhibitor for treatment of Alzheimer’s disease

Bibliography

• BORES GM, KOSLEY RW: Galantamine derivatives for the treatment of Alzheimer disease. Drugs Fut. (1996) 21(6):621–635.
   Google Scholar
• • An excellent review on the chemistry and biology of galantamine.
   Google Scholar
• LILIENFELD S: Galantamine — a novel cholinergic drug with a unique dual mode of action for the treatment of patients with Alzheimer's disease. CNS Drug Rev. (2002) 8(2):159–176.
   PubMedGoogle Scholar
• IRWIN RL, SMITH HJ: Cholinesterase inhibition by galantamine and lycoramine. Biochem. Pharmacol (1960) 3:147–148.
   PubMed Web of Science ®Google Scholar
• POULEV A, DEUS-NEUMANN B, ZENK MH: Enzyme immunoassay for the quantitative determination of galantamine. Planta Med. (1993) 59(5):442–446.
   PubMedGoogle Scholar
• BASTIDA J, VILADOMAT F, LLABRÉS JM, QUIROGA S, CODINA C, RUBIRALTA M: Narcissus alkaloids. Part IX. Narcissus nivalis: a new source of galantamine. Planta Med. (1990) 56(1):123–124.
   Google Scholar
• SHIEH WC, CARLSON JA: Asymmetric transformation of either enantiomer of narwedine via total spontaneous resolution process, a concise solution to the synthesis of (-)-galantamine. J. Org-. Chem. (1994) 59(18):5463–5465.
   Google Scholar
• BATTERSBY AR, TAYLOR WI: Oxidative coupling of phenols. Dekker, New York (1967).
   Google Scholar
• GIBSON SE, MIDDLETON RJ: The intramolecular Heck reaction. Contemp. Org-. Synth. (1996) 3(0:447–471.
   Google Scholar
• BARTON DHR, KIRBY GW: Phenol oxidation and biosynthesis. Part V The synthesis of galantamine. J. Chem. Soc. (1962):806–817.
   Google Scholar
• •• Seminal publication on this subject: thefirst synthesis of galantamine by using the phenol oxidative coupling strategy.
   Google Scholar
• BARTON DH, KIRBY GW, TAYLOR JB, THOMAS GM: Phenol oxidation and biosynthesis. Part VI. The biogenesis of Amaryllidaceae alkaloids. J. Chem. Soc. (1963):4545–4558.
   Google Scholar
• KAMETANI T, YAMAKI T, YAGI H, FUKUMOTO K: Studies on the syntheses of heterocyclic compounds. Part CCCXV. Modified total synthesis of (+)-galantamine through phenol oxidation. J. Chem. Soc. (1969):2602–2605.
   Google Scholar
• KRIKORIAN D, VLAHOV R, PARUSHEV S et al.: Synthesis of galantamine: intramolecular para–ortho coupling of diaryl ethers by anodic oxidation. Tetrahedron Lett. (1984) 25(28):2969–2972.
   Google Scholar
• KITA Y, ARISAWA M, GYOTEN M et al.: iodine(III) reagent: Leading to galantamine- (1998) 63(19): 6625–6633.
   Google Scholar
• • Important paper as PIFA was used the oxidant agent for the first time in the oxidative phenol coupling reaction.
   Google Scholar
• SZEWCZYKS J, LEWIN AH, CARROLL Fl: An improved synthesis of galantamine. J. Heterocyclic Chem. (1988) 25(6):1809–1811.
   Google Scholar
• SZEWCZYKS J, WILSON JW, LEWIN AH, CARROLL Fl: Facile
   Google Scholar
• NODE M, KODAMA S, HAMASHIMAY et al.: An efficient synthesis of (+)-narwedine and (2001) 40(16):3060–3062.
   Google Scholar
• KAMETANI T, PREMILA MS, FUKUMOTO K: The optical resolution of (+)-galantamine. Heterocycles (1976) 4(6):1111–1114.
   Google Scholar
• CHAPLIN DA, JOHNSON NB, PAUL JM, POTTER GA: Dynamic diastereomeric salt resolution of narwedine and its transformation to (-)-galantamine. Tetrahedron Lett. (1998) 39(37): 6777–6780.
   Google Scholar
• VLAHOV R, KRIKORIAN D, SPASSOV G et al.: Synthesis of 45(10:3329-3345.
   Google Scholar
• KDENBURG B, CZOLLNER L, FRC/LICH J, JORDIS U: Development of a pilot scale process for the anti-Alzheimer drug (-)-galantamine using large-scale phenolic oxidative coupling and crystallisation-induced chiral conversion. Org. Process. Res. Dev. (1999) 3(0:425–431.
   Google Scholar
• •• Important paper describing the industrial production of galantamine.
   Google Scholar
• KODAMA S, HAMASHIMA Y, NISHIDE K, NODE M: Total synthesis of (-)-galantamine by remote asymmetric induction. Angew. Chem. Int. Ed. (2004) 43(20):2659–2661.
   PubMedGoogle Scholar
• GUILLOU C, BEUNARD JL, GRAS E, THAL C: An efficient total synthesis of (+)-galantamine. Angew. Chem. Int. Ed (2001) 40 (24) :4745–4746.
   PubMedGoogle Scholar
• TROST BM, TOSTE FD: Enantioselective total synthesis of (-)-galantamine. J. Am. Chem. Soc. (2000) 122(45):11262–11263.
   Google Scholar
• TROST BM, TANG W: An efficient enantioselective total synthesis of (-)-galantamine. Angew. Chem. Int. Ed (2002) 41(15):2795–2797.
   PubMedGoogle Scholar
• HAN SY, SWEENEY JE, BACHMAN ES et al.: Chemical and pharmacological characterization of galantamine, an acetylcholinesterase inhibitor, and its derivatives. A potential application in Alzheimer's disease? Eur. J. Med. Chem. (1992) 27(7):673–687.
   Google Scholar
• MARY A, RENKO DZ, GUILLOU C, THAL C: Selective N-demethylation of galatamine to norgalantamine via a non classical Polonovski reaction. Tetrahedron Lett. (1997) 38 (29):5151–5152.
   Google Scholar
• MARY A, RENKO DZ, GUILLOU C, THAL C: Potent acetylcholinesterase inhibitors: design, synthesis, and structure-activity relationships of bis-interacting ligands in the galantamine series. Bioorg. Med. Chem. (1998) 6(10):1835–1850.
   PubMed Web of Science ®Google Scholar
• GUILLOU C, MARY A, RENKO DZ, GRAS E, THAL C: Potent acetylcholinesterase inhibitors: design, synthesis, and structure-activity relationships of alkylene linked bis-galantamine and galantamine-galantaminium salts. Bioorg. Med. Chem. Lett. (2000) 10(7): 637–639.
   PubMedGoogle Scholar
• HERLEM D, MARTIN MT, THAL C, GUILLOU C: Synthesis, and structure-activity relationships of open D-ring galantamine analogues. Bioorg. Med. Chem. Lett. (2003) 13(14):2389–2391.
   PubMedGoogle Scholar
• TREU M, JORDIS U, MEREITNER K: 12H- [2] -Benzothiepino [6,5a,5-bc]benzofuran: Synthesis of a sulfur-analog of galantamine. Heterocycles (2001) 55(9):1727–1735.
   Google Scholar
• TREU M, WELZIG S, JORDIS U: Bidirectional conversion of a galantamine and crinie type heterocycles. Heterocycles (2001) 55(12):2397–2404.
   Google Scholar
• POSCHALKO A, WELZIG S, TREU M et al.: Synthesis of (+)-6H-benzofuro[3a,3,2,ef] [3]benzazepine: an unnatural analog of (-)-galantamine. Tetrahedron (2002) 58(8):1513–1518.
   Google Scholar
• LIANG PH, HSIN LW, PONG SL et al.: Synthesis of galantamine analogs as acetylcholinesterase inhibitors via intramolecular Heck cyclization. J. Chin. Chem. Soc. (2003) 50(3A):449–456.
   Google Scholar
• HARVEY AL: The pharmacology of galantamine and its analogues. Pharmacol Ther. (1995) 68(1): 113–128.
   PubMed Web of Science ®Google Scholar
• SCHRATTENHOLZ A, PEREIRA EF, ROTH U et al.: Agonist responses of neuronal nicotinic acetylcholine receptors are potentiated by a novel class of allosterically acting ligands. MoL Pharmacol (1996) 49(1):1–6.
   PubMedGoogle Scholar
• PEREIRA EF, REINHARDT-MAELICKE S, SCHRATTENHOLZ A, MAELICKE A, ALBUQUERQUE EX: Identification and functional characterization of a new agonist site on nicotinic acetylcholine receptors of cultured hippocampal nuerons. Pharmacol Exp. (1993)265(3):1474–1491.
   Google Scholar