title: The gramine route to pyrido[4,3-b]indol-3-ones - identification of a new cytotoxic lead.
abstract: A novel approach to 3-oxo-γ-carbolines was worked out starting from methyl indol-2-ylacetate via a gramine derivative. After quaternization, ammonia and 4-methoxybenzylamine could be inserted giving appropriate 3-oxo-γ-carbolines. Condensation with 2-chlorobenzaldehyde under microwave irradiation gave a 4-(2-chlorobenzyl)-3-oxo-γ-carboline. N-methylation lead to a product with very promising antifungal and cytotoxic activities.
authors: Department of Pharmacy - Center for Drug Research, Ludwig-Maximilians University, Butenandtstr. 5-13, 81377 Munich, Germany.
authors: Uwe
authors: U
authors: Wollein
authors: Franz
authors: F
authors: Bracher
references: J Med Chem. 2010 Feb 11;53(3):1383-6
references: 20030343
references: J Nat Prod. 1994 Mar;57(3):419-21
references: 8201316
references: J Immunol Methods. 1983 Dec 16;65(1-2):55-63
references: 6606682
references: J Nat Prod. 2007 Mar;70(3):461-77
references: 17309302
references: Bioorg Med Chem Lett. 2007 Aug 15;17(16):4664-9
references: 17576063
references: Arch Neurol. 2010 Feb;67(2):154-60
references: 20142523
references: J Med Chem. 2008 Dec 25;51(24):7777-87
references: 19053769
references: J Med Chem. 1998 Jul 2;41(14):2588-603
references: 9651163
references: Int J Clin Pharmacol Ther. 1995 Jul;33(7):373-83
references: 7582391
references: Drugs. 2000 Mar;59(3):511-8; discussion 519-20
references: 10776833
references: Bioorg Med Chem Lett. 2009 Jun 15;19(12):3183-7
references: 19443217
references: Biochemistry. 1981 Jan 20;20(2):298-305
references: 7008841
references: Curr Med Chem. 2007;14(4):479-500
references: 17305548
references: Org Biomol Chem. 2005 Mar 7;3(5):911-6
references: 15731878