4468-59-1Relevant articles and documents
Synthesis of N-benzyl-des-D-ring lamellarin K via an acyl-Claisen/Paal-Knorr approach
Dittrich, Nora,Pilkington, Lisa I.,Leung, Euphemia,Barker, David
, p. 1881 - 1894 (2017/03/11)
Lamellarin K is a complex pyrrole natural product and member of the lamellarin family – a group of natural products known for their potent biological activities, such as, antiproliferative activity and inhibition of P-gp mediated drug efflux pumps. We herein describe the synthesis of the N-benzyl-des-D ring analogue of lamellarin K using a route that centres on an acyl-Claisen reaction to eventually prepare a highly-functionalised 1-aryl-4-methyl-1,4-diketone. Paal-Knorr pyrrole formation using this diketone undergoes auto-oxidation to give a fully-substituted 5-formyl pyrrole which was converted into the natural lactone B ring. Antiproliferative testing of the N-benzyl-des-D ring analogue gave an IC50 of 2.63?μM against the MDA-MB-231 breast cancer cell line.
Novel phenolic glycosides, adenophorasides A-E, from Adenophora roots
Koike, Yuka,Fukumura, Motonori,Hirai, Yasuaki,Hori, Yumiko,Usui, Shiho,Atsumi, Toshiyuki,Toriizuka, Kazuo
experimental part, p. 245 - 251 (2011/02/28)
Five novel phenolic glycosides, adenophorasides A (1), B (2), C (3), D (4), and E (5), were isolated from commercial Adenophora roots, together with vanilloloside (6), 3,4-dimethoxybenzyl alcohol 7-O-β-D-glucopyranoside (7), and lobetyolin (8). The structures of the new compounds (1-5) were characterized as 4-hydroxy-3-methoxyphenylacetonitrile 4-O-β-D- glucopyranoside (1), 4-hydroxy-3-methoxyphenylacetonitrile 4-O-β-D- glucopyranosyl-1→6)-b-D-glucopyranoside (2), 4-hydroxy-3- methoxyphenylacetonitrile 4-O-α-L-rhamnopyranosyl-(1→6)-β-D- glucopyranoside (3), 4-hydroxyphenylacetonitrile 4-O-β-D-glucopyranosyl- (1→6)-β-D-glucopyranoside (4),and 4-hydroxy-3-methoxybenzyl alcohol 4-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (5), respectively, by means of spectroscopic and chemical analyses. The Japanese Society of Pharmacognosy and Springer 2010.
Syntheses of NAMDA derivatives inhibiting NO production in BV-2 cells stimulated with lipopolysaccharide
Jai, Woong Seo,Srisook, Ekaruth,Hyo, Jin Son,Hwang, Onyou,Cha, Young-Nam,Dae, Yoon Chi
, p. 3369 - 3373 (2007/10/03)
Sixteen derivatives of N-acetyl-3-O-methyldopamine (NAMDA), an inhibitor of BH4 synthesis, were designed and synthesized. The ability of these derivatives to inhibit NO and BH4 production by lipopolysaccharide- stimulated BV-2 microglial cells was determined. While NAMDA at 100 μM inhibited NO and BH4 production by only about 20%, its catecholamide 8, indole 23 derivative, 13, and N-acetyl tetrahydroisoquinoline 25 inhibited the NO production by >50% at the same concentration. In particular, 13 and 25 inhibited both NO and BH4 production to similar degrees, which suggested that these compounds might inhibit NO production by blocking BH 4-dependent dimerization of the newly synthesized iNOS monomer.