Yuan, Rui published the artcileSynthesis of 1,7-bis (N-substituted-aminomethyl)-2,8-dihydroxy-Troger’s bases and their application in Aldol-Ullmann reaction, Quality Control of 86-51-1, the main research area is aminomethyl dihydroxy Troger base preparation anti tumor human; hydroxylcoumarin electrophile Aldol Ullmann.
1,7-Bis (N-substituted-aminomethyl)-2,8-dihydroxy-Troger’s bases I (R = CH3, n-C4H9, C6H11, etc.) were synthesized and used as efficient organocatalyst for the Aldol reaction of 4-hydroxylcoumarin and 2-benzylidenemalononitrile (or Me (ethyl)-2-cyano-3-phenylacrylate) to afford 2-amino-4-aryl-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitriles II (R1 = H, p-F, p-OCH3, etc.; R2 = CN, COOMe, COOEt). Subsequently, they were used as the efficient ligand to promote the Pd-catalyzed Aldol-Ullmann reaction to give III (R = 4-OH, 2-OCH3, 4-F, etc.) and IV (R = 5-CH3, 5-OCH3, 5-Cl, etc.), resp. The anti-cancer activity on human three pos. breast cancer cells (MCF-7), human three neg. breast cancer cells (MDA-MB-231), human hepatoma cells (HepG2), human hepatoma cells (MHCC-97H) and cytotoxicity on human hepatocyte cells (LO2) of catalyst I and all products in vitro were evaluated. I (R = CH3) had selective inhibition (inhibition rate>30%) on MCF-7 cells while I (R = 1-phenylmethyl) and I (R = pyridin-2-methyl) had selective inhibition on MDA-MB-231 cells. II (R1 = 3,4,5-(OCH3)3; R2 = CN) had strong inhibitory effects on three kinds of cancer cells except MDA-MB-231 while II (R1 = p-Br; R2 = CN), II (R1 = 2,4-Cl2; R2 = CN), II (R1 = o-F; R2 = CN) and II (R1 = o-Br; R2 = CN) had strong inhibitory effects on four kinds of cancer cells. However, all the compounds showed cytotoxicity to normal LO2 cells which prompts the necessary of structure modification to reduce the toxicity.
Youji Huaxue published new progress about Aldol addition. 86-51-1 belongs to class isoquinoline, name is 2,3-Dimethoxybenzaldehyde, and the molecular formula is C9H10O3, Quality Control of 86-51-1.
Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem