Synthesis and Biological Evaluation of Novel Compounds Related to 1-Arylnaphthalene Lignans and Isoquinolines

Abstract

Novel compounds designed as hybrids of 1-arylnaphthalene lignans with isoquinoline alkaloids were prepared and evaluated for their cytotoxicities on human tumor cell lines, such as A549, Hela, PC-3, CNE, BEL-7404, and KB. Some of the synthetic compounds exhibited their IC50 values on selected cell lines at 10(-6) M scale. The preliminary CoMFA molecular-modelling studies of these synthetic analogues were also performed.

Oxidation and Deprotection of Primary Benzylamines by Visible Light Flavin Photocatalysis

“…Tetraacetyl riboflavin, 10 N-propyl-4-methoxybenzylamine (3e), 15 2-(4-methoxyphenyl)ethanamine (3k), 16 Bzl-Phe-OMe (9), MobPhe-OMe (11), Mob-Ala-OMe (12), 17 Mob-Pro-OMe (14), 18 BzlPro-OMe (16), 19 Boc-Phe-OMob (21), 20 Boc-Phe-OBzl (23), 21 tertbutyl 1-(benzyloxy)-3-phenylpropan-2-ylcarbamate (27), 22 and Cbz-(OH)-Pro-OBzl (31), 23 were prepared as previously reported. All other chemicals were purchased from commercial suppliers and used as received.…”

Polyphosphoric Acid–Mediated, One-Pot, Novel Reactions to Build Polymethoxyarylnaphthalene Lignans

“…[5] However, because of their nonconventional structures and the presence of a number of sterically congested, strongly electron-donating groups in one molecule, such as methoxy groups and=or methylenedioxy groups, the synthesis of polymethoxyarylnaphthalene lignans and their methylenedioxy counterparts were considerably challenging. [1][2][3][4][5][6][7][8][9] During the total synthesis of 4 00 -O-acetylmananthoside B, [10][11][12][13] unexpectedly we found a polyphosphoric acid-mediated novel reaction of succinic anhydride 3 with 1,2-dimethoxybenzene 4 to produce two polymethoxyarylnaphthalene lignans, polymethoxyarylnaphthol 1 as the minor product and polymethoxynaphtho [1,2-b]oxacycloheptatrienone 2 as the major product (Scheme 1). An optimized reaction of 3 with 4 could provide 2 specifically in good yield (Scheme 2).…”

“…Polymethoxyarylnaphthalene lignans constitute an important class of naturally occurring bioactive products that possess hypocholesterolemic, [1] antirheumatic, [2] anti-HIV, [3] and antitumor [4] activities and can also be employed as apical sodium codependent bile acid transporter inhibitors. [5] However, because of their nonconventional structures and the presence of a number of sterically congested, strongly electron-donating groups in one molecule, such as methoxy groups and=or methylenedioxy groups, the synthesis of polymethoxyarylnaphthalene lignans and their methylenedioxy counterparts were considerably challenging.…”

Facile Synthesis of Isoquinolines, β‐Carbolines, and 3‐Deazapurines

“…A pale yellow solid: mp 234-2368C (lit [21]. 245-2468C);1 H NMR (500 MHz, CDCl 3 ) d 7.31 -7.35 (1H, m, 6-H), 7.50-7.62 (5H, m, ArH), 7.95-7.99 (3H, m, 7,8, 4-H), 8.16 -8.19 (1H, m, 5-H), 8.58 -8.60 (2H, m); IR (KBr) 1624, 1594, 1560, 1496 cm 21 ; eluent: CHCl 3 /MeOH 10/1, v/v. 3-Deazapurine (3e).…”

“…All melting points were measured on a melting-point apparatus with microscope and hot stage and are uncorrected. 1 H and 13 C NMR spectra were recorded on a Varian Inova 500 NMR spectrometer. IR spectra were recorded on a Thermo Nicolet Avatar 360 IR spectrometer.…”