Synthesis and study of antiinflammatory and analgesic activity of 1-hydrazino-3,3-dialkyl-3,4-dihydroisoquinoline derivatives

Abstract

As is known, the class of 3,4-dihydroisoquinoline derivafives exhibits a broad spectrum of pharmacological activity [1 -4], including compounds producing spasmolytic [5], antiarrhythmie and antiaggregative [6], and hypotensive effects [7]. Acid hydrazides and hydrazones of earbonyl compounds constitute another class of substances offering a broad spectrum of biological activity. Therefore, it would be of interest to study the compounds whose molecules include pharmacophore groups belonging to beth classes.For this study we have selected a previously described compound, l-hydrazono-3,3-dimethyl-1,2,3,4-tetrahydroiso quinoline ( 1,2,3A-tetrahydroisoquinoline (lib) synthesized by a similar procedure. According to [9], these compounds occur in the tautomer form of hydrazone. The conversions were carried out in accordance with the following scheme: 258Ia, lla: R I = Me; lb, lib: R I + R l =-(CH2)4-; Ilia: R I = Me, R 2 = Ph, R 3 = H; IIIb: R 1 = Me, R 2 = 2-CeH4OH, R 3 = H; llIc: R l = Me, R 2 = 2-furyl, R 3 = H; llld: R 1 = Me, R 2 = 4-pyfidyl, R 3 = H; llle: R t --Me, R 2 = 3-methyl-5-oxo-l-phenylpyrazolin-4-yl, R 3 = H; Illf: R l = Me, C(R2,R 3) = 5-bromo-2-oxoindolin-3-ilidene; lllg: R 1 --Me, R 2 = 6-methyl-2,4-dioxo-3,4-dihydro-2H-pyran-3-yl, R 3 = Me;IVa: R l = Me, R 4 --Et;IVb: R I = Me, R 4 = Ph;IVe: R 1 = Me, R 4 = 3,4,5-CtH2(OMe)3;0091 -150X/98/3205-0258520.00 9

The Design and Synthesis of Novel 2,3-Dihydrobenzo[f]isoquinolin-4(1H)-ones via Sequential Ugi-Heck Reactions by Using an Efficient Heterogeneous Palladium Nanocatalyst

“…3,4‐Dihydroisoquinolin‐1(2H)‐ones (Fig. (i)) and benzo‐fused analogs have been found to possess biological activities . In 1951, their potency as local anesthetics was discovered and reported .…”