Synthesis and antiinflammatory and analgesic activity of amidines of 3,4-dihydroisoquinoline series

Abstract

A series of substituted 1-arylamino-3,4-dihydroisoquinolines have been synthesized using reactions of 1-methylthio-3,3-dimethyl-3,4-dihydroisoquinolines with substituted anilines and 2-aminothiazoles. The products were tested for analgesic and antiinflammatory activity.Substituted 1-aminoisoquinolines, which can be also considered heterocyclic amidines, exhibit various types of biological activity. Compounds of this class were reported to act as antihypertensive agents [1], antitumor drugs [2], thrombin inhibitors (active upon peroral administration) [3], and specific DOPA receptor agonists [4]. Previously, we reported on the synthesis of 1-arylamino-3,3-dimethyl-3,4dihydroisoquinolines [5] with a general structure isosteric to 4-arylaminoquinazolines known to be protein kinase inhibitors [6].In continuation of these investigations, we have synthesized a series of amidines containing halogen-substituted arylimino (IIb -IId) or thiazolylamino (IIg -IIi) groups at the first position of the heterocycle, studied their antiinflammatory and analgesic properties, and compared their biologi-533 0091-150X/05/3910-0533

A novel and green method for the synthesis of highly substituted isoquinoline derivatives in ionic liquid

“…1 H NMR spectra were obtained from solution in DMSO-d 6 or CDCl 3 with Me 4 Si as internal standard using a Bruker-400 spectrometer. HRMS analyses were carried out using Bruker-micro TOF-Q-MS analyzer.…”

“…They have been reported to possess antifungal activity [3], antitumor activity [4], anticoagulant activity [5], anti-inflammatory, and analgesic activity [6]. 3-Cyanoisoquinoline I (Fig.…”

Synthesis and SAR Study of Novel Amidino 2-substituted Benzimidazoles as Potential Antibacterial Agents

“…[15] The amidine derivatives generally possess broad spectrum of biological activities: anticancer, [16] antimicrobial, [17] anti-HIV [18] and anti-inflammatory. [19,20] The positively charged amidine groups are attracted by electrostatic interactions to negatively charged DNA thus enabling selective binding. [21] In view of the afore-mentioned findings and in a continuation of our research on biologically active heterocycles, [22][23][24][25] we hereby describe the synthesis of a new 2,5(6)-disubstituted benzimidazole derivatives and their evaluation as antibacterial agents.…”

Synthesis of tert-butyl (substituted benzamido)phenylcarbamate derivatives: anti-inflammatory activity and docking studies

“…Amide formation from carboxylic acids and amines is a fundamental reaction in organic, biological, medicinal, polymer, and material chemistry for which a great amount of research is still pursued [10]. The amide derivatives were associated with a broad spectrum of biological activities including anti-inflammatory [11], antidegenerative [12], antiplatelet [13], anticancer [14,15], antimicrobial [16][17][18], urokinase…”