Synthesis and Antiinflammatory Activity of Certain 5,6,7,8-Tetrahydroquinolines and Related Compounds

Abstract

Modification of some 8-benzylidene-5,6,7,8-tetrahydroquinolines, which have good antiulcer activity, led to three distinct classes of compounds with good in vivo antiinflammatory activity. Initial efforts led to a series of alkenes derived from 5,6,7,8-tetrahydroquinolines substituted at the 8-position. A second approach concentrated on replacing the CH linkage of these 8-benzylidene-substituted compounds with other spacer groups and increasing the size of the cycloalkyl ring from a six- to seven-membered ring, which provided 6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine analogues. Finally, the substituent was switched from the cycloalkyl ring to the 2-position of the pyridine ring. Variation of the 2-substituent was also examined. Optimal antiinflammatory activity after oral administration was found in both the rat carrageenan paw edema and rat developing adjuvant arthritis models with 2-substituted 6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridines, and of particular interest was 27 (WY-28342).

Design, synthesis, and antitumor evaluation of novel methylene moiety-tetheredtetrahydroquinoline derivatives

“…The most potent effects among a variety of pharmacological activities are exhibited by 1,2,3,4-THQs [8][9][10][11][12], such as glucocorticoid receptor agonists [13], antagonists of vasopressin V 2 receptor [14], and antitumor agents targeting the colchicine site on tubulin [15]. A second type of THQ with the 5,6,7,8-THQ structure has appeared in some reports in which their potential biopharmaceutical effects were evaluated [16][17][18]. Recently, 5,6,7, derivatives have been presented to act as anti-HIV-1 agents [19], anticancer agents [20], and antagonists against metabotropic glutamate receptors (mGluRs) 1 (Figure 1), which play a crucial role in the prevention and control of acute neurological disorders [21].…”

Quinoline Derivatives: In Vitro Antimicrobial Study

“…Literature survey shows that various quinoline derivatives are known to possess a wide range of pharmacological properties, such as antiviral [14] , antitubercular [15] , antidiabetic [16] , antibacterial [17] , anticancer [18] , antiarthritic, analgesic [19] antiinflammatory [20] , antioxidant [21] etc. Owing to their interesting biological properties, in the present work some novel quinoline derivatives were synthesized from arylidine, dimidone and ammonium acetate.…”

Synthesis and Crystal Structure of Two Nitro-Regioisomers of cis-4-(4-Methoxyphenyl)-3-Methyl-2-Phenyl-1,2,3,4-Tetrahydroquinoline

“…A great number of natural and synthetic tetrahydroquinoline compounds are core structures in many important pharmaceutical agents (Katrizky et al 1996, Kouznetsov et al 1998. These heterocycle compounds play a key role in bioorganic and medicinal chemistry; they exhibit a wide range of biological activity, such as, antipsychotic (Singer et al 2005), anti-inflammatory (Calhoun et al 1995), anti-ulcers (Uchida et al 1989), estrogenic receptors (Chen et al 2007, Wallace et al 2007 and antimalarial activities (Bendale et al 2007), among others. Many methods have been developed for synthesis of tetrahydroquinoline derivatives (Sridharan et al 2011).…”