ω‐Dialkylaminoalkyl ethers of phenyl‐(5‐substituted 1‐phenyl‐1H‐pyrazol‐4‐yl)methanols with analgesic and anti‐inflammatory activity

Abstract

A series of carbinols 3a‐f was prepared starting from methanols 1a‐f via oxidation with pyridinium chlorochromate to aldehydes 2a‐f, followed by a Grignard reaction of the latter. Reaction of 3a‐f with ω‐chloroalkyldialkylamine hydrochlorides afforded a series of aminoether derivatives 4g‐t. Compounds 4i,m‐p,s showed a good analgesic activity in the acetic acid writhing test in mice. Moreover, compounds 4h,1,s exhibited a moderate anti‐inflammatory activity in the carrageenan‐induced edema assay in rats.

The crystal structure of 4-[(benzo[1,3]dioxol-5-ylmethylene)-amino]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one, C19H17N3O3

“…In this regard, pyrazole based molecules gained reasonable attention. Pyrazoles have found their applications in biological systems as analgesic [7], anti-in ammatory [8], antifungal [9], anti-hyperglycemic [10], antimicrobial [11], antitumor [12], antiviral [13] agents. The central pyrazole ring (N1/N2/C9/C8/C7) in the crystal structure of title compound is highly crowded.…”

Synthesis of Ferrocene-Modified Porphyrins by Reductive Amination Reaction

“…Starting ferrocenyl-(1-phenyl-5-ferrocenyl-3-formylpyrazole [28] 2a, 1-phenyl-5-ferrocenyl-4-formylpyrazole [29] 2b, 1-phenyl-3-ferrocenyl-4-formylpyrazole [30,31] 2c, formylferrocene [32] 2d) and phenylformylpyrazoles (1-phenyl-5-ferrocenyl-4-pyrazolecarboxaldehyde [33] 4a, and 1-phenyl-3-ferrocenyl-4-pyrazolecarboxaldehyde [34] 4b) were obtained by methods described in literature. …”

“…Noteworthy, pyrazole motif makes up the core structure of numerous biologically active compounds. [6] Some pyrazole compounds have affinity for the human CRF-1 receptor, [7] exhibit anti-viral/antitumor, [8] antibacterial, [9] anti-parasitic, [10] antipyretic, [11] antyflammatory, [9,11,12] analgesic, [12] fungistatic, [13] fungicidal, [14] and anti-hyperglycemic activity. [15] Ferrocene and porphyrins have already been associated by means of various methods.…”

Quantitative Structure Activity Relationship and Biological Activity Studies of 4-Methyl-2-(4-substituted phenyl)quinoline Derivatives

“…Quinoline and its derivatives are the important scaffold of biologically active compounds present in nature [1][2][3][4][5][6]. Many heterocyclic units contain quinoline scaffold as an integral part and show antiviral [7], antimalarial [8][9][10], antibacterial [8][9][10][11][12][13] and anticancer activities [14].…”