Synthesis of 3H-spiro[benzofuran-2,1′-cyclohexane] derivatives from naturally occurring filifolinol and their classical complement pathway inhibitory activity

Synthesis and classical pathway Complement inhibitory activity of C7-functionalized filifolinol derivatives, inspired in K-76 COOH

“…We have previously prepared some filifolinol derivatives as Complement inhibitors, demonstrating through compound 10 that the carboxylic acid moiety is important but not essential for the biological activity [21] and that chemical modifications at the C-3 0 substituent level yielded inhibitors such as 11, which were more potent than K-76 COOH itself; in addition, we found that 3 0 S alcohols and amines were more potent inhibitors than their 3 0 R counterparts [22,23].…”

Regioselective 5-exo-Trig Heterocyclization of 2-Allyl-1-naphthols under the Influence of N-Iodosuccinimide or Molecular Iodine in Aqueous Micelle

“…IR spectra were recorded on KBr discs on a Perkin Elmer L 120-000A apparatus ν max (in cm −1 ). Routine 1 H NMR (300, 400 and 500 MHz) and 13 C NMR (100 MHz) spectra were recorded on Bruker DPX-300, Bruker DPX-400, and Bruker DPX-500 instruments at 298 K. The chemical shifts (δ) are given in ppm and the coupling constants (J) in Hz. In all cases the solvent for the NMR experiments was CDCl 3 (99.9%) and the references were SiMe 4 [for 1 H and 13…”

“…Heterocyclic compounds, the vital building blocks in organic synthesis, are omnipresent in various natural products and bioactive compounds [1][2][3][4]. In general, heterocyclic compounds containing naphthalene moiety are well known for their antimicrobial activities, HIV-1 integrase inhibitory effect, anti-inflammatory activity, inhibition of protein tyrosine kinases, and inactivation of enveloped viruses [5][6][7][8][9][10][11][12][13][14][15]. Over the years, organic chemists are actively involved in the syntheses of oxygen, nitrogen, and sulphur containing benzofuran and benzopyran heterocycles [16][17][18][19][20], with different reagents such as N-iodosuccinimide [21][22][23][24], pyridine hydrotribromide [25][26][27], hexamethylenetetramine hydrotribromide [28], and mercuric acetate [29,30] and, subsequently, several new methodologies have been revealed.…”

Modulators of complement activation: a patent review (2008 – 2013)

“…Several Russian patents were granted to the isolation of betulinic acid sulfate (14), disulfate and its sodium salts [191][192][193][194]. In addition, tricyclic complement inhibitor 15 was disclosed [195], as a simplified analog of the recognized inhibitor K76-COOH (16) [196][197][198][199][200].…”