79623-17-9Relevant academic research and scientific papers
In silico design and synthesis of N-arylalkanyl 2-naphthamides as a new class of non-purine xanthine oxidase inhibitors
Ho, Sheau Ling,Lin, Ching-Ting,Lee, Shoei-Sheng
, p. 789 - 801 (2021/01/12)
A series of N-arylalkanyl 2-naphthamides (Xa~e), which were predicted from virtual molecular docking on a built xanthine oxidase template as potential inhibitors, were synthesized. Their inhibitory activity against xanthine oxidase was assayed. Among these prepared, compounds Xb (IC50 13.6?μM), Xc (IC50 13.1?μM), and Xd (IC50 12.5?μM) showed comparable inhibitory activity to allopurinol (IC50 22.1?μM). The in vitro assay result correlated well with molecular docking scores, ΔG?=??16.99, ?17.66, and ?17.13 Kcal/mol, respectively. On the potassium oxonate-induced hyperuricemic mice model, oral administration of Xc-Ac (40 mg/ Kg), the per-O-acetylated Xc, could reduce the blood uric acid level by 60% in comparison to the normal control group and is statistically significant (p .01) while compared with the hyperuricemic mice group.
Synthesis, in vitro and in silico evaluation of diaryl heptanones as potential 5LOX enzyme inhibitors
Meka, Bharani,Ravada, Suryachandra Rao,Muthyala, Murali Krishna Kumar,Kurre, Purna Nagasree,Golakoti, Trimurtulu
, p. 408 - 421 (2018/07/13)
A new series of diaryl heptanones (12a-q) were synthesized and their structures were confirmed by its 1H, 13C NMR and Mass spectral data. These analogs were evaluated for their anti-oxidant activity and potential to inhibit 5-lipoxygenase. Compounds 12k and 12o showed potent in vitro 5-lipoxygenase enzyme inhibitory activity with IC50 values of 22.2, 21.5 μM, which are comparable to curcumin (24.4 μM). Further they also have shown significant antioxidant activity. Molecular docking studies clearly showed correlation between binding energy and potency of these compounds.
The Enantiospecific Nicholas Reaction
Muehldorf, Alexander V.,Guzman-Perez, Angel,Kluge, Arthur F.
, p. 8755 - 8758 (2007/10/02)
The enantiospecific Nicholas reaction, i.e. cobalt-promoted Friedel-Crafts reaction leading from chiral reactant to chiral product, was demonstrated for the first time. - Key Words: Nicholas reaction; enantiospecific; cobalt-stabilized carborations; 1-ethynyltetralin
Synthesis of Alkylphenols and -catechols from Plectranthus albidus (Labiatae)
Buergi, Christoph,Liu, Gui,Rueedi, Peter
, p. 1901 - 1915 (2007/10/02)
In the preceding paper, we described the isolation and structure elucidation of a series of even-numbered phenol- or pyrocatechol-derived 1-arylalkane-5-ones.To establish the assigned structures unambiguously and to have larger quantities available for physiological testing, the following compounds were prepared: in the alkylphenol series, 1-(4'-hydroxyphenyl)tetradecan-5-one (2a), 1-(4'-hydroxyphenyl)hexadecan-5-one (2b), and 1-(4'-hydroxyphenyl)octadecan-5-one (2c); in the alkylcatechol series, 1-(3',4'-dihydroxyphenyl)decan-5-one (3a; not isolated as a natural compound), 1-(3',4'-dihydroxyphenyl)dodecan-5-one (3b), 1-(3',4'-dihydroxyphenyl)tetradecan-5-one (3c), 1-(3',4'-dihydroxyphenyl)hexadecan-5-one (3d), 1-(3',4'-dihydroxyphenyl)octadecan-5-one (3e), and 1-(3',4'-dihydroxyphenyl)icosan-5-one (3f); in the alkenylphenol series, (Z)-1-(4'-hydroxyphenyl)octadec-13-en-5-one (4a) and (E)-1-(4'-hydroxyphenyl)octadec-13-en-5-one (4b); in the alkenylcatechol series, (E,E)-1-(3',4'-dihydroxyphenyl)deca-1,3-dien-5-one (1) and (Z)-1-(3',4'-dihydroxyphenyl)octadec-13-en-5-one (5).All compounds proved to be identical with the previously assigned structures.Compound 1 was synthesized by regioselective aldol condensation of heptan-2-one with (E)-3-(3',4'-dimethoxyphenyl)prop-2-enal (6d; Scheme 1), the phenols 2a-c and the catechols 3a-f by addition of the corresponding alkyl Grignard reagent to 5-(4'-methoxyphenyl)- or 5-(3',4'-dimethoxyphenyl)pentanal (17c and 18c, resp.; Scheme 4), and the olefins 4a, 4b and 5 from 17c or 18c via the 9-O-silyl-protected 13-(4'-methoxyphenyl)- or 13-(3',4'-dimethoxyphenyl)tridecanals (26 and 27, resp.) and Wittig olefination as the key steps (Scheme 5).
