- Chiral spirodihydroindene skeleton compound and preparation method thereof
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The invention discloses a chiral spirodihydroindene skeleton compound and a preparation method thereof. The chiral spirodihydroindene skeleton compound is represented by formula I or I'. The preparation method of the chiral spirodihydroindene skeleton compound is characterized in that an intramolecular Friedel-Crafts reaction of a compound represented by formula III is carried out in a solvent under the action of a catalyst to prepare the compound represented by formula I, and the catalyst is a Bronsted acid or a Lewis acid. The preparation method has the advantages of no chiral initial raw material or chiral resolution reagent, no chiral resolution steps, simplicity, simplicity in post-treatment, good economic property, environmental protection, high product yield, and realization of high optical purity and high chemical purity of the product. Transition metal catalyzed asymmetric reaction catalysts prepared by adopting the chiral spirodihydroindene skeleton compound have a substantial catalysis effect, the product yield is greater than 99%, and the ee value of the product higher than 99%.
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Paragraph 0116-0119; 0121-0122
(2017/02/28)
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- Synthesis, molecular docking and in vitro antimicrobial studies of new hexahydroindazole derivatives of curcumin
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A series of hexahydroindazole analogues of curcumin were synthesized and investigated for in vitro and in silico antimicrobial activity. The structures of synthesized compounds were identified on the basis of satisfactory analytical and spectral data (1H NMR, 13C NMR, EI-MASS techniques and elemental analysis). Synthesized compounds showed moderate to high activity against both bacterial and fungal strains. All compounds were docked computationally to the active site of enzyme L-glutamine: D-fructose-6-phosphate amido-transferase [GlcN-6-P] (EC 2.6.1.16). The autodock programme 4.0 was employed to perform automated molecular docking. (E)-1-(7-(3-methoxybenzylidene) -3-(3- methoxyphenyl)-3,3a,4,5,6,7-hexahydro-2H-indazol-2-yl)ethanone (A7) turned out to be the most potent analogue of the series, showing best activity against bacterial and fungal strains. Compound A7 showed minimum binding and docking energy and may be considered as good inhibitor of GlcN-6-P synthase. Further investigation and optimization of this lead could provide new antimicrobial molecules.
- Kumar, Dileep,Harish,Gangwar, Mayank,Kumar, Manish,Kumar, Dharmendra,Tilak, Ragini,Nath, Gopal,Kumar, Ashok,Singh, Sushil Kumar
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p. 119 - 128
(2013/05/09)
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- Effects of diarylpentanoid analogues of curcumin on chemiluminescence and chemotactic activities of phagocytes
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Objectives A series of 43 curcumin diarylpentanoid analogues were synthesized and evaluated for their inhibitory effects on the chemiluminescence and chemotactic activity of phagocytes in vitro. Methods The effects of the compounds on the respiratory burst of human whole blood and isolated human polymorphonuclear leukocytes (PMNs) were evaluated using a luminol-based chemiluminescence assay and their effect on chemotactic migration of PMNs was investigated using the Boyden chamber technique. Key findings Compounds 6, 17, 25 and 30 exhibited significant inhibitory activity on the oxidative burst of PMNs. The presence of methoxy groups at positions 2 and 5, and methoxylation and fluorination at positions 4 and 2 of both phenyl rings, respectively, may contribute significantly to their reactive oxygen species inhibition activity. Compounds 7, 17, 18, 24 and 32 showed strong inhibition of the chemotaxis migration of PMNs. Chlorination at various positions of both phenyl rings of cyclohexanone diarylpentanoid resulted in compounds with potent inhibitory effects on PMN migration. Conclusions The results suggest that some of these diarylpentanoid analogues are able to modulate the innate immune response of phagocytes at different steps, emphasizing their potential as a source of new immunomodulatory agents.
- Jantan, Ibrahim,Bukhari, Syed Nasir Abbas,Lajis, Nordin Haji,Abas, Faridah,Wai, Lam Kok,Jasamai, Malina
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experimental part
p. 404 - 412
(2012/07/02)
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