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Synthesis and Crystal Structure of 6-Cyclohexyl-8-methylphenanthridine

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摘要 The target compound Ⅳ (C_(20)H_(21)N) was synthesized through four-step reactions and structurally determined by single-crystal X-ray diffraction.The crystal of compound Ⅳ is in the orthorhombic system,space group Fdd2 with a=41.178(19),b=30.389(8),c=4.8182(17)Å,β=90°,C_(20)H_(21)N,M_(r)=275.38,D_(c)=1.213g/cm^(3),V=6029(4)Å^(3),Z=16,F(000)=2368,μ(Mo Ka)=0.527 mm^(-1),T=240(2) K,2200 independent reflections with 1233 observed ones (I>2σ(I)),R=0.1285 and w R=0.2589 with GOF=1.050 (R=0.2058 and w R=0.3055for all data).A one-dimensional interaction model of the title compound was formed by one kind of π-π interactions between the two phenyl rings of the adjacent molecules at upper and lower levels.The inhibition to the strand transfer process of HIV-1 integrase of the target compound was also evaluated.
出处 《Chinese Journal of Structural Chemistry》 SCIE CAS CSCD 2021年第10期1284-1290,共7页 结构化学(英文)
基金 supported by the Natural Science Research Projects in Colleges and Universities of Anhui Province(No.KJ2019A0116) National Training Programs of Innovation and Entrepreneurship for Undergraduates(No.202010361076) Jiangxi Education Hall Science and Technology Foundation(GJJ160998)。
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  • 9General procedure for the preparation of 3: 4-nitrobenzene sulfonamide 2 were dissolved in EtOAc (50-100 mL) and SnCl2-2H2O (1.125 g per mmol nitro compound) was added. The mixture was heated under reflux for 4 h. Then, NaHCO3 solution was added until pH 7-8 was reached and the organic layer was separated. The aqueous layer was extracted three times with EtOAc. The combined organic layers were washed with brine and dried over MgSO4. Then, the solvent was removed in vacuo to obtain the crude products. General procedure for the preparation of 4: a mixture of diethyl ethoxymethylenemalonate (46 mmol) and 4-aminobenzene sulfonamide 3 (46 mmol) in 1,4-dioxane solution (25 mL) was refluxed for 3.5 h until the reaction was finished (monitor by thin lay chromatography). Then the solvent was removed under reduced pressure and the residue was recrystallized from Petroleum ether to obtain the pure products. General procedure for the preparation of 5: phenyl ether (40 mL) was heated under stirring at 250 ℃ containing catalytic p-chlorobenzoic acid. The aminomethylenemalonate 4 (10 mmol) was slowly added, and the resulting mixture was remained the temperature at 250 ℃ for 0.5 h. After the mixture was cooled at room temperature, the resulting precipitate was collected by filtration, washed with petroleum ether, and re.crystallized from DMF to provide quinolone 5. General procedure for the preparation of 6: quinolone 5 (1 mmol) was dissolved in the mixed solution of EtOH/H2O (25 mL) and NaOH ( 1.1 mmol) was added. The mixture was refluxed for 1 h. Removal of the solvents under reduced pressure and acidification with 10% H2SO4 gave a solid, which was washed with water, dichloromethane and dried. The resulting quinoline-3-carboxylic acid 6 was recrystallized from the appropriate solvent. 被引量:1
  • 10Y.E Suen, L. Robins, B.X. Yang, A.S. Verkman, Bioorg. Med. Chem. Lett. 16 (2006) 537. 被引量:1

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