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Synthesis of 6-sulfamoyl-4-oxoquinoline-3-carboxylic acid derivatives as integrase antagonists with anti-HIV activity 被引量：3

Synthesis of 6-sulfamoyl-4-oxoquinoline-3-carboxylic acid derivatives as integrase antagonists with anti-HIV activity
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摘要 A series of novel 6-sulfamoyl-4-oxoquinoline-3-carboxylic acids derivatives have been synthesized and screened for HIV integrase inhibition activity. Their structures were confirmed by ESI-MS, ^1H NMR and ^13C NMR. 2009 Li Ming Hu. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved. A series of novel 6-sulfamoyl-4-oxoquinoline-3-carboxylic acids derivatives have been synthesized and screened for HIV integrase inhibition activity. Their structures were confirmed by ESI-MS, ^1H NMR and ^13C NMR. 2009 Li Ming Hu. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
作者 Zai Gang Luo Cheng Chu Zeng Lei Fu Yang Hong Qiu He Cun Xin Wang Li Ming Hu
机构地区 College of Life Science and Bioengineering
出处 《Chinese Chemical Letters》 SCIE CAS CSCD 2009年第7期789-792,共4页 中国化学快报（英文版）
基金 the financial supports of the National Basic Research Program(No.2009CB930200) the Fund from Beijing City Education Committee(No.KM200610005029) Funding Project for Academic Human Resources Development in Institutions of Higher Learning Under the Jurisdiction of Beijing Municipality.
关键词 QUINOLINE INTEGRASE Anti-HIV-1 activity Quinoline Integrase Anti-HIV-1 activity
分类号 TQ630.49 [化学工程—精细化工] TQ463.24 [化学工程—制药化工]
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  • 8General 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.
  • 9Y.E Suen, L. Robins, B.X. Yang, A.S. Verkman, Bioorg. Med. Chem. Lett. 16 (2006) 537.
  • 10Selected data of title compounds: 6a: Yellow powder, yield 71%, mp: 284-286 ℃, ^1H NMR (DMSO-de, 400 MHz, δ ppm): 1.40-1.66 (m, 12H, -CH2-adamantane), 1.91 (s, 3H, CH-adamantane), 2.40 (d, 2H, J = 6.8 Hz, CH2- Adamantane), 7.74 (t, 1H, J = 3.4 Hz, NHSO2), 8.00 (d, IH, J = 8.8 Hz, HT), 8.21 (dd, 1 H, J = 2.0 and 8.8 Hz, H8), 8.67 (d, 1 H, J = 2.0 Hz, H5), 8.98 (s, 1H, H2), 13.66 (s, 1 H, COOH). 13C NMR (DMSO- de, 100 MHz, δ ppm): 178.62, 166.27, 147.03, 141.74, 138.68, 131.36, 124.59, 121.73, 109.13, 54.78, 36.86, 33.32, 28.06. MS (ESI)m/z: 417 [M + H]^+, 439 [M + Na]^+. 6b: white powder, yield 72%, mp> 290 ℃, ^1H NMR (DMSO-de, 400 MHz, δ ppm): 1.45-1.70 (m, 12H, CH2- adamantane), 1.92 (s, 3H, CH-adamantane), 7.83 (t, 1H, NHSO2), 7.99 (d, 1H, J = 8.8 Hz, H7), 8.25 (dd, 1H, J = 2.0 and 8.8 Hz, H8), 8.73 (d,1H, J -- 2.0 Hz, H5), 8.97 (s, 1H, H2), 13.65 (s, 1H, Nil), 14.87 (s, 1H, COOH). ^13C NMR (DMSO-d6, 100 MHz, δ ppm): 178.62, 166.29, 146.94, 142.79, 141.48, 131.20, 124.56, 124.04, 121.51, 109.11, 54.55, 42.93, 35.89, 29.29. 6e: White powder, yield 76%, mp>290 ℃, ^1H NMR (DMSO-d6, 400 MHz, δ ppm): 1.56 (m, 2H, CH2), 1.90 (m, 2H, CH2), 2.25 (m, 1H, CH), 2.46 (m, 2H, CH2), 3.54 (m, 2H, CH2), 8.03 (d, 1H, J =8.8 Hz, H7), 8.17 (dd, 1H, J = 2.4 and 8.8 Hz, H8), 8.54 (d, 1H, J = 2.0 Hz, H5), 9.03 (s, 1H, H2), 12.30 (s, 1H, COOH), 13.71 (s, 1H, NH), 14.77 (s, 1H, COOH). MS (ESI) m/z: 379 [M-H]^-, 759 [2M-H]^-. 6 h: White powder, yield 83%, mp: 265-268 ~C, 1H NMR (DMSO-d6, 400 MHz, δ ppm): 3.08 (m, 4H, CH2), 3.23 (In, 41-1, CH2), 6.80 (m, 1H, H-Ar), 6.89 (m, 2H, H-Ar), 7.18 (m, 2H, H-At), 8.05 (d, 1H, J = 8.4 Hz, H7), 8.20 (dd, 1H, J = 2.0 and 8.8 Hz, H8), 8.58 (d, 1H, J = 2.0 Hz, H5), 9.03 (s, 1H, H2), 13.71 (s, 1H, NH), 14.75 (s, 1H, COOH). MS (ESI) m/ z: 412 [M-H]^-, 825 [2M-H]^-.

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Chinese Chemical Letters
2009年 第7期

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