Convenient preparation of N-8-quinolinyl benzenesultams as novel NF-κB inhibitors

Tetrahedron Letters

Volumn 49, Issue 14, 2008, Pages 2320-2323

  Xie, Yuli ^a   Gong, Gangli ^a   Liu, Yidong ^a   Deng, Shixian ^a   Rinderspacher, Alison ^a   Branden, Lars ^b   Landry, Donald W ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

^b Department of Physiology and Cellular Biophysics ^*  (United States)

Author keywords

Benzenesultam; Cyclization; Diazotization; NF B

Indexed keywords

8 AMINOQUINOLINE DERIVATIVE; AMINOBENZENESULFONAMIDE DERIVATIVE; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; N 8 QUINOLYLBENZENESULTAM DERIVATIVE; PALLADIUM; PROTEIN INHIBITOR; SULFONAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DIAZOTIZATION; DRUG SYNTHESIS;

EID: 40049088500     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.01.136     Document Type: Article

References (10)

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3. Unpublished data from Columbia and NCGC MLSCN Center.
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9. A typical synthesis: Compound 9a: To a solution of 6-methoxy-2-methylquinolin-8-amine 2a (0.19 g, 1.0 mmol) in pyridine (5 ml) was added 4-methyl-2-nitrobenzenesulfonyl chloride (0.24 g, 1.0 mmol). The mixture was stirred at room temperature overnight and precipitated with H2O. The crude product was filtered and recrystallized from EtOH to afford nitrobenzenesulfonamide (0.31 g, 79%) as red crystal. 1H NMR (300 MHz, CDCl3) d 10.1 (br, 1H); 8.04 (d, 1H), 7.86 (d, 1H), 7.62 (m, 2H), 7.39 (d, 1H), 7.24 (d, 1H), 6.73 (s, 1H), 3.88 (s, 3H), 2.66 (s, 3H), 2.41 (s, 3H); ESI-MS (M++1): 388.0. To a suspension of above nitro compound (0.20 g, 0.56 mmol) in EtOH (5 ml) SnCl2 (0.32 g, 1.7 mmol) was slowly added. The mixture was refluxed for 2 h. After the removal of EtOH, the residue was treated with 1M NaOH. The aqueous solution was extracted with CH2Cl2. The combined organic phases were washed by brine, dried over Na2SO4, and concentrated to yield 9a (0.18 g, 92%) as a white solid. 1H NMR (300 MHz, CDCl3) d 9.42 (br, 1H); 7.83 (d, 1H), 7.65 (d, 1H), 7.30 (s, 1H), 7.23 (d, 1H), 6.64 (s, 1H), 6.48 (d, 1H), 6.42 (s, 1H), 3.80 (s, 3H), 2.61 (s, 3H), 2.17 (s, 3H); ESI-MS (M++1): 358.1. Compound 1a: To a solution of 9a (0.1 g, 0.28 mmol) in HOAc (1 ml) at 10 °C was added t-BuONO (0.05 ml, 0.42 mmol). The reaction was slowly warmed to room temperature over 10 min and quenched with H2O. The mixture was extracted with EtOAc. The combined organic phases were washed with saturated NaHCO3, dried over Na2SO4, and concentrated. Flash chromatography (EtOAc/CH2Cl2 1:10 v/v) gave 1a (74 mg, 78%) as a yellow solid. 1H NMR (300 MHz, CDCl3) d 8.49 (s, 1H), 7.98 (d, 1H), 7.92 (d, 1H), 7.37 (d, 1H), 7.25 (d, 1H), 6.87 (s, 1H), 4.00 (s, 3H), 2.69 (s, 3H), 2.52 (s, 3H); 13C NMR (75 MHz, CDCl3) d 156.2, 155.2, 142.2, 134.8, 134.5, 134.1, 132.2, 131.4, 130.1, 129.0, 126.8, 124.4, 122.0, 112.5, 100.0, 56.2, 25.2, 22.6; ESI-MS (M++1): 341.2.
10. Matsugi, M.; Tabusa, F.; Minamikawa, J. Tetrahedron Lett. 2000, 41, 8523.