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Letters in Organic Chemistry
Volumn 5, Issue 7, 2008, Pages 510-513
Facile synthesis of anticancer drug NCX 4040 in mild conditions
Author keywords

Anticancer drug; Design; LNCaP cancer cell lines; Mild conditions; NCX 4040; Prostate cancer; Synthesis
Indexed keywords

EID: 57349154368     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017808785982257     Document Type: Article
Times cited : (4)
References (25)
  • 9
    • 57349184535 scopus 로고    scopus 로고
    • PCT Int. Appl. WO 2002030867, 325420
    • Del Soldato, P. PCT Int. Appl. WO 2002030867, 2002; Chem. Abstr., 2002, 136, 325420.
    • (2002) Chem. Abstr , vol.136
    • Del Soldato, P.1
  • 11
    • 57349102258 scopus 로고    scopus 로고
    • PCT Int. Appl. WO 2000044705, 152268
    • Del Soldato, P.; Garufi, M. PCT Int. Appl. WO 2000044705, 2000; Chem. Abstr., 2002, 133, 152268.
    • (2000) Chem. Abstr , vol.133
    • Del Soldato, P.1    Garufi, M.2
  • 14
    • 57349188400 scopus 로고    scopus 로고
    • Compounds 2 and 3. To a one-neck round bottom flask, were added 4-hydroxybenzyl alcohol (2.3 g, 18.5 mmol, dimethylacetamide (20 mL, To the clear solution, were added imidazole (1.96 g, 23.5 mmol) and tert-butyldimethyl silyl chloride (6.02 g, 44 mmol, After stirring overnight, the resulting mixture was decomposed by adding onto water (40 mL) and extracted with ethyl acetate for three times (3 × 20 mL, The organic layers were combined and washed with water, and dried over anhydrous MgSO4. After removal of the solvent in vacuum, the residue was checked with TLC, which showed the mixture contained two products 2 and 3. The Rf values of the compounds 2 and 3 were 0.16 and 0.23 (2% ethyl acetate in hexane, respectively. The residue was then purified with flash column chromatography using a mixed solvent (2-20% of ethyl acetate in hexane in to give compounds 2 (1.65) and 3 0.96 g
    • 4. After removal of the solvent in vacuum, the residue was then purified with flash column chromatography using a mixed solvent (5-20% of ethyl acetate in hexane in volume) to give compounds 2 (0.49 g). The overall yield for compound 2 from 4-hydroxybenzyl alcohol was 52%.
  • 15
    • 57349153010 scopus 로고    scopus 로고
    • Compound 4. To a one-neck round bottom flask, were added aspirin (1.27 g, 7.05 mmol, acetonitrile (25 mL, compound 2 (1.65 g, 7.05 mmol) and a catalytic amount of DMAP (84 mg, To the clear solution was added DCC (1.586 g, 7.7 mmol, After stirring at rt overnight, the resulting mixture was concentrated and submitted for column chromatography using a mixed solvent (3-7% of ethyl acetate in hexane in to give compound 4 (1.76 g, 63, The Rf value of compound 4 was 0.17 in 5% of ethyl acetate in hexane. 1H NMR (CDCl3, ppm, 400 MHz) δ 3.23 (t, 2 H, J, 6.8 Hz, CH2, 1.82 (m, 2 H, CH2, 1.43 (m, 2 H, CH2, 0.92 (t, 3 H, J, 7.2 Hz, CH3, 1H NMR (CDCl3, ppm, 400 MHz) δ 0.087 (s, 6 H, CH3, 0.944 (s, 9 H, CH3, 4.75 (s, 2 H, CH2, 7.15 (m, 3 H, Ar-H, 7.40 (m, 3 H, Ar-H, 7.64 t, 1 H, J
    • 5SiNa, 423.1598. Found, 423.1607.
  • 16
    • 57349146211 scopus 로고    scopus 로고
    • 2); 7.17 (m, 3 H, Ar-H); 7.44 (m, 3 H, Ar-H); 7.64 (m, 1 H, Ar-H); 8.23 (dd, 1 H, J = 8.0, 1.6 Hz, Ar-H).
    • 2); 7.17 (m, 3 H, Ar-H); 7.44 (m, 3 H, Ar-H); 7.64 (m, 1 H, Ar-H); 8.23 (dd, 1 H, J = 8.0, 1.6 Hz, Ar-H).
  • 17
    • 57349177505 scopus 로고    scopus 로고
    • 2); 7.18 (m, 3 H, Ar-H); 7.46 (m, 3 H, Ar-H); 7.67 (m, 1 H, Ar-H); 8.23 (dd, 1 H, J = 7.6, 1.4 Hz, Ar-H).
    • 2); 7.18 (m, 3 H, Ar-H); 7.46 (m, 3 H, Ar-H); 7.67 (m, 1 H, Ar-H); 8.23 (dd, 1 H, J = 7.6, 1.4 Hz, Ar-H).
  • 18
    • 57349184534 scopus 로고    scopus 로고
    • Compound 1. To a one-neck round bottom flask was added compound 6 (0.11 g, 0.348 mmol) and acetonitrile (3 mL, To the clear solution was added solid AgNO3 (0.10 g, 0.60 mmol, After stirring at 70-73°C for 4.5 h, the resulting mixture was concentrated and submitted for column chromatography using a mixed solvent (5-20% of ethyl acetate in hexane in to give compound 1 (0.11 g, 92, The Rf value of compound 1 was 0.36 in 20% of ethyl acetate in hexane. 1H NMR (CDCl3, ppm, 400 MHz) δ 5.43 (s, 2 H, CH2, 7.25 (m, 3 H, Ar-H, 7.49 (m, 3 H, Ar-H, 7.68 (m, 1 H, Ar-H, 8.23 (dd, 1 H, J, 7.6, 1.4 Hz, Ar-H, 13C NMR (CDCl3, ppm, 400 MHz) δ 21.13, 74.11, 122.40, 124.19, 126.36, 130.21, 130.70, 132.32, 134.96, 151.35, 151.44, 162.82, 169.85. ESI-TOE-high-acc (M, Na) calcd. for C16H13O7Na, 354.0584. Found, 354.0583
    • 7Na, 354.0584. Found, 354.0583.
  • 19
    • 57349121949 scopus 로고    scopus 로고
    • She, Z.; Chen, Y.; Zhang, Q.; Wang, G. Huaxue Shiji, 2001, 23, 110. Chem. Abstr., 2001, 135, 137273.
    • She, Z.; Chen, Y.; Zhang, Q.; Wang, G. Huaxue Shiji, 2001, 23, 110. Chem. Abstr., 2001, 135, 137273.
  • 25
    • 57349197813 scopus 로고    scopus 로고
    • 2. For the negative control group, only medium (buffer) was added to the cells. For the positive control group, the cells were treated with staurosporine (0.5 μM, Sigma Chemical Co., St. Louis, MO). For the NCX 4040 treating group, the cells were treated with NCX 4040 (20 μM).
    • 2. For the negative control group, only medium (buffer) was added to the cells. For the positive control group, the cells were treated with staurosporine (0.5 μM, Sigma Chemical Co., St. Louis, MO). For the NCX 4040 treating group, the cells were treated with NCX 4040 (20 μM).

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