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ArH), 7.31 (s, 2H, –CH=), 6.85 (d, J = 8.1 Hz, 4H, ArH), 3.01
(s, 4H, –CH2–CH2–). LC–MS (m/z): 292. Anal. Calc. for
C19H16O3: C 78.06, H 5.52. Found: C 77.93, H 5.46.
5.1.2.16. 1,5-bis(3,4-Dihydroxyphenyl)-1,4-pentadiene-3-one C2.
Yield 90%. M.p. 150–154 °C. 1H NMR (DMSO-d6, 300 MHz)
δ (ppm): 9.58 (brs, 2H, –OH), 9.11 (brs, 2H, –OH), 7.54 (d,
J = 15.9 Hz, 2H, –CH=C–), 7.13 (s, 2H, ArH), 7.06 (d,
J = 8.1 Hz, 2H, ArH), 6.98 (d, J = 15.9 Hz, 2H, –C=CH–),
6.78 (d, J = 8.1 Hz, 2H, ArH). LC–MS (m/z): 298. Anal. Calc.
for C17H14O5: C 68.45, H 4.73. Found: C 68.26, H 4.67.
5.1.2.9. 2,5-bis(3,4-Dihydroxybenzylidene)cyclopentanone B2.
1
Yield 85%. M.p. > 300 °C. H NMR (DMSO-d6, 300 MHz)
δ (ppm): 9.53 (brs, 2H, –OH), 9.18 (brs, 2H, –OH), 7.23 (d,
2H, –CH=), 7.10 (s, 2H, ArH), 7.00 (d, J = 8.1 Hz, 2H, ArH),
6.82 (d, J = 8.1 Hz, 2H, ArH), 3.00 (s, 4H, –CH2–CH2–). LC–
MS (m/z): 324. Anal. Calc. for C19H16O5: C 70.36, H 4.97.
Found: C 70.18, H 4.89.
5.1.2.17. 1,5-bis(4-Hydroxy-3-methoxphenyl)-1,4-pentadiene-3-
1
one C3. Yield 98%. M.p. 99–100 °C. H NMR (DMSO-d6,
300 MHz)
δ (ppm): 9.60 (brs, 2H, –OH), 7.63 (d,
J = 15.9 Hz, 2H, –CH=C–), 7.35 (s, 2H, ArH), 7.18 (d,
J = 8.1 Hz, 2H, ArH), 7.12 (d, J = 15.9 Hz, 2H, –C=CH–),
6.81 (d, J = 8.1 Hz, 2H, ArH), 3.84 (s, 6H, OCH3). LC–MS
(m/z): 326. Anal. Calc. for C19H18O5: C 69.93, H 5.56. Found:
C 69.79, H 5.51.
5.1.2.10. 2,5-bis(4-Hydroxy-3-methoxybenzylidene)cyclopenta-
none B3. Yield 94%. M.p. 212–214 °C. H NMR (DMSO-d6,
1
300 MHz) δ (ppm): 9.64 (brs, 2H, –OH), 7.34 (s, 2H, –CH=),
7.23 (s, 2H, arom), 7.15 (d, J = 8.1 Hz, 2H, ArH), 6.87 (d,
J = 8.1 Hz, 2H, ArH), 3.83 (s, 6H, OCH3), 3.06 (s, 4H,
–H2C–CH2–). LC–MS (m/z): 352. Anal. Calc. for C21H20O5:
C 71.58, H 5.72. Found: C 71.50, H 5.68.
5.1.2.18. 1,5-bis(3,5-Di-tert-butyl-4-hydroxylphenyl)-1,4-penta-
diene-3-one C4. Yield 81%. M.p. 224–226 °C. 1H NMR
(DMSO-d6, 300 MHz) δ (ppm): 7.64 (d, J = 15.9 Hz, 2H,
–CH=C–), 7.50 (s, 4H, ArH), 7.14 (d, J = 15.9 Hz, 2H,
–C=CH–), 1.40 (s, 36H, C–CH3). LC–MS (m/z): 490. Anal.
Calc. for C33H46O3: C 80.77, H 9.45. Found: C 80.63, H 9.40.
5.1.2.11. 2,5-bis(3,5-Di-tert-butyl-4-hydroxylbenzylidene)cyclo-
pentanone B4. Yield 82%. M.p. 137–138 °C. 1H NMR
(DMSO-d6, 300 MHz) δ (ppm): 7.51 (s, 2H, –CH=), 7.43 (s,
4H, ArH), 7.35 (brs, 2H, –OH), 3.05 (4H, –H2C–CH2–), 1.45
(s, 36H, –C–CH3). LC–MS (m/z): 516. Anal. Calc. for
C35H48O3: C 81.35, H 9.36. Found: C 81.28, H 9.30.
5.1.2.19. 1,5-bis(3,4-Dimethoxyphenyl)-1,4-pentadiene-3-one C5
.
Yield 98%. M.p. 89–90 °C. 1H NMR (DMSO-d6, 300 MHz) δ
(ppm): 7.68 (d, J = 15.9 Hz, 2H, –CH=C–), 7.38 (s, 2H, ArH),
7.31 (d, J = 8.1 Hz, 2H, ArH), 7.21 (d, J = 15.9 Hz, 2H,
–C=CH–), 7.01 (d, J = 8.1 Hz, 2H, ArH), 3.84 (s, 6H,
OCH3), 3.81 (s, 6H, OCH3). LC–MS (m/z): 354. Anal. Calc.
for C21H22O5: C 71.17, H 6.26. Found: C 71.02, H 6.14.
5.1.2.12. 2,5-bis(3,4-Dimethoxybenzylidene)cyclopentanone B5
.
Yield 85%. M.p. 188–190 °C. 1H NMR (DMSO-d6,
300 MHz) δ (ppm): 7.35 (s, 2H, –CH=), 7.27 (d, J = 8.1 Hz,
4H, ArH), 7.06 (d, J = 8.1 Hz, 2H, ArH), 3.81 (12, O–CH3),
3.10 (4H, –CH2–CH2–). LC–MS (m/z): 380. Anal. Calc. for
C23H24O5: C 72.61, H 6.36. Found: C 72.52, H 6.32.
5.1.2.20. 1,5-bis(4-Hydroxy-3,5-dimethoxyphenyl)-1,4-pentadiene-
1
3-one C6. Yield 65%. M.p. 164–166 °C. H NMR (DMSO-d6,
300 MHz) δ (ppm): 9.00 (brs, 2H, –OH), 7.63 (d, J = 15.9 Hz,
2H, –CH=C–), 7.17 (d, J = 15.9 Hz, 2H, –C=CH–), 7.07 (s,
4H, ArH), 3.83 (s, 12H, OCH3). LC–MS (m/z): 386. Anal.
Calc. for C21H22O7: C 65.28, H 5.74. Found: C 65.16, H 5.65.
5.1.2.13. 2,5-bis(4-Hydroxy-3,5-dimethoxybenzylidene)cyclopen-
tanone B6. Yield 82%. M.p. 226–228 °C. 1H NMR (DMSO-d6,
300 MHz) δ (ppm): 9.03 (brs, 2H, –OH), 7.36 (s, 2H, –CH=),
6.96 (s, 4H, ArH), 3.82 (s, 12H, OCH3), 3.12 (t, J = 6.7 Hz,
4H, –CH2–CH2–). LC–MS (m/z): 412. Anal. Calc. for
C23H24O7: C 66.98, H 5.87. Found: C 66.83, H 5.82.
5.1.2.21. 3,5-bis(4-Hydroxyphenyl)-4-piperidone D1. Yield
90%. M.p. > 300 °C. 1H NMR (DMSO-d6, 300 MHz) δ
(ppm): 10.23 (brs, 2H, –OH), 9.50 (brs, 2H, –N+–H), 7.77 (s,
2H, –CH=), 7.38 (d, J = 8.1 Hz, 4H, ArH), 6.91 (d, J = 8.1 Hz,
4H, ArH), 4.45 (s, 4H, –CH2–). LC–MS (m/z):343. Anal. Calc.
for C19H18ClNO3: C 66.38, H 5.28, N 4.07. Found: C 66.18,
H5.20, N 4.04.
5.1.2.14. 2,5-bis(3-Bromo-4-hydroxy-5-methoxybenzylidene)
1
cyclopentanone B7. Yield 45%. M.p. 280–281 °C. H NMR
(DMSO-d6, 300 MHz) δ (ppm): 10.09 (brs, 2H, –OH), 7.41
(s, 2H, –CH=), 7.32 (s, 2H, ArH), 7.27 (s, 2H, ArH), 3.89 (s,
6H, OCH3), 3.07 (4H, –CH2–CH2–). LC–MS (m/z): 508. Anal.
Calc. for C21H18Br2O5: C 49.44, H 3.56. Found: C 49.32, H
3.52.
5.1.2.22. 3,5-bis(3,4-Dihydroxybenzylidene)-4-piperidone
D2.
1
Yield 90%. M.p. > 300 °C. H NMR (DMSO-d6, 300 MHz) δ
(ppm): 9.79 (brs, 2H, –OH), 9.60 (brs, 2H, –N+–H), 9.37 (brs,
2H, –OH), 7.67 (s, 2H, –CH=), 6.90 (s, 2H, ArH), 6.82 (d,
J = 8.1 Hz, 2H, ArH), 6.76 (d, J = 8.1 Hz, 2H, ArH), 4.43 (s, 4H,
–CH2–). LC–MS (m/z): 375. Anal. Calc. for C19H18ClNO5: C
60.72, H 4.83, N 3.73. Found: C 60.62, H4.78, N 3.69.
5.1.2.15. 1,5-bis(4-Hydroxyphenyl)-1,4-pentadiene-3-one C1.
Yield 95%. M.p. 243–245 °C. 1H NMR (DMSO-d6,
300 MHz) δ (ppm): 10.01 (brs, 2H, –OH), 7.64 (d,
J = 15.9 Hz, 2H, –CH=C–), 7.60 (d, J = 8.1 Hz, 4H, ArH),
7.08 (d, J = 15.9 Hz, 2H, –C=CH–), 6.82 (d, J = 8.1 Hz, 4H,
ArH). LC–MS (m/z): 266. Anal. Calc. for C17H14O3: C 76.68,
H 5.30. Found: C 76.56, H 5.23.
5.1.2.23. 3,5-bis(4-Hydroxy-3-methoxybenzyliden)-4-piperidone
D
3. C23H24O7:Yield 98%. M.p. 254–256 °C. 1H NMR