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S. Batra et al. / Bioorg. Med. Chem. 8 (2000) 2195±2209
3-[2-(N,N0-Diethylamino)ethylamino]-1-(4-bromophenyl)-
6-hydroxy-hex-2-ene-1-one (5b). (58%, oil): IR (neat)
3375, 1593cm
J=7 Hz, 2ÂCH3), 1.88 (m, 2H, CH2), 2.48 (t, 2H,
J=6Hz, CH2), 2.59 (t, 4H, 2ÂCH2), 2.70 (t, 2H, J=6Hz,
CH2), 3.46 (q, 2H, J=6Hz, CH2), 3.74 (t, 2H, J=6Hz,
CH2), 5.63 (s, 1H,CH), 7.50, 7.53 (d, 2H, J=9Hz, Ar-
H), 7.70, 7.73 (d, 2H, J=9 Hz, Ar-H), 11.50 (brs, 1H,
NH); mass (EI) m/z 268 (M+ 114). Anal. calcd for
C18H27BrN2O2 C, 56.40, H, 7.09, N, 7.30. Found C,
56.64, H, 7.20, N, 7.77%.
2.98 (t, 4H, 2ÂCH2), 3.05 (t, 2H, J=6Hz, CH2), 3.74 (t,
2H, J=6 Hz, CH2), 3.80 (q, 2H, J=8Hz, CH2), 5.70 (s,
1H,=CH), 7.52, 7.55 (d, 2H, J=9Hz, Ar-H), 7.69, 7.72 (d,
2H, J=9 Hz, Ar-H), 11.59 (brs, 1H, NH); mass (EI) m/z
266 (M+ 114). Anal. calcd for C18H25BrN2O2 C, 71.01,
H, 9.26, N, 9.20. Found C, 70.72, H, 9.06, N, 9.08%.
1
;
1H NMR (CDCl3) d 1.06 (t, 6H,
1-(4-Methylphenyl)-3-[(-2pyrrolidin-1-yl)ethylamino]-6-
hydroxy-hex-2-ene-1-one (6c). (43%, oil): IR (Neat)
1
3396, 1598 cm
;
1H NMR (CDCl3) d 1.90 (m, 4H,
2ÂCH2), 2.01 (m, 2H, CH2), 2.32 (m, 11H, 4ÂCH2 and
Ar4-Me), 3.44 (q, 2H, J=6 Hz, CH2), 3.72 (t, 2H,
J=6 Hz, CH2), 5.69 (s, 1H,CH), 7.19, 7.22 (d, 2H,
J=9 Hz, Ar-H), 7.74, 7.77 (d, 2H, J=9 Hz, Ar-H), 11.51
(brs, 1H, NH); mass (EI) m/z 316 (M+).(Anal. calcd for
C18H28N2O2 C, 72.11, H, 8.91, N, 8.85. Found C, 72.23,
H, 8.64, N, 8.68%.
3-[2-(N,N0-Diethylamino)ethylamino]-6-hydroxy-1-(4-me-
thylphenyl)-hex-2-ene-1-one (5c). (50%, oil): IR (neat)
1
3386, 1595 cm
;
1H NMR (CDCl3) d 1.06 (t, 6H,
J=7 Hz, 2ÂCH3), 1.91 (m, 2H, CH2), 2.48 (s, 3H, Ar4-
Me), 2.48 (t, 2H, J=6 Hz, CH2), 2.59 (t, 4H, 2ÂCH2),
2.66 (t, 2H, J=6 Hz, CH2), 3.48 (q, 2H, J=6 Hz, CH2),
3.76 (t, 2H, J=6 Hz, CH2), 5.70 (s, 1H,CH), 7.21, 7.24
(d, 2H, J=9 Hz, Ar-H), 7.77, 7.80 (d, 2H, J=9 Hz, Ar-
H), 11.50 (brs, 1H, NH); mass (EI) m/z 318 (M+). Anal.
calcd for C19H30BrN2O2 C, 71.66, H, 9.49, N, 8.79.
Found C, 71.45, H, 9.25, N, 8.40%.
1-(4-Chlorophenyl)-3-[2-(pyrrolidin-1-yl) ethylamino]-6-
hydroxy-hex-2-ene-1-one (6d). (45%, 87±88 ꢀC): IR
(KBr) 3388, 1596cm 1; 1H NMR (CDCl3) d 1.88 (m, 6H,
3ÂCH2), 2.49 (t, 2H, J=6Hz, CH2), 2.72 (t, 4H, J=6Hz,
2ÂCH2), 2.79 (t, 2H, J=9Hz, CH2), 3.54 (q, 2H, J=8Hz,
CH2), 3.73 (t, 2H, J=6Hz, CH2), 5.65 (s, 1H,CH), 7.34,
7.37 (d, 2H, J=9Hz, Ar-H), 7.69, 7.72 (d, 2H, J=9Hz,
Ar-H), 11.55 (brs, 1H, NH); mass (EI) m/z 338 (M++2).
Anal. calcd for C18H25ClN2O2 C, 67.47, H, 7.48, N, 8.31.
Found C, 67,95, H, 7.51, N, 7.96%.
3-[2-(N,N0-Diethylamino)ethylamino]-1-(4-chlorophenyl)-
6-hydroxy-hex-2-ene-1-one (5d). (64%, oil): IR (neat)
1
3386, 1596cm
;
2H NMR (CDCl3) d 1.06 (t, 6H,
J=7Hz, 2ÂCH3), 1.88 (m, 2H, CH2), 2.48 (t, 2H,
J=6Hz, CH2), 2.58 (t, 4H, 2ÂCH2), 2.67 (t, 2H, J=6Hz,
CH2), 3.45 (q, 2H, J=6Hz, CH2), 3.76 (t, 2H, J=6Hz,
CH2), 5.60 (s, 1H,CH), 7.33, 7.36 (d, 2H, J=9Hz, Ar-
H), 7.77, 7.80 (d, 2H, J=9Hz, Ar-H), 11.50 (brs, 1H,
NH); 13C NMR 11.54 (CH3), 28.74 (CH2), 30.90 (CH2),
41.68 (CH2), 47.37 (CH2), 61.26 (CH2), 90.88 (CH2),
128.26, 128.87 (2ÂCH), 136.31 (C), 139.02 (C), 168.57
(C), 186.28 (C) ppm; mass (EI) m/z 338 (M+). Anal.
calcd for C18H27ClN2O2 C, 63.79, H, 8.02, N, 8.26.
Found C, 63.55, H, 8.19, N, 7.97%.
1-(4-Flourophenyl)-3-[2-(pyrrolidin-1-yl) ethylamino]-6-
hydroxy-hex-2-ene-1-one (6e). (41%, oil): IR (neat) 3365,
1
1595cm 1; H NMR (CDCl3) d 1.86 (m, 6H, 3ÂCH2),
2.46 (m, 4H, 2ÂCH2), 2.59 (t, 2H, J=6Hz, 2ÂCH2), 2.79
(t, 2H, J=9Hz, CH2), 3.54 (q, 2H, J=8Hz, CH2), 3.70 (t,
2H, J=6 Hz, CH2), 5.65 (s, 1H,=CH), 7.34, 7.37 (d,
2H, J=9 Hz, Ar-H), 7.69, 7.72 (d, 2H, J=9 Hz, Ar-H),
11.56 (brs, 1H, NH); mass (EI) m/z 320 (M+). Anal.
calcd for C18H25FN2O2 C, 67.50, H, 7.86, N, 8.74.
Found C, 67.35, H, 7.56, N, 8.56%.
3-[2-(N,N0-Diethylamino)ethylamino]-1-(4-¯uorophenyl)-
6-hydroxy-hex-2-ene-1-one (5e). (67%, oil): IR (neat)
3-[2-(Morpholin-4-yl) ethylamino]-1-phenyl-6-hydroxy-
hex-2-ene-1-one (7a). (42%, 62±63 ꢀC): IR (KBr) 3188,
1591 cm 1; 1H NMR (CDCl3) d 1.88 (m, 2H, CH2), 2.48
(t, 2H, J=6 Hz, CH2), 2.62 (m, 4H, 2ÂCH2), 2.64 (t,
2H, J=6 Hz, CH2), 3.50 (q, 2H, J=6 Hz, CH2), 3.75
(m, 6H, 3ÂCH2), 5.70 (s, 1H,CH), 7.39 (m, 3H, Ar-
H), 7.84 (m, 2H, Ar-H), 11.48 (brs, 1H, NH); mass (EI)
m/z 318(M+). Anal. calcd for C18H26N2O3 C, 67.89, H,
8.23, N, 8.80. Found C, 67.54, H, 8.14, N, 8.60%).
1
3369, 1595cm
;
1H NMR (CDCl3) d 1.07 (t, 6H,
J=7 Hz, 2ÂCH3), 1.89 (m, 2H, CH2), 2.49 (t, 2H,
J=6Hz, CH2), 2.62 (t, 4H, 2ÂCH2), 2.71 (t, 2H, J=6Hz,
CH2), 3.50 (q, 2H, J=6Hz, CH2), 3.75 (t, 2H, J=6Hz,
CH2), 5.63 (s, 1H,=CH), 7.07 (m, 2H, Ar-H), 7.85 (m,
2H, Ar-H), 11.46 (brs, 1H, NH); mass (EI) m/z 322
(M+). Anal. calcd for C18H27FN2O2 C, 71.01, H, 9.26,
N, 9.20. Found C, 70.92, H, 9.06, N, 9.08%.
1-Phenyl-3-[2-(pyrrolidin-1-yl)ethylamino]-6-hydroxy-hex-
1
1-(4-Bromophenyl)-3-[2-(morpholin-4-yl)ethylamino]-6-
hydroxy-hex-2-ene-1-one (7b). (49%, 118±120 ꢀC): IR
(KBr) 3176, 1587 cm 1; 1H NMR (CDCl3) d 1.88 (m, 2H,
CH2), 2.46 (t, 2H, J=6 Hz, CH2), 2.53 (m, 4H, 2ÂCH2),
2.63 (t, 2H, J=6 Hz, CH2), 3.49 (q, 2H, J=6 Hz, CH2),
3.75 (m, 6H, 3ÂCH2), 5.63 (s, 1H,=CH), 7.50, 7.53 (d,
2H, J=9 Hz, Ar-H), 7.70, 7.73 (d, 2H, J=9 Hz, Ar-H),
11.48 (brs, 1H, NH); mass (EI) m/z 397(M+). Anal.
calcd for C18H25BrN2O3 C, 54.41, H, 6.34, N, 7.04.
Found C, 54.65, H, 6.47, N, 7.26%.
2-ene-1-one (6a). (44%, oil): IR (neat) 3358, 1594 cm
;
1H NMR (CDCl3) d 1.88 (m, 2H, CH2), 2.26 (brs, 4H,
CH2), 2.53 (m, 4H, 2ÂCH2), 3.47 (m, 2H, CH2), 3.72 (t,
2H, J=6 Hz, CH2), 5.68 (s, 1H,CH), 7.40 (m, 3H, Ar-
H), 7.84 (m, 2H, Ar-H), 11.57 (brs, 1H, NH); mass (EI)
m/z 304 (M+). Anal. calcd for C18H26N2O2 C, 71.01, H,
9.20, N, 9.20. Found C, 70.75, H, 9.05, N, 9.07%.
1-(4-Bromophenyl)-3-[2-(pyrrolidin-1-yl)ethylamino]-6-
hydroxy-hex-2-ene-1-one (6b). (41%, 117±118ꢀC): IR
(KBr) 3360, 1596 cm 1; 1H NMR (CDCl3) d 1.90 (m, 4H,
2ÂCH2), 1.99 (m, 2H, CH2), 2.58 (t, 2H, J=6 Hz, CH2),
1-(4-Methylphenyl)-3-[(2-morpholin-4-yl) ethylamino)]-6-
hydroxy-hex-2-ene-1-one (7c). (46%, 69±70 ꢀC): IR