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4.2.28.9. (4S,5S)-1-{3-[4-(4,5-Diphenyl-1,4-dioxolan-
4.2.28.14. (meso/trans)-1-{3-[4-(4,5-Diphenyl-1,4-dioxo-
lan-2-yl)phenoxy]propyl}-4-(5,5-diphenylpentyl)piperazine
(27/trans). Compound 27/trans was obtained according
to method B by use of 8-b/trans and 17d. Yield 63%;
1H NMR (base in CDCl3): d [ppm] = 1.24–1.31 (m,
2H, –CH2–CH2–CH2–CH–), 1.52–1.56 (m, 2H, –CH2–
CH2–CH2–CH–), 1.95–2.07 (m, 4H, –O–CH2–CH2–,
–CH2–CH–), 2.28–2.53 (m, 12H, –N–CH2–), 3.87 (t,
1H, –CH–Ph2), 4.02 (t, 2H, –O–CH2–), 5.39 (s, 2H,
–O–CHPh–CHPhO–), 6.75 (s, 1H, –CHOO–), 6.92–
7.52 (m, 20H, –ArH); Anal. C53H58N2O11 (salt) requires
C, 70.81; H, 6.50; N, 3.12. Found: C, 70.76; H, 6.53; N,
3.14; MS (ES+) m/z 667.9 (M+H).
2-yl)phenoxy]propyl}-4-methylpiperazine (22/SS). Com-
pound 22/SS 36 was obtained according to method A
by use of 8-b/SS and N-methylpiperazine. Yield 84%;
1H NMR (base in CDCl3): d [ppm] = 1.98–2.01 (m,
2H, –CH2–), 2.38 (s, 3H, –N–CH3), 2.58–2.61 (m,
10H, –CH2–), 4.04 (t, 2H, –O–CH2–), 4.91–4.94 (m,
2H, –O–CHPh–CHPh–O–), 6.34 (s, 1H, –CHOO–),
6.93–7.58 (m, 14H, –ArH); Anal. C37H42N2O11 (salt)
C, 64.34; H, 6.13; N, 4.06. Found: C, 64.37; H, 6.19;
N, 4.05; MS (ES+) m/z 459.6 (M+H).
4.2.28.10. (meso/cis)-1-{3-[4-(4,5-Diphenyl-1,4-dioxo-
lan-2-yl)phenoxy]propyl}-4-(diphenylmethyl)piperazine
(23). Compound 23 was obtained according to method
B by use of 8-b/cis and N-(diphenylmethyl)piperazine.
4.2.28.15. (meso/cis)-1-{3-[4-(4,5-Diphenyl-1,4-dioxo-
lan-2-yl)phenoxy]propyl}-4-(5,5-diphenylpentyl)piperazine
(27/cis). Compound 27/cis was obtained according to
method B by use of 8-b/cis and 17d. Yield 65%; 1H
NMR (base in CDCl3): d [ppm] = 1.24–1.30 (m, 2H,
–CH2–CH2–CH2–CH–), 1.53–1.56 (m, 2H, –CH2–
CH2–CH2–CH–), 1.97–2.07 (m, 4H, –O–CH2–CH2–,
–CH2–CH–), 2.29–2.57 (m, 12H, –N–CH2–), 3.87 (t,
1H, –CH–Ph2), 4.05 (t, 2H, –O–CH2–), 5.48 (s, 2H,
–O–CHPh–CHPh–O–), 6.13 (s, 1H, –CHOO–), 6.97–
7.66 (m, 20H, –ArH); Anal. C53H58N2O11 (salt) requires
C, 70.81; H, 6.50; N, 3.12. Found: C, 70.89; H, 6.56; N,
3.20; MS (ES+) m/z 667.9 (M+H).
1
Yield 52%; H NMR (base in CDCl3): d [ppm] = 1.94–
2.00 (m, 2H, –CH2–), 2.43–2.55 (m, 10H, –N–CH2–),
4.04 (t, 2H, –O–CH2–), 4.21 (s, 1H, –N–CH-Ph2),
5.48 (s, 2H, –O–CHPh–CHPh–O–), 6.13 (s, 1H,
–CHOO–), 6.96–7.65 (m, 20H, –ArH); Anal.
C49H50N2O11 (salt) requires C, 69.82; H, 5.98; N,
3.32. Found: C, 69.75; H, 6.06; N, 3.21; MS (ES+)
m/z 611.8 (M+H).
4.2.28.11. (meso/cis)-1-{3-[4-(4,5-Diphenyl-1,4-dioxo-
lan-2-yl)phenoxy]propyl}-4-(2,2-diphenylethyl)pipera-
zine (24). Compound 24 was obtained according to
method B by use of 8-b/cis and 17a. Yield 68%; 1H
NMR (base in CDCl3): d [ppm] = 1.92–1.97 (m, 2H,
–CH2–), 2.40–2.49 (m, 10H, –N–CH2–), 2.97 (d, 2H,
–N–CH2–CH–), 4.04 (t, 2H, –O–CH2–), 4.19 (t, 1H,
–CH–Ph2), 5.48 (s, 2H, –O–CHPh–CHPh–O–), 6.13
(s, 1H, –CHOO–), 6.90–7.65 (m, 20H, –ArH); Anal.
C50H52N2O11 (salt) requires C, 70.08; H, 6.12; N, 3.27.
Found: C, 70.15; H, 6.11; N, 3.30; MS (ES+) m/z
625.8 (M+H).
4.2.28.16. (4R,5R)-1-{3-[4-(4,5-Diphenyl-1,4-dioxolan-
2-yl)phenoxy]propyl}-4-(5,5-diphenylpentyl)piperazine (27/
RR). Compound 27/RR was obtained according to meth-
1
od B by use of 8-b/RR and 17d. Yield 63%; H NMR
(base in CDCl3): d [ppm] = 1.24–1.30 (m, 2H, –CH2–
CH2–CH2–CH–), 1.53–1.58 (m, 2H, –CH2–CH2–CH2–
CH–), 1.95–2.07 (m, 4H, –O–CH2–CH2–, –CH2–CH–),
2.29–2.54 (m, 12H, –N–CH2–), 3.87 (t, 1H, –CH–Ph2),
4.03 (t, 2H, –O–CH2–), 4.91–4.95 (m, 2H, –O–CHPh–
CHPh–O–), 6.34 (s, 1H, –CHOO–), 6.93–7.57 (m, 20H,
–ArH); Anal. C53H58N2O11 (salt) requires C, 70.81; H,
6.50; N, 3.12. Found: C, 70.83; H, 6.52; N, 3.08; MS
(ES+) m/z 667.9 (M+H).
4.2.28.12. (meso/cis)-1-{3-[4-(4,5-Diphenyl-1,4-dioxo-
lan-2-yl)phenoxy]propyl}-4-(3,3-diphenylpropyl)piperazine
(25). Compound 25 was obtained according to method
B by use of 8-b/cis and 17b. Yield 62%; 1H NMR
(base in CDCl3): d [ppm] = 1.94–1.97 (m, 2H, –O–
CH2–CH2–), 2.22–2.26 (m, 2H, –N–CH2–CH2–),
2.34–2.52 (m, 12H, –N–CH2–), 3.96 (t, 1H, –CH–
Ph2), 4.05 (t, 2H, –O–CH2–), 5.48 (s, 2H,
–O–CHPh–CHPh–O–), 6.13 (s, 1H, –CHOO–),
6.96–7.66 (m, 20H, –ArH); Anal. C51H54N2O11 (salt)
requires C, 70.33; H, 6.25; N, 3.22. Found: C, 70.36;
H, 6.19; N, 3.24; MS (ES+) m/z 639.8 (M+H).
4.2.28.17. (4S,5S)-1-{3-[4-(4,5-Diphenyl-1,4-dioxolan-2-
yl)phenoxy]propyl}-4-(5,5-diphenylpentyl)piperazine (27/SS).
Compound 27/SS was obtained according to method B by
1
use of 8-b/SS and 17d. Yield 62%; H NMR (base in
CDCl3): d [ppm] = 1.23–1.29 (m, 2H, –CH2–CH2–CH2–
CH–), 1.52–1.57 (m, 2H, –CH2–CH2–CH2–CH–), 1.93–
2.07 (m, 4H, –O–CH2–CH2–, –CH2–CH–), 2.26–2.53 (m,
12H, –N–CH2–), 3.87 (t, 1H, –CH–Ph2), 4.03 (t, 2H,
–O–CH2–), 4.91–4.95 (m, 2H, –O–CHPh–CHPh–O–),
6.34 (s, 1H, –CHOO–), 6.93–7.57 (m, 20H, –ArH); Anal.
C53H58N2O11 (salt) requires C, 70.81; H, 6.50; N, 3.12.
Found: C, 70.75; H, 6.46; N, 3.20; MS (ES+) m/z 667.9
(M+H).
4.2.28.13. (meso/cis)-1-{3-[4-(4,5-Diphenyl-1,4-dioxo-
lan-2-yl)phenoxy]propyl}-4-(4,4-diphenylbutyl)piperazine
(26). Compound 26 was obtained according to method
1
B by use of 8-b/cis and 17c. Yield 69%; H NMR (base
in CDCl3): d [ppm] = 1.45–1.48 (m, 2H, –CH2–CH2–
CH–), 1.94–2.07 (m, 4H, –O–CH2–CH2–, –CH2–CH–),
2.33–2.53 (m, 12H, –N–CH2–), 3.88 (t, 1H, –CH–Ph2),
4.05 (t, 2H, –O–CH2–), 5.48 (s, 2H, –O–CHPh–CHPh–
O–), 6.13 (s, 1H, –CHOO–), 6.97–7.66 (m, 20H,
–ArH); Anal. C52H56N2O11 (salt) requires C, 70.57; H,
6.38; N, 3.17. Found: C, 70.63; H, 6.36; N, 3.23; MS
(ES+) m/z 653.9 (M+H).
4.2.28.18.
(meso/cis)-1-{3-[4-(4,5-Bis[2-chlorophenyl]-
1,4-dioxolan-2-yl)phenoxy]propyl}-4-methylpiperazine (28).
Compound 28 was obtained according to method A by
use of 8-d/cis and N-methylpiperazine. Yield 82%; 1H
NMR (base in CDCl3): d [ppm] = 1.93–2.00 (m, 2H,
–CH2–), 2.28 (s, 3H, –N–CH3), 2.50–2.54 (m, 10H,
–CH2–), 4.03 (t, 2H, –O–CH2–), 6.02 (s, 2H, –O–