Novel thalidomide analogues with potent NFκB and TNF expression inhibitionElectronic supplementary information (ESI) available: Experimental details. CCDC reference numbers 834073 and 834074. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c1md00184aCrystal data: Compound 9. C19H15N3O4, M = 349.34, monoclinic, space group P21/c, a = 8.0529(6), b = 16.0380(8), c = 12.8344(7) Å, β = 101.335(6)°, V = 1625.26(17) Å3, Z = 4, T = 100 K, μ = 0.103 mm−1, reflections

A series of N -phenyl thalidomide analogues have been prepared efficiently through a Buchwald-Hartwig cross coupling reaction as the key step. Several of these compounds have extraordinary TNF expression inhibition compared to both thalidomide and the current pharmaceutical agent Revlimid (Lenalidom...

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Bibliographic Details
Main Authors Yeung, Sing Yee, Kampmann, Sven, Stubbs, Keith A, Skelton, Brian W, Kaskow, Belinda J, Abraham, Lawrence J, Stewart, Scott G
Format Journal Article
LanguageEnglish
Published 01.11.2011
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Summary:A series of N -phenyl thalidomide analogues have been prepared efficiently through a Buchwald-Hartwig cross coupling reaction as the key step. Several of these compounds have extraordinary TNF expression inhibition compared to both thalidomide and the current pharmaceutical agent Revlimid (Lenalidomide). A series of N -phenyl thalidomide analogues have been prepared efficiently through a Buchwald-Hartwig cross coupling reaction as the key step. Several of these compounds have extraordinary TNF expression inhibition compared to both thalidomide and the current pharmaceutical agent Revlimid (Lenalidomide).
Bibliography:79.600(3)
100 K
349.34, monoclinic, space group
1625.26(17) Å
10
(int) = 0.0377
78.108(3)
834074
15
834073
101.335(6)
(
19
,
.
/
Crystal data: Compound
α
1
β
2
γ
3
4
8
9
0.103 mm
μ
63.344(4)
C
σ
(int) = 0.0447
1&cmb.macr
12.8344(7) Å
H
0.0495, w
I
M
(all data) = 0.117. CCDC
N
O
0.0751, w
P
For ESI and crystallographic data in CIF or other electronic format see DOI
R
14.0273(5)
T
349.34, triclinic, space group
reflections measured = 17482, independent reflections = 5757
and
V
16.2753(6) Å
Z
(all data) = 0.1589. CCDC
a
b
16.0380(8)
reflections measured = 38940, independent reflections = 18586
Compound
Electronic supplementary information (ESI) available: Experimental details. CCDC reference numbers
0.105 mm
8.0529(6)
10.1039/c1md00184a
3188.9(2) Å
16.0539(6)
ISSN:2040-2503
2040-2511
DOI:10.1039/c1md00184a