Erratum: Structure-based design and synthesis of novel P2/P3 modified, non-peptidic β-secretase (BACE-1) inhibitors (Bioorganic and Medicinal Chemistry Letters (2010) 20 (1924-1927))

Full text of DOI:10.1016/j.bmcl.2013.01.001

Bioorganic & Medicinal Chemistry Letters 23 (2013) 2460–2461
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Bioorganic & Medicinal Chemistry Letters
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Corrigendum
Corrigendum to ‘‘Structure-based design and synthesis of novel P2/P3
modified, non-peptidic b-secretase (BACE-1) inhibitors’’ [Bioorg. Med.
Chem. Lett. 20 (2010) 1924–1927]
a
b
b
Stephen Hanessian a, , Zhihui Shao , Claudia Betschart , Jean-Michel Rondeau ,
⇑
Ulf Neumann b, Marina Tintelnot-Blomley b
a Department of Chemistry, Université de Montréal, C. P. 6128, Succ. Centre-Ville, Montréal, P.Q., Canada H3C 3J7
b Novartis Institutes for BioMedical Research, Novartis Pharma AG, PO Box, CH-4002 Basel, Switzerland
The stereochemistries of the hydroxyl group in structures 23, 24 and 25 in Scheme 3 as well as in the structure in Table 3 should be
reversed. The updated Table and Scheme appear below.
NO
2
1, Raney-Ni, H2,
H2PtCl6, MeOH
H
H
HN
CO Me
H
H
2
CO Me
2
Br
2,
NaHCO3, MeCN
64%
18
12
5 mol% Grubbs 1st
generation catalyst,
n
N
COCl
O
n
CH2Cl2, reflux
H
H
CO Me
2
Et3N, CH2Cl2
19, n=0, (66%)
20
, n=1, (61%)
1, 1% Pd/C, H2 MeOH
n()
O
N
2, 1 M LiOH in H2O/MeOH (1:1)
3, PyBop, DIEA, CH2Cl2
H
H
CO Me
2
Ph
21
22
, n=1, (85%)
H N
N
H
2
, n=2, (80%)
OH
23
Ph
()
O
N
O
n
H
24, n=1, (62%)
25
H
, n=2, (60%)
N
H
N
H
OH
Scheme 3.
DOI of original article: http://dx.doi.org/10.1016/j.bmcl.2010.01.139
⇑
Corresponding author. Tel.: +1 514 343 6738; fax: +1 514 343 5728.
E-mail address: stephen.hanessian@umontreal.ca (S. Hanessian).
0960-894X/$ - see front matter Ó 2013 Elsevier Ltd. All rights reserved.
http://dx.doi.org/10.1016/j.bmcl.2013.01.001

S. Hanessian et al. / Bioorg. Med. Chem. Lett. 23 (2013) 2460–2461
2461
Table 3
SAR in P3 for P2/P3 cyclohexyl hydroxyethylamines
O
R
N
H
N
H
OH
Compound
R
BACE-1
BACE-2
CathD
Ab40ÁCHO
a
IC50
(l
M)
IC50 (lM)
O
26
27
4.2
3.8
3.7
7.9
7.1
No data
No data
N
H
O
0.58
0.15
N
H
O
28
24
0.20
0.96
0.41
0.56
0.66
0.13
N
O
0.025
N
O
25
0.0025
0.14
0.12
0.067
N