Design of small-molecule thrombin inhibitors based on the cis-5-phenylproline scaffold
K V Kudryavtsev
1
,
D A Shulga
1
,
V I Chupakhin
2
,
A.V. Churakov
3
,
N G Datsuk
1
,
D V Zabolotnev
1
,
N. S. Zefirov
1, 2
Publication type: Journal Article
Publication date: 2011-04-01
scimago Q3
SJR: 0.305
CiteScore: 2.8
Impact factor: —
ISSN: 10665285, 15739171
General Chemistry
Abstract
The design of novel organic compounds containing no strongly basic amidine or guanidine functional groups typical of serine protease inhibitors was performed to develop an oral anticoagulant drug. A three-dimensional computational model for thrombin active site was constructed and optimized for docking of small-molecule organic compounds and calculating the energies of inhibitor-enzyme interactions. Novel racemic derivatives of 1-[2-(4-chlorophenylthio)acetyl]-5-phenylpyrrolidine-2,4-dicarboxylic acids were synthesized for which Cl-π interactions between the inhibitors and the S1 pocket of thrombin active site are predicted by modeling. The compounds synthesized deactivate thrombin in vitro and the inhibition properties show good correlations with the results of calculations.
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Kudryavtsev K. V. et al. Design of small-molecule thrombin inhibitors based on the cis-5-phenylproline scaffold // Russian Chemical Bulletin. 2011. Vol. 60. No. 4. pp. 685-693.
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Kudryavtsev K. V., Shulga D. A., Chupakhin V. I., Churakov A., Datsuk N. G., Zabolotnev D. V., Zefirov N. S. Design of small-molecule thrombin inhibitors based on the cis-5-phenylproline scaffold // Russian Chemical Bulletin. 2011. Vol. 60. No. 4. pp. 685-693.
Cite this
RIS
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TY - JOUR
DO - 10.1007/s11172-011-0107-x
UR - http://link.springer.com/10.1007/s11172-011-0107-x
TI - Design of small-molecule thrombin inhibitors based on the cis-5-phenylproline scaffold
T2 - Russian Chemical Bulletin
AU - Kudryavtsev, K V
AU - Shulga, D A
AU - Chupakhin, V I
AU - Churakov, A.V.
AU - Datsuk, N G
AU - Zabolotnev, D V
AU - Zefirov, N. S.
PY - 2011
DA - 2011/04/01
PB - Springer Nature
SP - 685-693
IS - 4
VL - 60
SN - 1066-5285
SN - 1573-9171
ER -
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BibTex (up to 50 authors)
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@article{2011_Kudryavtsev,
author = {K V Kudryavtsev and D A Shulga and V I Chupakhin and A.V. Churakov and N G Datsuk and D V Zabolotnev and N. S. Zefirov},
title = {Design of small-molecule thrombin inhibitors based on the cis-5-phenylproline scaffold},
journal = {Russian Chemical Bulletin},
year = {2011},
volume = {60},
publisher = {Springer Nature},
month = {apr},
url = {http://link.springer.com/10.1007/s11172-011-0107-x},
number = {4},
pages = {685--693},
doi = {10.1007/s11172-011-0107-x}
}
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MLA
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Kudryavtsev, K. V., et al. “Design of small-molecule thrombin inhibitors based on the cis-5-phenylproline scaffold.” Russian Chemical Bulletin, vol. 60, no. 4, Apr. 2011, pp. 685-693. http://link.springer.com/10.1007/s11172-011-0107-x.