441600
Captopril
97%
Synonym(s):
N-[(S)-3-Mercapto-2-methylpropionyl]-L-proline
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About This Item
Empirical Formula (Hill Notation):
C9H15NO3S
CAS Number:
Molecular Weight:
217.29
Beilstein/REAXYS Number:
477887
EC Number:
MDL number:
UNSPSC Code:
12352103
assay
97%
optical activity
[α]20/D −129°, c = 1.7 in ethanol
mp
104-108 °C (lit.)
SMILES string
C[C@H](CS)C(=O)N1CCC[C@H]1C(O)=O
InChI
1S/C9H15NO3S/c1-6(5-14)8(11)10-4-2-3-7(10)9(12)13/h6-7,14H,2-5H2,1H3,(H,12,13)/t6-,7+/m1/s1
InChI key
FAKRSMQSSFJEIM-RQJHMYQMSA-N
Gene Information
human ... ACE(1636)
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Biochem/physiol Actions
Angiotensin converting enzyme inhibitor. Inhibits the formation of angiotensin II, a bioactive peptide that stimulates angiogenesis and increases microvessel density.
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Andreas G Tzakos et al.
Bioorganic & medicinal chemistry letters, 16(19), 5084-5087 (2006-08-08)
Enzyme-inhibitor recognition is considered one of the most fundamental aspects in the area of drug discovery. However, the molecular mechanism of this recognition process (induced fit or prebinding and adaptive selection among multiple conformers) in several cases remains unexplored. In
Ioanna Ntai et al.
Bioorganic & medicinal chemistry letters, 18(10), 3068-3071 (2007-12-22)
The naturally occurring phosphonotripeptide K-26 is a potent angiotensin converting enzyme (ACE) inhibitor containing an alpha-amino phosphonic acid analogue of tyrosine. Previous studies have demonstrated that canonical peptide analogues of K-26 are micromolar inhibitors of ACE. To ascertain the structure-activity
Guo-Xiang Li et al.
European journal of medicinal chemistry, 44(12), 4841-4847 (2009-08-21)
Antioxidant capacities of captopril (CAP), 6-mercaptopurine (6-MP) and 9-(beta-D-ribofuranosyl)-6-mercaptopurine (6-MPR) were investigated by interacting them with 2,2'-diphenyl-1-picrylhydrazyl (DPPH), galvinoxyl radical, and 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cation radical (ABTS(+)(*)), and by protecting DNA and erythrocyte against 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH) induced oxidation. It was found
A Ma Velázquez et al.
European journal of medicinal chemistry, 43(3), 486-500 (2007-06-22)
We present in this work the synthesis and cardiovascular effects of new methylthiomorpholine compounds and they were compared with cardiovascular drugs such as captopril, losartan and omapatrilat.
Hiroshi Enomoto et al.
Bioorganic & medicinal chemistry letters, 18(16), 4529-4532 (2008-08-05)
We studied the synthetic modification of structurally similar N-mercaptoacyl-L-proline and (4R)-N-mercaptoacylthiazolidine-4-carboxylic acid to obtain potent leukotriene A(4) (LTA(4)) hydrolase inhibitors. An N-mercaptoacyl group, (2S)-3-mercapto-2-methylpropionyl group, was effective for both scaffolds. Additional introduction of a large substituent such as 4-isopropylbenzylthio (3f)
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