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
EC Number:
263-607-1
UNSPSC Code:
12352103
MDL number:
Beilstein/REAXYS Number:
477887
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
SMILES string
C[C@H](CS)C(=O)N1CCC[C@H]1C(O)=O
assay
97%
optical activity
[α]20/D −129°, c = 1.7 in ethanol
mp
104-108 °C (lit.)
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.
Regulatory Information
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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
Jie Liu et al.
Bioorganic & medicinal chemistry letters, 19(6), 1822-1824 (2009-02-24)
This letter describes the total synthesis, preliminary biological evaluation and mechanism studies of a novel and structurally unique isochromanone, (+/-)7,8-dihydroxy-3-methyl-isochromanone-4 (1), a nature product contained in banana (Musa sapientum L.) peel. The bioassay showed that compound 1 displays potent antihypertensive
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
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.
Francesca Olimpieri et al.
Bioorganic & medicinal chemistry letters, 19(16), 4715-4719 (2009-07-15)
A novel family of peptidomimetics incorporating fluoroalkyl groups, mainly a trifluoromethyl, in alpha-position to a zinc(II)-binding thiol function, was synthesized in solution as well as in solid-phase. These compounds showed inhibitory potency in the nanomolar range against both angiotensin-converting enzyme
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