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:
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.
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
Maria C Breschi et al.
Journal of medicinal chemistry, 49(8), 2628-2639 (2006-04-14)
In a preliminary work, we reported two NO-sartans, possessing the characteristics of an AT(1) antagonist and a "slow NO donor", obtained by adding NO-donor side chains to losartan 1. The NO release from an NO-sartan should be modulated in order
Mohamed A H Ismail et al.
Bioorganic & medicinal chemistry, 17(10), 3739-3746 (2009-05-01)
A series of new 3-mercapto-2-methyl-propanoyl-pyrrolidine derivatives (V, VIa-e) were designed. A new validated ACE inhibitors pharmacophore model (hypothesis) was generated for the first time in this research from the biologically active (frozen) conformation of Lisinopril-Human ACE complex that was downloaded
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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