| Identification | Back Directory | [Name]
HFI-419 | [CAS]
1110650-72-0 | [Synonyms]
HFI-419
4H-1-Benzopyran-3-carboxylic acid, 2-(acetylamino)-7-hydroxy-4-(3-pyridinyl)-, ethyl ester | [Molecular Formula]
C19H18N2O5 | [MDL Number]
MFCD32671930 | [MOL File]
1110650-72-0.mol | [Molecular Weight]
354.36 |
| Chemical Properties | Back Directory | [Boiling point ]
584.9±50.0 °C(Predicted) | [density ]
1.36±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO: 100mg/mL | [form ]
powder | [pka]
9.13±0.70(Predicted) | [color ]
off-white | [InChI]
1S/C19H18N2O5/c1-3-25-19(24)17-16(12-5-4-8-20-10-12)14-7-6-13(23)9-15(14)26-18(17)21-11(2)22/h4-10,16,23H,3H2,1-2H3,(H,21,22) | [InChIKey]
GGBHINRNYAAYMX-UHFFFAOYSA-N | [SMILES]
CCOC(=O)C1=C(OC2=C(C1C3=CN=CC=C3)C=CC(=C2)O)NC(=O)C |
| Hazard Information | Back Directory | [Uses]
The racemic mixture of an aqueous soluble (at least 50 µg/mL or 140 µM at pH 6.5) pyridinyl-4H-benzopyran compound that inhibits insulin-regulated (IRAP) aminopeptidase activity by competing against substrate for IRAP extracellular catalytic site binding (Ki = 0.48 µM; using 25 µM Leu-AMC as substrate) with concomitant interaction with active site zinc via its acetamide, while displaying little potency against glucose-6-phosphatase, aminopeptidase N, ACE1, leukotriene A4 hydrolase, or ER-associated aminopeptidases 1 & 2 (≤13% inhibition at 100 µM). Reported to boost 1 mM dibutyryl cAMP-evoked glucose uptake in cultured rat hippocampal slices (68% higher uptake in 5 min than dbcAMP alone without 100 nM HFI-419) in vitro and exhibit in vivo memory-enhancing efficacay in an object recognition test when administered directly into the cerebral lateral ventricle of rats via a cannula implant (0.1 or 1.0 nmol/2 µL/rat). HFI-419 is reported to hydrolyze into slightly less potent HFI-142 (Ki = 2.0 µM) after i.v. (plasma t1/2 = 11 min; 2 mg/kg) or i.p (plasma t1/2 = 4.6 h; 10 mg/kg) injection in rats, although HFI-142 is more stable and likely exhibits better blood-brain permeability (Blood:Brain HFI-142 ratio = 3.36 and 0.38, respectively, 0.5 and 4 h post single 3 mg HFI-419/kg i.v. injection). | [Biological Activity]
Cell permeable: yes''Primary Target
IRAP''Reversible: yes |
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| Company Name: |
Merck KGaA
|
| Tel: |
21-20338288 |
| Website: |
www.sigmaaldrich.cn |
| Company Name: |
Enamine Ltd
|
| Tel: |
+1 732 274 9150 |
| Website: |
www.enaminestore.com |
|