Indacrinone - CAS 57296-63-6
Catalog number:
57296-63-6
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C18H14Cl2O4
Molecular Weight:
365.21
COA:
Inquire
Description:
Indacrinone is a loop diuretic. It can be used as an antihypertensive in patients of gout with hypertension because it decreases reabsorption of uric acid.
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Purity:
98%
Appearance:
Solid powder
Synonyms:
Indacrinic acid;Indacrynic acid;MK-196;[(6,7-Dichloro-2-methyl-1-oxo-2-phenyl-2,3-dihydro-1H-inden-5-yl) oxy]acetic acid;Indacrinonum;2-[(6,7-dichloro-2-methyl-1-oxo-2-phenyl-3H-inden-5-yl)oxy]acetic acid;MK196;Acidum indacrinicum;Acetic acid, ((2,3-dihyd
Solubility:
Soluble in DMSO, not in water
Storage:
-20°C Freezer
MSDS:
Inquire
Application:
Indacrinone can be used as an antihypertensive in patients of gout with hypertension.
Quality Standard:
In-house standard
Quantity:
Milligrams-Grams
Boiling Point:
553.6±50.0 °C | Condition: Press: 760 Torr
Melting Point:
167-168 °C | Condition: Solv: acetic acid (64-19-7)
Density:
1.422±0.06 g/cm3 | Condition: Temp: 20 °C Press: 760 Torr
InChIKey:
PRKWVSHZYDOZLP-UHFFFAOYSA-N
InChI:
InChI=1S/C18H14Cl2O4/c1-18(11-5-3-2-4-6-11)8-10-7-12(24-9-13(21)22)15(19)16(20)14(10)17(18)23/h2-7H,8-9H2,1H3,(H,21,22)
Canonical SMILES:
CC1(CC2=CC(=C(C(=C2C1=O)Cl)Cl)OCC(=O)O)C3=CC=CC=C3
1.Organocatalytic tandem Morita-Baylis-Hillman-Michael reaction for asymmetric synthesis of a drug-like oxa-spirocyclic indanone scaffold.
Li X1, Yang L, Peng C, Xie X, Leng HJ, Wang B, Tang ZW, He G, Ouyang L, Huang W, Han B. Chem Commun (Camb). 2013 Oct 7;49(77):8692-4. doi: 10.1039/c3cc44004d.
A novel multicatalytic MBH-Michael tandem reaction has been developed for the asymmetric assembly of ninhydrin, nitroolefins and aldehydes into a structurally complex oxa-spirocyclic indanone backbone. Successive iodocyclization allowed us to convert these multifunctional allylic products into fused chiral natural product mimics.
2.Novel indanone derivatives as potential imaging probes for β-amyloid plaques in the brain.
Qiao JP1, Gan CS, Wang CW, Ge JF, Nan DD, Pan J, Zhou JN. Chembiochem. 2012 Jul 23;13(11):1652-62. doi: 10.1002/cbic.201200223. Epub 2012 Jul 6.
Molecular imaging probes to detect senile plaques (SPs) might help the early diagnosis of Alzheimer's disease (AD). In this study, a novel series of indanone derivatives were synthesized and characterized. In in vitro binding studies, compound 2e exhibited a K(i) value of 16 nM with a human AD brain homogenate. Although they displayed relatively low affinities for 2i and 2j--with K(i) values of 99 and 237 nM, respectively--the SPs in AD brain sections were positively stained by 2j. A method for in situ micro-autoradiography of AD brain was developed in this study and showed clear labeling of SPs by [(125)I]2i and [(125)I]2j. Both [(125)I]2i and [(125)I]2j had suitable lipophilicities and displayed high initial uptake and rapid clearance from the mouse brains. Furthermore, [(125)I]2i and [(125)I]2j were more stable in human brain homogenates than in mouse brain homogenates. These data suggest that such indanone derivatives might represent potential amyloid imaging agents for the detection of SPs in AD.
3.Discovery of indanone derivatives as multi-target-directed ligands against Alzheimer's disease.
Huang L1, Miao H1, Sun Y1, Meng F1, Li X2. Eur J Med Chem. 2014 Nov 24;87:429-39. doi: 10.1016/j.ejmech.2014.09.081. Epub 2014 Sep 26.
A series of indanone derivatives were designed, synthesized, and tested using a variety of assays to assess their potential as anti-Alzheimer's disease (AD) agents. The investigations assessed the activities of the agents for the inhibition of cholinesterases (AChE and BuChE), the inhibition of amyloid beta (Aβ) self-assembly, and the catalysis of the disassembly of preformed Aβ oligomers and measured their antioxidant activities. Our results demonstrate that most of the synthesized compounds demonstrated good inhibitory activity against AChE with IC50 values in the nanomolar range. In particular, compounds 9 (IC50 = 14.8 nM) and 14 (IC50 = 18.6 nM) exhibited markedly higher inhibitory activities than tacrine and similar activities to donepezil. In addition, 9 and 14 significantly inhibited Aβ aggregation (inhibition rates of 85.5% and 83.8%, respectively), catalysed the disaggregation of Aβ fibrils generated by self-induced Aβ aggregation, and exhibited antioxidant activity.
4.CH-activating oxidative hydroxylation of 1-tetralones and related compounds with high regio- and stereoselectivity.
Roiban GD1, Agudo R, Ilie A, Lonsdale R, Reetz MT. Chem Commun (Camb). 2014 Nov 28;50(92):14310-3. doi: 10.1039/c4cc04925j.
Mutants of P450-BM3 evolved by directed evolution are excellent catalysts in the CH-activating oxidative hydroxylation of 1-tetralone derivatives and of indanone, with unusually high regio- and enantioselectivity being observed. Similar results were achieved in the oxidative hydroxylation of tetralin and indane. The products are useful building blocks in the synthesis of a number of biologically active compounds.
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CAS 57296-63-6 Indacrinone

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