| Identification | Back Directory | [Name]
BAY 36-7620 | [CAS]
232605-26-4 | [Synonyms]
BAY 36-7620
(3aS,6aS)-Hexahydro-5-methylene-6a-(2-naphthalenylmethyl)-1H-cyclopenta[c]furan-1-one
1H-Cyclopenta[c]furan-1-one, hexahydro-5-methylene-6a-(2-naphthalenylmethyl)-, (3aS,6aS)-
(3aS,6aS)-5-methylidene-3a-(naphthalen-2-ylmethyl)-1,4,6,6a-tetrahydrocyclopenta[c]furan-3-one | [Molecular Formula]
C19H18O2 | [MDL Number]
MFCD03700725 | [MOL File]
232605-26-4.mol | [Molecular Weight]
278.35 |
| Chemical Properties | Back Directory | [Boiling point ]
471.9±34.0 °C(Predicted) | [density ]
1.19±0.1 g/cm3(Predicted) | [storage temp. ]
Store at +4°C | [solubility ]
<27.84mg/ml in ethanol; <27.84mg/ml in DMSO | [form ]
solid | [color ]
White | [Optical Rotation]
[α]/D -43 to -35°, c =0.5 in chloroform-d | [InChI]
1S/C19H18O2/c1-13-8-17-12-21-18(20)19(17,10-13)11-14-6-7-15-4-2-3-5-16(15)9-14/h2-7,9,17H,1,8,10-12H2/t17-,19+/m1/s1 | [InChIKey]
CVIRWLJKDBYYOG-MJGOQNOKSA-N | [SMILES]
C=C1C[C@@](CC2=CC3=C(C=C2)C=CC=C3)(C(OC4)=O)[C@]4([H])C1 |
| Hazard Information | Back Directory | [Uses]
Bay 36-7620, is an inhibitor of metabotropic glutamate receptor 1 (mGlu1 receptor), and thus suppresses tumor growth and angiogenesis in experimental non-small cell lung cancer (NSCLC). | [Biological Activity]
Selective mGlu 1 receptor non-competitive antagonist (IC 50 = 0.16 μ M) with inverse agonist activity. Impairs classical conditioning and associated synaptic plasticity in hippocampal neurons. Exhibits neuroprotective and anticonvulsive effects in vivo following systemic administration. | [in vitro]
bay36-7620 is a potent and selective antagonist at mglu1receptors and inhibits >60% of mglu1a receptor constitutive activity (ic50 = 0.38 μm). bay36-7620 is thus the first described mglu1 receptor inverse agonist. moreover, bay36-7620 did not displace the [3h]quisqualate binding from the glu-binding pocket, indicating that bay36-7620 is a noncompetitive mglu1 antagonist [2]. | [in vivo]
bay 36-7620 protected against pentylenetetrazole-induced convulsions in the mouse. as assessed in rats, bay 36-7620 was devoid of the typical side effects of the ionotropic glutamate (iglu) receptor antagonists phencyclidine and mk-801. therefore, bay 36-7620 did not disrupt sensorimotor gating, induce phencyclidine-like discriminative effects or stereotypical behavior, or facilitate intracranial self-stimulated behavior [3]. | [IC 50]
mGluR 1: 0.16 μM (IC50); mGluR1a: 0.38 μM (IC50); mGluR2: 0.14 μM (IC50); mGluR 5: 0.24 μM (IC50) | [storage]
Store at +4°C | [References]
[1] carroll fy, stolle a, beart pm, voerste a, brabet i, mauler f, joly c, antonicek h, bockaert j, müller t, pin jp, prézeau l. bay36-7620: a potent non-competitive mglu1 receptor antagonist with inverse agonist activity. mol pharmacol. 2001 may;59(5):965-73.
[2] de vry j, horváth e, schreiber r. neuroprotective and behavioral effects of the selective metabotropic glutamate mglu(1) receptor antagonist bay 36-7620. eur j pharmacol. 2001 oct 5;428(2):203-14. |
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