L-701324

L-701324

Names
IUPAC name 7-Chloro-4-hydroxy-3-(3-phenoxyphenyl)-1H-quinolin-2-one
Identifiers
CAS Number	142326-59-8
3D model (JSmol)	Interactive image
ChEBI	CHEBI:92140
ChEMBL	ChEMBL31741
ChemSpider	103009.html : 103009
ECHA InfoCard	100.162.301
EC Number	634-309-2
IUPHAR/BPS	4240
PubChem CID	54682505
UNII	I9WY146163
CompTox Dashboard (EPA)	DTXSID00162016
InChI InChI=1S/C21H14ClNO3/c22-14-9-10-17-18(12-14)23-21(25)19(20(17)24)13-5-4-8-16(11-13)26-15-6-2-1-3-7-15/h1-12H,(H2,23,24,25) Key: FLVRDMUHUXVRET-UHFFFAOYSA-N
SMILES C1=CC=C(C=C1)OC2=CC=CC(=C2)C3=C(C4=C(C=C(C=C4)Cl)NC3=O)O
Properties
Chemical formula	C21H14ClNO3
Molar mass	363.80 g·mol−1
Hazards
GHS labelling: [1]
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

L-701324 is an antagonist of the NMDA receptor. It appears to have activity in animal models of depression.

Pharmacology

L-701324 appears to be an antagonist of the NMDA receptor and acts at the glycine binding site. ^[2] This means that it prevents the receptor from activating by blocking the binding of glycine, a required co-agonist in addition to glutamate.

Potential use as an antidepressant

L-701324 exhibited antidepressant behavior in mice by reducing depression-like behavior caused by the forced swimming test, the tail suspension test, and the chronic unpredictable mild stress model. ^[3]

In another animal study, a combination of an adenosine receptor antagonist, such as caffeine, with an NMDA receptor antagonist, such as L-701324, showed a synergistic effect that might have use as an antidepressant. ^[4]

References

1. "7-Chloro-4-hydroxy-3-(3-phenoxyphenyl)quinolin-2(1H)-one". PubChem. U.S. National Library of Medicine.
2. Priestley T, Laughton P, Macaulay AJ, Hill RG, Kemp JA (1996). "Electrophysiological characterisation of the antagonist properties of two novel NMDA receptor glycine site antagonists, L-695,902 and L-701,324". Neuropharmacology. 35 (11): 1573–1581. doi:10.1016/s0028-3908(96)00141-4. PMID   9025105.
3. Liu L, Ji CH, Wang Y, Zhao J, Liu Y, Tang WQ, et al. (February 2021). "Antidepressant-like activity of L-701324 in mice: A behavioral and neurobiological characterization". Behavioural Brain Research. 399 113038. doi:10.1016/j.bbr.2020.113038. PMID   33276033.
4. Serefko A, Szopa A, Wlaź A, Wośko S, Wlaź P, Poleszak E (April 2016). "Synergistic antidepressant-like effect of the joint administration of caffeine and NMDA receptor ligands in the forced swim test in mice". Journal of Neural Transmission. 123 (4): 463–472. doi:10.1007/s00702-015-1467-4. PMC   4805709 . PMID   26510772.