Target Information

Target General Information

Target ID

T62276 (Former ID: TTDR01259)

Target Name

Glutamate receptor ionotropic NMDA 1 (NMDAR1)

Synonyms

NmethylDaspartate receptor subunit NR1; NMDR1; NMD-R1; N-methyl-D-aspartate receptor subunit NR1; Glutamate receptor ionotropic, NMDA 1; Glutamate [NMDA] receptor subunit zeta1; Glutamate [NMDA] receptor subunit zeta-1; GluN1

Gene Name

GRIN1

Target Type

Successful target

[1]

Disease

[+] 2 Target-related Diseases

Bacterial infection [ICD-11: 1A00-1C4Z]

HIV-infected patients with tuberculosis [ICD-11: 1B10-1B14]

Function

Channel activation requires binding of the neurotransmitter glutamate to the epsilon subunit, glycine binding to the zeta subunit, plus membrane depolarization to eliminate channel inhibition by Mg(2+). Sensitivity to glutamate and channel kinetics depend on the subunit composition. Component of NMDA receptor complexes that function as heterotetrameric, ligand-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium.

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BioChemical Class

Glutamate-gated ion channel

UniProt ID

NMDZ1_HUMAN

Sequence

MSTMRLLTLALLFSCSVARAACDPKIVNIGAVLSTRKHEQMFREAVNQANKRHGSWKIQL
NATSVTHKPNAIQMALSVCEDLISSQVYAILVSHPPTPNDHFTPTPVSYTAGFYRIPVLG
LTTRMSIYSDKSIHLSFLRTVPPYSHQSSVWFEMMRVYSWNHIILLVSDDHEGRAAQKRL
ETLLEERESKAEKVLQFDPGTKNVTALLMEAKELEARVIILSASEDDAATVYRAAAMLNM
TGSGYVWLVGEREISGNALRYAPDGILGLQLINGKNESAHISDAVGVVAQAVHELLEKEN
ITDPPRGCVGNTNIWKTGPLFKRVLMSSKYADGVTGRVEFNEDGDRKFANYSIMNLQNRK
LVQVGIYNGTHVIPNDRKIIWPGGETEKPRGYQMSTRLKIVTIHQEPFVYVKPTLSDGTC
KEEFTVNGDPVKKVICTGPNDTSPGSPRHTVPQCCYGFCIDLLIKLARTMNFTYEVHLVA
DGKFGTQERVNNSNKKEWNGMMGELLSGQADMIVAPLTINNERAQYIEFSKPFKYQGLTI
LVKKEIPRSTLDSFMQPFQSTLWLLVGLSVHVVAVMLYLLDRFSPFGRFKVNSEEEEEDA
LTLSSAMWFSWGVLLNSGIGEGAPRSFSARILGMVWAGFAMIIVASYTANLAAFLVLDRP
EERITGINDPRLRNPSDKFIYATVKQSSVDIYFRRQVELSTMYRHMEKHNYESAAEAIQA
VRDNKLHAFIWDSAVLEFEASQKCDLVTTGELFFRSGFGIGMRKDSPWKQNVSLSILKSH
ENGFMEDLDKTWVRYQECDSRSNAPATLTFENMAGVFMLVAGGIVAGIFLIFIEIAYKRH
KDARRKQMQLAFAAVNVWRKNLQDRKSGRAEPDPKKKATFRAITSTLASSFKRRRSSKDT
STGGGRGALQNQKDTVLPRRAIEREEGQLQLCSRHRES

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3D Structure

Click to Show 3D Structure of This Target

PDB

HIT2.0 ID

T86CQC

Drugs and Modes of Action

Top

Approved Drug(s)

[+] 1 Approved Drugs

Cycloserine

Drug Info

Approved

Tuberculosis

[2], [3]

Clinical Trial Drug(s)

[+] 2 Clinical Trial Drugs

ELIPRODIL

Drug Info

Phase 2

Multiple sclerosis

[4]

NBQX

Drug Info

Phase 1

Neurological disorder

[5]

Discontinued Drug(s)

[+] 6 Discontinued Drugs

YM-90K

Drug Info

Discontinued in Phase 2

Convulsion

[6]

DIZOCILPINE

Drug Info

Terminated

Cerebrovascular ischaemia

[7], [8]

L-689560

Drug Info

Terminated

Neurodegenerative disorder

[9], [10]

L-698532

Drug Info

Terminated

Neurological disorder

[11]

L-698544

Drug Info

Terminated

Alzheimer disease

[12]

L-701324

Drug Info

Terminated

Cerebrovascular ischaemia

[13], [14], [15]

Mode of Action

[+] 3 Modes of Action

Inhibitor

[+] 94 Inhibitor drugs

Cycloserine

Drug Info

[1]

D-Serine

Drug Info

[16]

ELIPRODIL

Drug Info

[17]

NBQX

Drug Info

[18]

YM-90K

Drug Info

[19]

AM-92016

Drug Info

[20]

DIZOCILPINE

Drug Info

[21]

L-687414

Drug Info

[22]

L-695902

Drug Info

[22]

L-698532

Drug Info

[24]

L-698544

Drug Info

[22]

L-701324

Drug Info

[24]

MDL-105519

Drug Info

[25]

RPR-104632

Drug Info

[26]

SPERMINE

Drug Info

[27]

(D)-Ala-Pro-Glu

Drug Info

[28]

(R)-2-Amino-5-phosphono-pentanoic acid

Drug Info

[29]

(R)-2-Amino-7-phosphono-heptanoic acid

Drug Info

[29]

1,3-ditolylguanidine

Drug Info

[30]

2-(4-Phenoxy-benzyl)-1H-benzoimidazole

Drug Info

[31]

2-(4-Phenoxy-benzyl)-3H-benzoimidazol-4-ol

Drug Info

[31]

2-(4-Phenoxy-benzyl)-3H-benzoimidazol-5-ol

Drug Info

[31]

2-(4-Phenoxy-benzyl)-3H-benzoimidazol-5-ylamine

Drug Info

[31]

2-Methylamino-succinic acid(NMDA)

Drug Info

[23], [32]

2-Pyridin-4-yl-1,2,3,4-tetrahydro-isoquinoline

Drug Info

[33]

3-Benzoyl-7-chloro-4-hydroxy-1H-quinolin-2-one

Drug Info

[22]

3-Carbamoyl-6-chloro-1H-indole-2-carboxylic acid

Drug Info

[34]

3-Hydroxy-1H-benzo[b]azepine-2,5-dione

Drug Info

[35]

3-Hydroxy-6-methyl-1H-benzo[b]azepine-2,5-dione

Drug Info

[35]

3-Hydroxy-7-nitro-1H-benzo[b]azepine-2,5-dione

Drug Info

[35]

3-Hydroxy-8-methyl-1H-benzo[b]azepine-2,5-dione

Drug Info

[35]

3-phenyl-4-hydroxyquinolin-2(1H)-one

Drug Info

[24]

4,5,7-Trichloro-3-hydroxy-1H-quinolin-2-one

Drug Info

[36]

4,6-Dichloro-1H-indole-2-carboxylic acid

Drug Info

[37]

4-(3,4-Dihydro-1H-isoquinolin-2-yl)-quinoline

Drug Info

[33]

4-Benzyl-1-(2-phenoxy-ethyl)-piperidine

Drug Info

[17]

4-Benzyl-1-phenethyl-piperidine hydrochloride

Drug Info

[38]

4-Bromo-3-hydroxy-1H-quinolin-2-one

Drug Info

[36]

4-Bromo-5,7-dichloro-3-hydroxy-1H-quinolin-2-one

Drug Info

[36]

4-Chloro-3-hydroxy-1H-quinolin-2-one

Drug Info

[36]

4-hydroxy-5-phenylthieno[2,3-b]pyridin-6(7H)-one

Drug Info

[24]

4-[2-(3-Phenyl-propylamino)-ethyl]-phenol

Drug Info

[38]

4-[2-(4-Benzyl-piperidin-1-yl)-ethoxy]-phenol

Drug Info

[17]

4-[2-(4-Phenyl-butoxy)-ethyl]-phenol

Drug Info

[38]

4-[2-(4-Phenyl-butylamino)-ethyl]-phenol

Drug Info

[38]

4-[2-(4-Phenyl-piperidin-1-yl)-ethoxy]-phenol

Drug Info

[17]

4-[2-(5-Phenyl-pentylamino)-ethyl]-phenol

Drug Info

[38]

4-[2-(6-Phenyl-hexylamino)-ethyl]-phenol

Drug Info

[38]

4-[3-(4-Phenyl-butylamino)-propyl]-phenol

Drug Info

[39]

4-[3-(5-Phenyl-pentylamino)-propyl]-phenol

Drug Info

[38]

4-{2-[Ethyl-(4-phenyl-butyl)-amino]-ethyl}-phenol

Drug Info

[38]

5,6,7-Trichloro-1,4-dihydro-quinoxaline-2,3-dione

Drug Info

[40]

5,7-Dibromo-1,4-dihydro-quinoxaline-2,3-dione

Drug Info

[40]

5,7-Dichloro-1,4-dihydro-quinoxaline-2,3-dione

Drug Info

[40]

5,7-Dichloro-3-hydroxy-1H-quinazoline-2,4-dione

Drug Info

[41]

5,7-Dichloro-4-hydroxy-3-phenyl-1H-quinolin-2-one

Drug Info

[22]

5,7-Dichlorokynurenic Acid

Drug Info

[42]

5,7-Dinitro-1,4-dihydro-quinoxaline-2,3-dione

Drug Info

[22]

6,7-Dichloro-1,4-dihydro-quinoxaline-2,3-dione

Drug Info

[40]

6,7-Dichloro-3-hydroxy-1H-quinazoline-2,4-dione

Drug Info

[41]

6-Chloro-1,4-dihydro-quinoxaline-2,3-dione

Drug Info

[43]

6-Methoxy-2-(4-phenoxy-benzyl)-1H-benzoimidazole

Drug Info

[31]

6-Nitro-1,4-dihydro-quinoxaline-2,3-dione

Drug Info

[43]

6-Nitro-2-(4-phenoxy-benzyl)-1H-benzoimidazole

Drug Info

[31]

7-chloro-3-hydroxyquinazoline-2,4-dione

Drug Info

[44]

8-Bromo-3-hydroxy-1H-benzo[b]azepine-2,5-dione

Drug Info

[35]

8-Chloro-3-hydroxy-1H-benzo[b]azepine-2,5-dione

Drug Info

[35]

8-Ethyl-3-hydroxy-1H-benzo[b]azepine-2,5-dione

Drug Info

[35]

8-Fluoro-3-hydroxy-1H-benzo[b]azepine-2,5-dione

Drug Info

[35]

Ala-Pro-Glu

Drug Info

[28]

AP-7

Drug Info

[45]

Benzyl 4-aminobutyl(3-aminopropyl)carbamate

Drug Info

[46]

Cycloleucine

Drug Info

[47]

DNQX

Drug Info

[48]

Gly-Amp-Glu

Drug Info

[28]

Gly-b7Pro-Glu

Drug Info

[28]

Gly-Hyp-Glu

Drug Info

[28]

Gly-Pip-Glu

Drug Info

[28]

H-Gly-D-dmP-Glu-OH

Drug Info

[49]

H-Gly-dmP-Glu-OH

Drug Info

[49]

N,N'-Bis-(4-butoxy-phenyl)-guanidine

Drug Info

[30]

N,N'-Bis-(4-butyl-phenyl)-guanidine

Drug Info

[30]

N,N'-Bis-(4-ethyl-phenyl)-guanidine

Drug Info

[30]

N,N'-Bis-(4-hexyl-phenyl)-guanidine

Drug Info

[30]

N,N'-Bis-(4-isopropyl-phenyl)-guanidine

Drug Info

[30]

N,N'-Bis-(4-sec-butyl-phenyl)-guanidine

Drug Info

[30]

N-(2-methoxybenzyl)cinnamamidine

Drug Info

[50]

Nle-Pro-Glu

Drug Info

[28]

Phe-Pro-Glu

Drug Info

[28]

PHENCYCLIDINE

Drug Info

[51]

Phenethyl-(3-phenyl-propyl)-amine

Drug Info

[38]

Phenethyl-(4-phenyl-butyl)-amine

Drug Info

[38]

RPR-118723

Drug Info

[26]

TRANSTORINE

Drug Info

[37]

Antagonist

[+] 7 Antagonist drugs

L-689560

Drug Info

[23]

CGP61594

Drug Info

[23]

[3H]CGP39653

Drug Info

[23]

[3H]CGS19755

Drug Info

[23]

[3H]CPP

Drug Info

[23]

[3H]dizocilpine

Drug Info

[23]

[3H]MDL105519

Drug Info

[23]

Agonist

[+] 5 Agonist drugs

(+)-HA966

Drug Info

[23]

(RS)-(tetrazol-5-yl)glycine

Drug Info

[23]

D-aspartic acid

Drug Info

[23]

homoquinolinic acid

Drug Info

[23]

L-aspartic acid

Drug Info

[23]

Chemical Structure based Activity Landscape of Target

Top

Drug Property Profile of Target

Top

(1) Molecular Weight (mw) based Drug Clustering

(2) Octanol/Water Partition Coefficient (xlogp) based Drug Clustering

(3) Hydrogen Bond Donor Count (hbonddonor) based Drug Clustering

(4) Hydrogen Bond Acceptor Count (hbondacc) based Drug Clustering

(5) Rotatable Bond Count (rotbonds) based Drug Clustering

(6) Topological Polar Surface Area (polararea) based Drug Clustering

"RO5" indicates the cutoff set by lipinski's rule of five; "D123AB" colored in GREEN denotes the no violation of any cutoff in lipinski's rule of five; "D123AB" colored in PURPLE refers to the violation of only one cutoff in lipinski's rule of five; "D123AB" colored in BLACK represents the violation of more than one cutoffs in lipinski's rule of five

Co-Targets

Top

Co-Targets

Co-Targets Info

Target Poor or Non Binders

Top

Target Poor or Non Binders

Target Poor or Non Binders Info

Target Profiles in Patients

Top

Target Expression
Profile (TEP)

Target Expression Profile Info

Target Affiliated Biological Pathways		Top
KEGG Pathway	[+] 15 KEGG Pathways	+
1	Ras signaling pathway
2	Rap1 signaling pathway
3	Calcium signaling pathway
4	cAMP signaling pathway
5	Neuroactive ligand-receptor interaction
6	Circadian entrainment
7	Long-term potentiation
8	Glutamatergic synapse
9	Alzheimer's disease
10	Amyotrophic lateral sclerosis (ALS)
11	Huntington's disease
12	Cocaine addiction
13	Amphetamine addiction
14	Nicotine addiction
15	Alcoholism
Panther Pathway	[+] 5 Panther Pathways	+
1	Huntington disease
2	Ionotropic glutamate receptor pathway
3	Metabotropic glutamate receptor group III pathway
4	Metabotropic glutamate receptor group I pathway
5	Muscarinic acetylcholine receptor 1 and 3 signaling pathway
Reactome	[+] 5 Reactome Pathways	+
1	EPHB-mediated forward signaling
2	Unblocking of NMDA receptor, glutamate binding and activation
3	CREB phosphorylation through the activation of CaMKII
4	Ras activation uopn Ca2+ infux through NMDA receptor
5	RAF/MAP kinase cascade
WikiPathways	[+] 6 WikiPathways	+
1	SIDS Susceptibility Pathways
2	Hypothetical Network for Drug Addiction
3	Neurotransmitter Receptor Binding And Downstream Transmission In The Postsynaptic Cell
4	Spinal Cord Injury
5	BDNF signaling pathway
6	Alzheimers Disease

Target-Related Models and Studies

Top

Target Validation

Target Validation Info

References

Top

REF 1

How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.

REF 2

Novel agents in the management of Mycobacterium tuberculosis disease. Curr Med Chem. 2007;14(18):2000-8.

REF 3

Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015

REF 4

ClinicalTrials.gov (NCT00001929) Treatment of Parkinson's Disease With Eliprodil. U.S. National Institutes of Health.

REF 5

URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4264).

REF 6

Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800002155)

REF 7

REF 8

Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800000713)

REF 9

REF 10

Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800001828)

REF 11

Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800006620)

REF 12

Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800003218)

REF 13

REF 14

Anticonvulsant and behavioral profile of L-701,324, a potent, orally active antagonist at the glycine modulatory site on the N-methyl-D-aspartate receptor complex. J Pharmacol Exp Ther. 1996 Nov;279(2):492-501.

REF 15

L-701,324, a selective antagonist at the glycine site of the NMDA receptor, counteracts haloperidol-induced muscle rigidity in rats. Psychopharmacology (Berl). 1999 Apr;143(3):235-43.

REF 16

Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5.

REF 17

4-Hydroxy-1-[2-(4-hydroxyphenoxy)ethyl]-4-(4-methylbenzyl)piperidine: a novel, potent, and selective NR1/2B NMDA receptor antagonist. J Med Chem. 1999 Jul 29;42(15):2993-3000.

REF 18

Synthesis, ionotropic glutamate receptor binding affinity, and structure-activity relationships of a new set of 4,5-dihydro-8-heteroaryl-4-oxo-1,2,... J Med Chem. 2001 Sep 13;44(19):3157-65.

REF 19

4,10-Dihydro-4-oxo-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-2-carboxylic acid derivatives: highly potent and selective AMPA receptors antagonists with... Bioorg Med Chem Lett. 2000 May 15;10(10):1133-7.

REF 20

Enantiomeric propanolamines as selective N-methyl-D-aspartate 2B receptor antagonists. J Med Chem. 2008 Sep 25;51(18):5506-21.

REF 21

Synthesis and evaluation of 6,11-ethanohexahydrobenzo[b]quinolizidines: a new class of noncompetitive N-methyl-D-aspartate antagonists. J Med Chem. 1995 Jun 23;38(13):2483-9.

REF 22

Amino acid bioisosteres: design of 2-quinolone derivatives as glycine-site N-methyl-D-aspartate receptor antagonists, Bioorg. Med. Chem. Lett. 3(2):299-304 (1993).

REF 23

REF 24

Synthesis of thieno[2,3-b]pyridinones acting as cytoprotectants and as inhibitors of [3H]glycine binding to the N-methyl-D-aspartate (NMDA) receptor. J Med Chem. 2006 Feb 9;49(3):864-71.

REF 25

CoMFA, synthesis, and pharmacological evaluation of (E)-3-(2-carboxy-2-arylvinyl)-4,6-dichloro-1H-indole-2-carboxylic acids: 3-[2-(3-aminophenyl)-2... J Med Chem. 2005 Feb 24;48(4):995-1018.

REF 26

Indeno[1,2-b]pyrazin-2,3-diones: a new class of antagonists at the glycine site of the NMDA receptor with potent in vivo activity. J Med Chem. 2000 Jun 15;43(12):2371-81.

REF 27

Bivalent beta-carbolines as potential multitarget anti-Alzheimer agents. J Med Chem. 2010 May 13;53(9):3611-7.

REF 28

New Gly-Pro-Glu (GPE) analogues: expedite solid-phase synthesis and biological activity. Bioorg Med Chem Lett. 2006 Mar 1;16(5):1392-6.

REF 29

Synthesis and pharmacology of N1-substituted piperazine-2,3-dicarboxylic acid derivatives acting as NMDA receptor antagonists. J Med Chem. 2005 Apr 7;48(7):2627-37.

REF 30

Synthesis and pharmacological evaluation of N,N'-diarylguanidines as potent sodium channel blockers and anticonvulsant agents. J Med Chem. 1998 Aug 13;41(17):3298-302.

REF 31

NR2B-selective N-methyl-D-aspartate antagonists: synthesis and evaluation of 5-substituted benzimidazoles. J Med Chem. 2004 Apr 8;47(8):2089-96.

REF 32

2,4-Dihydro-3H-1,2,4-triazol-3-ones as anticonvulsant agents. J Med Chem. 1990 Oct;33(10):2772-7.

REF 33

4-(3,4-dihydro-1H-isoquinolin-2yl)-pyridines and 4-(3,4-dihydro-1H-isoquinolin-2-yl)-quinolines as potent NR1/2B subtype selective NMDA receptor an... Bioorg Med Chem Lett. 2003 May 19;13(10):1759-62.

REF 34

2-carboxy indolines and indoles as potential glycine/NMDA antagonists: effect of five-membered ring conformation on affinity. Bioorg. Med. Chem. Lett. 2(12):1627-1630 (1992).

REF 35

Analogs of 3-hydroxy-1H-1-benzazepine-2,5-dione: structure-activity relationship at N-methyl-D-aspartate receptor glycine sites. J Med Chem. 1996 Nov 8;39(23):4643-53.

REF 36

3-Hydroxy-quinolin-2-ones: Inhibitors of [3H]-glycine binding to the site associated with the NMDA receptor, Bioorg. Med. Chem. Lett. 6(5):499-504 (1996).

REF 37

3-(2-carboxyindol-3-yl)propionic acid derivatives: antagonists of the strychnine-insensitive glycine receptor associated with the N-methyl-D-aspart... J Med Chem. 1990 Nov;33(11):2944-6.

REF 38

Structure-activity relationships for a series of bis(phenylalkyl)amines: potent subtype-selective inhibitors of N-methyl-D-aspartate receptors. J Med Chem. 1998 Aug 27;41(18):3499-506.

REF 39

Structure-activity relationship for a series of 2-substituted 1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indoles: potent subtype-selective inhibitors of N-... Bioorg Med Chem Lett. 1999 Jun 7;9(11):1619-24.

REF 40

1-Hydroxy-1,4-dihydroquinoxaline-2,3-diones: Novel antagonists at NMDA receptor glycine sites, Bioorg. Med. Chem. Lett. 6(4):439-440 (1996).

REF 41

3-hydroxy-quinazoline-2,4-dione as a useful scaffold to obtain selective Gly/NMDA and AMPA receptor antagonists. Bioorg Med Chem Lett. 2004 May 3;14(9):2345-9.

REF 42

The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.

REF 43

5-(N-oxyaza)-7-substituted-1,4-dihydroquinoxaline-2,3-diones: novel, systemically active and broad spectrum antagonists for NMDA/glycine, AMPA, and... J Med Chem. 1997 Oct 24;40(22):3679-86.

REF 44

Structural investigation of the 7-chloro-3-hydroxy-1H-quinazoline-2,4-dione scaffold to obtain AMPA and kainate receptor selective antagonists. Syn... J Med Chem. 2006 Oct 5;49(20):6015-26.

REF 45

Bioisosteric replacement of the alpha-amino carboxylic acid functionality in 2-amino-5-phosphonopentanoic acid yields unique 3,4-diamino-3-cyclobut... J Med Chem. 1992 Dec 11;35(25):4720-6.

REF 46

Polyamines and the NMDA receptor: modifying intrinsic activities with aromatic substituents. Bioorg Med Chem Lett. 2006 Jun 1;16(11):2837-41.

REF 47

Effects of D-cycloserine and cycloleucine, ligands for the NMDA-associated strychnine-insensitive glycine site, on brain-stimulation reward and spontaneous locomotion. Pharmacol Biochem Behav. 1990 Aug;36(4):735-8.

REF 48

Kynurenic acid derivatives. Structure-activity relationships for excitatory amino acid antagonism and identification of potent and selective antago... J Med Chem. 1991 Apr;34(4):1243-52.

REF 49

The neuroprotective activity of GPE tripeptide analogues does not correlate with glutamate receptor binding affinity. Bioorg Med Chem Lett. 2006 Jul 1;16(13):3396-400.

REF 50

Indole-2-carboxamidines as novel NR2B selective NMDA receptor antagonists. Bioorg Med Chem Lett. 2005 Dec 15;15(24):5439-41.

REF 51

Synthesis and biological activity of conformationally restricted analogs of milnacipran: (1S,2R)-1-phenyl-2-[(S)-1-aminopropyl]-N,N-diethylcyclopro... J Med Chem. 1996 Nov 22;39(24):4844-52.

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