(-)-threo 4-[2-(4-Benzyl-piperidin-1-yl)-1-hydroxy-propyl]-phenol

ID: ALA319706

Chembl Id: CHEMBL319706

PubChem CID: 11771731

Max Phase: Preclinical

Molecular Formula: C21H27NO2

Molecular Weight: 325.45

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  C[C@@H]([C@@H](O)c1ccc(O)cc1)N1CCC(Cc2ccccc2)CC1

Standard InChI:  InChI=1S/C21H27NO2/c1-16(21(24)19-7-9-20(23)10-8-19)22-13-11-18(12-14-22)15-17-5-3-2-4-6-17/h2-10,16,18,21,23-24H,11-15H2,1H3/t16-,21+/m0/s1

Standard InChI Key:  UYNVMODNBIQBMV-HRAATJIYSA-N

Alternative Forms

  1. Parent:

Associated Targets(Human)

KCNH2 Tclin HERG (29587 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GRIN2B Tclin Glutamate [NMDA] receptor subunit epsilon 2 (467 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GRIN1 Tclin Glutamate NMDA receptor; GRIN1/GRIN2B (726 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SIGMAR1 Tclin Sigma opioid receptor (6358 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SH-SY5Y (11521 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GRIN1 Tclin Glutamate [NMDA] receptor (933 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR6 Tchem Serotonin 6 (5-HT6) receptor (9749 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR7 Tclin Serotonin 7 (5-HT7) receptor (5576 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Grin1 Glutamate NMDA receptor (6467 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Adra1b Adrenergic receptor alpha-1 (5652 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Grin2c Glutamate [NMDA] receptor subunit epsilon 3 (367 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SIGMAR1 Sigma-1 receptor (3326 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Tmem97 Sigma intracellular receptor 2 (922 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: YesOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 325.45Molecular Weight (Monoisotopic): 325.2042AlogP: 3.77#Rotatable Bonds: 5
Polar Surface Area: 43.70Molecular Species: BASEHBA: 3HBD: 2
#RO5 Violations: HBA (Lipinski): 3HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: 9.67CX Basic pKa: 9.03CX LogP: 3.57CX LogD: 2.30
Aromatic Rings: 2Heavy Atoms: 24QED Weighted: 0.88Np Likeness Score: 0.06

References

1. Chenard BL, Shalaby IA, Koe BK, Ronau RT, Butler TW, Prochniak MA, Schmidt AW, Fox CB..  (1991)  Separation of alpha 1 adrenergic and N-methyl-D-aspartate antagonist activity in a series of ifenprodil compounds.,  34  (10): [PMID:1681106] [10.1021/jm00114a018]
2. Chenard BL, Shalaby IA, Koe BK, Ronau RT, Butler TW, Prochniak MA, Schmidt AW, Fox CB..  (1991)  Separation of alpha 1 adrenergic and N-methyl-D-aspartate antagonist activity in a series of ifenprodil compounds.,  34  (10): [PMID:1681106] [10.1021/jm00114a018]
3. Chenard BL, Shalaby IA, Koe BK, Ronau RT, Butler TW, Prochniak MA, Schmidt AW, Fox CB..  (1991)  Separation of alpha 1 adrenergic and N-methyl-D-aspartate antagonist activity in a series of ifenprodil compounds.,  34  (10): [PMID:1681106] [10.1021/jm00114a018]
4. Chenard BL, Bordner J, Butler TW, Chambers LK, Collins MA, De Costa DL, Ducat MF, Dumont ML, Fox CB, Mena EE..  (1995)  (1S,2S)-1-(4-hydroxyphenyl)-2-(4-hydroxy-4-phenylpiperidino)-1-propanol: a potent new neuroprotectant which blocks N-methyl-D-aspartate responses.,  38  (16): [PMID:7636876] [10.1021/jm00016a017]
5. Chenard B, Butler T, Shalaby I, Prochniak M, Koe B, Fox C.  (1993)  Oxindole N-Methyl-D-Aspartate (NMDA) antagonists,  (1): [10.1016/S0960-894X(00)80098-0]
6. Kawai M, Nakamura H, Sakurada I, Shimokawa H, Tanaka H, Matsumizu M, Ando K, Hattori K, Ohta A, Nukui S, Omura A, Kawamura M..  (2007)  Discovery of novel and orally active NR2B-selective N-methyl-D-aspartate (NMDA) antagonists, pyridinol derivatives with reduced HERG binding affinity.,  17  (20): [PMID:17768047] [10.1016/j.bmcl.2007.08.039]
7. Gawaskar S, Schepmann D, Bonifazi A, Robaa D, Sippl W, Wünsch B..  (2015)  Benzo[7]annulene-based GluN2B selective NMDA receptor antagonists: Surprising effect of a nitro group in 2-position.,  25  (24): [PMID:26531150] [10.1016/j.bmcl.2015.10.076]
8. Dey S, Schepmann D, Wünsch B..  (2016)  Role of the phenolic OH moiety of GluN2B-selective NMDA antagonists with 3-benzazepine scaffold.,  26  (3): [PMID:26750254] [10.1016/j.bmcl.2015.12.067]
9. Lütnant I, Schepmann D, Wünsch B..  (2016)  Benzimidazolone bioisosteres of potent GluN2B selective NMDA receptor antagonists.,  116  [PMID:27061977] [10.1016/j.ejmech.2016.03.065]
10. Rath S, Schepmann D, Wünsch B..  (2017)  Replacement of benzylic hydroxy group by vinyl or hydroxymethyl moiety at the 3-benzazepine scaffold retaining GluN2B affinity.,  25  (20): [PMID:28797770] [10.1016/j.bmc.2017.07.059]
11. Zhang L, Zhao Y, Wang J, Yang D, Zhao C, Wang C, Ma C, Cheng M..  (2018)  Design, synthesis and bioevaluation of 1,2,3,9-tetrahydropyrrolo[2,1-b]quinazoline-1-carboxylic acid derivatives as potent neuroprotective agents.,  151  [PMID:29604542] [10.1016/j.ejmech.2018.03.052]
12. Zhang L, Quan J, Zhao Y, Yang D, Zhao Q, Liu P, Cheng M, Ma C..  (2019)  Design, synthesis and biological evaluation of 1-benzyl-5-oxopyrrolidine-2-carboximidamide derivatives as novel neuroprotective agents.,  182  [PMID:31494474] [10.1016/j.ejmech.2019.111654]
13. Bechthold E,Schreiber JA,Lehmkuhl K,Frehland B,Schepmann D,Bernal FA,Daniliuc C,Álvarez I,Garcia CV,Schmidt TJ,Seebohm G,Wünsch B.  (2021)  Ifenprodil Stereoisomers: Synthesis, Absolute Configuration, and Correlation with Biological Activity.,  64  (2.0): [PMID:33426889] [10.1021/acs.jmedchem.0c01912]

Source