(+/-)-3-(4-Phenylbutyl)-2,3,4,5-tetrahydro-1H-3-benzazepine-1,7-diol

ID: ALA1289626

Chembl Id: CHEMBL1289626

PubChem CID: 49832807

Max Phase: Preclinical

Molecular Formula: C20H25NO2

Molecular Weight: 311.43

Molecule Type: Small molecule

Names and Identifiers

Synonyms: WMS-1410 | CHEMBL1289626|SCHEMBL3424183|WMS-1410|BDBM50331291|(+/-)-3-(4-Phenylbutyl)-2,3,4,5-tetrahydro-1H-3-benzazepine-1,7-diol

Canonical SMILES:  Oc1ccc2c(c1)CCN(CCCCc1ccccc1)CC2O

Standard InChI:  InChI=1S/C20H25NO2/c22-18-9-10-19-17(14-18)11-13-21(15-20(19)23)12-5-4-8-16-6-2-1-3-7-16/h1-3,6-7,9-10,14,20,22-23H,4-5,8,11-13,15H2

Standard InChI Key:  KKLZGWQBNXJWGZ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1289626

   (+/-)-3-(4-Phenylbutyl)-2,3,4,5-tetrahydro-1H-3-benzazepine-1,7-diol

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 311.43

Molecular Weight (Monoisotopic): 311.1885

AlogP: 3.31

#Rotatable Bonds: 5

Polar Surface Area: 43.70

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.70

CX Basic pKa: 8.93

CX LogP: 3.46

CX LogD: 2.24

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.83

Np Likeness Score: 0.26

References

1. Tewes B, Frehland B, Schepmann D, Schmidtke KU, Winckler T, Wünsch B..  (2010)  Conformationally constrained NR2B selective NMDA receptor antagonists derived from ifenprodil: Synthesis and biological evaluation of tetrahydro-3-benzazepine-1,7-diols.,  18  (22): [PMID:20965739] [10.1016/j.bmc.2010.09.026]

2. 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]

3. 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]

4. Dey S, Schepmann D, Wünsch B..  (2018)  2-Methyltetrahydro-3-benzazepin-1-ols - The missing link in SAR of GluN2B selective NMDA receptor antagonists.,  26  (2): [PMID:29254894] [10.1016/j.bmc.2017.12.010]

5. Dey S, Temme L, Schreiber JA, Schepmann D, Frehland B, Lehmkuhl K, Strutz-Seebohm N, Seebohm G, Wünsch B..  (2017)  Deconstruction - reconstruction approach to analyze the essential structural elements of tetrahydro-3-benzazepine-based antagonists of GluN2B subunit containing NMDA receptors.,  138  [PMID:28704758] [10.1016/j.ejmech.2017.06.068]

6. Thum S, Schepmann D, Ayet E, Pujol M, Nieto FR, Ametamey SM, Wünsch B..  (2019)  Tetrahydro-3-benzazepines with fluorinated side chains as NMDA and σ₁ receptor antagonists: Synthesis, receptor affinity, selectivity and antiallodynic activity.,  177  [PMID:31129453] [10.1016/j.ejmech.2019.05.034]

7. Temme L,Bechthold E,Schreiber JA,Gawaskar S,Schepmann D,Robaa D,Sippl W,Seebohm G,Wünsch B.  (2020)  Negative allosteric modulators of the GluN2B NMDA receptor with phenylethylamine structure embedded in ring-expanded and ring-contracted scaffolds.,  190  [PMID:32070917] [10.1016/j.ejmech.2020.112138]

Source

Source(1):

• Scientific Literature