1'-benzyl-3-methoxyspiro[1,3-dihydroisobenzofuran-1,4'-(hexahydropyridine)]

ID: ALA138809

Chembl Id: CHEMBL138809

PubChem CID: 10357986

Max Phase: Preclinical

Molecular Formula: C20H23NO2

Molecular Weight: 309.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC1OC2(CCN(Cc3ccccc3)CC2)c2ccccc21

Standard InChI:  InChI=1S/C20H23NO2/c1-22-19-17-9-5-6-10-18(17)20(23-19)11-13-21(14-12-20)15-16-7-3-2-4-8-16/h2-10,19H,11-15H2,1H3

Standard InChI Key:  RZZAEVQHACUOGI-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA138809

   1'-Benzyl-3-methoxyspiro[isobenzofuran-1(3H),4'-piperidine]

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: 309.41

Molecular Weight (Monoisotopic): 309.1729

AlogP: 3.85

#Rotatable Bonds: 3

Polar Surface Area: 21.70

Molecular Species: BASE

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.75

CX LogP: 3.55

CX LogD: 2.19

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.86

Np Likeness Score: 0.05

References

1. Maier CA, Wünsch B..  (2002)  Novel spiropiperidines as highly potent and subtype selective sigma-receptor ligands. Part 1.,  45  (2): [PMID:11784148] [10.1021/jm010992z]

2. Maier CA, Wünsch B..  (2002)  Novel sigma receptor ligands. Part 2. SAR of spiro[[2]benzopyran-1,4'-piperidines] and spiro[[2]benzofuran-1,4'-piperidines] with carbon substituents in position 3.,  45  (22): [PMID:12383018] [10.1021/jm020889p]

3. Schläger T, Schepmann D, Würthwein EU, Wünsch B..  (2008)  Synthesis and structure-affinity relationships of novel spirocyclic sigma receptor ligands with furopyrazole structure.,  16  (6): [PMID:18221879] [10.1016/j.bmc.2007.12.045]

4. Grosse Maestrup E, Wiese C, Schepmann D, Hiller A, Fischer S, Scheunemann M, Brust P, Wünsch B..  (2009)  Synthesis of spirocyclic sigma1 receptor ligands as potential PET radiotracers, structure-affinity relationships and in vitro metabolic stability.,  17  (10): [PMID:19394833] [10.1016/j.bmc.2009.03.060]

5. Maestrup EG, Fischer S, Wiese C, Schepmann D, Hiller A, Deuther-Conrad W, Steinbach J, Wünsch B, Brust P..  (2009)  Evaluation of spirocyclic 3-(3-fluoropropyl)-2-benzofurans as sigma1 receptor ligands for neuroimaging with positron emission tomography.,  52  (19): [PMID:19791807] [10.1021/jm900909e]

6. Schläger T, Schepmann D, Lehmkuhl K, Holenz J, Vela JM, Buschmann H, Wünsch B..  (2011)  Combination of two pharmacophoric systems: synthesis and pharmacological evaluation of spirocyclic pyranopyrazoles with high σ₁ receptor affinity.,  54  (19): [PMID:21859078] [10.1021/jm200585k]

7. Oberdorf C, Schepmann D, Vela JM, Buschmann H, Holenz J, Wünsch B..  (2012)  Thiophene bioisosteres of spirocyclic σ receptor ligands: relationships between substitution pattern and σ receptor affinity.,  55  (11): [PMID:22515405] [10.1021/jm300302p]

8. Meyer C, Neue B, Schepmann D, Yanagisawa S, Yamaguchi J, Würthwein EU, Itami K, Wünsch B..  (2013)  Improvement of σ1 receptor affinity by late-stage C-H-bond arylation of spirocyclic lactones.,  21  (7): [PMID:23462714] [10.1016/j.bmc.2013.01.038]

9. Knappmann I, Schepmann D, Wünsch B..  (2016)  Oxa-Pictet-Spengler reaction as key step in the synthesis of novel σ receptor ligands with 2-benzopyran structure.,  24  (18): [PMID:27396684] [10.1016/j.bmc.2016.06.046]

10. Zhao Z, Kang K, Yue J, Ji X, Qiao H, Fan P, Zheng X..  (2021)  Research progress in biological activities of isochroman derivatives.,  210  [PMID:33310287] [10.1016/j.ejmech.2020.113073]

Source

Source(1):

• Scientific Literature