1'-benzyl-3-methoxyspiro[3,4-dihydro-1H-isochromene-1,4'-(hexahydropyridine)]

ID: ALA141209

Chembl Id: CHEMBL141209

Cas Number: 398476-28-3

PubChem CID: 10019102

Max Phase: Preclinical

Molecular Formula: C21H25NO2

Molecular Weight: 323.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC1Cc2ccccc2C2(CCN(Cc3ccccc3)CC2)O1

Standard InChI:  InChI=1S/C21H25NO2/c1-23-20-15-18-9-5-6-10-19(18)21(24-20)11-13-22(14-12-21)16-17-7-3-2-4-8-17/h2-10,20H,11-16H2,1H3

Standard InChI Key:  POOPPNNSPMKABZ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA141209

   1'-Benzyl-3-methoxyspiro[isochroman-1,4'-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: 323.44

Molecular Weight (Monoisotopic): 323.1885

AlogP: 3.72

#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: 8.80

CX LogP: 3.61

CX LogD: 2.20

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.86

Np Likeness Score: 0.20

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. Oberdorf C, Schepmann D, Vela JM, Diaz JL, Holenz J, Wünsch B..  (2008)  Thiophene bioisosteres of spirocyclic sigma receptor ligands. 1. N-substituted spiro[piperidine-4,4'-thieno[3,2-c]pyrans].,  51  (20): [PMID:18816044] [10.1021/jm8007739]

4. Jasper A, Schepmann D, Lehmkuhl K, Vela JM, Buschmann H, Holenz J, Wünsch B..  (2009)  Synthesis of sigma receptor ligands with unsymmetrical spiro connection of the piperidine moiety.,  44  (11): [PMID:19709783] [10.1016/j.ejmech.2009.07.017]

5. Rack E, Fröhlich R, Schepmann D, Wünsch B..  (2011)  Design, synthesis and pharmacological evaluation of spirocyclic σ(1) receptor ligands with exocyclic amino moiety (increased distance 1).,  19  (10): [PMID:21531141] [10.1016/j.bmc.2011.04.002]

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. Jasper A, Schepmann D, Lehmkuhl K, Vela JM, Buschmann H, Holenz J, Wünsch B..  (2012)  Microwave assisted synthesis of spirocyclic pyrrolidines -σ1 receptor ligands with modified benzene-N-distance.,  53  [PMID:22578786] [10.1016/j.ejmech.2012.04.018]

8. Yous S, Wallez V, Belloir M, Caignard DH, McCurdy CR, Poupaert JH.  (2005)  Novel 2(3H)-Benzothiazolones as Highly Potent and Selective Sigma-1 Receptor Ligands,  14  (3): [10.1007/s00044-005-0131-1]

9. 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]

10. Miyata K, Möller G, Schepmann D, Wünsch B..  (2014)  Pyridine analogues of spirocyclic σ₁ receptor ligands.,  22  (15): [PMID:24913984] [10.1016/j.bmc.2014.05.033]

11. 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]

12. Kronenberg E, Weber F, Brune S, Schepmann D, Almansa C, Friedland K, Laurini E, Pricl S, Wünsch B..  (2019)  Synthesis and Structure-Affinity Relationships of Spirocyclic Benzopyrans with Exocyclic Amino Moiety.,  62  (8): [PMID:30939014] [10.1021/acs.jmedchem.9b00449]

13. Kronenberg, Elisabeth, Weber, Frauke, Schepmann, Dirk, Wunsch, Bernhard.  (2021)  Synthesis and sigma receptor affinity of spiro[[2]benzopyran-1,1-cyclohexanes] with an exocyclic amino moiety in the 3-position,  12  (2): [PMID:34046612] [10.1039/d0md00307g]

14. 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