3-(4-((6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)methyl)-7-methoxybenzofuran-2-yl)benzonitrile

ID: ALA247056

PubChem CID: 44438154

Max Phase: Preclinical

Molecular Formula: C28H26N2O4

Molecular Weight: 454.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1OC)CN(Cc1ccc(OC)c3oc(-c4cccc(C#N)c4)cc13)CC2

Standard InChI:  InChI=1S/C28H26N2O4/c1-31-24-8-7-21(23-14-25(34-28(23)24)20-6-4-5-18(11-20)15-29)16-30-10-9-19-12-26(32-2)27(33-3)13-22(19)17-30/h4-8,11-14H,9-10,16-17H2,1-3H3

Standard InChI Key:  UZCLTQVKERFKSX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    2.8807    0.9352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5956    0.5223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5938    2.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3091    1.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5946   -0.3027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3086   -0.7160    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3100   -1.5381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0199   -1.9513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0257   -0.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7401   -0.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.8736   -0.3126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8692   -1.9586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5851   -1.5485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5888    2.9968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8731    3.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4155    1.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5861   -0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8295    0.6524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6537    0.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0628    1.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6417    2.0887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8188    2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0493    2.8040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4551    3.5223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  2  0
  6  7  1  0
 16 17  1  0
  7  8  2  0
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  8  9  1  0
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  9  5  1  0
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  4  1  2  0
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  3 10  1  0
  5  6  2  0
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 18 22  1  0
 10 11  1  0
 11 12  1  0
 24 25  1  0
  4 24  1  0
  8 26  1  0
  2  3  2  0
 21 27  1  0
  3  6  1  0
 26 28  2  0
 11 14  1  0
 28 29  1  0
 12 13  1  0
 29 30  2  0
 13 16  1  0
 30 31  1  0
 15 14  1  0
 31 32  2  0
 32 26  1  0
  1  2  1  0
  5  4  1  0
 33 34  3  0
 31 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA247056

   3-[4-[(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)methyl]-7-methoxy-1-benzofuran-2-yl]benzonitrile

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: 454.53

Molecular Weight (Monoisotopic): 454.1893

AlogP: 5.56

#Rotatable Bonds: 6

Polar Surface Area: 67.86

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 7.63

CX LogP: 4.79

CX LogD: 4.36

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.38

Np Likeness Score: -0.59

References

1. Hagihara K, Kashima H, Iida K, Enokizono J, Uchida S, Nonaka H, Kurokawa M, Shimada J..  (2007)  Novel 4-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)methylbenzofuran derivatives as selective alpha(2C)-adrenergic receptor antagonists.,  17  (6): [PMID:17257841] [10.1016/j.bmcl.2006.12.094]

Source

Source(1):

• Scientific Literature