1-(3,4-Dimethoxy-benzyl)-6,8-difluoro-2,3,4,9-tetrahydro-1H-beta-carboline

ID: ALA94655

PubChem CID: 10618362

Max Phase: Preclinical

Molecular Formula: C20H20F2N2O2

Molecular Weight: 358.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CC2NCCc3c2[nH]c2c(F)cc(F)cc32)cc1OC

Standard InChI:  InChI=1S/C20H20F2N2O2/c1-25-17-4-3-11(8-18(17)26-2)7-16-20-13(5-6-23-16)14-9-12(21)10-15(22)19(14)24-20/h3-4,8-10,16,23-24H,5-7H2,1-2H3

Standard InChI Key:  HGPUOFMXABMTJJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    4.9792   -6.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4667   -7.0500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -5.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7417   -5.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917   -6.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8125   -6.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9625   -7.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667   -6.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2000   -5.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0500   -5.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2750   -6.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3125   -5.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2500   -7.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7167   -6.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4542   -6.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0750   -7.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3292   -7.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9167   -7.9542    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.9167   -4.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5042   -7.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7417   -4.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6167   -5.4125    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.6542   -5.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5417   -6.9542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4792   -5.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9792   -7.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  3  1  0
  5  2  1  0
  6  1  1  0
  7  5  2  0
  8  7  1  0
  9  6  1  0
 10  4  2  0
 11 15  2  0
 12 10  1  0
 13  6  1  0
 14 17  2  0
 15 16  1  0
 16 13  1  0
 17 20  1  0
 18  7  1  0
 19  3  1  0
 20 16  2  0
 21  9  1  0
 22 12  1  0
 23 11  1  0
 24 14  1  0
 25 23  1  0
 26 24  1  0
  4  5  1  0
 21 19  1  0
 12  8  2  0
 11 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA94655

   1-[(3,4-dimethoxyphenyl)methyl]-6,8-difluoro-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

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: 358.39

Molecular Weight (Monoisotopic): 358.1493

AlogP: 3.89

#Rotatable Bonds: 4

Polar Surface Area: 46.28

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.22

CX LogP: 3.63

CX LogD: 1.82

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.74

Np Likeness Score: 0.18

References

1. Audia JE, Evrard DA, Murdoch GR, Droste JJ, Nissen JS, Schenck KW, Fludzinski P, Lucaites VL, Nelson DL, Cohen ML..  (1996)  Potent, selective tetrahydro-beta-carboline antagonists of the serotonin 2B (5HT2B) contractile receptor in the rat stomach fundus.,  39  (14): [PMID:8709108] [10.1021/jm960062t]

2. Beato A, Gori A, Boucherle B, Peuchmaur M, Haudecoeur R..  (2021)  β-Carboline as a Privileged Scaffold for Multitarget Strategies in Alzheimer's Disease Therapy.,  64  (3.0): [PMID:33528252] [10.1021/acs.jmedchem.0c01887]

Source

Source(1):

• Scientific Literature