5-(4-Pyrrolidin-1-ylmethyl-phenyl)-2,3-dihydro-imidazo[2,1-a]isoquinoline

ID: ALA78642

PubChem CID: 10042229

Max Phase: Preclinical

Molecular Formula: C22H23N3

Molecular Weight: 329.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C1=C(c2ccc(CN3CCCC3)cc2)N2CCN=C2c2ccccc21

Standard InChI:  InChI=1S/C22H23N3/c1-2-6-20-19(5-1)15-21(25-14-11-23-22(20)25)18-9-7-17(8-10-18)16-24-12-3-4-13-24/h1-2,5-10,15H,3-4,11-14,16H2

Standard InChI Key:  SSMILBSXSKDVOF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 29  0  0  0  0  0  0  0  0999 V2000
    1.4500   -1.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9375   -2.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4792   -1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9667   -0.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4167   -1.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9375   -2.6167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4375   -1.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0792   -1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2917   -0.7000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8750   -1.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3750   -0.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792   -1.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667   -2.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667   -2.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2750   -1.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9792   -1.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667   -0.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1125   -1.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0750   -0.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8750   -0.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2667   -0.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6250   -1.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2000   -0.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8250    0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6083   -1.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  3  2  0
  5  2  1  0
  6  2  2  0
  7  4  1  0
  8  3  1  0
  9 10  1  0
 10 15  1  0
 11  8  1  0
 12  8  2  0
 13  1  1  0
 14 13  1  0
 15 16  2  0
 16 12  1  0
 17 11  2  0
 18  5  1  0
 19  7  1  0
 20  9  1  0
 21  9  1  0
 22 18  2  0
 23 20  1  0
 24 21  1  0
 25 19  2  0
 14  6  1  0
  7  5  2  0
 15 17  1  0
 25 22  1  0
 24 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA78642

   5-(4-Pyrrolidin-1-ylmethyl-phenyl)-2,3-dihydro-imidazo[2,1-a]isoquinoline

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: 329.45

Molecular Weight (Monoisotopic): 329.1892

AlogP: 3.86

#Rotatable Bonds: 3

Polar Surface Area: 18.84

Molecular Species: BASE

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.26

CX LogP: 3.41

CX LogD: 1.37

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.85

Np Likeness Score: -0.63

References

1. Houlihan WJ, Munder PG, Handley DA, Cheon SH, Parrino VA..  (1995)  Antitumor activity of 5-aryl-2,3-dihydroimidazo[2,1-a]isoquinolines.,  38  (2): [PMID:7830265] [10.1021/jm00002a004]

Source

Source(1):

• Scientific Literature