5-(4-tert-Butyl-phenyl)-8-chloro-2,3-dihydro-imidazo[2,1-a]isoquinoline

ID: ALA80443

PubChem CID: 11724601

Max Phase: Preclinical

Molecular Formula: C21H21ClN2

Molecular Weight: 336.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1ccc(C2=Cc3cc(Cl)ccc3C3=NCCN23)cc1

Standard InChI:  InChI=1S/C21H21ClN2/c1-21(2,3)16-6-4-14(5-7-16)19-13-15-12-17(22)8-9-18(15)20-23-10-11-24(19)20/h4-9,12-13H,10-11H2,1-3H3

Standard InChI Key:  SAIHPDTXXDQRSJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    4.2750   -0.9042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7625   -1.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3042   -0.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7917    0.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2625   -0.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417   -0.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7625   -1.8042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9042   -0.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7125   -1.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7500    0.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7000   -0.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1000   -0.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2000    0.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2042   -0.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8042   -0.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7917    0.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7917   -1.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2167   -0.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7917   -1.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1917   -0.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6292   -0.0917    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.0000    0.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3000   -0.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0042   -0.8292    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  4  1  0
  6  2  1  0
  7  2  2  0
  8  3  1  0
  9  6  1  0
 10  5  1  0
 11 12  1  0
 12 15  2  0
 13  8  1  0
 14  8  2  0
 15 14  1  0
 16 13  2  0
 17  1  1  0
 18 10  2  0
 19 17  1  0
 20  9  2  0
 21 18  1  0
 22 11  1  0
 23 11  1  0
 24 11  1  0
  7 19  1  0
  6  5  2  0
 16 12  1  0
 18 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA80443

   5-(4-tert-Butyl-phenyl)-8-chloro-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: 336.87

Molecular Weight (Monoisotopic): 336.1393

AlogP: 5.21

#Rotatable Bonds: 1

Polar Surface Area: 15.60

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 7.02

CX LogP: 5.21

CX LogD: 5.06

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.70

Np Likeness Score: -0.68

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