3-Chloro-6-(3-(1H-Imidazol-1-yl)propyl)-9-methoxy-5H-pyrido-[3',2':4,5]cyclopenta[1,2-c]isoquinoline-5,11(6H)-dione

ID: ALA4103520

PubChem CID: 137656446

Max Phase: Preclinical

Molecular Formula: C22H17ClN4O3

Molecular Weight: 420.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cnc2c(c1)C(=O)c1c-2n(CCCn2ccnc2)c(=O)c2cc(Cl)ccc12

Standard InChI:  InChI=1S/C22H17ClN4O3/c1-30-14-10-17-19(25-11-14)20-18(21(17)28)15-4-3-13(23)9-16(15)22(29)27(20)7-2-6-26-8-5-24-12-26/h3-5,8-12H,2,6-7H2,1H3

Standard InChI Key:  RHUBXYGWGVODBD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    5.7478   -6.1867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7467   -7.0062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4547   -7.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4529   -5.7778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1615   -6.1831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1604   -7.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8666   -7.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5785   -7.0057    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8689   -5.7715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5779   -6.1809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0393   -4.9707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4926   -4.3634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8535   -4.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1842   -5.6327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9952   -5.7188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4763   -5.0582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1407   -4.3095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3307   -4.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8643   -8.2300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2855   -7.4155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2841   -8.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9911   -8.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9897   -9.4597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6191   -3.6470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4321   -3.7301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0386   -7.4142    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.3294   -9.9378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5806  -10.7155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3978  -10.7169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6516   -9.9401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5  9  1  0
  6  7  1  0
  7  8  1  0
  8 10  1  0
  9 10  2  0
 10 14  1  0
 13 11  1  0
 11  9  1  0
 11 12  2  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  7 19  2  0
  8 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 17 24  1  0
 24 25  1  0
  2 26  1  0
 23 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4103520

   ---

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: 420.86

Molecular Weight (Monoisotopic): 420.0989

AlogP: 3.56

#Rotatable Bonds: 5

Polar Surface Area: 79.01

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.79

CX LogP: 1.70

CX LogD: 1.63

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.43

Np Likeness Score: -0.68

References

1. Elsayed MSA, Su Y, Wang P, Sethi T, Agama K, Ravji A, Redon CE, Kiselev E, Horzmann KA, Freeman JL, Pommier Y, Cushman M..  (2017)  Design and Synthesis of Chlorinated and Fluorinated 7-Azaindenoisoquinolines as Potent Cytotoxic Anticancer Agents That Inhibit Topoisomerase I.,  60  (13): [PMID:28657311] [10.1021/acs.jmedchem.6b01870]

Source

Source(1):

• Scientific Literature