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

ID: ALA4063586

PubChem CID: 137635101

Max Phase: Preclinical

Molecular Formula: C22H19FN4O3S

Molecular Weight: 438.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cnc2c(c1)C(=O)c1c-2n(CCCNC2=NCCS2)c(=O)c2cc(F)ccc12

Standard InChI:  InChI=1S/C22H19FN4O3S/c1-30-13-10-16-18(26-11-13)19-17(20(16)28)14-4-3-12(23)9-15(14)21(29)27(19)7-2-5-24-22-25-6-8-31-22/h3-4,9-11H,2,5-8H2,1H3,(H,24,25)

Standard InChI Key:  YRTKFQZVICPSAQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
   11.5324   -8.9582    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0237   -4.5150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8215   -6.8947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1677   -3.0905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3854   -4.3403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9639   -6.8943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6848   -3.7593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1072   -5.6484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5345   -6.8933    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.2492   -6.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3915   -5.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6763   -6.4790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9621   -5.2415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2503   -5.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5338   -8.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3868   -7.7168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8201   -7.7196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5635   -4.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5379   -5.1818    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8671   -3.6760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6775   -5.6505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7193   -5.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3892   -6.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1078   -6.4810    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0116   -3.8136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9884   -3.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2394   -9.3680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3268  -10.1781    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.1258  -10.3494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5357   -9.6423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9898   -9.0342    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
 23 16  2  0
  5 22  2  0
 24  3  1  0
 10  6  1  0
  6 12  2  0
 18 11  1  0
  8 22  1  0
 18 25  2  0
 21 11  1  0
 12 23  1  0
  7 20  2  0
  3 17  1  0
 17 15  1  0
 21 12  1  0
 20  5  1  0
 14 10  2  0
 24  8  1  0
  5 18  1  0
 22 19  1  0
 10  9  1  0
 11  8  2  0
 21 13  2  0
 19  2  2  0
 23 24  1  0
  2  7  1  0
  4 26  1  0
  7  4  1  0
 15  1  1  0
  1 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4063586

   ---

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: 438.48

Molecular Weight (Monoisotopic): 438.1162

AlogP: 2.84

#Rotatable Bonds: 5

Polar Surface Area: 85.58

Molecular Species: BASE

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.14

CX LogP: 1.64

CX LogD: -0.02

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.48

Np Likeness Score: -0.66

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