7-phenyl-3-propyl-3H-pyrrolo[3,2-f]quinolin-9(6H)-one

ID: ALA392818

PubChem CID: 23634555

Max Phase: Preclinical

Molecular Formula: C20H18N2O

Molecular Weight: 302.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCn1ccc2c3c(=O)cc(-c4ccccc4)[nH]c3ccc21

Standard InChI:  InChI=1S/C20H18N2O/c1-2-11-22-12-10-15-18(22)9-8-16-20(15)19(23)13-17(21-16)14-6-4-3-5-7-14/h3-10,12-13H,2,11H2,1H3,(H,21,23)

Standard InChI Key:  CGRNFPWJMANHOE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
    9.6662   -0.1742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6650   -1.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3807   -1.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0979   -1.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0951   -0.1705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3789    0.2409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8088    0.2469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5270   -0.1697    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5230    1.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8053    1.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5227    2.3053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2398    1.0699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2359    0.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9424   -0.1687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6573    0.2424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9459    1.4762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6552    1.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2674    1.6100    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9380    2.3605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1223    2.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0742    1.4367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6298    2.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4367    1.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  9 11  2  0
  5  6  2  0
  6  1  1  0
 12 13  2  0
  1  2  2  0
 13 14  1  0
  5  7  1  0
 14 15  2  0
 15 17  1  0
 16 12  1  0
 16 17  2  0
  7  8  1  0
  3  4  2  0
  4  5  1  0
  7 10  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 16  1  0
  8 13  1  0
 18 21  1  0
 12  9  1  0
 21 22  1  0
  9 10  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA392818

   7-phenyl-3-propyl-6H-pyrrolo[3,2-f]quinolin-9-one

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: 302.38

Molecular Weight (Monoisotopic): 302.1419

AlogP: 4.56

#Rotatable Bonds: 3

Polar Surface Area: 37.79

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.49

CX LogP: 4.45

CX LogD: 4.45

Aromatic Rings: 4

Heavy Atoms: 23

QED Weighted: 0.59

Np Likeness Score: -0.69

References

1. Gasparotto V, Castagliuolo I, Ferlin MG..  (2007)  3-substituted 7-phenyl-pyrroloquinolinones show potent cytotoxic activity in human cancer cell lines.,  50  (22): [PMID:17915851] [10.1021/jm070534b]

2. Carta D, Bortolozzi R, Hamel E, Basso G, Moro S, Viola G, Ferlin MG..  (2015)  Novel 3-Substituted 7-Phenylpyrrolo[3,2-f]quinolin-9(6H)-ones as Single Entities with Multitarget Antiproliferative Activity.,  58  (20): [PMID:26418966] [10.1021/acs.jmedchem.5b00805]

Source

Source(1):

• Scientific Literature