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

ID: ALA393477

PubChem CID: 23636403

Max Phase: Preclinical

Molecular Formula: C21H18N2O

Molecular Weight: 314.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1cc(-c2ccccc2)[nH]c2ccc3c(ccn3CC3CC3)c12

Standard InChI:  InChI=1S/C21H18N2O/c24-20-12-18(15-4-2-1-3-5-15)22-17-8-9-19-16(21(17)20)10-11-23(19)13-14-6-7-14/h1-5,8-12,14H,6-7,13H2,(H,22,24)

Standard InChI Key:  PVUYLVHBXLYPDV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 28  0  0  0  0  0  0  0  0999 V2000
   10.2519   -6.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2508   -6.8670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9665   -7.2779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6838   -6.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6809   -6.0355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9647   -5.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3948   -5.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1130   -6.0347    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1090   -4.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3912   -4.7964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1087   -3.5594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8259   -4.7950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8220   -5.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5286   -6.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2435   -5.6226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5321   -4.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2414   -4.7988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8534   -4.2548    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5243   -3.5043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7085   -3.5870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6380   -4.5105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2537   -3.9582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0575   -3.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5052   -3.1702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
 23 22  1  0
 24 23  1  0
 22 24  1  0
  9 10  1  0
  2  3  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA393477

   3-(cyclopropylmethyl)-7-phenyl-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: 314.39

Molecular Weight (Monoisotopic): 314.1419

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: 4.35

CX LogD: 4.35

Aromatic Rings: 4

Heavy Atoms: 24

QED Weighted: 0.59

Np Likeness Score: -0.56

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