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

ID: ALA236555

PubChem CID: 11514447

Max Phase: Preclinical

Molecular Formula: C17H12N2O

Molecular Weight: 260.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1cc(-c2ccccc2)[nH]c2ccc3[nH]ccc3c12

Standard InChI:  InChI=1S/C17H12N2O/c20-16-10-15(11-4-2-1-3-5-11)19-14-7-6-13-12(17(14)16)8-9-18-13/h1-10,18H,(H,19,20)

Standard InChI Key:  KPEBIZFOKQFEBS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 23  0  0  0  0  0  0  0  0999 V2000
   11.0230   -3.4703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0218   -4.2986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7373   -4.7120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4546   -4.2981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4517   -3.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7355   -3.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1654   -3.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8774   -3.4620    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8681   -1.8126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5899   -2.2227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5923   -3.0473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3065   -3.4558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0187   -3.0408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6173   -1.6626    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2797   -0.9147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4642   -1.0048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2977   -1.8082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0104   -2.2149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8621   -0.9868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1475   -2.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  2  3  1  0
 10 11  1  0
  5  6  2  0
 11 12  2  0
  6  1  1  0
 12 13  1  0
 13 18  2  0
 17 10  2  0
 17 18  1  0
  1  2  2  0
  5  7  1  0
 15 16  2  0
  3  4  2  0
  7  8  1  0
  8 11  1  0
 14 15  1  0
 16 17  1  0
 18 14  1  0
  9 19  2  0
  7 20  2  0
 10  9  1  0
  9 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA236555

   7-Phenyl-3,6-dihydropyrrolo[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: 260.30

Molecular Weight (Monoisotopic): 260.0950

AlogP: 3.68

#Rotatable Bonds: 1

Polar Surface Area: 48.65

Molecular Species: NEUTRAL

HBA: 1

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.52

CX LogP: 3.35

CX LogD: 3.35

Aromatic Rings: 4

Heavy Atoms: 20

QED Weighted: 0.54

Np Likeness Score: 0.03

References

1. Gasparotto V, Castagliuolo I, Chiarelotto G, Pezzi V, Montanaro D, Brun P, Palù G, Viola G, Ferlin MG..  (2006)  Synthesis and biological activity of 7-phenyl-6,9-dihydro-3H-pyrrolo[3,2-f]quinolin-9-ones: a new class of antimitotic agents devoid of aromatase activity.,  49  (6): [PMID:16539377] [10.1021/jm0510676]

2. 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]

3. Carta D, Bortolozzi R, Sturlese M, Salmaso V, Hamel E, Basso G, Calderan L, Quintieri L, Moro S, Viola G, Ferlin MG..  (2017)  Synthesis, structure-activity relationships and biological evaluation of 7-phenyl-pyrroloquinolinone 3-amide derivatives as potent antimitotic agents.,  127  [PMID:27823884] [10.1016/j.ejmech.2016.10.026]

Source

Source(1):

• Scientific Literature