7-phenyl-3-(diethylamino-ethyl)-6,9-dihydro-pyrrolo[3,2-f]quinolin-9-one

ID: ALA379229

PubChem CID: 11681981

Max Phase: Preclinical

Molecular Formula: C23H25N3O

Molecular Weight: 359.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)CCn1ccc2c3c(O)cc(-c4ccccc4)nc3ccc21

Standard InChI:  InChI=1S/C23H25N3O/c1-3-25(4-2)14-15-26-13-12-18-21(26)11-10-19-23(18)22(27)16-20(24-19)17-8-6-5-7-9-17/h5-13,16H,3-4,14-15H2,1-2H3,(H,24,27)

Standard InChI Key:  ABRLJDSDABFAQX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    4.9604  -10.5308    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3729   -9.8149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9604   -9.1032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1354   -9.1032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7229   -9.8149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8979   -9.8149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4854  -10.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8979  -11.2425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7229  -11.2425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1354  -10.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6794  -10.3584    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3448   -9.2026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5945   -9.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7229   -8.3873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0629  -10.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2824  -10.6544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3298  -11.2074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1188  -12.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6761  -12.2175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1186  -10.9503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309  -11.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1979   -9.8149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6104   -9.1032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4354   -9.1032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8479   -9.8149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4354  -10.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6104  -10.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  1 10  1  0
  5 10  1  0
 12 13  2  0
 11 13  1  0
  6 12  1  0
  7 11  1  0
  4 14  1  0
 15 16  1  0
 18 19  1  0
 17 18  1  0
 20 21  1  0
 17 20  1  0
 16 17  1  0
 11 15  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 22 27  1  0
  2 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA379229

   3-[2-(diethylamino)ethyl]-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: 359.47

Molecular Weight (Monoisotopic): 359.1998

AlogP: 4.90

#Rotatable Bonds: 6

Polar Surface Area: 41.29

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.40

CX Basic pKa: 9.66

CX LogP: 4.55

CX LogD: 2.58

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.53

Np Likeness Score: -1.09

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]

Source

Source(1):

• Scientific Literature