3,6-Dimethyl-9-(3-fluoro-5-trifluoromethylphenyl)-3,4,6,7-tetrahydroacridine-1,8-(2H,5H,9H,10H)-dione

ID: ALA2263263

PubChem CID: 76312281

Max Phase: Preclinical

Molecular Formula: C22H21F4NO2

Molecular Weight: 407.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1CC(=O)C2=C(C1)NC1=C(C(=O)CC(C)C1)C2c1cc(F)cc(C(F)(F)F)c1

Standard InChI:  InChI=1S/C22H21F4NO2/c1-10-3-15-20(17(28)5-10)19(21-16(27-15)4-11(2)6-18(21)29)12-7-13(22(24,25)26)9-14(23)8-12/h7-11,19,27H,3-6H2,1-2H3

Standard InChI Key:  PQULMGOXXBKUJU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    2.6910   -3.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6910   -4.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3962   -5.1467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3962   -3.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1015   -3.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1026   -4.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8069   -5.1476    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8048   -3.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5136   -3.9232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5139   -4.7378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2157   -5.1427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9216   -4.7373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9214   -3.9227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2151   -3.5134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2137   -2.6962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3962   -2.6951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6289   -5.1467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9838   -5.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8038   -2.7001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5120   -2.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5102   -1.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8008   -1.0662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0919   -1.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0972   -2.2962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2237   -1.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2219   -0.2347    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.9391   -1.4706    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.0206   -0.8462    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.3749   -1.0730    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  2  0
  5  8  1  0
  6  7  1  0
  7 10  1  0
  9  8  1  0
  9 10  2  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
  4 16  2  0
 12 17  1  0
  2 18  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
  8 19  1  0
 21 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
 23 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2263263

   9-[3-Fluoro-5-(trifluoromethyl)phenyl]-3,6-dimethyl-2,3,4,5,6,7,9,10-octahydroacridine-1,8-dione

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: 407.41

Molecular Weight (Monoisotopic): 407.1508

AlogP: 5.04

#Rotatable Bonds: 1

Polar Surface Area: 46.17

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.00

CX LogD: 4.00

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.66

Np Likeness Score: -0.77

References

1. Gozde Gunduz M, Evrim Dogan A, Simsek R, Erol K, Safak C.  (2009)  Substituted 9-aryl-1,8-acridinedione derivatives and their effects on potassium channels,  18  (4): [10.1007/s00044-008-9129-9]

Source

Source(1):

• Scientific Literature