2,2,7,7-Tetramethyl-9-(5-bromo-1H-indol-3-yl)-3,4,6,7-tetrahydroacridine-1,8-(2H,5H,9H,10H)-dione

ID: ALA3121555

PubChem CID: 76318025

Max Phase: Preclinical

Molecular Formula: C25H27BrN2O2

Molecular Weight: 467.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CCC2=C(C1=O)C(c1c[nH]c3ccc(Br)cc13)C1=C(CCC(C)(C)C1=O)N2

Standard InChI:  InChI=1S/C25H27BrN2O2/c1-24(2)9-7-17-20(22(24)29)19(15-12-27-16-6-5-13(26)11-14(15)16)21-18(28-17)8-10-25(3,4)23(21)30/h5-6,11-12,19,27-28H,7-10H2,1-4H3

Standard InChI Key:  SKVTUFGQCAUSLE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
   10.2879  -15.6923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8734  -14.9790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4629  -15.6947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5677  -15.7050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3926  -15.7081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9829  -14.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8446  -16.9407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2879  -16.5173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0000  -16.9257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0000  -15.2756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7120  -15.6923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7085  -16.5173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4174  -16.9306    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4243  -15.2806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1377  -15.6983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1339  -16.5259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8523  -15.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8549  -14.4606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0000  -14.4506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4267  -14.4555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0967  -13.9764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8475  -13.1911    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5668  -16.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7618  -13.9725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0183  -13.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4700  -12.5800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6653  -12.7496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4117  -13.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9616  -14.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6050  -13.7088    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  1  3  1  0
  5  4  1  0
  4  6  1  0
  1  8  1  0
  1 10  1  0
  8  9  1  0
  9 12  1  0
 11 10  1  0
 11 12  2  0
 11 14  1  0
 12 13  1  0
 13 16  1  0
 15 14  1  0
 15 16  2  0
 15 17  1  0
 16  7  1  0
  7 23  1  0
  4 17  1  0
 17 18  2  0
 10 19  2  0
 14 20  1  0
 20 21  2  0
 21 22  1  0
 24 20  1  0
 25 22  1  0
 23  4  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 28 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3121555

   9-(5-bromo-1H-indol-3-yl)-2,2,7,7-tetramethyl-3,4,5,6,9,10-hexahydroacridine-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: 467.41

Molecular Weight (Monoisotopic): 466.1256

AlogP: 5.90

#Rotatable Bonds: 1

Polar Surface Area: 61.96

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.47

CX LogD: 5.47

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.55

Np Likeness Score: 0.04

References

1. Gündüz MG, Işli F, El-Khouly A, Yıldırım S, Öztürk Fincan GS, Şimşek R, Şafak C, Sarıoğlu Y, Öztürk Yıldırım S, Butcher RJ..  (2014)  Microwave-assisted synthesis and myorelaxant activity of 9-indolyl-1,8-acridinedione derivatives.,  75  [PMID:24534541] [10.1016/j.ejmech.2014.01.059]

Source

Source(1):

• Scientific Literature