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

ID: ALA3121556

PubChem CID: 76325358

Max Phase: Preclinical

Molecular Formula: C25H27BrN2O2

Molecular Weight: 467.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CC(=O)C2=C(C1)NC1=C(C(=O)CC(C)(C)C1)C2c1c[nH]c2ccc(Br)cc12

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

Standard InChI Key:  ARSQLZZMTFSCJW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
   24.0284  -17.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4375  -18.2223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8534  -17.5097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7498  -17.4915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9248  -17.4927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3383  -18.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7498  -16.6665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0293  -16.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3064  -17.9148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4618  -17.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4618  -16.2498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1738  -16.6665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1704  -17.4915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8791  -17.9047    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8861  -16.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5994  -16.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5955  -17.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3139  -16.2598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3166  -15.4348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4618  -15.4248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8884  -15.4298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5584  -14.9506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3093  -14.1654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2236  -14.9468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4800  -14.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9318  -13.5544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1271  -13.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8735  -14.5098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4234  -15.1172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0670  -14.6831    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
  7  4  1  0
  7 11  1  0
  4 10  1  0
 10 13  1  0
 12 11  1  0
 12 13  2  0
 12 15  1  0
 13 14  1  0
 14 17  1  0
 16 15  1  0
 16 17  2  0
 16 18  1  0
 17  9  1  0
  9  1  1  0
  8 18  1  0
 18 19  2  0
 11 20  2  0
 15 21  1  0
 21 22  2  0
 22 23  1  0
 24 21  1  0
 25 23  1  0
  1  8  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:

   

   ALA3121556

   9-(5-bromo-1H-indol-3-yl)-3,3,6,6-tetramethyl-2,4,5,7,9,10-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: 4.45

CX LogD: 4.45

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.55

Np Likeness Score: -0.42

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