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

ID: ALA3121557

PubChem CID: 76336193

Max Phase: Preclinical

Molecular Formula: C21H19BrN2O2

Molecular Weight: 411.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1CCCC2=C1C(c1c[nH]c3cc(Br)ccc13)C1=C(CCCC1=O)N2

Standard InChI:  InChI=1S/C21H19BrN2O2/c22-11-7-8-12-13(10-23-16(12)9-11)19-20-14(3-1-5-17(20)25)24-15-4-2-6-18(26)21(15)19/h7-10,19,23-24H,1-6H2

Standard InChI Key:  YFJHXBINOQRNCY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    2.4209  -23.9089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7006  -23.9216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9775  -25.1572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4209  -24.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1329  -25.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1329  -23.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8450  -23.9089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8415  -24.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5503  -25.1471    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5572  -23.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2706  -23.9149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2668  -24.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9852  -23.5022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9878  -22.6772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1329  -22.6672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5596  -22.6721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2295  -22.1929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9805  -21.4077    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6997  -24.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8948  -22.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1512  -21.4074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6030  -20.7966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983  -20.9662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5446  -21.7521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0946  -22.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2461  -20.3531    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0
  1  6  1  0
  4  5  1  0
  5  8  1  0
  7  6  1  0
  7  8  2  0
  7 10  1  0
  8  9  1  0
  9 12  1  0
 11 10  1  0
 11 12  2  0
 11 13  1  0
 12  3  1  0
  3 19  1  0
  2 13  1  0
 13 14  2  0
  6 15  2  0
 10 16  1  0
 16 17  2  0
 17 18  1  0
 20 16  1  0
 21 18  1  0
 19  2  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3121557

   9-(6-bromo-1H-indol-3-yl)-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: 411.30

Molecular Weight (Monoisotopic): 410.0630

AlogP: 4.63

#Rotatable Bonds: 1

Polar Surface Area: 61.96

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.27

CX LogD: 3.27

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.72

Np Likeness Score: -0.41

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