1'-(2,4-dichlorobenzylideneamino)-5'-oxo-1',5'-dihydro-10H-spiro[acridine-9,2'-pyrrole]-4'-carbonitrile

ID: ALA4864938

PubChem CID: 164622220

Max Phase: Preclinical

Molecular Formula: C24H14Cl2N4O

Molecular Weight: 445.31

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#CC1=CC2(c3ccccc3Nc3ccccc32)N(/N=C\c2ccc(Cl)cc2Cl)C1=O

Standard InChI:  InChI=1S/C24H14Cl2N4O/c25-17-10-9-15(20(26)11-17)14-28-30-23(31)16(13-27)12-24(30)18-5-1-3-7-21(18)29-22-8-4-2-6-19(22)24/h1-12,14,29H/b28-14-

Standard InChI Key:  BAHZLBHWIJXOFJ-MUXKCCDJSA-N

Molfile:  

 
     RDKit          2D

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   32.7124   -4.7728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4248   -4.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2488   -3.5497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4274   -3.4679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0959   -4.2238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5695   -5.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5683   -6.0232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2831   -6.4360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2813   -4.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9967   -5.1922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9955   -6.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7084   -6.4336    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.4284   -5.1942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4266   -6.0190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1390   -6.4311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8534   -6.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8512   -5.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1383   -4.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2899   -4.3999    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.7345   -3.7899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9850   -3.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7893   -2.8327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0400   -2.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4843   -1.4366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6747   -1.6161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4278   -2.4010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0108   -2.7558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.7961   -2.9347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3447   -2.3184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.7338   -0.6502    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   29.6228   -2.5816    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  6  7  2  0
  7  8  1  0
  8 11  2  0
 10  9  2  0
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 10 11  1  0
 10  1  1  0
 11 12  1  0
 12 14  1  0
 13  1  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  5 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
  4 27  2  0
 28 29  3  0
  3 28  1  0
 24 30  1  0
 26 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4864938

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 445.31

Molecular Weight (Monoisotopic): 444.0545

AlogP: 5.62

#Rotatable Bonds: 2

Polar Surface Area: 68.49

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 0.19

CX LogP: 5.49

CX LogD: 5.49

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.52

Np Likeness Score: -0.64

References

1. Almeida FS, Sousa GLS, Rocha JC, Ribeiro FF, de Oliveira MR, de Lima Grisi TCS, Araújo DAM, de C Nobre MS, Castro RN, Amaral IPG, Keesen TSL, de Moura RO..  (2021)  In vitro anti-Leishmania activity and molecular docking of spiro-acridine compounds as potential multitarget agents against Leishmania infantum.,  49  [PMID:34311084] [10.1016/j.bmcl.2021.128289]

Source

Source(1):

• Scientific Literature