N*9*-(4-Dimethylamino-phenyl)-acridine-3,9-diamine

ID: ALA34930

PubChem CID: 44283267

Max Phase: Preclinical

Molecular Formula: C21H20N4

Molecular Weight: 328.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)c1ccc(Nc2c3ccccc3nc3cc(N)ccc23)cc1

Standard InChI:  InChI=1S/C21H20N4/c1-25(2)16-10-8-15(9-11-16)23-21-17-5-3-4-6-19(17)24-20-13-14(22)7-12-18(20)21/h3-13H,22H2,1-2H3,(H,23,24)

Standard InChI Key:  TVEFLIUQTOCYTL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   -2.0792   -1.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0804   -2.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3660   -2.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3678   -0.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6529   -1.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6521   -2.2342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0627   -2.6448    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0571   -0.9940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7725   -1.4009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7761   -2.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4947   -2.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2102   -2.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2025   -1.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4834   -0.9832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9272   -2.6282    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0527   -0.1696    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7645    0.2464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760   -0.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1873    0.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1834    1.0752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4622    1.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7539    1.0658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8946    1.4922    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6113    1.0846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8891    2.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  2  0
  5  6  1  0
 12 13  1  0
  3  6  2  0
 13 14  2  0
 14  9  1  0
  6  7  1  0
 12 15  1  0
  7 10  2  0
  8 16  1  0
  1  2  2  0
 16 17  1  0
  9  8  2  0
 17 18  2  0
  8  5  1  0
 18 19  1  0
  5  4  2  0
 19 20  2  0
  4  1  1  0
 20 21  1  0
  9 10  1  0
 21 22  2  0
 22 17  1  0
 20 23  1  0
 10 11  1  0
 23 24  1  0
  2  3  1  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA34930

   9-N-[4-(dimethylamino)phenyl]acridine-3,9-diamine

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: 328.42

Molecular Weight (Monoisotopic): 328.1688

AlogP: 4.78

#Rotatable Bonds: 3

Polar Surface Area: 54.18

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.60

CX LogP: 4.23

CX LogD: 2.62

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.42

Np Likeness Score: -0.95

References

1. Gamage SA, Tepsiri N, Wilairat P, Wojcik SJ, Figgitt DP, Ralph RK, Denny WA..  (1994)  Synthesis and in vitro evaluation of 9-anilino-3,6-diaminoacridines active against a multidrug-resistant strain of the malaria parasite Plasmodium falciparum.,  37  (10): [PMID:8182707] [10.1021/jm00036a014]

2. Acharya BN, Saraswat D, Kaushik MP..  (2008)  Pharmacophore based discovery of potential antimalarial agent targeting haem detoxification pathway.,  43  (12): [PMID:18395298] [10.1016/j.ejmech.2008.02.005]

3. Acharya BN, Saraswat D, Kaushik MP..  (2008)  Pharmacophore based discovery of potential antimalarial agent targeting haem detoxification pathway.,  43  (12): [PMID:18395298] [10.1016/j.ejmech.2008.02.005]

4. Prado-Prado FJ, García-Mera X, González-Díaz H..  (2010)  Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.,  18  (6): [PMID:20185316] [10.1016/j.bmc.2010.01.068]

Source

Source(1):

• Scientific Literature