4-(3,6-Dichloro-acridin-9-ylamino)-benzenesulfonamide

ID: ALA36532

PubChem CID: 9979401

Max Phase: Preclinical

Molecular Formula: C19H13Cl2N3O2S

Molecular Weight: 418.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)c1ccc(Nc2c3ccc(Cl)cc3nc3cc(Cl)ccc23)cc1

Standard InChI:  InChI=1S/C19H13Cl2N3O2S/c20-11-1-7-15-17(9-11)24-18-10-12(21)2-8-16(18)19(15)23-13-3-5-14(6-4-13)27(22,25)26/h1-10H,(H,23,24)(H2,22,25,26)

Standard InChI Key:  HPDKFWFFTQAQET-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   -2.9122   -1.3658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9134   -2.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1990   -2.6054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2008   -0.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4858   -1.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4850   -2.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7701   -2.5993    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7758   -0.9482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0604   -1.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0568   -2.1844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6620   -2.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776   -2.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3699   -1.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6506   -0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7801   -0.1238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0684    0.2922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6433   -0.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3547    0.2957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3507    1.1211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6295    1.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0790    1.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0946   -2.5827    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.6278   -2.6044    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.0620    1.5381    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.7734    1.9571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4798    0.8272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6433    2.2484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
  3  6  2  0
 13 14  2  0
 14  9  1  0
  6  7  1  0
  8 15  1  0
  7 10  2  0
 15 16  1  0
  1  2  2  0
 16 17  2  0
  9  8  2  0
 17 18  1  0
  8  5  1  0
 18 19  2  0
  5  4  2  0
 19 20  1  0
  4  1  1  0
 20 21  2  0
 21 16  1  0
  9 10  1  0
 12 22  1  0
  2 23  1  0
 10 11  1  0
 19 24  1  0
  2  3  1  0
 24 25  1  0
 11 12  2  0
 24 26  2  0
  5  6  1  0
 24 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA36532

   4-[(3,6-Dichloroacridin-9-yl)amino]benzenesulfonamide

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: 418.31

Molecular Weight (Monoisotopic): 417.0106

AlogP: 5.09

#Rotatable Bonds: 3

Polar Surface Area: 85.08

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.80

CX Basic pKa: 6.93

CX LogP: 4.76

CX LogD: 4.64

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.45

Np Likeness Score: -1.19

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. 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