N-[4-(3,6-Diamino-acridin-9-ylamino)-phenyl]-methanesulfonamide

ID: ALA37647

Cas Number: 76015-35-5

PubChem CID: 127111

Max Phase: Preclinical

Molecular Formula: C20H19N5O2S

Molecular Weight: 393.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)Nc1ccc(Nc2c3ccc(N)cc3nc3cc(N)ccc23)cc1

Standard InChI:  InChI=1S/C20H19N5O2S/c1-28(26,27)25-15-6-4-14(5-7-15)23-20-16-8-2-12(21)10-18(16)24-19-11-13(22)3-9-17(19)20/h2-11,25H,21-22H2,1H3,(H,23,24)

Standard InChI Key:  DFPFHWONJWGBDW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   -2.2595   -9.5528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2606  -10.3801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5459  -10.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5477   -9.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8324   -9.5492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8317  -10.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1165  -10.7868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1221   -9.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5937   -9.5423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5973  -10.3718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3163  -10.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0322  -10.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0246   -9.5304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3050   -9.1243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7496  -10.7702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1265   -8.3102    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5857   -7.8940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2976   -8.3060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0093   -7.8905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0054   -7.0647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2838   -6.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5751   -7.0742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9753  -10.7919    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7170   -6.6476    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4341   -7.0552    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.1452   -7.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8442   -6.3395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0275   -7.7729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
  2 23  1  0
 10 11  1  0
 20 24  1  0
  2  3  1  0
 24 25  1  0
 11 12  2  0
 25 26  1  0
  5  6  1  0
 25 27  2  0
 12 13  1  0
 25 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA37647

   3,6-Diamino-9-(4-(methylsulfonyl)aminophenyl)aminoacridine

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: 393.47

Molecular Weight (Monoisotopic): 393.1259

AlogP: 3.67

#Rotatable Bonds: 4

Polar Surface Area: 123.13

Molecular Species: BASE

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.43

CX Basic pKa: 10.30

CX LogP: 1.45

CX LogD: -0.01

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.31

Np Likeness Score: -0.87

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. Denny WA, Cain BF, Atwell GJ, Hansch C, Panthananickal A, Leo A..  (1982)  Potential antitumor agents. 36. Quantitative relationships between experimental antitumor activity, toxicity, and structure for the general class of 9-anilinoacridine antitumor agents.,  25  (3): [PMID:7069706] [10.1021/jm00345a015]

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