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

ID: ALA36405

PubChem CID: 10341452

Max Phase: Preclinical

Molecular Formula: C21H19N3O4S

Molecular Weight: 409.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c(Nc3ccc(S(N)(=O)=O)cc3)c3ccc(OC)cc3nc2c1

Standard InChI:  InChI=1S/C21H19N3O4S/c1-27-14-5-9-17-19(11-14)24-20-12-15(28-2)6-10-18(20)21(17)23-13-3-7-16(8-4-13)29(22,25)26/h3-12H,1-2H3,(H,23,24)(H2,22,25,26)

Standard InChI Key:  MJQDOQLIFBCNNJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    5.7167   -8.2667    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8792  -10.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875  -12.4042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5917  -11.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1667  -11.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6000  -11.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1667  -11.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8750   -9.9292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0042   -8.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3167  -12.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4542  -12.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3042  -10.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4542  -10.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7167   -7.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7167   -9.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5417   -8.2667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0125   -9.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2875   -8.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5875   -9.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7417  -12.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0292  -11.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7417  -11.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0250  -11.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3000   -9.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5792   -8.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7542  -12.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0250  -12.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4625  -11.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6875  -12.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  8  1  0
  3  7  1  0
  4  2  2  0
  5  2  1  0
  6  4  1  0
  7  5  1  0
  8 19  1  0
  9  1  1  0
 10  6  1  0
 11  7  2  0
 12  4  1  0
 13  5  2  0
 14  1  2  0
 15  1  2  0
 16  1  1  0
 17  9  2  0
 18  9  1  0
 19 25  1  0
 20 22  2  0
 21 23  1  0
 22 13  1  0
 23 12  2  0
 24 17  1  0
 25 18  2  0
 26 21  1  0
 27 20  1  0
 28 26  1  0
 29 27  1  0
 24 19  2  0
  6  3  2  0
 20 11  1  0
 21 10  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA36405

   4-[(3,6-Dimethoxyacridin-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: 409.47

Molecular Weight (Monoisotopic): 409.1096

AlogP: 3.80

#Rotatable Bonds: 5

Polar Surface Area: 103.54

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.80

CX Basic pKa: 8.51

CX LogP: 3.24

CX LogD: 2.19

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.49

Np Likeness Score: -0.90

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]

Source

Source(1):

• Scientific Literature