1-[4-(Acridin-9-ylamino)-phenyl]-3-phenyl-urea

ID: ALA49272

PubChem CID: 149541

Max Phase: Preclinical

Molecular Formula: C26H20N4O

Molecular Weight: 404.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccccc1)Nc1ccc(Nc2c3ccccc3nc3ccccc23)cc1

Standard InChI:  InChI=1S/C26H20N4O/c31-26(28-18-8-2-1-3-9-18)29-20-16-14-19(15-17-20)27-25-21-10-4-6-12-23(21)30-24-13-7-5-11-22(24)25/h1-17H,(H,27,30)(H2,28,29,31)

Standard InChI Key:  GZNSAGOUDBUPIM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
    0.5000   -2.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042   -4.1042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2083   -2.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2167   -2.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542   -0.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2167   -3.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2083   -3.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917   -1.6250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417    0.0375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7667    0.0458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0625   -1.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2042   -1.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292   -0.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4875   -0.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2000   -0.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167   -1.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292   -1.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9042    0.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9250   -2.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9292   -2.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9375   -4.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9250   -4.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4875   -1.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1917    0.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6417   -2.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6375   -2.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6375   -3.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6542   -3.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9042   -0.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2042   -1.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9167   -1.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  2  0
  3  1  1  0
  4  1  2  0
  5  9  1  0
  6  4  1  0
  7  3  1  0
  8  1  1  0
  9 13  1  0
 10  5  1  0
 11  5  2  0
 12  8  1  0
 13 17  2  0
 14 10  1  0
 15 12  1  0
 16 12  2  0
 17 16  1  0
 18 15  2  0
 19  3  2  0
 20  4  1  0
 21  6  1  0
 22  7  2  0
 23 14  2  0
 24 14  1  0
 25 20  2  0
 26 19  1  0
 27 26  2  0
 28 25  1  0
 29 24  2  0
 30 23  1  0
 31 29  1  0
  2  7  1  0
 13 18  1  0
 28 21  2  0
 27 22  1  0
 31 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA49272

   1-[4-(Acridin-9-ylamino)phenyl]-3-phenyl-urea

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: 404.47

Molecular Weight (Monoisotopic): 404.1637

AlogP: 6.78

#Rotatable Bonds: 4

Polar Surface Area: 66.05

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.77

CX Basic pKa: 8.50

CX LogP: 6.09

CX LogD: 5.06

Aromatic Rings: 5

Heavy Atoms: 31

QED Weighted: 0.29

Np Likeness Score: -0.85

References

1. Baguley BC, Denny WA, Atwell GJ, Cain BF..  (1981)  Potential antitumor agents. 34. Quantitative relationships between DNA binding and molecular structure for 9-anilinoacridines substituted in the anilino ring.,  24  (2): [PMID:7205885] [10.1021/jm00134a009]

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. Medapi B, Meda N, Kulkarni P, Yogeeswari P, Sriram D..  (2016)  Development of acridine derivatives as selective Mycobacterium tuberculosis DNA gyrase inhibitors.,  24  (4): [PMID:26787274] [10.1016/j.bmc.2016.01.011]

Source

Source(1):

• Scientific Literature