2-(4-Amino-2-chloro-5-methoxy-phenyl)-2-(5-chloro-2-methoxy-phenylamino)-indan-1,3-dione

ID: ALA2297447

PubChem CID: 76320470

Max Phase: Preclinical

Molecular Formula: C23H18Cl2N2O4

Molecular Weight: 457.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C2(Nc3cc(Cl)ccc3OC)C(=O)c3ccccc3C2=O)c(Cl)cc1N

Standard InChI:  InChI=1S/C23H18Cl2N2O4/c1-30-19-8-7-12(24)9-18(19)27-23(15-10-20(31-2)17(26)11-16(15)25)21(28)13-5-3-4-6-14(13)22(23)29/h3-11,27H,26H2,1-2H3

Standard InChI Key:  BRWFNHGDICGMTB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   12.4156  -21.0268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0063  -20.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7088  -20.6155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7076  -21.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4220  -21.8549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4202  -20.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1351  -20.6119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1354  -21.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9252  -21.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1203  -20.5949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8452  -20.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5488  -20.5617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5279  -19.7355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7975  -19.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0970  -19.7744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2968  -19.5457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9171  -22.5226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2305  -19.3041    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0913  -18.9458    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.2729  -20.9557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2938  -21.7800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8206  -21.7356    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8165  -22.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0981  -22.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0936  -23.7905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8061  -24.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5245  -23.7941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5255  -22.9718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2402  -22.5608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9535  -22.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3773  -24.1988    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  4  2  0
  4  5  1  0
  5  8  2  0
  7  6  2  0
  6  3  1  0
  7  8  1  0
  8  9  1  0
  9  1  1  0
  2  7  1  0
  1 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  2 16  2  0
  9 17  2  0
 13 18  1  0
 15 19  1  0
 12 20  1  0
 20 21  1  0
  1 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 28 29  1  0
 29 30  1  0
 25 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2297447

   2-(4-Amino-2-chloro-5-methoxyphenyl)-2-(5-chloro-2-methoxyanilino)indene-1,3-dione

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: 457.31

Molecular Weight (Monoisotopic): 456.0644

AlogP: 4.98

#Rotatable Bonds: 5

Polar Surface Area: 90.65

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.91

CX Basic pKa: 3.22

CX LogP: 4.32

CX LogD: 4.32

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.42

Np Likeness Score: -0.29

References

1. Sahu KB, Banerjee M, Ghosh S, Maity A, Mondal S, Paira R, Hazra A, Karmakar S, Samanta A, Mondal NB.  (2013)  I2 catalyzed FriedelCrafts alkylation reaction of substituted anilines with ninhydrin: formation of novel products and their antimicrobial evaluation,  22  (4): [10.1007/s00044-012-0202-z]

Source

Source(1):

• Scientific Literature