3-(2-Chloro-phenyl)-2-[2-(4-chloro-phenylamino)-4-methyl-thiazol-5-yl]-3H-quinazolin-4-one

ID: ALA475112

PubChem CID: 25017850

Max Phase: Preclinical

Molecular Formula: C24H16Cl2N4OS

Molecular Weight: 479.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc(Nc2ccc(Cl)cc2)sc1-c1nc2ccccc2c(=O)n1-c1ccccc1Cl

Standard InChI:  InChI=1S/C24H16Cl2N4OS/c1-14-21(32-24(27-14)28-16-12-10-15(25)11-13-16)22-29-19-8-4-2-6-17(19)23(31)30(22)20-9-5-3-7-18(20)26/h2-13H,1H3,(H,27,28)

Standard InChI Key:  VLFNQZMEZRAGHC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
    6.0250   -8.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0250   -9.6431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7394  -10.0556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7394   -8.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4539   -8.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4539   -9.6431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1684  -10.0556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8829   -9.6431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8829   -8.8181    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1684   -8.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1684   -7.5806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5973   -8.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3118   -8.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0263   -8.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0263   -7.5806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3118   -7.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5973   -7.5806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5973  -10.0556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6836  -10.8761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4905  -11.0476    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9030  -10.3332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3510   -9.7201    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.7235  -10.2469    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2084  -10.9144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0705  -11.4282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0289  -10.8281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5138  -11.4956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1783  -12.2493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3578  -12.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8729  -11.6681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8829   -7.1681    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.6632  -12.9167    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0
 15 16  1  0
  4  1  1  0
 16 17  2  0
 17 12  1  0
  5 10  1  0
  8 18  1  0
 18 19  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 18  1  0
  5  6  1  0
 21 23  1  0
 10 11  2  0
 23 24  1  0
 19 25  1  0
  9 12  1  0
 24 26  2  0
  2  3  1  0
 26 27  1  0
 12 13  2  0
 27 28  2  0
  3  6  2  0
 28 29  1  0
 13 14  1  0
 29 30  2  0
 30 24  1  0
  1  2  2  0
 17 31  1  0
 14 15  2  0
 28 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA475112

   2-[2-(4-Chloroanilino)-4-methyl-1,3-thiazol-5-yl]-3-(2-chlorophenyl)quinazolin-4-one

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: 479.39

Molecular Weight (Monoisotopic): 478.0422

AlogP: 6.87

#Rotatable Bonds: 4

Polar Surface Area: 59.81

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.71

CX Basic pKa: ┄

CX LogP: 6.76

CX LogD: 6.76

Aromatic Rings: 5

Heavy Atoms: 32

QED Weighted: 0.31

Np Likeness Score: -1.46

References

1. Giri RS, Thaker HM, Giordano T, Williams J, Rogers D, Sudersanam V, Vasu KK..  (2009)  Design, synthesis and characterization of novel 2-(2,4-disubstituted-thiazole-5-yl)-3-aryl-3H-quinazoline-4-one derivatives as inhibitors of NF-kappaB and AP-1 mediated transcription activation and as potential anti-inflammatory agents.,  44  (5): [PMID:19064304] [10.1016/j.ejmech.2008.10.031]

Source

Source(1):

• Scientific Literature