[4-Amino-2-(4-chlorophenylamino)-thiazol-5-yl]-phenylmethanone

ID: ALA564732

Cas Number: 196877-94-8

PubChem CID: 1484799

Max Phase: Preclinical

Molecular Formula: C16H12ClN3OS

Molecular Weight: 329.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(Nc2ccc(Cl)cc2)sc1C(=O)c1ccccc1

Standard InChI:  InChI=1S/C16H12ClN3OS/c17-11-6-8-12(9-7-11)19-16-20-15(18)14(22-16)13(21)10-4-2-1-3-5-10/h1-9H,18H2,(H,19,20)

Standard InChI Key:  LFUAJHRRAYJVBI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    7.6990    1.5423    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.4441    0.7577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6191    0.7577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3642    1.5423    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0316    2.0273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9290    0.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7495    0.1765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5935   -0.6634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0316    2.8523    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7461    3.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7461    4.0898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4605    4.5023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1750    4.0898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1750    3.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4605    2.8523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0784   -1.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7428   -2.0845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9224   -2.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4374   -1.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7730   -0.7496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1342    0.0903    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8895    4.5023    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 10 11  2  0
  1  2  1  0
 11 12  1  0
  2  6  1  0
 12 13  2  0
 13 14  1  0
  6  7  2  0
 14 15  2  0
 15 10  1  0
  2  3  2  0
  8 16  2  0
  6  8  1  0
 16 17  1  0
  3  4  1  0
 17 18  2  0
  5  9  1  0
 18 19  1  0
  4  5  2  0
 19 20  2  0
 20  8  1  0
  9 10  1  0
  3 21  1  0
  5  1  1  0
 13 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA564732

   [4-Amino-2-(4-chloroanilino)-1,3-thiazol-5-yl](phenyl)methanone

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: 329.81

Molecular Weight (Monoisotopic): 329.0390

AlogP: 4.35

#Rotatable Bonds: 4

Polar Surface Area: 68.01

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.32

CX Basic pKa: 1.46

CX LogP: 5.37

CX LogD: 5.37

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.70

Np Likeness Score: -1.58

References

1. Romagnoli R, Baraldi PG, Carrion MD, Cruz-Lopez O, Cara CL, Basso G, Viola G, Khedr M, Balzarini J, Mahboobi S, Sellmer A, Brancale A, Hamel E..  (2009)  2-Arylamino-4-amino-5-aroylthiazoles. "One-pot" synthesis and biological evaluation of a new class of inhibitors of tubulin polymerization.,  52  (17): [PMID:19663386] [10.1021/jm9001692]

Source

Source(1):

• Scientific Literature