2-[1-(4-chlorophenylamino)-4,5-dimethyl-1H-imidazol-2-ylthio]-N-(thiazol-2-yl)acetamide

ID: ALA2296449

PubChem CID: 54613444

Max Phase: Preclinical

Molecular Formula: C16H16ClN5OS2

Molecular Weight: 393.93

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc(SCC(=O)Nc2nccs2)n(Nc2ccc(Cl)cc2)c1C

Standard InChI:  InChI=1S/C16H16ClN5OS2/c1-10-11(2)22(21-13-5-3-12(17)4-6-13)16(19-10)25-9-14(23)20-15-18-7-8-24-15/h3-8,21H,9H2,1-2H3,(H,18,20,23)

Standard InChI Key:  IHKFKYOOSMMSOZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   28.4939   -8.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1652   -9.2165    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.8131   -8.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5421   -7.9518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.7269   -7.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2305   -7.3228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7232   -9.0249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1853  -10.0334    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.4878  -10.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7722  -10.0641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0751  -10.4892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0948  -11.3071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8172  -11.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5113  -11.2705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5962   -8.9545    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   30.7856   -9.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5688   -9.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7582  -10.7778    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.1625   -9.4214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.5414  -11.0112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8160  -11.7781    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   33.6330  -11.7581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8664  -10.9749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1937  -10.5111    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.3978  -11.7338    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  1  2  0
  5  6  1  0
  1  7  1  0
  2  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  3 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 20  2  0
 12 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2296449

   2-[1-(4-chloroanilino)-4,5-dimethylimidazol-2-yl]sulfanyl-N-(1,3-thiazol-2-yl)acetamide

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: 393.93

Molecular Weight (Monoisotopic): 393.0485

AlogP: 4.22

#Rotatable Bonds: 6

Polar Surface Area: 71.84

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.86

CX Basic pKa: 4.66

CX LogP: 3.48

CX LogD: 3.36

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.61

Np Likeness Score: -2.70

References

1. Duran M, Demirayak S.  (2013)  Synthesis of 2-[4,5-dimethyl-1-(phenylamino)-1H-imidazol-2-ylthio]-N-(thiazole-2-yl)acetamide derivatives and their anticancer activities,  22  (9): [10.1007/s00044-012-0411-5]

Source

Source(1):

• Scientific Literature