2-(2-Fluoro-4-biphenylyl)-N-[2-(2,6-difluorophenyl)-4-oxo-1,3-thiazolidine-3-yl]propanamide

ID: ALA2281776

PubChem CID: 76319876

Max Phase: Preclinical

Molecular Formula: C24H19F3N2O2S

Molecular Weight: 456.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C(=O)NN1C(=O)CSC1c1c(F)cccc1F)c1ccc(-c2ccccc2)c(F)c1

Standard InChI:  InChI=1S/C24H19F3N2O2S/c1-14(16-10-11-17(20(27)12-16)15-6-3-2-4-7-15)23(31)28-29-21(30)13-32-24(29)22-18(25)8-5-9-19(22)26/h2-12,14,24H,13H2,1H3,(H,28,31)

Standard InChI Key:  LFTOCSUGPMYXAL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    4.8180   -5.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5261   -6.0532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2357   -5.6438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2329   -4.8211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243   -4.4158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9361   -4.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6456   -4.8188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3513   -4.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3486   -3.5901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6344   -3.1844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.7640   -3.5829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0501   -2.3607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7682   -4.4001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.1794   -3.5757    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6478   -5.6359    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.2658   -4.3851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0660   -4.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4710   -3.8411    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.9210   -3.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6603   -4.9339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0844   -2.4381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8611   -2.1806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0252   -1.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4134   -0.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6349   -1.0999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4746   -1.8991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7001   -2.1596    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.4720   -2.7234    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  5  7  1  0
 10 13  1  0
 13 14  1  0
 13 15  1  0
 14 16  2  0
 14 17  1  0
 17 18  1  0
  8 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 18  1  0
 20 24  2  0
 25 26  2  0
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 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 23 25  1  0
 30 31  1  0
 26 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2281776

   N-[2-(2,6-difluorophenyl)-4-oxo-1,3-thiazolidin-3-yl]-2-(3-fluoro-4-phenylphenyl)propanamide

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: 456.49

Molecular Weight (Monoisotopic): 456.1119

AlogP: 5.18

#Rotatable Bonds: 5

Polar Surface Area: 49.41

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.82

CX Basic pKa: ┄

CX LogP: 5.16

CX LogD: 5.16

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.58

Np Likeness Score: -0.79

References

1. Ckla P, Tatar E, Kucukguzel I, Sahin F, Yurdakul D, Basu A, Krishnan R, Nichols DB, Kaushik-Basu N, Kucukguzel SG.  (2013)  Synthesis and characterization of flurbiprofen hydrazide derivatives as potential anti-HCV, anticancer and antimicrobial agents,  22  (12): [10.1007/s00044-013-0550-3]

Source

Source(1):

• Scientific Literature