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

ID: ALA2281777

PubChem CID: 72722223

Max Phase: Preclinical

Molecular Formula: C24H20ClFN2O2S

Molecular Weight: 454.95

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C(=O)NN1C(=O)CSC1c1ccc(Cl)cc1)c1ccc(-c2ccccc2)c(F)c1

Standard InChI:  InChI=1S/C24H20ClFN2O2S/c1-15(18-9-12-20(21(26)13-18)16-5-3-2-4-6-16)23(30)27-28-22(29)14-31-24(28)17-7-10-19(25)11-8-17/h2-13,15,24H,14H2,1H3,(H,27,30)

Standard InChI Key:  ZAVGCLBBIKPCED-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   14.3820   -4.6596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3808   -5.4791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0889   -5.8881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7985   -5.4787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7957   -4.6560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0871   -4.2507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4988   -4.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2084   -4.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9141   -4.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9114   -3.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1972   -3.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4944   -3.4322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6170   -3.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3268   -3.4178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6129   -2.1957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3310   -4.2350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0324   -3.0056    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7422   -3.4106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2106   -5.4709    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.8286   -4.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6288   -4.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0338   -3.6760    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.4838   -3.0716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2231   -4.7688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6472   -2.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4239   -2.0155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5879   -1.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9762   -0.6726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1977   -0.9348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0374   -1.7340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1389    0.1282    0.0000 Cl  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
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 23 25  1  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2281777

   N-[2-(4-chlorophenyl)-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: 454.95

Molecular Weight (Monoisotopic): 454.0918

AlogP: 5.56

#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: 10.20

CX Basic pKa: ┄

CX LogP: 5.48

CX LogD: 5.48

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.55

Np Likeness Score: -0.98

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