2-(2-Fluoro-4-biphenylyl)-N-[2-(5-nitrofuran-2-yl)-4-oxo-1,3-thiazolidine-3-yl]propanamide

ID: ALA2281802

PubChem CID: 72722210

Max Phase: Preclinical

Molecular Formula: C22H18FN3O5S

Molecular Weight: 455.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C(=O)NN1C(=O)CSC1c1ccc([N+](=O)[O-])o1)c1ccc(-c2ccccc2)c(F)c1

Standard InChI:  InChI=1S/C22H18FN3O5S/c1-13(15-7-8-16(17(23)11-15)14-5-3-2-4-6-14)21(28)24-25-19(27)12-32-22(25)18-9-10-20(31-18)26(29)30/h2-11,13,22H,12H2,1H3,(H,24,28)

Standard InChI Key:  BGPVRFYZOGJGNF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   15.7027  -21.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7015  -21.8766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4096  -22.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1192  -21.8761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1164  -21.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4078  -20.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8196  -20.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5291  -21.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2348  -20.6406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2321  -19.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5179  -19.4168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8152  -19.8297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9377  -19.4103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6475  -19.8153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9336  -18.5931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6517  -20.6325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3531  -19.4031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0629  -19.8081    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5313  -21.8683    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.1493  -20.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9495  -20.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3545  -20.0735    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.8045  -19.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5438  -21.1663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9675  -18.6676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7115  -18.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6199  -17.5175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8193  -17.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4162  -18.0645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4812  -16.6078    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6678  -16.5286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9564  -15.9430    0.0000 O   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 25  1  0
 23 25  1  0
 30 31  2  0
 30 32  1  0
 28 30  1  0
M  CHG  2  30   1  32  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2281802

   2-(3-fluoro-4-phenylphenyl)-N-[2-(5-nitrofuran-2-yl)-4-oxo-1,3-thiazolidin-3-yl]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: 455.47

Molecular Weight (Monoisotopic): 455.0951

AlogP: 4.40

#Rotatable Bonds: 6

Polar Surface Area: 105.69

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.78

CX Basic pKa: ┄

CX LogP: 3.97

CX LogD: 3.96

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.44

Np Likeness Score: -1.12

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