2-(2-Fluorobiphenyl-4-yl)-N'-[(5-nitro-2-furyl)methylene]propanehydrazide

ID: ALA2281791

PubChem CID: 76308970

Max Phase: Preclinical

Molecular Formula: C20H16FN3O4

Molecular Weight: 381.36

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H16FN3O4/c1-13(20(25)23-22-12-16-8-10-19(28-16)24(26)27)15-7-9-17(18(21)11-15)14-5-3-2-4-6-14/h2-13H,1H3,(H,23,25)/b22-12+

Standard InChI Key:  PPEWAWKYMKNUHU-WSDLNYQXSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   -2.0952   -2.3484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0941   -3.1679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3906   -3.5769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6805   -3.1674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6777   -2.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3888   -1.9395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0271   -1.9348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7366   -2.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4423   -1.9318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4397   -1.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7254   -0.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0227   -1.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1453   -0.7016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8550   -1.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1411    0.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8592   -1.9238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5607   -0.6944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2704   -1.0994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7388   -3.1596    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.9761   -0.6872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6858   -1.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7739   -1.9062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5741   -2.0720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9791   -1.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4291   -0.7578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7941   -1.2698    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1226   -0.5216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2778   -1.9285    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  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 21  1  0
 26 27  2  0
 26 28  1  0
 24 26  1  0
M  CHG  2  26   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2281791

   2-(3-fluoro-4-phenylphenyl)-N-[(E)-(5-nitrofuran-2-yl)methylideneamino]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: 381.36

Molecular Weight (Monoisotopic): 381.1125

AlogP: 4.25

#Rotatable Bonds: 6

Polar Surface Area: 97.74

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.71

CX Basic pKa: ┄

CX LogP: 4.37

CX LogD: 4.37

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.39

Np Likeness Score: -1.54

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