rac-ethyl 6,8-difluoro-1-(oxiran-2-ylmethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

ID: ALA2381920

PubChem CID: 71624136

Max Phase: Preclinical

Molecular Formula: C15H13F2NO4

Molecular Weight: 309.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cn(CC2CO2)c2c(F)cc(F)cc2c1=O

Standard InChI:  InChI=1S/C15H13F2NO4/c1-2-21-15(20)11-6-18(5-9-7-22-9)13-10(14(11)19)3-8(16)4-12(13)17/h3-4,6,9H,2,5,7H2,1H3

Standard InChI Key:  GGLBPJLVEJTFGV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    4.2384   -2.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9481   -2.3255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9452   -1.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2366   -1.0975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5303   -2.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5345   -1.5064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8307   -1.0953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1183   -1.4993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1141   -2.3188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8224   -2.7344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8359   -0.2781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4132   -1.0861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4184   -0.2690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7029   -1.4902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6976   -2.3074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0203   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8195   -3.5516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1103   -3.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2899   -3.9588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6960   -4.6680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2382   -3.5521    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.6514   -1.0915    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  7 11  2  0
  8 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 10 17  1  0
 17 18  1  0
 19 18  1  0
 20 19  1  0
 18 20  1  0
  1 21  1  0
  3 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2381920

   Ethyl 6,8-difluoro-1-(oxiran-2-ylmethyl)-4-oxoquinoline-3-carboxylate

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: 309.27

Molecular Weight (Monoisotopic): 309.0813

AlogP: 1.86

#Rotatable Bonds: 4

Polar Surface Area: 60.83

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.24

CX LogD: 2.24

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.64

Np Likeness Score: -0.91

References

1. Cui SF, Ren Y, Zhang SL, Peng XM, Damu GL, Geng RX, Zhou CH..  (2013)  Synthesis and biological evaluation of a class of quinolone triazoles as potential antimicrobial agents and their interactions with calf thymus DNA.,  23  (11): [PMID:23602443] [10.1016/j.bmcl.2013.03.118]

2. Cui SF, Peng LP, Zhang HZ, Rasheed S, Vijaya Kumar K, Zhou CH..  (2014)  Novel hybrids of metronidazole and quinolones: synthesis, bioactive evaluation, cytotoxicity, preliminary antimicrobial mechanism and effect of metal ions on their transportation by human serum albumin.,  86  [PMID:25173851] [10.1016/j.ejmech.2014.08.063]

Source

Source(1):

• Scientific Literature