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

ID: ALA2382006

PubChem CID: 71624258

Max Phase: Preclinical

Molecular Formula: C15H13Cl2NO4

Molecular Weight: 342.18

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H13Cl2NO4/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:  DMUDHDAODVCDBV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    9.7400   -8.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4496   -8.5081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4468   -7.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7382   -7.2801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0319   -8.5085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0361   -7.6890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3323   -7.2779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6198   -7.6818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6157   -8.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3240   -8.9170    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3375   -6.4607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9148   -7.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9200   -6.4516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2045   -7.6728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1992   -8.4900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4889   -8.8940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3211   -9.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6119  -10.1402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7915  -10.1414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1975  -10.8506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7398   -9.7347    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.1530   -7.2741    0.0000 Cl  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:

   

   ALA2382006

   Ethyl 6,8-dichloro-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: 342.18

Molecular Weight (Monoisotopic): 341.0222

AlogP: 2.88

#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: 3.16

CX LogD: 3.16

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.63

Np Likeness Score: -0.79

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