Rac-4-bromo-N-(4-(2,4-dichlorophenyl)-1-(4-methoxyphenyl)azetidin-2-ylidene)aniline

ID: ALA4872499

PubChem CID: 164623008

Max Phase: Preclinical

Molecular Formula: C22H17BrCl2N2O

Molecular Weight: 476.20

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(N2/C(=N/c3ccc(Br)cc3)CC2c2ccc(Cl)cc2Cl)cc1

Standard InChI:  InChI=1S/C22H17BrCl2N2O/c1-28-18-9-7-17(8-10-18)27-21(19-11-4-15(24)12-20(19)25)13-22(27)26-16-5-2-14(23)3-6-16/h2-12,21H,13H2,1H3/b26-22+

Standard InChI Key:  BJHKFNCZPOTFPY-XTCLZLMSSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   15.5682  -21.2746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5682  -22.0999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3935  -22.0999    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3935  -21.2746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9768  -22.6842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7627  -23.4823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3426  -24.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1408  -23.8502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3520  -23.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7705  -22.4713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9738  -20.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7718  -20.9084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3523  -20.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7609  -19.9006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9834  -22.6846    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1860  -22.4721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9758  -21.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1793  -21.4595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5935  -22.0446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8139  -22.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6099  -23.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7265  -24.4343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3378  -19.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1358  -19.5283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7997  -21.8345    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   18.7152  -18.9464    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.9668  -19.6916    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.5193  -24.2206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  1  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  3  5  1  0
 11 12  2  0
 12 13  1  0
 13 24  2  0
 23 14  2  0
 14 11  1  0
  4 11  1  0
  2 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
  8 22  1  0
 23 24  1  0
 19 25  1  0
 24 26  1  0
 14 27  1  0
 22 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4872499

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 476.20

Molecular Weight (Monoisotopic): 473.9901

AlogP: 7.45

#Rotatable Bonds: 4

Polar Surface Area: 24.83

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 6.75

CX LogP: 6.99

CX LogD: 6.90

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.39

Np Likeness Score: -0.94

References

1. Romero E, Oueslati S, Benchekroun M, D'Hollander ACA, Ventre S, Vijayakumar K, Minard C, Exilie C, Tlili L, Retailleau P, Zavala A, Elisée E, Selwa E, Nguyen LA, Pruvost A, Naas T, Iorga BI, Dodd RH, Cariou K..  (2021)  Azetidinimines as a novel series of non-covalent broad-spectrum inhibitors of β-lactamases with submicromolar activities against carbapenemases KPC-2 (class A), NDM-1 (class B) and OXA-48 (class D).,  219  [PMID:33862516] [10.1016/j.ejmech.2021.113418]

Source

Source(1):

• Scientific Literature