6-(4-chlorophenyl)-4-(4-(2-chlorophenyl)piperazin-1-yl)-2-oxo-2H-pyran-3-carbonitrile

ID: ALA4866825

PubChem CID: 164622290

Max Phase: Preclinical

Molecular Formula: C22H17Cl2N3O2

Molecular Weight: 426.30

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#Cc1c(N2CCN(c3ccccc3Cl)CC2)cc(-c2ccc(Cl)cc2)oc1=O

Standard InChI:  InChI=1S/C22H17Cl2N3O2/c23-16-7-5-15(6-8-16)21-13-20(17(14-25)22(28)29-21)27-11-9-26(10-12-27)19-4-2-1-3-18(19)24/h1-8,13H,9-12H2

Standard InChI Key:  HQRDEOMKAHWDMF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   21.9540  -24.6462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6661  -24.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6661  -23.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9540  -22.9962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2420  -24.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2374  -23.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9572  -22.1712    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3818  -23.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0974  -22.5921    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3799  -24.6514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6804  -21.7629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6855  -20.9414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9744  -20.5225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2565  -20.9309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2497  -21.7586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9806  -19.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6999  -19.2938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7065  -18.4696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9946  -18.0509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2747  -18.4624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2716  -19.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4102  -19.7136    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.5292  -24.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8160  -24.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1037  -24.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1067  -25.4834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8280  -25.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5373  -25.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3946  -25.8998    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0
  5  1  1  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  5  6  2  0
  4  7  1  0
  3  8  1  0
  8  9  3  0
  2 10  2  0
  7 11  1  0
  7 15  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 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
 17 22  1  0
  5 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4866825

   ---

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: 426.30

Molecular Weight (Monoisotopic): 425.0698

AlogP: 4.81

#Rotatable Bonds: 3

Polar Surface Area: 60.48

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.40

CX LogP: 4.58

CX LogD: 4.58

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.60

Np Likeness Score: -0.98

References

1. Mishra S, Parmar N, Chandrakar P, Sharma CP, Parveen S, Vats RP, Seth A, Goel A, Kar S..  (2021)  Design, synthesis, in vitro and in vivo biological evaluation of pyranone-piperazine analogs as potent antileishmanial agents.,  221  [PMID:33992928] [10.1016/j.ejmech.2021.113516]

Source

Source(1):

• Scientific Literature