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

ID: ALA4866054

PubChem CID: 12027945

Max Phase: Preclinical

Molecular Formula: C23H20BrN3O3

Molecular Weight: 466.33

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccccc1N1CCN(c2cc(-c3ccc(Br)cc3)oc(=O)c2C#N)CC1

Standard InChI:  InChI=1S/C23H20BrN3O3/c1-29-21-5-3-2-4-19(21)26-10-12-27(13-11-26)20-14-22(30-23(28)18(20)15-25)16-6-8-17(24)9-7-16/h2-9,14H,10-13H2,1H3

Standard InChI Key:  FCGNIPCNZMQZBX-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   37.5475  -23.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5475  -22.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8354  -22.0265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1233  -23.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1187  -22.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8385  -21.2014    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.2632  -22.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9789  -21.6223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.2614  -23.6819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.5618  -20.7931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5668  -19.9717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8558  -19.5526    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.1378  -19.9612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1311  -20.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8620  -18.7275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5814  -18.3240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5879  -17.4997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8760  -17.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1560  -17.4925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1530  -18.3154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2917  -18.7437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.4106  -23.6838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6973  -23.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9850  -23.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9880  -24.5138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7093  -24.9231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4186  -24.5059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2757  -24.9303    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   39.0103  -18.3384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  5 23  1  0
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 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 26 29  1  0
 22 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4866054

   6-(4-Bromophenyl)-4-[4-(2-methoxyphenyl)piperazin-1-yl]-2-oxopyran-3-carbonitrile

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: 466.33

Molecular Weight (Monoisotopic): 465.0688

AlogP: 4.28

#Rotatable Bonds: 4

Polar Surface Area: 69.71

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.24

CX LogP: 3.98

CX LogD: 3.98

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.57

Np Likeness Score: -0.76

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