Dimethyl 2,6-dimethyl-4-{3-[2-(4-methylpiperazin-1-yl)-2-oxoethoxy]-phenyl}-1,4-dihydropyridine-3,5-dicarboxylate

ID: ALA2237190

PubChem CID: 76333490

Max Phase: Preclinical

Molecular Formula: C24H31N3O6

Molecular Weight: 457.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cccc(OCC(=O)N2CCN(C)CC2)c1

Standard InChI:  InChI=1S/C24H31N3O6/c1-15-20(23(29)31-4)22(21(16(2)25-15)24(30)32-5)17-7-6-8-18(13-17)33-14-19(28)27-11-9-26(3)10-12-27/h6-8,13,22,25H,9-12,14H2,1-5H3

Standard InChI Key:  OOWKVRPAFXWENV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
   14.9702   -9.3672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0791  -11.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2811   -7.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3555  -11.8650    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6629  -10.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8296   -9.4137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9299  -11.8418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7032   -8.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5605   -8.1905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7894  -11.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3824  -10.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1329   -8.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4226   -7.7407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5269  -10.1675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2430  -10.2624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9569  -10.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6494  -11.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3958   -9.3905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8162  -10.2386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2332  -10.5949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2948   -6.9629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1194   -8.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0926  -10.6414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6897   -8.9685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5223  -10.6648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8535   -7.7641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9860   -8.2093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9693   -9.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6702   -9.4518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3900   -9.0556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4045   -8.2335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6992   -7.8076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0932   -9.4797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 18  1  0
  2  4  1  0
 19 25  1  0
 12 26  1  0
 24  8  2  0
 11 23  1  0
  5 16  1  0
 17  7  1  0
 16 20  1  0
 17  4  1  0
 13 12  2  0
 26  9  1  0
 12 22  1  0
 20 14  1  0
  9  3  1  0
 18 24  1  0
  2 10  1  0
 25 15  1  0
  3 21  2  0
 16  1  2  0
 23  2  2  0
 18 22  2  0
  5 11  1  0
 17  5  2  0
 19  6  2  0
 23 19  1  0
  8 13  1  0
  3 27  1  0
 27 28  1  0
 27 32  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 30 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2237190

   Dimethyl 2,6-dimethyl-4-[3-[2-(4-methylpiperazin-1-yl)-2-oxoethoxy]phenyl]-1,4-dihydropyridine-3,5-dicarboxylate

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: 457.53

Molecular Weight (Monoisotopic): 457.2213

AlogP: 1.42

#Rotatable Bonds: 6

Polar Surface Area: 97.41

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.90

CX LogP: 0.68

CX LogD: 0.56

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.64

Np Likeness Score: -0.95

References

1. Bansal R, Jain P, Calle C, Carron R, Pemberton K, Harvey AL.  (2012)  Synthesis of a New Series of 4-Aryl-1,4-Dihydropyridines with Calcium Channel Blocking and Vasodilatory Activity,  21  (6): [10.1007/s00044-011-9600-x]

Source

Source(1):

• Scientific Literature