rac-tert-Butyl 4-(2-Chloro-4-fluorophenyl)-5-cyano-2,6-dimethyl-1,4-dihydropyridine-3-carboxylate

ID: ALA1094114

PubChem CID: 46237842

Max Phase: Preclinical

Molecular Formula: C19H20ClFN2O2

Molecular Weight: 362.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C(C#N)C(c2ccc(F)cc2Cl)C(C(=O)OC(C)(C)C)=C(C)N1

Standard InChI:  InChI=1S/C19H20ClFN2O2/c1-10-14(9-22)17(13-7-6-12(21)8-15(13)20)16(11(2)23-10)18(24)25-19(3,4)5/h6-8,17,23H,1-5H3

Standard InChI Key:  MPFVEJCVRPLSQN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    6.9527   -4.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9516   -5.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6664   -5.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3828   -5.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3800   -4.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6646   -3.9580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6667   -6.4311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9504   -6.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9482   -7.6635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6607   -8.0801    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3771   -7.6690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3810   -6.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2321   -8.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0901   -8.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0960   -6.4298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2370   -6.4278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2392   -5.6028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5214   -6.8384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8080   -6.4240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0925   -6.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8102   -5.5990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0875   -6.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6621   -3.1330    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.8083   -6.0125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0980   -5.6091    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  3  7  1  0
  6  1  1  0
  9 13  1  0
  7  8  1  0
 11 14  1  0
  1  2  2  0
 12 15  1  0
  3  4  2  0
  8 16  1  0
 16 17  2  0
  4  5  1  0
 16 18  1  0
  2  3  1  0
 18 19  1  0
  5  6  2  0
 19 20  1  0
  7 12  1  0
 19 21  1  0
  8  9  2  0
 19 22  1  0
  9 10  1  0
  6 23  1  0
 10 11  1  0
 15 24  3  0
 11 12  2  0
  4 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1094114

   Tert-butyl 4-(2-chloro-4-fluorophenyl)-5-cyano-2,6-dimethyl-1,4-dihydropyridine-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: 362.83

Molecular Weight (Monoisotopic): 362.1197

AlogP: 4.58

#Rotatable Bonds: 2

Polar Surface Area: 62.12

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.52

CX LogD: 3.52

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.78

Np Likeness Score: -1.45

References

1. Arhancet GB, Woodard SS, Dietz JD, Garland DJ, Wagner GM, Iyanar K, Collins JT, Blinn JR, Numann RE, Hu X, Huang HC..  (2010)  Stereochemical requirements for the mineralocorticoid receptor antagonist activity of dihydropyridines.,  53  (10): [PMID:20408553] [10.1021/jm1002827]

2. Arhancet GB, Woodard SS, Iyanar K, Case BL, Woerndle R, Dietz JD, Garland DJ, Collins JT, Payne MA, Blinn JR, Pomposiello SI, Hu X, Heron MI, Huang HC, Lee LF..  (2010)  Discovery of novel cyanodihydropyridines as potent mineralocorticoid receptor antagonists.,  53  (16): [PMID:20672820] [10.1021/jm100506y]

Source

Source(1):

• Scientific Literature