diethyl 2,6-dimethyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

ID: ALA1099206

Cas Number: 21881-54-9

PubChem CID: 210905

Max Phase: Preclinical

Molecular Formula: C19H22N2O6

Molecular Weight: 374.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1c1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C19H22N2O6/c1-5-26-18(22)15-11(3)20-12(4)16(19(23)27-6-2)17(15)13-7-9-14(10-8-13)21(24)25/h7-10,17,20H,5-6H2,1-4H3

Standard InChI Key:  HGYFEULCVACRRI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
    3.6496    0.9253    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3794    1.3515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9170    1.3427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9402   -0.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9391   -1.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6539   -1.5527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3703   -1.1394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3675   -0.3088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6521    0.1003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6537   -2.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9394   -2.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9388   -3.6115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6537   -4.0250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3707   -3.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3677   -2.7853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2240   -4.0234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0865   -4.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0804   -2.3698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7966   -2.7793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0769   -1.5448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5093   -2.3638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2256   -2.7732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2257   -2.3734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2272   -1.5484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5104   -2.7846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7967   -2.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0815   -2.7819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
  7  8  1  0
 14 15  2  0
 15 10  1  0
  4  5  2  0
 12 16  1  0
  8  9  2  0
 14 17  1  0
  9  4  1  0
 15 18  1  0
  1  3  2  0
 18 19  1  0
  6 10  1  0
 18 20  2  0
  5  6  1  0
 19 21  1  0
 10 11  1  0
 21 22  1  0
 11 23  1  0
 11 12  2  0
 23 24  2  0
  6  7  2  0
 23 25  1  0
 12 13  1  0
 25 26  1  0
  1  2  1  0
 26 27  1  0
  9  1  1  0
M  CHG  2   1   1   2  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1099206

   Diethyl 2,6-dimethyl-4-(4-nitrophenyl)-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: 374.39

Molecular Weight (Monoisotopic): 374.1478

AlogP: 2.96

#Rotatable Bonds: 6

Polar Surface Area: 107.77

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.53

CX LogD: 2.53

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.46

Np Likeness Score: -0.80

References

1. Chang CC, Cao S, Kang S, Kai L, Tian X, Pandey P, Dunne SF, Luan CH, Surmeier DJ, Silverman RB..  (2010)  Antagonism of 4-substituted 1,4-dihydropyridine-3,5-dicarboxylates toward voltage-dependent L-type Ca2+ channels Ca V 1.3 and Ca V 1.2.,  18  (9): [PMID:20382537] [10.1016/j.bmc.2010.03.038]

2. Visentin S, Ermondi G, Medana C, Pedemonte N, Galietta L, Caron G..  (2012)  Ligand-based design, in silico ADME-Tox filtering, synthesis and biological evaluation to discover new soluble 1,4-DHP-based CFTR activators.,  55  [PMID:22889557] [10.1016/j.ejmech.2012.07.017]

3. Tale RH, Rodge AH, Hatnapure GD, Keche AP, Patil KM, Pawar RP.  (2013)  The synthesis, anti-inflammatory, and anti-microbial activity evaluation of new series of 4-(3-arylureido)phenyl-1,4-dihydropyridine urea derivatives,  22  (3): [10.1007/s00044-012-0109-8]

4. Niaz H, Kashtoh H, Khan JA, Khan A, Wahab AT, Alam MT, Khan KM, Perveen S, Choudhary MI..  (2015)  Synthesis of diethyl 4-substituted-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylates as a new series of inhibitors against yeast α-glucosidase.,  95  [PMID:25817770] [10.1016/j.ejmech.2015.03.018]

Source

Source(1):

• Scientific Literature