diethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydro-3,5-pyridinedicarboxylate

ID: ALA1099207

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)C1c1cccc([N+](=O)[O-])c1

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

Standard InChI Key:  ITAOFSSOVNYZCS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
   15.3679    0.6230    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1093    0.2174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3480    1.4659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2277    0.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2266   -0.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9414   -1.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6578   -0.6227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6550    0.2078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9396    0.6170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9412   -1.8610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2269   -2.2706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2263   -3.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9412   -3.5083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6582   -3.0915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6552   -2.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5115   -3.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3740   -3.5017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3679   -1.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0841   -2.2626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3644   -1.0282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7968   -1.8471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5131   -2.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5132   -1.8567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5147   -1.0317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7979   -2.2679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0842   -1.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3690   -2.2653    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
  8  1  1  0
M  CHG  2   1   1   2  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1099207

   ---

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: -0.92

References

1. Joslyn AF, Luchowski E, Triggle DJ..  (1988)  Dimeric 1,4-dihydropyridines as calcium channel antagonists.,  31  (8): [PMID:2840498] [10.1021/jm00403a002]

2. van Rhee AM, Jiang JL, Melman N, Olah ME, Stiles GL, Jacobson KA..  (1996)  Interaction of 1,4-dihydropyridine and pyridine derivatives with adenosine receptors: selectivity for A3 receptors.,  39  (15): [PMID:8709132] [10.1021/jm9600205]

3. 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]

4. 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]

5. Murthy YL, Rajack A, Taraka Ramji M, Jeson babu J, Praveen Ch, Aruna Lakshmi K..  (2012)  Design, solvent free synthesis, and antimicrobial evaluation of 1,4 dihydropyridines.,  22  (18): [PMID:22901391] [10.1016/j.bmcl.2012.05.003]

6. PubChem BioAssay data set, 

7. Amgoth SN, Porika M, Abbagani S, Garlapati A, Vanga MR.  (2013)  Synthesis, anticancer and MRP1 inhibitory activities of 4-alkyl/aryl-3,5-bis(carboethoxy/carbomethoxy)-1,4-dihydro-2,6-dimethylpyridines,  22  (1): [10.1007/s00044-012-9994-0]

8. 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(2):

• Scientific Literature
• PubChem BioAssays