2-(6-Cyclopropyl-pyridin-3-yl)-N-[1-(3,4-difluoro-benzyl)-1H-pyrazol-3-yl]-acetamide

ID: ALA4202684

PubChem CID: 118560466

Max Phase: Preclinical

Molecular Formula: C20H18F2N4O

Molecular Weight: 368.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Cc1ccc(C2CC2)nc1)Nc1ccn(Cc2ccc(F)c(F)c2)n1

Standard InChI:  InChI=1S/C20H18F2N4O/c21-16-5-1-14(9-17(16)22)12-26-8-7-19(25-26)24-20(27)10-13-2-6-18(23-11-13)15-3-4-15/h1-2,5-9,11,15H,3-4,10,12H2,(H,24,25,27)

Standard InChI Key:  UZGLRIDSOPLPQJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   23.6511  -13.1528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9464  -13.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2309  -13.1631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9724  -12.3781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1511  -12.3781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8967  -13.1631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5638  -13.6451    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1895  -13.5750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4768  -13.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7658  -13.5777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0573  -13.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3479  -13.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6358  -13.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6338  -12.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3498  -11.9429    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0590  -12.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4753  -12.3423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3609  -13.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0651  -13.1397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0558  -12.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3365  -11.9186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6353  -12.3383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7581  -11.9017    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   25.7774  -13.5402    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.9249  -11.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5168  -11.2409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1077  -11.9483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  3  1  0
  5  4  2  0
  6  5  1  0
  7  6  2  0
  3  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  9 17  2  0
  1 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  1  1  0
 20 23  1  0
 19 24  1  0
 26 25  1  0
 27 26  1  0
 25 27  1  0
 14 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4202684

   2-(6-cyclopropylpyridin-3-yl)-N-[1-[(3,4-difluorophenyl)methyl]pyrazol-3-yl]acetamide

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: 368.39

Molecular Weight (Monoisotopic): 368.1449

AlogP: 3.66

#Rotatable Bonds: 6

Polar Surface Area: 59.81

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.30

CX Basic pKa: 5.13

CX LogP: 3.77

CX LogD: 3.77

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.72

Np Likeness Score: -2.28

References

1. Bezençon O, Heidmann B, Siegrist R, Stamm S, Richard S, Pozzi D, Corminboeuf O, Roch C, Kessler M, Ertel EA, Reymond I, Pfeifer T, de Kanter R, Toeroek-Schafroth M, Moccia LG, Mawet J, Moon R, Rey M, Capeleto B, Fournier E..  (2017)  Discovery of a Potent, Selective T-type Calcium Channel Blocker as a Drug Candidate for the Treatment of Generalized Epilepsies.,  60  (23): [PMID:29116786] [10.1021/acs.jmedchem.7b01236]

Source

Source(1):

• Scientific Literature