trans-4-(2-(2,6-Dichlorophenyl)acetamido)-N-(4-methoxycyclohexyl)-1H-pyrazole-3-carboxamide

ID: ALA3335123

Max Phase: Preclinical

Molecular Formula: C19H22Cl2N4O3

Molecular Weight: 425.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@H]1CC[C@H](NC(=O)c2n[nH]cc2NC(=O)Cc2c(Cl)cccc2Cl)CC1

Standard InChI:  InChI=1S/C19H22Cl2N4O3/c1-28-12-7-5-11(6-8-12)23-19(27)18-16(10-22-25-18)24-17(26)9-13-14(20)3-2-4-15(13)21/h2-4,10-12H,5-9H2,1H3,(H,22,25)(H,23,27)(H,24,26)/t11-,12-

Standard InChI Key:  HDOIATBUQVHXDJ-HAQNSBGRSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    5.0599   -7.3056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7403   -7.7722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3955   -7.2708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1191   -6.4907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2951   -6.5161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8745   -5.8065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5339   -5.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3589   -5.7804    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1238   -5.0618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7737   -5.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6001   -5.0739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0148   -4.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6082   -3.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7823   -3.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3630   -4.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0258   -2.9351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8508   -2.9409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0495   -5.8154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6294   -5.1054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6447   -6.5342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8044   -5.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3873   -4.4033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5631   -4.4117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1574   -5.1311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5821   -5.8435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4049   -5.8315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8280   -6.5397    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7975   -3.6784    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  1  2  0
  5  6  1  0
  4  7  1  0
  7  8  1  0
  7  9  2  0
 10  8  1  1
 10 11  1  0
 10 15  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  6
 16 17  1  0
  6 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 26 27  1  0
 22 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3335123

   ---

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: 425.32

Molecular Weight (Monoisotopic): 424.1069

AlogP: 3.59

#Rotatable Bonds: 6

Polar Surface Area: 96.11

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.84

CX Basic pKa: 0.01

CX LogP: 3.72

CX LogD: 3.72

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.66

Np Likeness Score: -1.52

References

1. Urich R, Grimaldi R, Luksch T, Frearson JA, Brenk R, Wyatt PG..  (2014)  The design and synthesis of potent and selective inhibitors of Trypanosoma brucei glycogen synthase kinase 3 for the treatment of human african trypanosomiasis.,  57  (18): [PMID:25198388] [10.1021/jm500239b]

Source

Source(1):

• Scientific Literature