4-(6,7-Dimethoxy-quinoxalin-2-ylamino)-cyclohexanecarboxylic acid methyl ester

ID: ALA2112462

Max Phase: Preclinical

Molecular Formula: C18H23N3O4

Molecular Weight: 345.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2ncc(N[C@H]3CC[C@H](C(=O)OC)CC3)nc2cc1OC

Standard InChI:  InChI=1S/C18H23N3O4/c1-23-15-8-13-14(9-16(15)24-2)21-17(10-19-13)20-12-6-4-11(5-7-12)18(22)25-3/h8-12H,4-7H2,1-3H3,(H,20,21)/t11-,12-

Standard InChI Key:  FTXKUBNATJTYSH-HAQNSBGRSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  1  0  0  0  0  0999 V2000
   -1.2296    3.0367    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9400    2.6171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2213    1.3791    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6503    3.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9400    1.7904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5068    2.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6503    1.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3607    2.6171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0533    1.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3607    1.7904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2036    3.0408    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429    1.8153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0575    0.5815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5068    1.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6243    1.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347    2.6379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9139    2.6379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7679    1.8153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0835    3.0367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0835    1.3791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6243    3.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9139    1.8071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4782    1.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0835    0.5566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7939    2.6171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3 14  2  0
  4  2  2  0
  5  2  1  0
  6  1  2  0
  7  5  2  0
  8  4  1  0
 12  9  1  1
 10  7  1  0
 11  6  1  0
 12 15  1  0
 13  9  2  0
 14  6  1  0
 15 22  1  0
 16 21  1  0
 17 11  1  6
 18  9  1  0
 19  8  1  0
 20 10  1  0
 21 17  1  0
 22 17  1  0
 23 18  1  0
 24 20  1  0
 25 19  1  0
  3  5  1  0
 10  8  2  0
 12 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2112462

   ---

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: 345.40

Molecular Weight (Monoisotopic): 345.1689

AlogP: 2.79

#Rotatable Bonds: 5

Polar Surface Area: 82.57

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.50

CX LogP: 2.22

CX LogD: 2.22

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.83

Np Likeness Score: -0.80

References

1. He W, Myers MR, Hanney B, Spada AP, Bilder G, Galzcinski H, Amin D, Needle S, Page K, Jayyosi Z, Perrone MH..  (2003)  Potent quinoxaline-based inhibitors of PDGF receptor tyrosine kinase activity. Part 2: the synthesis and biological activities of RPR127963 an orally bioavailable inhibitor.,  13  (18): [PMID:12941342] [10.1016/s0960-894x(03)00655-3]

Source

Source(1):

• Scientific Literature