8'-Chloro-6'-((3-fluoropyridin-4-yl)amino)-2'H-spiro[cyclohexane-1,3'-imidazo[1,5-a]pyridine]-1',5'-dione

ID: ALA4535537

PubChem CID: 155548047

Max Phase: Preclinical

Molecular Formula: C17H16ClFN4O2

Molecular Weight: 362.79

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1NC2(CCCCC2)n2c1c(Cl)cc(Nc1ccncc1F)c2=O

Standard InChI:  InChI=1S/C17H16ClFN4O2/c18-10-8-13(21-12-4-7-20-9-11(12)19)16(25)23-14(10)15(24)22-17(23)5-2-1-3-6-17/h4,7-9H,1-3,5-6H2,(H,20,21)(H,22,24)

Standard InChI Key:  CWUHWURRJXDZRD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   43.2410  -19.3072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6590  -19.8850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.8673  -20.6735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.6575  -20.8906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.2394  -20.3128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.0312  -19.5179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0577  -18.2424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0577  -19.0595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7630  -19.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7630  -17.8296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4682  -18.2424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4682  -19.0560    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.7204  -18.6492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.2421  -17.9910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7630  -17.0124    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   43.4946  -17.2138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.7645  -20.2812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.3506  -19.4692    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.6423  -19.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6440  -18.2454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9366  -17.8379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2285  -18.2476    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.2323  -19.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9403  -19.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9451  -20.2900    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  7  8  2  0
  7 10  1  0
  8  9  1  0
  9 12  1  0
 11 10  2  0
 11 12  1  0
 12  1  1  0
  1 13  1  0
 13 14  1  0
 14 11  1  0
 10 15  1  0
 14 16  2  0
  9 17  2  0
  8 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4535537

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 362.79

Molecular Weight (Monoisotopic): 362.0946

AlogP: 3.14

#Rotatable Bonds: 2

Polar Surface Area: 76.02

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.05

CX Basic pKa: 5.55

CX LogP: 1.58

CX LogD: 1.57

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.86

Np Likeness Score: -0.79

References

1. Abdelaziz AM, Basnet SKC, Islam S, Li M, Tadesse S, Albrecht H, Gerber C, Yu M, Wang S..  (2019)  Synthesis and evaluation of 2'H-spiro[cyclohexane-1,3'-imidazo[1,5-a]pyridine]-1',5'-dione derivatives as Mnk inhibitors.,  29  (18): [PMID:31362920] [10.1016/j.bmcl.2019.07.043]

2. Xu W, Kannan S, Verma CS, Nacro K..  (2022)  Update on the Development of MNK Inhibitors as Therapeutic Agents.,  65  (2.0): [PMID:34533957] [10.1021/acs.jmedchem.1c00368]

Source

Source(1):

• Scientific Literature