5-Fluoro-4-(5-fluoro-1,1-dimethyl-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazol-7-yl)-N-(5-(piperazin-1-ylmethyl)pyridin-2-yl)pyrimidin-2-amine

ID: ALA4209329

PubChem CID: 122657629

Max Phase: Preclinical

Molecular Formula: C26H28F2N8

Molecular Weight: 490.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CCc2nc3c(F)cc(-c4nc(Nc5ccc(CN6CCNCC6)cn5)ncc4F)cc3n21

Standard InChI:  InChI=1S/C26H28F2N8/c1-26(2)6-5-22-33-24-18(27)11-17(12-20(24)36(22)26)23-19(28)14-31-25(34-23)32-21-4-3-16(13-30-21)15-35-9-7-29-8-10-35/h3-4,11-14,29H,5-10,15H2,1-2H3,(H,30,31,32,34)

Standard InChI Key:  DHPLYCJQWJHXFH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   14.5311  -11.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7061  -11.6878    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2936  -10.9733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7061  -10.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5311  -10.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9436  -10.9733    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9436  -12.4022    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7686  -12.4022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1811  -11.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.4186  -12.4022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0061  -13.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1811  -13.1167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2436  -12.4022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6561  -13.1167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4811  -13.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.9253  -11.9653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0116  -11.1448    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8186  -10.9733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2311  -11.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6790  -12.3009    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3733  -12.5784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7858  -13.2929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5928  -13.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0561  -11.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4686  -10.9733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0561  -10.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2311  -10.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4178  -13.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6790  -13.9418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8186   -9.5444    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.2936   -9.5444    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
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  1  6  2  0
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  8  9  1  0
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 12 13  1  0
  8 13  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 15 20  1  0
 14 15  1  0
 11 14  1  0
  7  8  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 21 25  1  0
 26 27  1  0
 27 28  1  0
 25 28  1  0
 21 26  1  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 23 32  2  0
 24 29  2  0
 28 33  1  0
 28 34  1  0
 32 35  1  0
  3 30  1  0
  4 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4209329

   ---

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: 490.56

Molecular Weight (Monoisotopic): 490.2405

AlogP: 4.00

#Rotatable Bonds: 5

Polar Surface Area: 83.79

Molecular Species: BASE

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.31

CX Basic pKa: 9.18

CX LogP: 3.58

CX LogD: 2.02

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.44

Np Likeness Score: -1.13

References

1. Wang Y, Liu WJ, Yin L, Li H, Chen ZH, Zhu DX, Song XQ, Cheng ZZ, Song P, Wang Z, Li ZG..  (2018)  Design and synthesis of 4-(2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazol-7-yl)-N-(5-(piperazin-1-ylmethyl)pyridine-2-yl)pyrimidin-2-amine as a highly potent and selective cyclin-dependent kinases 4 and 6 inhibitors and the discovery of structure-activity relationships.,  28  (5): [PMID:29429832] [10.1016/j.bmcl.2017.12.068]

Source

Source(1):

• Scientific Literature