(3-chloropyrazolo[1,5-a]pyridin-2-yl)(4-(2,4-difluorophenethyl)piperazin-1-yl)methanone

ID: ALA1957802

PubChem CID: 57394859

Max Phase: Preclinical

Molecular Formula: C20H19ClF2N4O

Molecular Weight: 404.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(c1nn2ccccc2c1Cl)N1CCN(CCc2ccc(F)cc2F)CC1

Standard InChI:  InChI=1S/C20H19ClF2N4O/c21-18-17-3-1-2-7-27(17)24-19(18)20(28)26-11-9-25(10-12-26)8-6-14-4-5-15(22)13-16(14)23/h1-5,7,13H,6,8-12H2

Standard InChI Key:  HSSOKZQOZIZVNW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   -1.9252   -2.3627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9252   -3.1878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2131   -3.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5010   -3.1878    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5010   -2.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2131   -1.9460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6410   -1.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6434   -1.1272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3542   -2.3669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2129   -3.6014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9281   -3.1899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6420   -3.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6379   -4.4265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3509   -4.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0671   -4.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0656   -3.5990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3519   -3.1893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3491   -2.3642    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.7816   -4.8411    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1129   -2.0318    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4420   -3.1859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2485   -3.3600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6601   -2.6475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4809   -2.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8914   -3.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4748   -4.0747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6553   -4.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8286   -3.7378    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
  1  7  1  0
 14 15  2  0
  1  2  1  0
 15 16  1  0
  7  8  2  0
 16 17  2  0
 17 12  1  0
  1  6  1  0
 17 18  1  0
  7  9  1  0
 15 19  1  0
  9 20  2  0
  2  3  1  0
  4 10  1  0
 20 23  1  0
 22 21  2  0
 21  9  1  0
  3  4  1  0
 10 11  1  0
 22 23  1  0
  4  5  1  0
 23 24  1  0
 11 12  1  0
 24 25  2  0
  5  6  1  0
 25 26  1  0
 12 13  2  0
 26 27  2  0
 27 22  1  0
 21 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1957802

   (3-Chloropyrazolo[1,5-a]pyridin-2-yl)-[4-[2-(2,4-difluorophenyl)ethyl]piperazin-1-yl]methanone

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: 404.85

Molecular Weight (Monoisotopic): 404.1215

AlogP: 3.27

#Rotatable Bonds: 4

Polar Surface Area: 40.85

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.07

CX LogP: 3.94

CX LogD: 3.92

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.67

Np Likeness Score: -2.18

References

1. Xiong Y, Ullman B, Choi JS, Cherrier M, Strah-Pleynet S, Decaire M, Feichtinger K, Frazer JM, Yoon WH, Whelan K, Sanabria EK, Grottick AJ, Al-Shamma H, Semple G..  (2012)  Identification of fused bicyclic heterocycles as potent and selective 5-HT(2A) receptor antagonists for the treatment of insomnia.,  22  (5): [PMID:22325948] [10.1016/j.bmcl.2012.01.080]

Source

Source(1):

• Scientific Literature