(4-(2,4-difluorophenethyl)piperazin-1-yl)(pyrazolo[1,5-a]pyridin-7-yl)methanone

ID: ALA1957805

PubChem CID: 57400053

Max Phase: Preclinical

Molecular Formula: C20H20F2N4O

Molecular Weight: 370.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(c1cccc2ccnn12)N1CCN(CCc2ccc(F)cc2F)CC1

Standard InChI:  InChI=1S/C20H20F2N4O/c21-16-5-4-15(18(22)14-16)7-9-24-10-12-25(13-11-24)20(27)19-3-1-2-17-6-8-23-26(17)19/h1-6,8,14H,7,9-13H2

Standard InChI Key:  HGKUJSGVRNNXTO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   -3.3601   -9.0813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0344   -8.3185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1802   -9.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3643   -8.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6568   -7.7789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6682   -6.9580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3862   -6.5565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0943   -6.9819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0794   -7.8014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2380   -6.9558    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2380   -7.7809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5258   -8.1893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8137   -7.7809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8137   -6.9558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5258   -6.5390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9539   -6.5453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9563   -5.7201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0996   -8.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6156   -7.7829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3296   -8.1966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3255   -9.0197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0387   -9.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7549   -9.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7534   -8.1922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0397   -7.7824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0369   -6.9573    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.4695   -9.4344    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 10 15  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  3  1  1  0
 10 16  1  0
  7  8  1  0
 16 17  2  0
 13 18  1  0
  8  9  2  0
 18 19  1  0
  9  4  1  0
 19 20  1  0
 10 11  1  0
 20 21  2  0
  1  2  2  0
 21 22  1  0
  4  5  1  0
 22 23  2  0
  2  5  1  0
 23 24  1  0
  5  6  1  0
 24 25  2  0
 25 20  1  0
  4  3  2  0
 25 26  1  0
  6  7  2  0
 23 27  1  0
 16  6  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1957805

   [4-[2-(2,4-Difluorophenyl)ethyl]piperazin-1-yl]-pyrazolo[1,5-a]pyridin-7-ylmethanone

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: 370.40

Molecular Weight (Monoisotopic): 370.1605

AlogP: 2.61

#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: 6.24

CX LogP: 2.87

CX LogD: 2.84

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.71

Np Likeness Score: -2.03

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