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

ID: ALA1957801

PubChem CID: 57391358

Max Phase: Preclinical

Molecular Formula: C20H19BrF2N4O

Molecular Weight: 449.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(c1nn2ccccc2c1Br)N1CCN(CCc2ccc(F)cc2F)CC1

Standard InChI:  InChI=1S/C20H19BrF2N4O/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:  CELPFHKOYOVBDS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   18.0850    2.3044    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0850    1.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7971    1.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5092    1.4793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5092    2.3044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7971    2.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3693    2.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3668    3.5399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6559    2.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2231    1.0657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9382    1.4772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6522    1.0637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6480    0.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3612   -0.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0772    0.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0758    1.0680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3621    1.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3593    2.3028    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.7917   -0.1739    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.8973    2.6352    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5681    1.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7617    1.3071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3502    2.0197    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5292    2.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1188    1.3057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5353    0.5925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3549    0.5971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1816    0.9294    0.0000 Br  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:

   

   ALA1957801

   (3-Bromopyrazolo[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: 449.30

Molecular Weight (Monoisotopic): 448.0710

AlogP: 3.38

#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: 6.09

CX LogP: 4.10

CX LogD: 4.08

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.61

Np Likeness Score: -2.05

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