2-(((2-bromopyridin-4-yl)oxy)methyl)-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidine-5-carboxamide

ID: ALA4533083

PubChem CID: 155547618

Max Phase: Preclinical

Molecular Formula: C19H13BrFN5O2

Molecular Weight: 442.25

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  NC(=O)c1cc(-c2ccc(F)cc2)n2nc(COc3ccnc(Br)c3)cc2n1

Standard InChI:  InChI=1S/C19H13BrFN5O2/c20-17-8-14(5-6-23-17)28-10-13-7-18-24-15(19(22)27)9-16(26(18)25-13)11-1-3-12(21)4-2-11/h1-9H,10H2,(H2,22,27)

Standard InChI Key:  VEIVGBLYCNEWTO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   36.1788   -3.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8841   -3.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8841   -2.4928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1788   -2.0801    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.4735   -3.3100    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.4690   -2.4929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6905   -2.2446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2138   -2.9084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6978   -3.5668    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.5930   -2.0863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2995   -2.4970    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.5954   -1.2691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.3966   -2.9129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9919   -3.6229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.1784   -4.5309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4690   -4.9389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4687   -5.7553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1769   -6.1647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8870   -5.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8838   -4.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1780   -6.9819    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   32.1747   -3.6274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7650   -2.9235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9486   -2.9277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5431   -3.6382    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.9600   -4.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7751   -4.3383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5579   -5.0573    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  3 10  1  0
 10 11  1  0
 10 12  2  0
  8 13  1  0
 13 14  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
  1 15  1  0
 18 21  1  0
 14 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4533083

   ---

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: 442.25

Molecular Weight (Monoisotopic): 441.0237

AlogP: 3.37

#Rotatable Bonds: 5

Polar Surface Area: 95.40

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.86

CX Basic pKa: 2.81

CX LogP: 3.00

CX LogD: 3.00

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.48

Np Likeness Score: -1.57

References

1. Childress ES, Wieting JM, Felts AS, Breiner MM, Long MF, Luscombe VB, Rodriguez AL, Cho HP, Blobaum AL, Niswender CM, Emmitte KA, Conn PJ, Lindsley CW..  (2018)  Discovery of Novel Central Nervous System Penetrant Metabotropic Glutamate Receptor Subtype 2 (mGlu₂) Negative Allosteric Modulators (NAMs) Based on Functionalized Pyrazolo[1,5- a]pyrimidine-5-carboxamide and Thieno[3,2- b]pyridine-5-carboxamide Cores.,  62  (1): [PMID:30350962] [10.1021/acs.jmedchem.8b01266]

Source

Source(1):

• Scientific Literature