2-((4-Chloro-2,6-difluorobenzyl)amino)-7-oxo-5-propyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

ID: ALA3617078

Cas Number: 1800024-45-6

PubChem CID: 78319104

Max Phase: Preclinical

Molecular Formula: C17H14ClF2N5O

Molecular Weight: 377.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCc1cc(=O)n2nc(NCc3c(F)cc(Cl)cc3F)c(C#N)c2[nH]1

Standard InChI:  InChI=1S/C17H14ClF2N5O/c1-2-3-10-6-15(26)25-17(23-10)11(7-21)16(24-25)22-8-12-13(19)4-9(18)5-14(12)20/h4-6,23H,2-3,8H2,1H3,(H,22,24)

Standard InChI Key:  SFUVDTPAOHEGCQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   -1.0028    1.5132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9991   -2.7132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6217    1.4865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1783    2.6281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5503    3.7690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9153    0.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9598    1.3162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0872    0.0320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8506   -1.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3513   -1.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1161   -2.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6160   -2.5196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3512   -1.2122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5865    0.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0866    0.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5511   -1.1985    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.5280   -3.5826    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.4749    1.0936    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0
  5  1  1  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  2  0
  4 10  2  0
  2 11  1  0
  9 12  1  0
 12 13  3  0
 11 14  1  0
 14 15  1  0
  8 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 21 24  1  0
 19 25  1  0
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3617078

   Bcat-IN-2

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: 377.78

Molecular Weight (Monoisotopic): 377.0855

AlogP: 3.39

#Rotatable Bonds: 5

Polar Surface Area: 85.98

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.99

CX Basic pKa: ┄

CX LogP: 3.81

CX LogD: 3.81

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.71

Np Likeness Score: -1.67

References

1. Bertrand SM, Ancellin N, Beaufils B, Bingham RP, Borthwick JA, Boullay AB, Boursier E, Carter PS, Chung CW, Churcher I, Dodic N, Fouchet MH, Fournier C, Francis PL, Gummer LA, Herry K, Hobbs A, Hobbs CI, Homes P, Jamieson C, Nicodeme E, Pickett SD, Reid IH, Simpson GL, Sloan LA, Smith SE, Somers DO, Spitzfaden C, Suckling CJ, Valko K, Washio Y, Young RJ..  (2015)  The Discovery of in Vivo Active Mitochondrial Branched-Chain Aminotransferase (BCATm) Inhibitors by Hybridizing Fragment and HTS Hits.,  58  (18): [PMID:26090771] [10.1021/acs.jmedchem.5b00313]

2. Günther J, Hillig RC, Zimmermann K, Kaulfuss S, Lemos C, Nguyen D, Rehwinkel H, Habgood M, Lechner C, Neuhaus R, Ganzer U, Drewes M, Chai J, Bouché L..  (2022)  BAY-069, a Novel (Trifluoromethyl)pyrimidinedione-Based BCAT1/2 Inhibitor and Chemical Probe.,  65  (21.0): [PMID:36261130] [10.1021/acs.jmedchem.2c00441]

3. Bertrand, Sophie M SM and 31 more authors.  2015-09-24  The Discovery of in Vivo Active Mitochondrial Branched-Chain Aminotransferase (BCATm) Inhibitors by Hybridizing Fragment and HTS Hits.  [PMID:26090771]

Source

Source(1):

• Scientific Literature