[76Br]-8-(4-bromo-2-chlorophenyl)-N,N-bis(2-methoxyethyl)-2,7-dimethylpyrazolo[1,5-a][1,3,5]triazin-4-amine

ID: ALA1762817

PubChem CID: 10917602

Max Phase: Preclinical

Molecular Formula: C19H23BrClN5O2

Molecular Weight: 468.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCN(CCOC)c1nc(C)nc2c(-c3ccc([76Br])cc3Cl)c(C)nn12

Standard InChI:  InChI=1S/C19H23BrClN5O2/c1-12-17(15-6-5-14(20)11-16(15)21)18-22-13(2)23-19(26(18)24-12)25(7-9-27-3)8-10-28-4/h5-6,11H,7-10H2,1-4H3/i20-4

Standard InChI Key:  GQBIMIUJNCVMCR-BMILMZPDSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   -3.9014    1.4542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9026    0.6268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1878    0.2140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1896    1.8670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6174    0.2149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1920    2.6920    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4788    3.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7631    2.6962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0499    3.1109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3342    2.7005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9077    3.1023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6210    2.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3367    3.0981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0501    2.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6843    0.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1965    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6848    1.7147    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4742    1.4578    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4739    0.6277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3715    1.0435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2521   -0.3291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6915   -1.0287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3053   -1.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4800   -1.7867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0423   -1.0823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4309   -0.3570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0048    0.3436    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0922   -2.5149    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  4  6  1  0
 13 14  1  0
 18 19  1  0
  3 19  1  0
  6  7  1  0
 16 17  2  0
  1  2  1  0
  7  8  1  0
 18  4  1  0
 15 16  1  0
 17 18  1  0
 19 15  2  0
  8  9  1  0
 16 20  1  0
  4  1  2  0
  9 10  1  0
 21 22  2  0
 22 23  1  0
  6 11  1  0
 23 24  2  0
  2  5  1  0
 24 25  1  0
 11 12  1  0
 25 26  2  0
 26 21  1  0
 15 21  1  0
  2  3  2  0
 26 27  1  0
 12 13  1  0
 24 28  1  0
M  ISO  1  28  76
M  END

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: 468.78

Molecular Weight (Monoisotopic): 467.0724

AlogP: 3.92

#Rotatable Bonds: 8

Polar Surface Area: 64.78

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.63

CX LogP: 4.46

CX LogD: 4.46

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.50

Np Likeness Score: -1.51

References

1. Zuev D, Mattson RJ, Huang H, Mattson GK, Zueva L, Nielsen JM, Kozlowski ES, Huang XS, Wu D, Gao Q, Lodge NJ, Bronson JJ, Macor JE..  (2011)  Potential CRF1R PET imaging agents: N-fluoroalkyl-8-(6-methoxy-2-methylpyridin-3-yl)-2,7-dimethyl-N-alkylpyrazolo[1,5-a][1,3,5]triazin-4-amines.,  21  (8): [PMID:21411322] [10.1016/j.bmcl.2011.02.050]

2. Deskus JA, Dischino DD, Mattson RJ, Ditta JL, Parker MF, Denhart DJ, Zuev D, Huang H, Hartz RA, Ahuja VT, Wong H, Mattson GK, Molski TF, Grace JE, Zueva L, Nielsen JM, Dulac H, Li YW, Guaraldi M, Azure M, Onthank D, Hayes M, Wexler E, McDonald J, Lodge NJ, Bronson JJ, Macor JE..  (2012)  [18F](R)-5-chloro-1-(1-cyclopropyl-2-methoxyethyl)-3-(4-(2-fluoroethoxy)-2,5-dimethyl phenylamino)pyrazin-2(1H)-one: introduction of N3-phenylpyrazinones as potential CRF-R1 PET imaging agents.,  22  (21): [PMID:23010264] [10.1016/j.bmcl.2012.08.112]

3. Denhart DJ, Zuev D, Ditta JL, Hartz RA, Ahuja VT, Mattson RJ, Huang H, Mattson GK, Zueva L, Nielsen JM, Kozlowski ES, Lodge NJ, Bronson JJ, Macor JE..  (2013)  Potential CRF1R PET imaging agents: 1-fluoroalkylsubstituted 5-halo-3-(arylamino)pyrazin-2(1H)-ones.,  23  (7): [PMID:23465610] [10.1016/j.bmcl.2013.02.009]

Source

Source(1):

• Scientific Literature