1-(4-bromophenyl)-6-[(2-hydroxyanilino)methyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one

ID: ALA4791250

PubChem CID: 162671993

Max Phase: Preclinical

Molecular Formula: C18H14BrN5O2

Molecular Weight: 412.25

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=c1[nH]c(CNc2ccccc2O)nc2c1cnn2-c1ccc(Br)cc1

Standard InChI:  InChI=1S/C18H14BrN5O2/c19-11-5-7-12(8-6-11)24-17-13(9-21-24)18(26)23-16(22-17)10-20-14-3-1-2-4-15(14)25/h1-9,20,25H,10H2,(H,22,23,26)

Standard InChI Key:  QIUYCRNMXXOIQG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   18.0573  -14.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3481  -14.6308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3481  -15.4572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0600  -15.8615    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7670  -15.4519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7670  -14.6302    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4844  -15.8649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1975  -15.4519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9107  -15.8649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6283  -15.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3419  -15.8643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3419  -16.6907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6308  -17.1026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9107  -16.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6283  -14.6261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5631  -15.7107    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0752  -15.0439    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5632  -14.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3483  -16.5088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5494  -16.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3371  -17.5201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9220  -18.0977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7164  -17.8868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9313  -17.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7072  -18.8958    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   18.0573  -13.3945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  4  3  1  0
  5  4  2  0
  6  5  1  0
  1  6  1  0
  7  5  1  0
  7  8  1  0
  8  9  1  0
 10  9  2  0
 11 10  1  0
 12 11  2  0
 13 12  1  0
 14 13  2  0
  9 14  1  0
 10 15  1  0
  3 16  1  0
 16 17  1  0
 17 18  2  0
  2 18  1  0
 19 16  1  0
 19 20  1  0
 21 20  2  0
 22 21  1  0
 23 22  2  0
 24 23  1  0
 24 19  2  0
 22 25  1  0
  1 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4791250

   ---

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: 412.25

Molecular Weight (Monoisotopic): 411.0331

AlogP: 3.19

#Rotatable Bonds: 4

Polar Surface Area: 95.83

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.93

CX Basic pKa: 3.72

CX LogP: 2.56

CX LogD: 2.55

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.45

Np Likeness Score: -1.85

References

1. Shaaban MA,Elshaier YAMM,Hammad AH,Farag NA,Hassan Haredy H,AbdEl-Ghany AA,Mohamed KO.  (2020)  Design and synthesis of pyrazolo[3,4-d]pyrimidinone derivatives: Discovery of selective phosphodiesterase-5 inhibitors.,  30  (16): [PMID:32631538] [10.1016/j.bmcl.2020.127337]

Source

Source(1):

• Scientific Literature