2-bromo-5-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)benzoate

ID: ALA4517951

Cas Number: 1569260-18-9

PubChem CID: 71720884

Max Phase: Preclinical

Molecular Formula: C14H11BrN4O2

Molecular Weight: 347.17

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)c1cc(Nc2ncnc3[nH]ccc23)ccc1Br

Standard InChI:  InChI=1S/C14H11BrN4O2/c1-21-14(20)10-6-8(2-3-11(10)15)19-13-9-4-5-16-12(9)17-7-18-13/h2-7H,1H3,(H2,16,17,18,19)

Standard InChI Key:  YHDDNFHODNKNQV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    7.1165  -16.8669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8334  -16.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8304  -15.6223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1147  -15.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4013  -16.4539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3979  -15.6290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6124  -15.3772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1303  -16.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6178  -16.7118    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1120  -14.3875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8256  -13.9724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5400  -14.3851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2531  -13.9707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2508  -13.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5296  -12.7341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8194  -13.1508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5236  -11.9070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2358  -11.4895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8060  -11.4991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2302  -10.6640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9638  -12.7283    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
  4 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 17 18  1  0
 17 19  2  0
 15 17  1  0
 18 20  1  0
 14 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4517951

   Methyl 2-Bromo-5-(7h-Pyrrolo[2,3-D]pyrimidin-4-Ylamino)benzoate

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: 347.17

Molecular Weight (Monoisotopic): 346.0065

AlogP: 3.25

#Rotatable Bonds: 3

Polar Surface Area: 79.90

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.53

CX Basic pKa: 5.48

CX LogP: 3.32

CX LogD: 3.32

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.71

Np Likeness Score: -1.17

References

1. Nozal V, Martinez A..  (2019)  Tau Tubulin Kinase 1 (TTBK1), a new player in the fight against neurodegenerative diseases.,  161  [PMID:30342424] [10.1016/j.ejmech.2018.10.030]

2. Nozal V, Martínez-González L, Gomez-Almeria M, Gonzalo-Consuegra C, Santana P, Chaikuad A, Pérez-Cuevas E, Knapp S, Lietha D, Ramírez D, Petralla S, Monti B, Gil C, Martín-Requero A, Palomo V, de Lago E, Martinez A, Martinez A..  (2022)  TDP-43 Modulation by Tau-Tubulin Kinase 1 Inhibitors: A New Avenue for Future Amyotrophic Lateral Sclerosis Therapy.,  65  (2.0): [PMID:34978799] [10.1021/acs.jmedchem.1c01942]

Source

Source(1):

• Scientific Literature