2-(5-methyl-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridin-1-yl)-N-phenylacetamide

ID: ALA5286974

Max Phase: Preclinical

Molecular Formula: C16H15N3O2

Molecular Weight: 281.32

Names and Identifiers

Canonical SMILES:  Cn1ccc2c(ccn2CC(=O)Nc2ccccc2)c1=O

Standard InChI:  InChI=1S/C16H15N3O2/c1-18-9-8-14-13(16(18)21)7-10-19(14)11-15(20)17-12-5-3-2-4-6-12/h2-10H,11H2,1H3,(H,17,20)

Standard InChI Key:  GJWHQKJHWPWJSA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   -2.5539    1.4318    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8393    1.8441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1274    1.4323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1274    0.6070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8375    0.1953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5539    0.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3445    0.3612    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1475    1.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3233    1.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1309   -0.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6661   -0.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8797   -1.4464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6767   -1.6600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2604   -1.0767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0549   -1.2903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2685   -2.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6891   -2.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8912   -2.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2496   -0.0659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8393    2.6694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2685    1.8444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  4  7  1  0
  7  8  1  0
  9  8  2  0
  3  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 14 13  2  0
 15 14  1  0
 16 15  2  0
 17 16  1  0
 18 17  2  0
 13 18  1  0
 11 19  2  0
  2 20  2  0
  1 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5286974

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 281.32

Molecular Weight (Monoisotopic): 281.1164

AlogP: 1.98

#Rotatable Bonds: 3

Polar Surface Area: 56.03

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.34

CX Basic pKa: ┄

CX LogP: 1.68

CX LogD: 1.68

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.80

Np Likeness Score: -1.77

References

1. Mamai A, Chau AM, Wilson BJ, Watson ID, Joseph BB, Subramanian PR, Morshed MM, Morin JA, Prakesch MA, Lu T, Connolly P, Kuntz DA, Pomroy NC, Poda G, Nguyen K, Marcellus R, Strathdee G, Theriault B, Subramaniam R, Mohammed M, Abibi A, Chan M, Winston J, Kiyota T, Undzys E, Aman A, Austin N, Du Jardin M, Packman K, Phillippar U, Attar R, Edwards J, O'Meara J, Uehling DE, Al-Awar R, Privé GG, Isaac MB..  (2023)  Discovery of OICR12694: A Novel, Potent, Selective, and Orally Bioavailable BCL6 BTB Inhibitor.,  14  (2.0): [PMID:36793435] [10.1021/acsmedchemlett.2c00502]

2. Cardenas, Mariano G MG and 24 more authors.  2016-09-01  Rationally designed BCL6 inhibitors target activated B cell diffuse large B cell lymphoma.  [PMID:27482887]

3. Kamada, Yusuke Y and 11 more authors.  2017-05-25  Discovery of a B-Cell Lymphoma 6 Protein-Protein Interaction Inhibitor by a Biophysics-Driven Fragment-Based Approach.  [PMID:28471657]

4. McCoull, William W and 33 more authors.  2017-05-25  Discovery of Pyrazolo[1,5-a]pyrimidine B-Cell Lymphoma 6 (BCL6) Binders and Optimization to High Affinity Macrocyclic Inhibitors.  [PMID:28485934]

5. Yasui, Takeshi T and 18 more authors.  2017-09-01  Discovery of a novel B-cell lymphoma 6 (BCL6)-corepressor interaction inhibitor by utilizing structure-based drug design.  [PMID:28760529]

6. Guo, Weikai and 12 more authors.  2020-01-23  Synthesis and Biological Evaluation of B-Cell Lymphoma 6 Inhibitors of N-Phenyl-4-pyrimidinamine Derivatives Bearing Potent Activities against Tumor Growth.  [PMID:31895575]

7. Bellenie, Benjamin R and 29 more authors.  2020-04-23  Achieving In Vivo Target Depletion through the Discovery and Optimization of Benzimidazolone BCL6 Degraders.  [PMID:32275432]

8. Teng, Mingxing and 8 more authors.  2020-06-11  Rationally Designed Covalent BCL6 Inhibitor That Targets a Tyrosine Residue in the Homodimer Interface.  [PMID:32551010]

Source

Source(1):

• Scientific Literature