Ethyl-8-ethynyl-6-(pyridin-2-yl)-4H-benzo[f]imidazo[1,5-a][1,4]diazepine-3-carboxylate

ID: ALA475022

Chembl Id: CHEMBL475022

Cas Number: 612527-56-7

PubChem CID: 10309028

Max Phase: Preclinical

Molecular Formula: C21H16N4O2

Molecular Weight: 356.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#Cc1ccc2c(c1)C(c1ccccn1)=NCc1c(C(=O)OCC)ncn1-2

Standard InChI:  InChI=1S/C21H16N4O2/c1-3-14-8-9-17-15(11-14)19(16-7-5-6-10-22-16)23-12-18-20(21(26)27-4-2)24-13-25(17)18/h1,5-11,13H,4,12H2,2H3

Standard InChI Key:  ZSEDMNMFODMQRD-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA475022

   Mur6UE5SL3

2. Alternative Forms:

   

   ALA475022

   ---

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: 356.39

Molecular Weight (Monoisotopic): 356.1273

AlogP: 2.78

#Rotatable Bonds: 3

Polar Surface Area: 69.37

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.05

CX LogP: 2.97

CX LogD: 2.97

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.53

Np Likeness Score: -0.88

References

1. Rivas FM, Stables JP, Murphree L, Edwankar RV, Edwankar CR, Huang S, Jain HD, Zhou H, Majumder S, Sankar S, Roth BL, Ramerstorfer J, Furtmüller R, Sieghart W, Cook JM..  (2009)  Antiseizure activity of novel gamma-aminobutyric acid (A) receptor subtype-selective benzodiazepine analogues in mice and rat models.,  52  (7): [PMID:19275170] [10.1021/jm801652d]

2. Namjoshi OA, Wang ZJ, Rallapalli SK, Johnson EM, Johnson YT, Ng H, Ramerstorfer J, Varagic Z, Sieghart W, Majumder S, Roth BL, Rowlett JK, Cook JM..  (2013)  Search for α3β₂/₃γ2 subtype selective ligands that are stable on human liver microsomes.,  21  (1): [PMID:23218469] [10.1016/j.bmc.2012.10.057]

3. Poe MM, Methuku KR, Li G, Verma AR, Teske KA, Stafford DC, Arnold LA, Cramer JW, Jones TM, Cerne R, Krambis MJ, Witkin JM, Jambrina E, Rehman S, Ernst M, Cook JM, Schkeryantz JM..  (2016)  Synthesis and Characterization of a Novel γ-Aminobutyric Acid Type A (GABAA) Receptor Ligand That Combines Outstanding Metabolic Stability, Pharmacokinetics, and Anxiolytic Efficacy.,  59  (23): [PMID:27933953] [10.1021/acs.jmedchem.6b01332]

4. Maramai S, Benchekroun M, Ward SE, Atack JR..  (2020)  Subtype Selective γ-Aminobutyric Acid Type A Receptor (GABA_AR) Modulators Acting at the Benzodiazepine Binding Site: An Update.,  63  (7): [PMID:31738537] [10.1021/acs.jmedchem.9b01312]

Source

Source(1):

• Scientific Literature