Ethyl-8-acetyleno-6-(2'-fluorophenyl)-4H-benzo[f]imidazo[1,5-a][1,4]diazepine-3-carboxylate

ID: ALA514974

Chembl Id: CHEMBL514974

Cas Number: 612526-36-0

PubChem CID: 21065283

Max Phase: Preclinical

Molecular Formula: C22H16FN3O2

Molecular Weight: 373.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#Cc1ccc2c(c1)C(c1ccccc1F)=NCc1c(C(=O)OCC)ncn1-2

Standard InChI:  InChI=1S/C22H16FN3O2/c1-3-14-9-10-18-16(11-14)20(15-7-5-6-8-17(15)23)24-12-19-21(22(27)28-4-2)25-13-26(18)19/h1,5-11,13H,4,12H2,2H3

Standard InChI Key:  DANIDPUWXPDMNG-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA514974

   JY-XHe-053

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: 373.39

Molecular Weight (Monoisotopic): 373.1227

AlogP: 3.52

#Rotatable Bonds: 3

Polar Surface Area: 56.48

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.94

CX LogP: 3.94

CX LogD: 3.94

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.52

Np Likeness Score: -0.89

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]

Source

Source(1):

• Scientific Literature