ethyl 8-ethynyl-6-phenyl-4H-benzo[f]imidazo[1,5-a][1,4]diazepine-3-carboxylate

ID: ALA522055

Chembl Id: CHEMBL522055

PubChem CID: 21930923

Max Phase: Preclinical

Molecular Formula: C22H17N3O2

Molecular Weight: 355.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#Cc1ccc2c(c1)C(c1ccccc1)=NCc1c(C(=O)OCC)ncn1-2

Standard InChI:  InChI=1S/C22H17N3O2/c1-3-15-10-11-18-17(12-15)20(16-8-6-5-7-9-16)23-13-19-21(22(26)27-4-2)24-14-25(18)19/h1,5-12,14H,4,13H2,2H3

Standard InChI Key:  HZYHQJXUEKIREU-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA522055

   Ethyl 12-ethynyl-9-phenyl-2,4,8-triazatricyclo[8.4.0.0^{2,6}]tetradeca-1(10),3,5,8,11,13-hexaene-5-carboxylate

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: 355.40

Molecular Weight (Monoisotopic): 355.1321

AlogP: 3.38

#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: 4.86

CX LogP: 3.80

CX LogD: 3.80

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.53

Np Likeness Score: -0.72

References

1. Han D, Holger Försterling F, Li X, Deschamps JR, Parrish D, Cao H, Rallapalli S, Clayton T, Teng Y, Majumder S, Sankar S, Roth BL, Sieghart W, Furtmuller R, Rowlett JK, Weed MR, Cook JM..  (2008)  A study of the structure-activity relationship of GABA(A)-benzodiazepine receptor bivalent ligands by conformational analysis with low temperature NMR and X-ray analysis.,  16  (19): [PMID:18790643] [10.1016/j.bmc.2008.08.072]

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