Imidazenil

Base Information

• Chemical Name: Imidazenil
• CAS No.: 151271-08-8
• Molecular Formula: C18H12 Br F N4 O
• Molecular Weight: 399.222
• UNII: 7N95V6864R
• DSSTox Substance ID: DTXSID90164746
• Nikkaji Number: J554.226J
• Wikipedia: Imidazenil
• Wikidata: Q15409429
• Mol file: 151271-08-8.mol

Synonyms:6-(2-bromophenyl)-8-fluoro-4-H-imidazo(1,5-a)(1-4)benzodiazepine-3-carboxamide;imidazenil

Chemical Property of Imidazenil

Chemical Property:

• Vapor Pressure: 9.25E-14mmHg at 25°C
• Boiling Point: 587°Cat760mmHg
• PKA: 15.37±0.40(Predicted)
• Flash Point: 308.8°C
• PSA: 73.27000
• Density: 1.67g/cm³
• LogP: 3.35970
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 398.01785
• Heavy Atom Count: 25
• Complexity: 559

Purity/Quality:

98% ^*data from raw suppliers

IMIDAZENIL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2=C(N=CN2C3=C(C=C(C=C3)F)C(=N1)C4=CC=CC=C4Br)C(=O)N
• Description: Imidazenil is an imidazobenzodiazepine with the profile of a partial agonist. Animal studies have shown that it does not produce sedation or ataxia in rats nor does it potentiate the effects of alcohol (Guisti et al. 1993). Imidazenil has a low intrinsic activity at the GABAA receptor and therefore causes only slight enhancement of GABA-ergic tone. Its efficacy may, however, be increased when GABA tone is reduced, which could lead to its being active only in conditions where GABA tone is altered. This may well make it an ideal treatment for anxiety and epilepsy.
• Uses: Imidazenil, a new anxiolytic and anticonvulsant drug, attenuates a benzodiazepine-induced cognition deficit in monkeys.

Technology Process of Imidazenil

There total 5 articles about Imidazenil which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

6-(2-bromophenyl)-8-fluoro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid (153874-00-1) → Imidazenil (151271-08-8)

Guidance literature:

With ammonium hydroxide; phosphorus pentachloride; Yield given. Multistep reaction; 1.) CH₂Cl₂, RT, 2 h, 2.) CH₂Cl₂, 15 min;

DOI:10.1002/(SICI)1099-1344(199612)38:12<1121::AID-JLCR948>3.0.CO;2-V

Reference yield:

(2-amino-5-fluorophenyl)(2-bromophenyl)methanone (153873-94-0) → Imidazenil (151271-08-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / tetrahydrofuran / 24 h

2: 71 percent / NH₂NH₂*H₂O / methanol / 24 h

3: 1.) potassium tert-butoxide, diethyl chlorophosphate / 1.) THF, from -20 deg C to 10 deg C, 2.) THF, from -20 deg C to RT, 1.5 h

4: 90 percent / 6 N HCl / 24 h / 90 °C

5: 1.) PCl₅, 2.) NH₃ (gas), NH₄OH / 1.) CH₂Cl₂, RT, 2 h, 2.) CH₂Cl₂, 15 min

With hydrogenchloride; ammonium hydroxide; phosphorus pentachloride; potassium tert-butylate; diethyl chlorophosphate; hydrazine hydrate; In tetrahydrofuran; methanol;

DOI:10.1002/(SICI)1099-1344(199612)38:12<1121::AID-JLCR948>3.0.CO;2-V

Reference yield:

N-[2-(2-Bromo-benzoyl)-4-fluoro-phenyl]-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetamide (186351-08-6) → Imidazenil (151271-08-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 71 percent / NH₂NH₂*H₂O / methanol / 24 h

2: 1.) potassium tert-butoxide, diethyl chlorophosphate / 1.) THF, from -20 deg C to 10 deg C, 2.) THF, from -20 deg C to RT, 1.5 h

3: 90 percent / 6 N HCl / 24 h / 90 °C

4: 1.) PCl₅, 2.) NH₃ (gas), NH₄OH / 1.) CH₂Cl₂, RT, 2 h, 2.) CH₂Cl₂, 15 min

With hydrogenchloride; ammonium hydroxide; phosphorus pentachloride; potassium tert-butylate; diethyl chlorophosphate; hydrazine hydrate; In methanol;

DOI:10.1002/(SICI)1099-1344(199612)38:12<1121::AID-JLCR948>3.0.CO;2-V

upstream raw materials:

6-(2-bromophenyl)-8-fluoro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid

(2-amino-5-fluorophenyl)(2-bromophenyl)methanone

5-(2-bromophenyl)-7-fluoro-1,3-dihydro-1,4-benzodiazepine-2-one

6-(2-bromophenyl)-8-fluoro-4H-imidazo[1,5-a][1,4]benzo-diazepine-3-carboxylic acid ethyl ester

Refernces

• 1、 -. "Benzodiazepines and compositions for treating anxiety and panic disorders, and idiopathic and psychomotor epilepsy". . . Retrieved 2008/06/13.