2886-65-9

Usage

Uses

Used in Pharmaceutical Industry:
7-Chloro-5-(2-fluoro-phenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one is used as a controlled drug precursor for the synthesis of various benzodiazepines. Its application in this industry is primarily due to its role as a metabolite in the pharmacological action of several benzodiazepines, which are widely used for their anxiolytic, sedative, and hypnotic properties.
Used in Research and Forensic Applications:
In the fields of research and forensic science, 7-Chloro-5-(2-fluoro-phenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one serves as an analytical reference material. Its ability to inhibit L-type voltage-gated calcium channels and modulate GABAA receptors makes it a valuable compound for studying the mechanisms of action and potential interactions of benzodiazepines. Additionally, it can be detected in biological samples such as urine, serum, and meconium using LC-MS/MS, making it useful in forensic investigations and drug testing.

Mode of action

N-Desalkylflurazepam is a benzodiazepine analog and an active metabolite of several other benzodiazepine drugs including flurazepam, flutoprazepam, fludiazepam, midazolam, flutazolam, quazepam, and ethyl loflazepate. It is long-acting, prone to accumulation, and binds unselectively to the various benzodiazepine receptor subtypes. It has been sold as a designer drug from 2016 onward.

InChI:InChI=1/C15H10ClFN2O/c16-9-5-6-13-11(7-9)15(18-8-14(20)19-13)10-3-1-2-4-12(10)17/h1-7H,8H2,(H,19,20)

Upstream product

• 76488-08-9 7-chloro-5-(2-fluorophenyl)-N-methoxy-alpha-nitro-3H-1,4-benzodiazepine-2-methanimine 
• 1172-18-5 flurazepam dihydrochloride 
• 17617-23-1 flurazepam 
• 100-97-0 hexamethylenetetramine 
• 2836-40-0 2-(2-chloroacetyl)amino-4-chloro-2'-fluorobenzophenone 
• 1584-62-9 2?(2?bromoacetamido)?5?chloro?2'?fluorobenzophenone 
• 784-38-3 2-amino-5-chloro-2'-fluorobenzophenone 
• 106-47-8 4-chloro-aniline 
• 393-52-2 2-Fluorobenzoyl chloride 
• 76488-35-2 7-chloro-5-(2-fluorophenyl)-N-hydroxy-alpha-nitro-3H-1,4-benzodiazepine-2-methanimine 
• 59467-63-9 7-chloro-5-(2-fluorophenyl)-2-nitromethylene-1,3-dihydro-2H-1,4-benzodiazepine 
• 4530-20-5 BOC-glycine 
• 1350621-36-1 C₂₀H₂₀ClFN₂O₄ 

Downstream Products

• 67974-53-2 2-(2-dimethylaminoethylthio)-5-(2-fluorophenyl)-7-chloro-3H-1,4-benzodiazepine 
• 112634-59-0 7-chloro-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-ylidenecyanoacetic acid t-butyl ester 
• 1645-32-5 7-chloro-1,3-dihydro-5-(2-fluorophenyl)-2H-1,4-benzodiazepine-2-thione 
• 72012-91-0 7-chloro-1-ethyl-(o-fluorophenyl)-3H-[1,4]benzodiazepin-2-one 
• 3900-31-0 fludiazepam 
• 713517-39-6 7-chloro-5-(2-fluoro-phenyl)-1-(4-methoxy-benzyl)-1,3-dihydro-benzo[e][1,4]diazepin-2-one 
• 39256-30-9 2-(methylthio)-5-(o-fluorophenyl)-7-chloro-3H-1,4-benzodiazepine 
• 59467-70-8 Midazolam 
• 59467-62-8 7-chloro-5-(2-fluorophenyl)-2-(N-nitrosomethylamino)-3H-1,4-benzodiazepine 
• 59467-61-7 [7-chloro-5-(2-fluoro-phenyl)-1,3-dihydro-benzo[e][1,4]diazepin-2-ylidene]-methyl-amine 
• 819793-75-4 8?chloro?6?(2?fluorophenyl)?3?(4?toluenesulfonyl)?4H?imidazo[1,5?a][1,4]benzodiazepine 
• 819793-80-1 8?chloro?6?(2?fluorophenyl)?1?methyl?3?(4?toluenesulfonyl)?4H?imidazo[1,5?a][1,4]benzodiazepine 
• 109774-05-2 <7-chloro-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepine-2-ylidene>-acetonitrile 
• 112634-60-3 <7-chloro-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-ylidene>acetamide 

Relevant academic research and scientific papers

Improved and scalable methods for the synthesis of midazolam drug and its analogues using isocyanide reagents

Abstract: In this research, two improved and scalable methods for the synthesis of midazolam and its analogues have been described. Midazolam has been synthesized using isocyanide reagents in satisfactory yield. In this methodology, imidazobenzodiazepine intermediates can be easily prepared via an improved process. One-pot condensation of benzodiazepines with mono-anion of tosylmethyl isocyanide or ethyl isocyanoacetate under mild condition led to formation of imidazobenzodiazepine. In the first method, tosylmethyl isocyanide (Tos-MIC) is used and the number of synthetic steps are decreased in comparison to previous report. In the second method, ethyl isocyanoacetate which is commonly used for the synthesis of some imidazobenzodiazepines, is consumed to generate midazolam. The latter, a relatively different method for the synthesis of midazolam analogues has been reported. Graphical abstract: [Figure not available: see fulltext.].

One-pot microwave-assisted synthesis and antimalarial activity of ferrocenyl benzodiazepines

An efficient synthesis of 1,4-benzodiazepin-2-ones is described by condensation between 2-aminobenzophenone and Boc-protected amino acids via microwave-assisted irradiation. This produces higher yields in shorter reaction times than with traditional methods. The antiplasmodial activity of the corresponding ferrocenyl benzodiazepines was evaluated in vitro against Plasmodium falciparum F32 (chloroquine-sensitive) and FCB1 and K1 (chloroquine-resistant) strains and gabonese clinical isolates.

Synthesis and in vitro anti-hepatitis B virus activities of 4-aryl-6-chloro-quinolin-2-one and 5-aryl-7-chloro-1,4-benzodiazepine derivatives

A series of 4-aryl-6-chloro-quinolin-2-ones and 5-aryl-7-chloro-1,4-benzodiazepine were synthesized and assayed for their in vitro anti-hepatitis B virus activities and cytotoxicities for the first time. Some of the tested compounds were active against HBsAg and HBeAg secretion in Hep G2.2.15 cells. Compound 5c showed IC50 of 0.074 and 0.449 mM on HBsAg and HBeAg secretions, respectively, which were 10 times higher than that of its analog 4c and led to better selective index (SI) values (SI = 23.2 and 3.4, respectively).

Synthesis of?some?new substituted triazolo [4,3-a][1,4] benzodiazepine derivatives as?potent anticonvulsants

Novel 8-chloro-6-(2-fluorophenyl)-1-(aryl)-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepines (5a-f) were prepared by treating 7-chloro-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepine-2-thione with various aromatic acid hydrazides. The newly prepared compounds were characterized by spectral analysis. Compounds were tested for anticonvulsant activity. Four of the tested compounds such as 5a, 5d, 5e and 5f exhibited excellent anticonvulsant activity in comparison with standard drug, diazepam.

Novel benzo[1,4]diazepin-2-one derivatives as endothelin receptor antagonists

Since its discovery in 1988 by Yanagisawa et al., endothelin (ET), a potent vasoconstrictor, has been widely implicated in the pathophysiology of cardiovascular, cerebrovascular, and renal diseases. Many research groups have embarked on the discovery and development of ET receptor antagonists for the treatment of such diseases. While several compounds, e.g., ambrisentan 2, are in late clinical trials for various indications, one compound (bosentan, Tracleer) is being marketed to treat pulmonary arterial hypertension. Inspired by the structure of ambrisentan 2, we designed a novel class of ET receptor antagonists based on a 1,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-2-one scaffold. Here, we report on the preparation as well as the in vitro and in vivo structure-activity relationships of these derivatives. Potent dual ET A/ETB receptor antagonists with affinities in the low nanomolar range have been identified. In addition, several compounds efficiently reduced arterial blood pressure after oral administration to Dahl salt sensitive rats. In this animal model, the efficacy of the benzo[e] [1,4]diazepin-2-one derivative rac-39au was superior to that of racemic ambrisentan, rac-2.

Synthesis and spectral properties of 2-[(o- and p-substituted)aminophenyl]-3H-5-[(o- and p-substituted)phenyl]-7-chloro-1,4-benzodiazepines

A series of twelve new 2-[(o- and p-substituted)aminophenyl]-3H-5-[(o- and p-substituted)phenyl]-7-chloro-1,4-benzodiazepines, which have possible pharmacological properties has been obtained. The synthesis was carried out following six steps. The structure of all products was corroborated by ir, 1H nmr, 13C nmr and ms. In addition for the compound 2-(o-chloroaminophenyl)-3H-5-(o-fluorophenyl)-7-chloro-1,4-benzodiazepine 7, its structure was confirmed by X-ray diffraction.

Quinazolines and 1,4-benzodiazepines. XCIII. (1). Synthesis of imidazo[1,5-a][1,4]benzodiazepines from nitrooximes

The displacement of the nitro group in nitrooximes by other nucleophiles was used to prepare various 2-(hydroxyimino)methyl- and 2-(methoxyimino)methyl-1,4-benzodiazepines. These compounds were converted to imidazo[1,5-α][1,4]benzodiazepines bearing a tertiary amine, methoxy or thiomethyl group in the 3-position.

Screening, detection and biotransformation of lormetazepam, a new hypnotic agent from the 1,4-benzodiazepine series

The paper describes a screening procedure for 7-chloro-5-(2-chlorophenyl)-3-hydroxy-1-methyl-2,3-dihydro-1H-1,4-benzodiaze pin-2-one (lormetazepam, Noctamid) and other important analytical data (TLC, GLC, UV-, IR- and mass spectra) of this new benzodiazepine derivative. Screening results after a single p.o. dose of 1 mg lormetazepam (Noctamid-1) are also reported.

On determination and pharmacokinetics of flurazepam metabolites in human blood

The blood levels and the elimination kinetics of flurazepam and its major metabolites in blood were investigated in 10 volunteers after application of 60 mg flurazepam (Dalmadorm). Hydroxyethylflurazepam and desalkylflurazepam are the metabolites suitable for proving a previous flurazepam ingestion. Splitting of glucuronides is helpful for the determination of hydroxyethylflurazepam as the maximum blood concentration of the unconjugated metabolite does not exceed 1/3 of the concentration after glucuronidase splitting. Because of the different half-lives of formation and of elimination a characteristic time dependent pattern of flurazepam and its metabolites is observed in blood during 24 h after a single dosing. From this, conclusions may be drawn about the period of time between ingestion and sampling of the blood specimen. The accumulation of desalkylflurazepam is indicative of the dose applied or of previous multiple dosing. Parallel to the rise of the blood concentration of the metabolites the excretion of the corresponding hydroxyethylflurazepam glucuronide is detectable in urine. Within 30 min the concentrations are suitable for thin-layer chromatographic quantitation. An impaired performance of the volunteers was observed essentially during the absorption and the early distribution phase.