4059-71-6

Usage

Uses

Used in Pharmaceutical Industry:
Clonitazene is used as a potent analgesic for the management of severe pain. Its high potency and efficacy make it a valuable option for pain relief, particularly in cases where other analgesics may be insufficient.
Used in Research and Development:
Clonitazene is utilized in scientific research to study the mechanisms of opioid action and develop new therapeutic agents with improved safety profiles. Its structural similarity to fentanyl allows researchers to investigate the molecular interactions and signaling pathways involved in opioid analgesia and addiction.
Used in Drug Enforcement and Regulatory Agencies:
As a Schedule I controlled substance, Clonitazene is monitored and regulated by drug enforcement and regulatory agencies to prevent its illicit use and distribution. These agencies work to ensure that Clonitazene is only available for legitimate medical purposes and to mitigate the risks associated with its abuse and addiction potential.

Upstream product

• 32315-10-9 bis(trichloromethyl) carbonate 
• 19050-62-5 N-(2-phenylethyl)-2-aminobenzamide 
• 201230-82-2 carbon monoxide 
• 615-43-0 2-iodophenylamine 
• 64-04-0 phenethylamine 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 2158-04-5 (2-phenylethyl)urea 
• 118-48-9 isatoic anhydride 
• 530-62-1 1,1'-carbonyldiimidazole 
• 6919-61-5 N-methoxy-N-methylbenzamide 
• 5344-90-1 2-Aminobenzyl alcohol 
• 541-41-3 chloroformic acid ethyl ester 
• 85-44-9 phthalic anhydride 

Downstream Products

• 2252395-44-9 4-((2,4-dioxo-3-phenethyl-3,4-dihydroquinazolin-1(2H)-yl)methyl)-N-hydroxybenzamide 
• 29745-29-7 3-(2-phenylethyl)-2-thioxo-1,2-dihydro-4(3H)-quinazolinone 

Relevant academic research and scientific papers

Synthesis and structural analysis of 3-phenylethyl-2,4(1H,3H)-quinazolinediones

This article presents the unexpected synthesis of 3-phenylethyl-2,4(1H,3H)-quinazolinediones by means of oxidative expansion of the 3-phenylethylimino-2-indolinone ring promoted by sodium borohydride. The 1H NMR spectroscopic patterns showed the presence of two conformational isomers in equilibrium, the first was a staggered conformation and the second was a gauche structure. The crystal structure of 3-phenylethyl-2,4(1H,3H)-quinazolinedione revealed a staggered conformation with the quinazoline fragment and the phenyl ring in anti-arrangement. The molecules of quinazolinedione are associated in centrosymmetric dimers through two N–H?O hydrogen bonds between the NH moieties and the adjacent carbonyl groups.

Design, synthesis, biological evaluation, and molecular docking study of thioxo-2,3-dihydroquinazolinone derivative as tyrosinase inhibitors

Tyrosinase is known to be a key enzyme in melanogenesis and hyperpigmentation. In this study, a series of thioxo-dihydroquinazolinone compounds were designed and synthesized as tyrosinase inhibitors. Among the investigated compounds, 4m demonstrated the best inhibitory activity with an IC50 value of 15.48 μM compared to kojic acid as a positive control with IC50 value of 9.30 μM. In kinetic evaluation against tyrosinase, 4m depicted a mixed inhibition pattern. Additionally, antioxidant evaluations exhibited moderate to weak potency in 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. The detailed interactions and binding mode toward tyrosinase of the most potent derivative were explicated by molecular docking study. Moreover, the computer-aided drug-likeness and pharmacokinetic studies were also carried out.

1,3,4-OXADIAZOLE HOMOPHTHALIMIDE DERIVATIVE COMPOUNDS AS HISTONE DEACETYLASE 6 INHIBITOR, AND THE PHARMACEUTICAL COMPOSITION COMPRISING THE SAME

The present invention relates to novel compounds having a histone deacetylase 6 (HDAC6) inhibitory activity, stereoisomers thereof or pharmaceutically acceptable salts thereof, a medicinal use thereof, and a method for preparing the same. The novel compounds according to the present invention, stereoisomers thereof or pharmaceutically acceptable salts thereof have the histone deacetylase 6 (HDAC6) inhibitory activity, and are effective in preventing or treating HDAC6-related diseases, comprising infectious diseases; neoplasm; endocrinopathy; nutritional and metabolic diseases; mental and behavioral disorders; neurological diseases; eye and ocular adnexal diseases; circulatory diseases; respiratory diseases; digestive diseases; skin and subcutaneous tissue diseases; musculoskeletal system and connective tissue diseases; and teratosis or deformities, or chromosomal aberration.

Iridium-Catalyzed C-H Amination of Weinreb Amides: A Facile Pathway toward Anilines and Quinazolin-2,4-diones

C-H amination of arenes directed by weakly coordinating Weinreb amides has been achieved with an iridium catalyst and 2,2,2-trichloroethoxycarbonyl (Troc) azide as an aminating agent, providing a robust method of producing synthetic useful ortho-TrocNH aryl Weinreb amides. Taking advantage of the reactivity of Weinreb amide and Troc groups in the amination products, selective hydrolysis was achieved as an attractive process for the synthesis of ortho-NH2 aryl Weinreb amides, which are the building blocks useful in the synthesis of bioactive compounds, and cascade aminocyclization with primary amines was successful and provided an efficient pathway for the construction of quinazolin-2,4-diones, which are present in various alkaloids and natural products.

High-selective HDAC6 inhibitor promotes HDAC6 degradation following autophagy modulation and enhanced antitumor immunity in glioblastoma

Glioblastoma is the most fatal type of primary brain cancer, and current treatments for glioblastoma are insufficient. HDAC6 is overexpressed in glioblastoma, and siRNA-mediated knockdown of HDAC6 inhibits glioma cell proliferation. Herein, we report a high-selective HDAC6 inhibitor, J22352, which has PROTAC (proteolysis-targeting chimeras)-like property resulted in both p62 accumulation and proteasomal degradation, leading to proteolysis of aberrantly overexpressed HDAC6 in glioblastoma. The consequences of decreased HDAC6 expression in response to J22352 decreased cell migration, increased autophagic cancer cell death and significant tumor growth inhibition. Notably, J22352 reduced the immunosuppressive activity of PD-L1, leading to the restoration of host anti-tumor activity. These results demonstrate that J22352 promotes HDAC6 degradation and induces anticancer effects by inhibiting autophagy and eliciting the antitumor immune response in glioblastoma. Therefore, this highly selective HDAC6 inhibitor can be considered a potential therapeutic for the treatment of glioblastoma and other cancers.

Quinazolin-2,4-dione-Based Hydroxamic Acids as Selective Histone Deacetylase-6 Inhibitors for Treatment of Non-Small Cell Lung Cancer

We designed and synthesized quinazolin-2,4-dione-based hydroxamic acids to serve as selective competitive inhibitors of histone deacetylase-6 (HDAC6). The most potent and selective compound, 3d (IC50, 4 nM, HDAC6; IC50 > 10 μM, HDAC1

One-pot Syntheses of Some New 2,4(1H,3H)-quinazolinedione Derivatives in the Absence of Catalyst

A facile, rapid and one-pot procedure for the synthesis of some new 2,4(1H,3H)-quinazolinediones is described. The method involves the one-pot condensation of isatoic anhydride, primary amine and carbonyl diimidazole (CDI) in the absence of organic or inorganic catalyst. It affords the corresponding product in high yield.

Traceless synthesis of quinazoline-2,4-diones by curtius rearrangement reaction using poly(ethylene glycol) as soluble polymeric support

(Chemical Equation Presented) We have developed an efficient method to synthesize various quinazoline-2,4-diones using polyethylene glycol) as soluble polymeric support. The procedure of this reaction included: formation of acyl azide, efficient Curtius rearrangement, nucleophlic addition with amines to produce ureas, cyclization and concurrent cleavage of the resulted six-membered heterocycle from PEG-support in excellent yields. This method is mild and manipulation is easy.

Tandem palladium-catalyzed urea arylation-intramolecular ester amidation: Regioselective synthesis of 3-alkylated 2,4-quinazolinediones

(Chemical Equation Presented) o-Halo benzoates can be combined with monoalkyl ureas in a tandem palladium-catalyzed arylation-ester amidation sequence to deliver quinazolinedione products. The reactions are regioselective for formation of the 3-N-alkyl isomers. Significant variation of both coupling partners is possible, allowing the synthesis of a diverse array of substituted quinazolinediones, exemplified by the preparation of a simple unsymmetric-dialkylated natural product.