72908-87-3

Usage

Uses

Used in Pharmaceutical Industry:
Etazene is used as an analgesic agent for the management of severe pain, particularly in cases where other opioids may be less effective or where a longer duration of action is required. Its high potency and selectivity for the μ-opioid receptor make it a potentially valuable asset in the treatment of chronic and acute pain conditions.
Used in Medical Research:
In the field of medical research, etazene is utilized for studying the mechanisms of opioid action and the development of novel analgesics. Its unique structure and properties provide insights into the design of new drugs with improved efficacy and safety profiles.
Used in Drug Abuse Prevention and Control:
Due to its classification as a controlled substance, etazene is also used in efforts to prevent and control drug abuse. Regulatory bodies and law enforcement agencies monitor its distribution and use to minimize the risks associated with its potential for misuse and addiction.

InChI:InChI=1/C8H8N2O2/c11-6-2-4-10-8(12)7-5(6)1-3-9-7/h1,3,9H,2,4H2,(H,10,12)

Upstream product

• 125118-55-0 (Z)-debromohymenialdisine 
• 129053-83-4 3-[(1H-pyrrole-2-carbonyl)-amino]-propionic acid ethyl ester 
• 161200-30-2 methyl 3-<(1H-pyrrole-2-carbonyl)amino>propionate 
• 5427-82-7 1H-pyrrole-2-carbonyl chloride 
• 136975-50-3 benzyl 3-(2-pyrrolecarboxamido)propionate 
• 634-97-9 pyrrole-2-carboxyl acid 
• 35302-72-8 pyrrol-2-yl trichloromethyl ketone 
• 129053-84-5 3-<(1H-pyrrole-2-carbonyl)amino>propionic acid 

Downstream Products

• 1234505-93-1 C₂₄H₂₄N₂O₃ 
• 1234505-94-2 C₂₄H₂₄N₂O₃ 
• 1233710-90-1 C₂₅H₂₆N₂O₃ 
• 1413996-17-4 (E)-4-(benzyloxyimino)-4,5,6,7-tetrahydropyrrolo[2,3-c]azepin-8(1H)-one 
• 1233710-89-8 C₁₄H₁₂N₂O₂ 
• 1234505-92-0 C₂₃H₂₂N₂O₃ 
• 1323444-38-7 C₁₆H₁₄N₂O₃ 
• 1233710-92-3 C₁₅H₁₃BrN₂O₂ 
• 1323444-40-1 C₂₂H₁₇N₃O₂ 
• 150159-15-2 C₁₅H₁₄N₂O₂ 
• 1233710-91-2 C₂₁H₂₅BN₂O₄ 
• 1323444-44-5 C₂₇H₂₅N₅O₂ 
• 1234505-95-3 C₂₃H₂₂N₂O₃ 
• 1323444-43-4 C₂₁H₁₉N₃O₂ 

Relevant academic research and scientific papers

Synthesis of indolo/pyrroloazepinone-oxindoles as potential cytotoxic, DNA-intercalating and Topo I inhibitors

A series of 17 indolo/pyrroloazepinone-oxindole conjugates was synthesized and evaluated for their antiproliferative activity against a panel of selected human cancer cell lines including A549 (lung cancer), HCT116 (colon cancer), MCF7 (breast cancer), and SK-MEL-28 (melanoma). Among the synthesized molecules (14a-m and 15a-d), compound 14d displayed remarkable activity against A549, HCT116 and SK-MEL-28 cells with IC50 values 50 value of 2.33 μM) over the normal rat kidney cells (NRK). Further, 14d-mediated apoptosis affected the cellular and nuclear morphology of the cancer cells in a dose-dependent manner. Wound healing and clonogenic assays inferred the inhibition of cell growth and migration. Target-based studies of compound 14d corroborated its DNA-intercalative capability and Topo I inhibitory activity which have been fortified by molecular modeling studies. Finally, the drug-likeness of the potent compound was determined by performing in silico ADME/T prediction studies.

Synthesis and antibacterial evaluation of (E)-1-(1H-indol-3-yl) ethanone O-benzyl oxime derivatives against MRSA and VRSA strains

Infections caused due to multidrug resistant organisms have emerged as a constant menace to human health. Even though numerous antibiotics are currently available for treating infectious diseases, a great number of bacterial strains have acquired resistance to many of them. Among these, infections caused due to Staphylococcus aureus are predominant in adult and paediatric population. Indole is a prominent chemical scaffold found in many pharmacologically active natural products and synthetic drugs. A number of oxime ether containing compounds have attracted attention of researchers owing to their interesting biological properties. Current work details the synthesis of indole containing oxime ether derivatives and their evaluation for antimicrobial activity against a panel of bacterial and mycobacterial strains. Synthesized compounds demonstrated good to moderate activity against drug-resistant S. aureus including resistant to vancomycin. Among all, compound 5h was found to possess potent activity against susceptible as well as MRSA and VRSA strains of S. aureus with MIC of 1 μg/mL and 2–4 μg/mL respectively. In addition, compound 5h was found to be non-toxic to Vero cells and exhibited good selectivity index of >40. Further, 5h, E-9a and E-9b possessed good biofilm inhibition against S. aureus. With these assuring biological properties, synthesized compounds could be potential prospective antimicrobial agents.

Synthesis and evaluation of novel anti-proliferative pyrroloazepinone and indoloazepinone oximes derived from the marine natural product hymenialdisine

The tetrahydroazepinone pharmacophore is a component of many interesting compounds, including several marine natural products, with anti-cancer properties. The synthesis and biological evaluation of a novel series of pyrroloazepinone and indoloazepinone oximes is reported. These compounds showed promising growth inhibition activity against four human cancer cell lines but did not significantly inhibit the cell cycle regulator cyclin dependent kinase 2. The most active compounds in this series displayed improved anti-proliferative activity over the related synthetic indoloazepine kenpaullone. The structure activity relationships exhibited by the azepinone pharmacophore suggests several novel lead compounds for anti-cancer drug discovery.

Pyrrolo[2,3-c]azepine derivatives: A new class of potent protein tyrosine phosphatase 1B inhibitors

A series of pyrrolo[2,3-c]azepine derivatives was designed, synthesized, and evaluated as a new class of inhibitors against protein tyrosine phosphatase 1B (PTP1B) in vitro. The results demonstrated that compounds bearing a biphenyl moiety were proved to

Stereoselective synthesis of (Z)-axino- and (Z)-debromoaxinohydantoin

(Z)-Axinohydantoin and (Z)-debromoaxinohydantoin, two pyrrole-imidazole alkaloids isolated from different marine sponges, possess moderate activities in inhibiting the progress of the cell cycle at different phases. A stereoselective synthesis of both nat

WNT SIGNALING INHIBITORS, AND METHODS FOR MAKING AND USING THEM

The invention provides dBHD-based compositions and dBHD analog compositions, and pharmaceutical compositions comprising them, e.g., in the form of liposomes and nanoparticles comprising them, and methods of making and using them. In one embodiment, these dBHD analogs are used to inhibit a dysfunctional stem cell and/or a cancer (tumor) stem cell.

A new glycociamidine ring precursor: Syntheses of (Z)-hymenialdisine, (Z)-2-debromohymenialdisine, and (±)-endo-2-debromohymenialdisine

(Chemical Equation Presented) The synthesis of the C11H 5 marine sponge alkaloids, (Z)-hymenialdisine and (Z)-2-debromohymenialdisine, is described. A key step was the condensation between aldisine or its monobromo derivative and a n

An expeditious multigram preparation of the marine protein kinase inhibitor debromohymenialdisine

A short synthesis of the protein kinase inhibitor debromohymenialdisine is described, which allowed the preparation of several grams of the desired compound.

Synthesis and pharmacological evaluation of pyrroloazepine derivatives as potent antihypertensive agents with antiplatelet aggregation activity

A series of 1-aminoalkyl-pyrrolo[2,3-c]azepin-8-one derivatives was synthesized and evaluated as α1 adrenergic and serotonin 2 (5-HT2) receptor antagonists, with the aim of finding a novel antihypertensive agent potently exhibiting b

Synthesis of pyrroloazepines. Facile synthesis of 2-substituted pyrrole derivatives by the phosgene method

A highly convenient method for the synthesis of 2-substituted pyrrole derivatives 7a-c from pyrrole using phosgene was developed. Successively, 7-methyl-6,7-dihydro-1H,5H-pyrrolo[2,3-c]azepine-4,8-dione 1a and 6,7-dihydro-1H,5H-pyrrolo[2,3-c]azepine-4,8-dione 1b (aldisin) were synthesized by phosphorus pentoxide/methanesulfonate and polyphosphoric acid cyclization.