72908-87-3

Basic information

• Product Name: 6,7-DIHYDRO-1H,5H-PYRROLO[2,3-C]AZEPINE-4,8-DIONE
• Synonyms: 6,7-DIHYDRO-1H,5H-PYRROLO[2,3-C]AZEPINE-4,8-DIONE;aldisine;3,10-diazabicyclo[5.3.0]deca-8,11-diene-2,6-dione;6,7-dihydropyrrolo[2,3-c]azepine-4,8(1H,5H)-dione;aldisin;Aldisin 6,7-Dihydropyrrolo[2,3-c]azepine-4,8(1H,5H)-dione;6,7-Dihydropyrrolo[2,3-c]azepine-4,8(1H,5H)
• CAS NO: 72908-87-3
• Molecular Formula: C₈H₈N₂O₂
• Molecular Weight: 164.16
• Product Categories: pharmacetical
• Mol File: 72908-87-3.mol
• Article Data: 13

Chemical Properties

• Melting Point: 286-288℃
• Boiling Point: 555.896°C at 760 mmHg
• Flash Point: 289.996°C
• Appearance: /
• Density: 1.353g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.592
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 6,7-DIHYDRO-1H,5H-PYRROLO[2,3-C]AZEPINE-4,8-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6,7-DIHYDRO-1H,5H-PYRROLO[2,3-C]AZEPINE-4,8-DIONE(72908-87-3)
• EPA Substance Registry System: 6,7-DIHYDRO-1H,5H-PYRROLO[2,3-C]AZEPINE-4,8-DIONE(72908-87-3)

Safety Data

• Hazardous Substances Data: 72908-87-3(Hazardous Substances Data)

Usage

General Description

6,7-Dihydro-1H,5H-pyrrolo[2,3-c]azepine-4,8-dione, also known as etazene, is a chemical compound with a unique bicyclic structure. It is a potent and long-acting opioid analgesic that has been studied and used in medical research. Etazene acts as a selective agonist for the μ-opioid receptor, producing powerful analgesic and sedative effects. Due to its high potency and potential for abuse, etazene is classified as a controlled substance in many countries, and its use is regulated by law. The compound has garnered attention as a novel opioid with potential medical applications, but also as a drug of abuse with associated risks and dangers.

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

• 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 
• 35302-72-8 pyrrol-2-yl trichloromethyl ketone 
• 125118-55-0 (Z)-debromohymenialdisine 
• 129053-84-5 3-<(1H-pyrrole-2-carbonyl)amino>propionic acid 
• 136975-50-3 benzyl 3-(2-pyrrolecarboxamido)propionate 
• 634-97-9 pyrrole-2-carboxyl acid 

Downstream Products

• 1413996-17-4 (E)-4-(benzyloxyimino)-4,5,6,7-tetrahydropyrrolo[2,3-c]azepin-8(1H)-one 
• 1233710-90-1 C₂₅H₂₆N₂O₃ 
• 1234505-94-2 C₂₄H₂₄N₂O₃ 
• 1234505-93-1 C₂₄H₂₄N₂O₃ 
• 125118-55-0 (Z)-debromohymenialdisine 
• 130749-84-7 1,7-di(4-methylphenylsulfonyl)-6,7-dihydropyrrolo<2,3-c>azepine-4,8(1H,5H)-dione 
• 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 

Relevant articles and documents

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 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.

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