68724-84-5

Basic information

• Product Name: 3,4-Dihydro-2H,10H-azepino[3,4-β]indole-1,5-dione
• Synonyms: 3,4-Dihydro-2H,10H-azepino[3,4-β]indole-1,5-dione;3,4-Dihydro-azepino[3,4-β]indole-1,5(2H,10H)-dione;3,4-Dihydro-2H,10H-azepino[3,4-b]indole-1,5-dione;3,4-Dihydro-azepino[3,4-b]indole-1,5(2H,10H)-dione
• CAS NO: 68724-84-5
• Molecular Formula: C₁₂H₁₀N₂O₂
• Molecular Weight: 214.22
• Product Categories: All Inhibitors;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Protein Kinase Inhibitors and Activators
• Mol File: 68724-84-5.mol

Chemical Properties

• Boiling Point: 603.389°C at 760 mmHg
• Flash Point: 318.719°C
• Appearance: /
• Density: 1.378g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.683
• CAS DataBase Reference: 3,4-Dihydro-2H,10H-azepino[3,4-β]indole-1,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Dihydro-2H,10H-azepino[3,4-β]indole-1,5-dione(68724-84-5)
• EPA Substance Registry System: 3,4-Dihydro-2H,10H-azepino[3,4-β]indole-1,5-dione(68724-84-5)

Safety Data

• Hazardous Substances Data: 68724-84-5(Hazardous Substances Data)

Usage

Uses

Used in Cancer Treatment:
3,4-Dihydro-2H,10H-azepino[3,4-β]indole-1,5-dione is used as a myt1 kinase inhibitor for the treatment of cancer. Its ability to inhibit myt1 kinase activity can help control the cell cycle, thereby preventing the uncontrolled growth and proliferation of cancer cells. This makes it a promising candidate for the development of targeted cancer therapies.
Used in Proliferative Disease Treatment:
In addition to cancer treatment, 3,4-Dihydro-2H,10H-azepino[3,4-β]indole-1,5-dione is also used as a myt1 kinase inhibitor for the treatment of other proliferative diseases. These diseases are characterized by abnormal cell growth and proliferation, which can lead to various health complications. By inhibiting myt1 kinase, 3,4-Dihydro-2H,10H-azepino[3,4-β]indole-1,5-dione can help regulate cell growth and mitigate the effects of these diseases.
Used in Pharmaceutical Industry:
3,4-Dihydro-2H,10H-azepino[3,4-β]indole-1,5-dione is used as a key component in the development of pharmaceutical drugs targeting cancer and proliferative diseases. Its role as a myt1 kinase inhibitor makes it a valuable asset in the creation of novel therapeutic agents that can offer more effective treatment options for patients suffering from these conditions.

InChI:InChI=1/C12H10N2O2/c15-9-5-6-13-12(16)11-10(9)7-3-1-2-4-8(7)14-11/h1-4,14H,5-6H2,(H,13,16)

Upstream product

• 68724-79-8 3-[(1H-indole-2-carbonyl)amino]propionic acid 
• 1477-50-5 Indole-2-carboxylic acid 
• 68724-78-7 3-[(1H-indole-2-carbonyl)amino]propionic acid ethyl ester 
• 1221227-25-3 C₂₃H₂₅F₃N₂O₈S 
• 1146622-75-4 methyl 3-(1H-indole-2-carboxamido)propanoate 

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 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.

Novel diindoloazepinone derivatives as DNA minor groove binding agents with selective topoisomerase I inhibition: Design, synthesis, biological evaluation and docking studies

We present here-in the molecular design and chemical synthesis of a novel series of diindoloazepinone derivatives as DNA minor groove binding agents with selective topoisomerase I inhibition. The in vitro cytotoxicity of the synthesized compounds was evaluated against four human cancer cell lines including DU143, HEPG2, RKO and A549 in addition to non-cancerous immortalized human embryonic kidney cells (HEK-293). Compound 11 showed significant cytotoxicity against all the four human cancer cell lines with IC50 values ranging from 4.2 to 6.59 μM. 11 was also found to display 13-fold selective cytotoxicity towards A549 cancerous cells compared to the non-cancerous cell lines (HEK-293). The decatenation, DNA relaxation and intercalation assays revealed that the investigational compounds 10 and 11 act as highly selective inhibitors of Topo-I with DNA minor groove binding ability which was also supported by the results obtained from circular dichroism (CD), UV-visible spectroscopy and viscosity studies. Apoptosis induced by the lead 11 was observed using morphological observations, AO/EB and DAPI staining procedures. Further, dose-dependent increase in the depolarization of mitochondrial membrane was also observed through JC-1 staining. Annexin V-FITC/PI assay confirmed that 11 induced early apoptosis. Additionally, cell cycle analysis indicated that the cells were arrested at sub-G1 phase. Gratifyingly, in silico studies demonstrated promising interactions of 11 with the DNA and Topo I, thus supporting their potential DNA minor groove binding property with relatively selective Topo I inhibition compared to Topo II.

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

Synthesis of novel annulated hymenialdisine analogues via palladium-catalyzed cross-coupling reactions with aryl boronic acids

Palladium-catalyzed Suzuki cross-coupling reactions of an indole vinyl triflate provides an efficient pathway for the synthesis of a diverse class of novel hymenialdisine analogues. Georg Thieme Verlag Stuttgart - New York.

Preparation of novel unsymmetrical bisindoles under solvent-free conditions: Synthesis, crystal structures, and mechanistic aspects

(Chemical Equation Presented) Indole aziridines and their hydroxyl derivatives have been used for the preparation of a small library of novel functionalized bisindoles. Diversification of these building blocks by solvent-free C-C-bond formation on solid s

New synthetic protocols for the preparation of unsymmetrical bisindoles

(Diagram presented) Novel unsymmetrical bisindoles were synthesized by a solvent-free C-C bond-formation reaction under mild conditions. Starting from aziridines or hydroxyl precursors, indoles have been used as C-nucleophiles to form new pharmacologicall

Potent inhibition of checkpoint kinase activity by a hymenialdisine-derived indoloazepine

The marine sponge metabolite hymenialdisine is a potent inhibitor of a variety of kinases including MEK-1, GSK-3β, and CK1. In addition, hymenialdisine and debromohymenialdisine exhibit inhibition of the G2 cell cycle checkpoint at micromolar c

Inhibition of cytokine production by hymenialdisine derivatives

We describe herein the synthesis and biological activity of two indoloazepines that are structurally related to the marine sponge metabolite hymenialdisine. The natural product hymenialdisine was found to be a potent inhibitor of interleukin-2 (IC50