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Usage

Uses

Used in Pharmaceutical Industry:
7-Oxabicyclo(2.2.1)hept-5-ene-2,3-dicarboximide is used as a precursor in the synthesis of various pharmaceutical compounds. Its ability to form stable intermediates and participate in key organic reactions makes it a valuable component in the development of new drugs.
Used in Agrochemical Industry:
In the agrochemical industry, 7-Oxabicyclo(2.2.1)hept-5-ene-2,3-dicarboximide serves as a starting material for the production of various agrochemicals. Its versatility in organic synthesis allows for the creation of compounds with specific properties, such as herbicidal or insecticidal activity.
Used in Dye Industry:
7-Oxabicyclo(2.2.1)hept-5-ene-2,3-dicarboximide is used as a building block in the synthesis of dyes. Its chemical properties enable the formation of a wide range of colored compounds, which are utilized in various applications, such as textiles, plastics, and printing inks.
Used in Organic Synthesis:
As a reagent in organic synthesis, 7-Oxabicyclo(2.2.1)hept-5-ene-2,3-dicarboximide is employed in various reactions, such as the Gabriel synthesis and the phthalimide deprotection reaction. Its ability to form stable intermediates and participate in key organic transformations makes it a valuable tool in the synthesis of complex organic molecules.
Used in Heterocyclic Compound Synthesis:
7-Oxabicyclo(2.2.1)hept-5-ene-2,3-dicarboximide is recognized for its potential as a reactive intermediate in the synthesis of various heterocyclic compounds. Its unique structure allows for the formation of diverse heterocyclic systems, which are important in various fields, such as pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C8H7NO3/c10-7-5-3-1-2-4(12-3)6(5)8(11)9-7/h1-6H,(H,9,10,11)

Upstream product

• 110-00-9 furan 
• 541-59-3 maleiimide 
• 60-29-7 diethyl ether 
• 19878-26-3 (3aR,4R,7S,7aS)-3a,4,7,7a-tetrahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione 
• 141-78-6 ethyl acetate 
• 71-43-2 benzene 
• 6118-51-0 exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride 
• 7732-18-5 water 
• 28871-62-7 7-Oxa-bicyclo-<2.2.1>-hept-5-en-2,3-exo,exo-dicarbonsaeure 

Downstream Products

• 28871-91-2 norcantharidimide 
• 272449-67-9 (+/-)-(3aR,4S,7R,7aS)-2-benzyl-3a,4,7,7a-tetrahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione 
• 58617-31-5 (+/-)-(3aR,4S,7R,7aS)-2-methyl-3a,4,7,7a-tetrahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione 
• 1353387-22-0 C₁₆H₂₁NO₃ 

Relevant academic research and scientific papers

An array-based nanosensor for detecting cellular responses in macrophages induced by femtomolar levels of pesticides

Environmental agents can induce cellular responses at concentrations far below the limits of detection for current viability and biomarker-based cell sensing platforms. Hypothesis-free cell sensor platforms can be engineered to maximize sensitivity to phenotypic changes, providing a tool for lowering the threshold for detecting cellular changes. Pesticides are one of the most prevalent sources of chemical exposure due to their use in food and agriculture fields. We report here a FRET-based nanosensor array engineered to maximize responses to changes at cell surfaces after pesticide exposure. This sensor array robustly detected macrophage responses to femtomolar concentrations of common pesticides-orders of magnitude lower concentrations than traditional toxicological and biomarker-based strategies. Significantly, this platform was able to classify these responses by pesticide class, demonstrating the ability to distinguish between changes induced by these different agents. Taken together, hypothesis-free cell surface sensing is a promising tool for detecting the effects of ultra-trace environmental chemicals on human health, as well as detecting threshold responses for use in drug discovery and diagnostics.

Synthesis and bioactivity evaluation of 5,6-epoxynorcantharidin mono-amide and imide derivatives

A series of 5,6-epoxynorcantharidin mono-amide and imide derivatives were designed and synthesized. MTT cell inhibition experiment shows that 5,6-epoxy compounds have good biological activity compared with the corresponding 5,6-olefin compounds and their hydrogenated products. Graphical abstract: [Figure not available: see fulltext.]

Erratum: Direct cytosolic delivery of proteins through coengineering of proteins and polymeric delivery vehicles (Journal of the American Chemical Society (2020) 142:9 (4349-4355) DOI: 10.1021/jacs.9b12759)

In this revised Supporting Information file, Figure S15 was misplaced in the text. The corrected figure is shown in the corrected Supporting Information file. This change does not affect any conclusions of the article, but this correction of the record is important.

Spherical Nucleic Acids for Topical Treatment of Hyperpigmentation

Oligonucleotide-based materials such as spherical nucleic acid (SNA) have been reported to exhibit improved penetration through the epidermis and the dermis of the skin upon topical application. Herein, we report a self-assembled, skin-depigmenting SNA structure, which is based upon a bifunctional oligonucleotide amphiphile containing an antisense oligonucleotide and a tyrosinase inhibitor prodrug. The two components work synergistically to increase oligonucleotide cellular uptake, enhance drug solubility, and promote skin penetration. The particles were shown to reduce melanin content in B16F10 melanoma cells and exhibited a potent antimelanogenic effect in an ultraviolet B-induced hyperpigmentation mouse model.

Aiming at the tumor-specific accumulation of MGMT-inhibitors: First description of a synthetic strategy towards inhibitor-peptide conjugates

In the therapy of cancer, alkylating agents are an efficient and often-used substance class. However, cells can repair the resulting alkyl modifications in the O6-position of guanine using the repair protein methylguanine methyltransferase (MGM

Cysteine-Targeted Insecticides against A. gambiae Acetylcholinesterase Are Neither Selective nor Reversible Inhibitors

Acetylcholinesterase cysteine-targeted insecticides against malaria vector Anopheles gambia and other mosquitos have already been introduced. We have applied the olefin metathesis for the preparation of cysteine-targeted insecticides in high yields. The prepared compounds with either a succinimide or maleimide moiety were evaluated on Anopheles gambiae and human acetylcholinesterase with relatively high irreversible inhibition of both enzymes but poor selectivity. The concept of cysteine binding was not proved by several methods, and poor stability was observed of the chosen most potent/selective compounds in a water/buffer environment. Thus, our findings do not support the proposed concept of cysteine-targeted selective insecticides for the prepared series of succinimide or maleimide compounds.

Direct Cytosolic Delivery of Proteins through Coengineering of Proteins and Polymeric Delivery Vehicles

Nanocarrier-mediated protein delivery is a promising strategy for fundamental research and therapeutic applications. However, the efficacy of the current platforms for delivery into cells is limited by endosomal entrapment of delivered protein cargo with concomitantly inefficient access to the cytosol and other organelles, including the nucleus. We report here a robust, versatile polymeric-protein nanocomposite (PPNC) platform capable of efficient (≥90%) delivery of proteins to the cytosol. We synthesized a library of guanidinium-functionalized poly(oxanorborneneimide) (PONI) homopolymers with varying molecular weights to stabilize and deliver engineered proteins featuring terminal oligoglutamate "E-tags". The polymers were screened for cytosolic delivery efficiency using imaging flow cytometry with cytosolic delivery validated using confocal microscopy and activity of the delivered proteins demonstrated through functional assays. These studies indicate that the PPNC platform provides highly effective and tunable cytosolic delivery over a wide range of formulations, making them robust agents for therapeutic protein delivery.

Inverse electron-demand Diels-Alder (iEDDA) bioorthogonal conjugation of half-sandwich transition metallocarbonyl entities to a model protein

Novel transition metallocarbonyl complexes carrying a norbornene or an oxanorbornene group were synthesized by [4 + 2] cycloaddition between the organometallic maleimide dienophiles and cyclopentadiene or furan, respectively. The oxanorbornene adduct was obtained as a mixture of endo and exo isomers as confirmed by X-ray diffraction and NMR spectroscopy. The (oxa)norbornene groups further provided convenient chemical reporters to carry out inverse electron demand Diels-Alder (iEDDA) reactions with tetrazine derivatives. Detailed kinetic studies with a model tetrazine revealed that faster rates of reaction were determined with both isomers of the oxanorbornene complex with respect to the norbornene complexes. Eventually, incorporation of metallocarbonyl entities into bovine serum albumin equipped with tetrazine handles was achieved as shown by IR spectroscopy of the protein conjugates.

Dendritic architectures by orthogonal thiol-maleimide "click" and furan-maleimide dynamic covalent chemistries

A set of dendrons and dendrimers is synthesized divergently using an orthogonal combination of kinetically-driven thiol-maleimide "click" chemistry and thermodynamically reversible furan-maleimide cycloaddition/retrocycloaddition reactions. Growth is controlled by taking advantage of the selective thiol-ene addition of thiols to the electron withdrawn alkene of maleimide in the presence of electron rich alkene of oxanorbornene. Subsequent activation of growing dendrons/dendrimers requires only heat to induce the dynamic covalent liberation of peripheral furan protecting groups. The methodology introduced provides a new route to multifunctional dendrimers that could, in principle, be synthesized by introducing different branched monomers at any stage of dendrimer growth, allowing dendrimer architectures and properties to be better tailored to their intended applications.

“Dial-In” Emission from a Unique Flexible Material with Polarization Tuneable Spectral Intensity

The development of organic photoluminescent materials, which show promising roles as catalysts, sensors, organic light-emitting diodes, logic gates, etc., is a major demand and challenge for the global scientific community. In this context, a photoclick polymerization method is adopted for the growth of a unique photoluminescent three-dimensional (3D) polymer film, E, as a model system that shows emission tunability over the range 350–650 nm against the excitation range 295–425 nm. The DFT analysis of energy calculations and π-stacking supports the spectroscopic observations for the material exhibiting a broad range of emission owing to newly formed chromophoric units within the film. Full polarization spectroscopic Mueller matrix studies were employed to extract and quantify the molecular orientational order of both the ground (excitation) and excited (emission) state anisotropies through a set of newly defined parameters, namely the fluorescence diattenuation and fluorescence polarizance. The information contained in the recorded fluorescence Mueller matrix of the organic polymer material provided a useful way to control the spectral intensity of emission by using pre- and post-selection of polarization states. The observation was based on the assumption that the longer lifetime of the excited dipolar orientation is attributed to the compactness of the film.