7507-93-9

Usage

Uses

Used in Pharmaceutical and Medicinal Chemistry:
3-NITRO-6,7,8,9-TETRAHYDRO-5H-BENZO[7]ANNULEN-5-ONE is used as an intermediate in the synthesis of various organic compounds for pharmaceutical and medicinal chemistry. Its unique structure and functional groups make it a valuable building block for developing new drugs and therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, 3-NITRO-6,7,8,9-TETRAHYDRO-5H-BENZO[7]ANNULEN-5-ONE is used as a key component in the creation of complex organic molecules. Its presence in the synthesis process can lead to the development of novel compounds with diverse applications across various industries.
Used in Research and Development:
3-NITRO-6,7,8,9-TETRAHYDRO-5H-BENZO[7]ANNULEN-5-ONE is also utilized in research and development settings to explore its chemical properties and potential applications. This can lead to a better understanding of its reactivity and the discovery of new uses in various fields.

InChI:InChI=1/C11H11NO3/c13-11-4-2-1-3-8-5-6-9(12(14)15)7-10(8)11/h5-7H,1-4H2

Upstream product

• 826-73-3 1-Benzosuberone 

Downstream Products

• 95207-68-4 3-amino-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one 

Relevant academic research and scientific papers

Towards Waltheriones C and D: Synthesis of the Oxabicyclic Core

A route to the oxabicyclic cores of the HIV cytoprotective quinolone alkaloids, waltheriones C and D, is described. The approach relies on a stereospecific transannular bromoetherification followed by reductive debromination. The route can also be rendere

Benzimidazolone bioisosteres of potent GluN2B selective NMDA receptor antagonists

Overactivation of the NMDA receptor is associated with excitotoxic events leading to neurodegenerative processes as observed during the development of Alzheimer's disease, ParFnson's disease, Chorea Huntington and epilepsy. Negative allosteric modulators

Light Harvesting for Rapid and Selective Reactions: Click Chemistry with Strain-Loadable Alkenes

Intramolecular strain is a powerful driving force for rapid and selective chemical reactions, and it is the cornerstone of strain-induced bioconjugation. However, the use of molecules with built-in strain is often complicated as a result of instability or selectivity issues. Here, we show that such strain, and subsequent cycloadditions, can be mediated by visible light via the harvesting of photochemical energy. Through theoretical investigations and molecular engineering of strain-loadable cycloalkenes, we demonstrate the rapid chemoselective cycloaddition of alkyl azides with unstrained cycloalkenes via the transiently (reversibly) formed trans-cycloalkene. We assess this system via the rapid bioconjugation of azide-functionalized insulin. An attractive feature of this process is the cleavable nature of the linker, which makes a catch-and-release strategy possible. In broader terms, we show that conversion of photochemical energy to intramolecular ring strain is a powerful strategy that can facilitate complex chemical transformations, even in biomolecular systems. Probing, isolating, and/or manipulating biologically relevant macromolecules is central to the study of their function in living systems. However, the synthetic tools available for performing the chemistry necessary for such studies are often difficult to use or limited in utility. In the approach presented here, light is converted to molecular strain energy, which can in turn be used for performing rapid and highly selective chemistry on macromolecular systems. Because it involves chemically stable and chemoselective reactions, this research not only opens up new possibilities for biomolecular functionalization and manipulation but also promises to make such experiments accessible to a broader class of researchers. The central concept of strain-loadable alkenes is general and provides a firm foundation for light-activated chemistry in complex environments. Strain-loadable alkenes are cycloalkenes that, when irradiated in the presence of a visible-light-absorbing photocatalyst, undergo double-bond isomerization. Because of engineered geometrical constraints, this isomerization results in significant molecular strain. Weaver and colleagues exploit this strain to dramatically accelerate the cycloaddition with azides, which are otherwise unreactive, in mixed molecular environments.

A cell-permeable and triazole-forming fluorescent probe for glycoconjugate imaging in live cells

A new fluorescence-forming probe, coumOCT, designed by fusing cyclooctyne with a coumarin fluorophore was successfully used for the imaging of azido-glycoconjugates in living HeLa cells. This probe is cell-permeable and generates fluorescence after triazole formation, thus minimizing the background signal and enabling the real-time intracellular imaging of glycoconjugate trafficking.

SUBSTITUTED POLYCYCLIC ANTIBACTERIAL COMPOUNDS

The present description relates to substituted polycyclic compounds of Formula (I), Formula (II) or Formula (III): wherein the dashed line represents an optional double bond and Rl, R2, R4, R5, R7, X and Z are as defined herein, and forms and compositions thereof, and also relates to uses of a compound of Formula (I), Formula (II) or Formula (III) or a form thereof and methods for treating or ameliorating Neisseria gonorrhoeae (N. gonorrhoeae) in a subject in need thereof comprising, administering an effective amount of the compound to the subject.

REACTIVE LABELLING COMPOUNDS AND USES THEREOF

Provided are azido-BODIPY compounds of formula (I), cyclooctyne-based fluorogenic probes of formula (IV), and activity-based probes of formula (VI). These compounds undergo azide-alkyne cycloadditions (AAC) with to form triazolyl products. The provided compounds are useful for detection and imaging of alkyne-, or azide-containing molecules. Methods for detection and imaging biomolecules using compounds of the present disclosure are disclosed.

REACTIVE LABELLING COMPOUNDS AND USES THEREOF

Provided are azido-BODIPY compounds of formula (I), cyclooctyne-based fluorogenic probes of formula (IV), and activity-based probes of formula (VI). These compounds undergo azide alkyne cycloadditions (AAC) with to form triazolyl products. The provided compounds are useful for detection and imaging of alkyne-, or azide-containing molecules. Methods for detection and imaging biomolecules using compounds of the present disclosure are disclosed.

BENZOCYCLOOCTYNE COMPOUNDS AND USES THEREOF

Provided are benzocyclooctyne compounds of formula (I). These compounds undergo strain-promoted azide-alkyne cyclo additions (SPAAC) without presence of toxic metal catalysts. The provided compounds are useful for diagnosis and imaging of azide-containing molecules. Methods for detection and imaging biomolecules using compounds of the present disclosure are disclosed.

Nitration chemistry in continuous flow using fuming nitric acid in a commercially available flow reactor

The paper will describe the use of flow chemistry for scaling up exothermic or hazardous nitration reactions. Such reactions often cause time delays to the delivery of larger batches of intermediates or final compounds for medicinal chemistry projects, be

Tricyclic [1,2,4]triazine 1,4-dioxides as hypoxia selective cytotoxins

A series of novel tricyclic triazine-di-N-oxides (TTOs) related to tirapazamine have been designed and prepared. A wide range of structural arrangements with cycloalkyl, oxygen-, and nitrogen-containing saturated rings fused to the triazine core, coupled with various side chains linked to either hemisphere, resulted in TTO analogues that displayed hypoxia-selective cytotoxicity in vitro. Optimal rates of hypoxic metabolism and tissue diffusion coefficients were achieved with fused cycloalkyl rings in combination with both the 3-aminoalkyl or 3-alkyl substituents linked to weakly basic soluble amines. The selection was further refined using pharmacokinetic/pharmacodynamic model predictions of the in vivo hypoxic potency (AUCreq) and selectivity (HCD) with 12 TTO analogues predicted to be active in vivo, subject to the achievement of adequate plasma pharmacokinetics.