30132-23-1

Usage

Uses

Used in Chemical Synthesis:
Ethyl 3-bromo-2-oxocyclohexanecarboxylate is used as an intermediate in the synthesis of trans-1,2-Dimethylcyclopentane (D464925), a hydrocarbon found in sedimentary rocks. ethyl 3-bromo-2-oxocyclohexanecarboxylate is important for determining the maturation history of these rocks, providing valuable insights into their geological formation and potential applications in the energy and chemical industries.
Used in Petroleum Industry:
In the petroleum industry, ethyl 3-bromo-2-oxocyclohexanecarboxylate plays a crucial role in the synthesis of trans-1,2-Dimethylcyclopentane, which is used to study the maturation history of sedimentary rocks. Understanding the maturation history of these rocks is essential for assessing their potential as sources of hydrocarbons and other valuable resources.
Used in Organic Chemistry Research:
Ethyl 3-bromo-2-oxocyclohexanecarboxylate is also used in organic chemistry research as a versatile building block for the synthesis of various organic compounds. Its unique molecular structure allows for a wide range of chemical reactions, making it a valuable tool for the development of new compounds with potential applications in various industries, such as pharmaceuticals, materials science, and agrochemicals.

InChI:InChI=1/C9H13BrO3/c1-2-13-9(12)6-4-3-5-7(10)8(6)11/h6-7H,2-5H2,1H3

Upstream product

• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 
• 35244-51-0 ethyl-2-(1-piperidinyl)-2-cyclohexenecarboxylate 
• 35244-45-2 ethyl-2-(1-piperidinyl)-1-cyclohexenecarboxylate 
• 7726-95-6 bromine 

Downstream Products

• 3400-80-4 ethyl 2-oxocyclohex-3-ene-1-carboxylate 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 
• 118-61-6 2-hydroxy-benzoic acid ethyl ester 
• 942-01-8 1,2,3,4-tetrahydrocarbazole 
• 53512-43-9 Ethyl-6-methylthiocyclohexanon-2-carboxylat 
• 1154-73-0 3-(2-Aethoxycarbonyl-aethylmercapto)-2-oxo-cyclohexan-1-carbonsaeure-aethylester 
• 76488-59-0 2-m-Tolylamino-4,5,6,7-tetrahydro-benzothiazole-4-carboxylic acid ethyl ester 
• 76488-60-3 2-p-Tolylamino-4,5,6,7-tetrahydro-benzothiazole-4-carboxylic acid ethyl ester 
• 76488-58-9 2-o-Tolylamino-4,5,6,7-tetrahydro-benzothiazole-4-carboxylic acid ethyl ester 
• 76488-54-5 2-(3-Chloro-phenylamino)-4,5,6,7-tetrahydro-benzothiazole-4-carboxylic acid ethyl ester 
• 76488-64-7 2-(4-Ethoxy-phenylamino)-4,5,6,7-tetrahydro-benzothiazole-4-carboxylic acid ethyl ester 
• 76488-57-8 2-(4-Bromo-phenylamino)-4,5,6,7-tetrahydro-benzothiazole-4-carboxylic acid ethyl ester 
• 76488-56-7 2-(2-Bromo-phenylamino)-4,5,6,7-tetrahydro-benzothiazole-4-carboxylic acid ethyl ester 
• 76488-63-6 2-(2-Ethoxy-phenylamino)-4,5,6,7-tetrahydro-benzothiazole-4-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Construction of the Fused Pentacycle of Talatisamine via a Combination of Radical and Cationic Cyclizations

The fused 6/7/5/6/6-membered (ABCDE) ring system of talatisamine was synthesized in 22 steps. After preparation of the AE-ring structure from 2-(ethoxycarbonyl)cyclohexanone, elaboration of the carboskeleton was realized by sequential additions of allyl magnesium bromide and the lithiated C-ring. The C11-bridgehead radical derived from the ACE-ring underwent the 7-endo cyclization with the enone moiety to form the B-ring in C10-stereoselective and C11-stereospecific manners. The 6-endo cyclization of the remaining D-ring was in turn attained by using the silyl enol ether as the nucleophile and the PhSeCl-activated olefin as the electrophile. These radical and cationic cyclizations were demonstrated to be highly chemoselective, and they significantly contributed to streamlining the route to the intricately fused pentacycle of talatisamine.

Expeditious synthesis of the fused hexacycle of puberuline C: Via a radical-based cyclization/translocation/cyclization process

The fused 6/7/5/6/6/6-hexacyclic ring system of puberuline C was assembled in 18 steps from 2-(ethoxycarbonyl)cyclohexanone. After the azabicyclo[3.3.1]nonane derivative was sequentially coupled with propargyl magnesium bromide, 2-iodo cyclopentenone and allyl bromide, the pentacycle was constructed in a single step via a radical-based cyclization/translocation/cyclization process. The C11-bridgehead radical generated via C-Br homolysis participated in a 7-endo cyclization, and the 1,5-hydrogen translocation of the resultant radical was followed by transannular 6-exo cyclization to simultaneously realize the construction of the two rings and the introduction of the five contiguous stereocenters. The last 6-exo cyclization was induced by the Mukaiyama aldol reaction, and the C16-ketone was stereoselectively reduced by the action of SmI2/t-BuOH, leading for the first time to the synthesis of the entire hexacycle of puberuline C.

METHODS AND MATERIALS FOR INCREASING OR MAINTAINING NICOTINAMIDE MONONUCLEOTIDE ADENYLYL TRANSFERASE-2 (NMNAT2) POLYPEPTIDE LEVELS

This document provides methods and materials for increasing or maintaining NMNAT2 polypeptide levels within cells. For example, compounds (e.g., organic compounds) having the ability to increase or maintain NMNAT2 polypeptide levels within cells, formulations containing compounds having the ability to increase or maintain NMNAT2 polypeptide levels within cells, methods for making compounds having the ability to increase or maintain NMNAT2 polypeptide levels within cells, methods for making formulations containing compounds having the ability to increase or maintain NMNAT2 polypeptide levels within cells, methods for increasing or maintain NMNAT2 polypeptide levels within cells, and methods for treating mammals (e.g., humans) having a condition responsive to an increase in NMNAT2 polypeptide levels are provided (or for preventing said condition).

Tetrahydrocarbazole small molecular organic compounds, application thereof to preparation of antibacterial medicines and preparation method thereof

The invention discloses tetrahydrocarbazole small molecular organic compounds shown as a structural formula (I), or pharmaceutically acceptable salts and medicinal compositions, application thereof topreparation of antibacterial medicines. The tetrahydrocarbazole small molecular organic compounds can effectively inhibit gram-positive bacteria, and have a very good inhibitory effect on multidrug-resistant staphylococcus aureus and gram-negative bacteria which are clinically difficult to treat, and can be used for preparing highly-efficient anti-bacterial infection medicines. The invention further discloses a preparation method of the tetrahydrocarbazole small molecular organic compounds.

Tetrahydrocarbazole Inhibitors Of SIRT1 Receptors

Described are deuterium-substituted tetrahydrocarbazole compounds of Formulae I, II, or III which are inhibitors of sirtuin 1 (SIRT1). Also described are pharmaceutical compositions comprising the deuterium-substituted tetrahydrocarbazole compounds, and methods of use thereof.

Discovery of α-Substituted Imidazole-4-acetic Acid Analogues as a Novel Class of ρ1γ-Aminobutyric Acid Type A Receptor Antagonists with Effect on Retinal Vascular Tone

The ρ-containing γ-aminobutyric acid type A receptors (GABAARs) play an important role in controlling visual signaling. Therefore, ligands that selectively target these GABAARs are of interest. In this study, we demonstrate that the partial GABAAR agonist imidazole-4-acetic acid (IAA) is able to penetrate the blood–brain barrier in vivo; we prepared a series of α- and N-alkylated, as well as bicyclic analogues of IAA to explore the structure–activity relationship of this scaffold focusing on the acetic acid side chain of IAA. The compounds were prepared via IAA from l-histidine by an efficient minimal-step synthesis, and their pharmacological properties were characterized at native rat GABAARs in a [3H]muscimol binding assay and at recombinant human α1β2γ2Sand ρ1GABAARs using the FLIPR membrane potential assay. The (+)-α-methyl- and α-cyclopropyl-substituted IAA analogues ((+)-6 a and 6 c, respectively) were identified as fairly potent antagonists of the ρ1GABAAR that also displayed significant selectivity for this receptor over the α1β2γ2SGABAAR. Both 6 a and 6 c were shown to inhibit GABA-induced relaxation of retinal arterioles from porcine eyes.

Design, synthesis, and evaluation of conformationally restricted acetanilides as potent and selective β3 adrenergic receptor agonists for the treatment of overactive bladder

A series of conformationally restricted acetanilides were synthesized and evaluated as β3-adrenergic receptor agonists (β3-AR) for the treatment of overactive bladder (OAB). Optimization studies identified a five-membered ring as the preferred conformational lock of the acetanilide. Further optimization of both the aromatic and thiazole regions led to compounds such as 19 and 29, which have a good balance of potency and selectivity. These compounds have significantly reduced intrinsic clearance compared to our initial series of pyridylethanolamine β3-AR agonists and thus have improved unbound drug exposures. Both analogues demonstrated dose dependent β3-AR mediated responses in a rat bladder hyperactivity model.

An improved, regioselective synthesis of the radiolabelling precursor for the translocator protein targeting positron emission tomography imaging radiotracer [18F]GE-180

[18F]GE-180 has been demonstrated to be a promising new positron emission tomography radiotracer for targeting translocator protein. PET imaging of TSPO will enable measurement of neuroinflammation and microglia activity in vivo. The synthetic route used in the initial discovery of GE-180, whilst enabling the rapid evaluation of the structure-activity relationships (SAR) in this molecular class, was not high yielding and not suitable for scale-up. Here we present an optimised route towards GE-180 and the radiolabelling precursor of [18F]GE-180 with significantly improved yields due to a strategy which improves the regioselectivity of the key indole formation step of the synthesis.

PROCESSES FOR THE PREPARATION OF 6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-1-CARBOXAMIDE AND OF ITS PRECURSORS

The invention relates to a novel process for the preparation of rac-6-Chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxamide (I) through the conversion of a 3-bromo-2-oxo-cyclohexanecarboxylic acid alkyl ester (I'-a) into 6-chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxylic acid alkyl ester (I'-b), which in turn is processed to yield the final product (I).

GE-180: A novel fluorine-18 labelled PET tracer for imaging Translocator protein 18 kDa (TSPO)

A series of tricyclic compounds have been synthesised and evaluated in vitro for affinity against Translocator protein 18 kDa (TSPO) and for preferred imaging properties. The most promising of the compounds were radiolabelled and evaluated in vivo to determine biodistribution and specificity for high expressing TSPO regions. Metabolite profiling in brain and plasma was also investigated. Evaluation in an autoradiography model of neuroinflammation was also carried out for the best compound, 12a ([18F]GE-180).