23680-40-2

Usage

Synthesis Reference(s)

Synthetic Communications, 22, p. 567, 1992 DOI: 10.1080/00397919208019255

InChI:InChI=1/C4H3BrO2/c1-7-4(6)2-3-5/h1H3

Upstream product

• 67-56-1 methanol 
• 16900-53-1 3-bromopropiolic acid 
• 922-67-8 propynoic acid methyl ester 
• 128-08-5 N-Bromosuccinimide 

Downstream Products

• 56904-83-7 methyl-5 heptene-4 yne-2 oate de methyle (Z) 
• 95081-58-6 (E)-3-aziridino-3-bromopropenoic acid methyl ester 
• 98236-76-1 1-(2-bromoethyl)-2-(methoxycarbonylmethylene)imidazolidine 
• 88474-06-0 3-aziridinopropynoic acid methyl ester 
• 142968-10-3 methyl 3-bromo-7-oxabicyclo[2.2.1]hepta-2,5-diene-2-carboxylate 
• 140455-72-7 1-[1-Methoxycarbonyl-meth-(E)-ylidene]-8-oxa-2-aza-5-azonia-spiro[4.5]decane; bromide 
• 95081-57-5 (2,2-Dimethyl-aziridin-1-yl)-propynoic acid methyl ester 
• 135923-04-5 3-methyl-2-(methoxycarbonylmethylene)-1,3-oxazoline 
• 136136-84-0 (Z)-3,3-dimethyl-2-(methoxycarbonylmethylene)-1,3-oxazolidinium bromide 
• 136136-83-9 (E)-3,3-dimethyl-2-(methoxycarbonylmethylene)-1,3-oxazolidinium bromide 
• 73587-82-3 (Z)-3-Chloro-4,5-dimethyl-hexa-2,5-dienoic acid methyl ester 
• 70230-24-9 2-Chloro-3,4,4-trimethyl-cyclobut-1-enecarboxylic acid methyl ester 
• 136136-85-1 5-Dimethylaminomethyl-2-[1-methoxycarbonyl-meth-(Z)-ylidene]-3,3-dimethyl-oxazolidin-3-ium; bromide 
• 136136-86-2 {2-[1-Methoxycarbonyl-meth-(Z)-ylidene]-3-methyl-oxazolidin-5-ylmethyl}-trimethyl-ammonium; bromide 

Relevant academic research and scientific papers

Synthesis of Epibatidine Analogues by Pyrrole Diels–Alder Reactions: Rapid Access to Azabicyclo[2.2.1]heptane and 3,8-Diazabicyclo[3.2.1]octane Scaffolds for Library Synthesis

Analogues of the nicotinic acetylcholine antagonist epibatidine, suitable for diversification, were synthesized by application of a pyrrole Diels–Alder strategy, allowing rapid generation of azabicyclo[2.2.1]heptane bicyclic cores. Further molecular complexity could be accessed by using intramolecular Diels–Alder reactions, or ring expansion by ozonolysis–reductive amination chemistry. Scaffolds were designed such that they could be orthogonally deprotected, yielding three points of diversity for library synthesis, exemplified by 24 compounds synthesized from four cores.

Silica gel-promoted convenient synthesis of 2-bromo-3-hydroxybenzoate derivatives

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Development of an enolate alkynylation approach towards the synthesis of the taiwanschirin natural products

Through the use of model studies, an approach was conceived towards the synthesis of the taiwanschirin family of natural products. These are structurally complex compounds which represent highly challenging and biologically active targets for total synthesis. This work describes a successful synthesis of the complex taiwanschirin fused [8,6,5] core through a novel alkynylation reaction coupled with an intramolecular Heck reaction used to construct the 8-membered ring.

Stable Pyrrole-Linked Bioconjugates through Tetrazine-Triggered Azanorbornadiene Fragmentation

An azanorbornadiene bromovinyl sulfone reagent for cysteine-selective bioconjugation has been developed. Subsequent reaction with dipyridyl tetrazine leads to bond cleavage and formation of a pyrrole-linked conjugate. The latter involves ligation of the tetrazine to the azanorbornadiene-tagged protein through inverse electron demand Diels–Alder cycloaddition with subsequent double retro-Diels–Alder reactions to form a stable pyrrole linkage. The sequence of site-selective bioconjugation followed by bioorthogonal bond cleavage was efficiently employed for the labelling of three different proteins. This method benefits from easy preparation of these reagents, selectivity for cysteine, and stability after reaction with a commercial tetrazine, which has potential for the routine preparation of protein conjugates for chemical biology studies.

Intermolecular cyclotrimerization of haloketoalkynes and internal alkynes: Facile access to arenes and phthalides

A highly chemo-and regioselective cyclo(co)trimerization between 3-halopropiolamides and symmetrical internal alkynes is reported. The reaction is catalyzed by CpRuCl(COD) and proceeds under air at ambient temperature in ethanol with no additional precautions. Iodo-, bromo-, and chloropropiolamides, esters, and ketones are viable coupling partners and, in a 2?:?1 stoichiometry relative to internal alkyne, yield fully-substituted arenes in a single step. The highest regioselectivities (96% single isomer) were observed when employing 2° and 3°-halopropiolamides. A mechanistic hypothesis accounting for this selectivity is proposed. Notably, by using 1,4-butynediol as the internal alkyne, in situ lactonization following [2+2+2]-cycloaddition generates therapeutically-relevant phthalide pharmacophores directly. This journal is

5-HYDROXY-7-OXABICYCLO[2.2.1]HEPTANE-2-CARBOXAMIDE DERIVATIVES FOR INDUCING CHONDROGENESIS FOR TREATING JOINT DAMAGE

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CERAMIDE GALACTOSYLTRANSFERASE INHIBITORS FOR THE TREATMENT OF DISEASE

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COMPOUNDS AND COMPOSITIONS FOR INDUCING CHONDROGENESIS

The present invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof; (I) or a pharmaceutically acceptable salt, tautomer, or stereoisomer thereof, wherein the variables are as defined herein. The present invention further provides pharmaceutical compositions comprising such compounds; and methods of using such compounds for treating joint damage or injury in a mammal, for inducing hyaline cartilage production or for inducing differentiation of chondrogenic progenitor cells into mature chondrocytes.

Discovery of aminocyclohexene analogues as selective and orally bioavailable hNav1.7 inhibitors for analgesia

hNav1.7 receives a lot of attention owing to its attractive mechanism of action in pain processing pathway. We have previously reported our design of a novel series of tetrahydropyridine analogues towards hNav1.7 selective inhibitors. Herein, we disclose further efforts to the optimization of hit compound (?)-6, which led to the identification of aminocyclohexene analogues (?)-9 and (?)-17 with good potency, high selectivity, and minimal CYP inhibition. Both compounds (?)-9 and (?)-17 demonstrated improved pharmacokinetic profiles in rats, and robust efficacy in rat formalin-induced nociception and spinal nerve ligation (SNL) models.