20549-68-2

Upstream product

• 588-63-6 3-phenoxypropyl bromide 
• 1746-13-0 allyl phenyl ether 
• 108-95-2 phenol 
• 6180-61-6 3-phenoxypropanol 
• 718638-46-1 (C₅H₅)2ZrCl(CH₂)3OC₆H₅ 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 3384-04-1 3-chloropropyl phenyl ether 

Downstream Products

• 32599-03-4 1-(3-phenoxypropyl)piperidine 
• 622-85-5 propoxybenzene 
• 1746-13-0 allyl phenyl ether 
• 10125-18-5 1,6-diphenoxyhexane 
• 66291-15-4 (3-nitro-propyl)-phenyl ether 
• 108847-05-8 trimethyl-(3-phenoxy-propyl)-ammonium; iodide 
• 119794-95-5 2,3-dihydro-6-(3-phenoxypropyl)-5-benzofuranol 
• 139-02-6 sodium phenoxide 
• 75-19-4 cyclopropane 
• 108-95-2 phenol 
• 380364-11-4 3-[[(methyl)(3-phenoxypropyl)amino]methyl]phenol 
• 802920-01-0 1,1-difluoro-4-phenoxybutyl phenyl sulfone 
• 861571-88-2 (5-iodo-hexyl)-phenyl ether 
• 1286739-96-5 2-(1,1-difluoro-4-phenoxybutylsulfonyl)pyridine 

Relevant academic research and scientific papers

Substrate-Dependent Cleavage Site Selection by Unconventional Radical S-Adenosylmethionine Enzymes in Diphthamide Biosynthesis

S-Adenosylmethionine (SAM) has a sulfonium ion with three distinct C-S bonds. Conventional radical SAM enzymes use a [4Fe-4S] cluster to cleave homolytically the C5′,adenosine-S bond of SAM to generate a 5′-deoxyadenosyl radical, which catalyzes various downstream chemical reactions. Radical SAM enzymes involved in diphthamide biosynthesis, such as Pyrococcus horikoshii Dph2 (PhDph2) and yeast Dph1-Dph2 instead cleave the Cγ,Met-S bond of methionine to generate a 3-amino-3-carboxylpropyl radical. We here show radical SAM enzymes can be tuned to cleave the third C-S bond to the sulfonium sulfur by changing the structure of SAM. With a decarboxyl SAM analogue (dc-SAM), PhDph2 cleaves the Cmethyl-S bond, forming 5′-deoxy-5′-(3-aminopropylthio) adenosine (dAPTA, 1). The methyl cleavage activity, like the cleavage of the other two C-S bonds, is dependent on the presence of a [4Fe-4S]+ cluster. Electron-nuclear double resonance and mass spectroscopy data suggests that mechanistically one of the S atoms in the [4Fe-4S] cluster captures the methyl group from dc-SAM, forming a distinct EPR-active intermediate, which can transfer the methyl group to nucleophiles such as dithiothreitol. This reveals the [4Fe-4S] cluster in a radical SAM enzyme can be tuned to cleave any one of the three bonds to the sulfonium sulfur of SAM or analogues, and is the first demonstration a radical SAM enzyme could switch from an Fe-based one electron transfer reaction to a S-based two electron transfer reaction in a substrate-dependent manner. This study provides an illustration of the versatile reactivity of Fe-S clusters.

Transition Metal Free Stannylation of Alkyl Halides: The Rapid Synthesis of Alkyltrimethylstannanes

A transition metal free stannylation reaction of alkyl bromides and iodides with hexamethyldistannane has been developed. This protocol is operationally convenient and features a rapid reaction and good functional group tolerance. A wide range of functionalized primary and secondary alkyl and benzyl trimethyl stannanes are prepared in moderate to excellent yields. The success of the gram-scale procedure and tandem Stille coupling reaction has allowed this protocol to demonstrate potential for application in organic synthesis. Both experimental and theoretical studies reveal the mechanistic details of this stannylation reaction.

PROSTAGLANDIN E2 (PGE2) EP4 RECEPTOR ANTAGONISTS

The present invention relates to novel compounds of formula (I) and pharmaceutical compositions containing these compounds. The compounds provided herein can act as prostaglandin E2 (PGE2) EP4 receptor antagonists, which renders them highly advantageous for use in therapy, particularly in the treatment or prevention of cancer, a neovascular eye disease, inflammatory pain, or an inflammatory disease, such as, e.g., multiple sclerosis, rheumatoid arthritis or endometriosis.

Transition-Metal-Free Borylation of Alkyl Iodides via a Radical Mechanism

We describe an operationally simple transition-metal-free borylation of alkyl iodides. This method uses commercially available diboron reagents as the boron source and exhibits excellent functional group compatibility. Furthermore, a diverse range of prim

Halogenation through Deoxygenation of Alcohols and Aldehydes

An efficient reagent system, Ph3P/XCH2CH2X (X = Cl, Br, or I), was very effective for the deoxygenative halogenation (including fluorination) of alcohols (including tertiary alcohols) and aldehydes. The easily available 1,2-dihaloethanes were used as key reagents and halogen sources. The use of (EtO)3P instead of Ph3P could also realize deoxy-halogenation, allowing for a convenient purification process, as the byproduct (EtO)3Pa?O could be removed by aqueous washing. The mild reaction conditions, wide substrate scope, and wide availability of 1,2-dihaloethanes make this protocol attractive for the synthesis of halogenated compounds.

Copper-Catalyzed Reductive Trifluoromethylation of Alkyl Iodides with Togni's Reagent

This work illustrates a reductive cross-electrophile coupling protocol for trifluoromethylation of alkyl iodides under Cu-catalyzed/Ni-promoted reaction conditions. The use of diboron esters as the terminal reductant allows the effective generation of the alkyl-CF3 products with excellent functional group tolerance and broad substrate scope. A mechanism involving a reaction of alkyl-Cu with Togni's reagent was proposed.

Transmetalation of Alkylzirconocenes in Copper-Catalyzed Alkyl–Alkynyl Cross-Coupling Reactions

A simple copper-catalyzed alkyl–alkynyl cross-coupling strategy has been developed using the reaction between alkynyl bromides and alkylzirconocenes. The alkylzirconocenes were generated in situ via regioselective addition of Schwartz's reagent (ZrCp2HCl) on to alkenes. The reaction has a broad scope, a range of functionalized bromoalkynes and alkylzirconium reagents were successfully coupled, resulting in moderate to good yields of the desired internal alkynes. (Figure presented.).

Unexpected conversion of alkyl azides to alkyl iodides and of aryl azides to N-tert-butyl anilines

In the presence of tert-butyl iodide, alkyl azides are converted into the corresponding iodides at room temperature, whereas, N-t-Bu anilines are obtained from aryl azides under the same experimental conditions. A mechanism is proposed to explain this unusual reactivity.

Acetylcholinesterase inhibitors: SAR and kinetic studies on ω-[N-methyl-N-(3-alkylcarbamoyloxyphenyl]methyl] aminoalkoxyaryl derivatives

In this work, we further investigated a class of carbamic cholinesterase inhibitors introduced in a previous paper (Rampa et al. J. Med. Chem. 1998, 41, 3976). Some new ω-[N-methyl-N-(3-alkylcarbamoyloxyphenyl)methyl]aminoalkoxyaryl analogues were designed, synthesized, and evaluated for their inhibitory activity against both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). The structure of the lead compound (xanthostigmine) was systematically varied with the aim to optimize the different parts of the molecule. Moreover, such a structure-activity relationships (SAR) study was integrated with a kinetic analysis of the mechanism of AChE inhibition for two representative compounds. The structural modifications lead to a compound (12b) showing an IC50 value for the AChE inhibition of 0.32 ± 0.09 nM and to a group of BuChE inhibitors also active at the nanomolar level, the most potent of which (15d) was characterized by an IC50 value of 3.3 ± 0.4 nM. The kinetic analysis allowed for clarification of the role played by different molecular moieties with regard to the rate of AChE carbamoylation and the duration of inhibition. On the basis of the results presented here, it was concluded that the cholinesterase inhibitors of this class possess promising characteristics in view of a potential development as drugs for the treatment of Alzheimer's disease.

Quaternary ammonium ions can externally block voltage-gated K+ channels. Establishing a theoretical and experimental model that predicts KDS and the selectivity of K+ over Na+ ions

The physicochemical basis for the high ion selectivity of potassium channels is poorly understood. In the present studies, external blockade of cloned voltage-gated potassium channels with alkyl quaternary ammonium ions are analyzed from a model derived from theory and experimental data. Atomic mass units, electrostatic potential residing on the nitrogen atom, the COSMO van der Waals solvent accessible surface, the Onsager solvation model, and the isodensity PCM solvation model are computed at the semi-empirical and the ab initio levels of theory. A structure-activity relationship (SAR) exists between the calculated values and the experimentally obtained KD (mM). The SAR model gives us KD predictions and when K+ and Na+ are incorporated into the model, it dramatically predicts the selectivity of K+ over Na+ ions.