63066-74-0

Usage

Synthesis Reference(s)

Synthetic Communications, 25, p. 395, 1995 DOI: 10.1080/00397919508011371

InChI:InChI=1/C14H14O3/c15-10-11-16-12-6-8-14(9-7-12)17-13-4-2-1-3-5-13/h1-9,15H,10-11H2

Upstream product

• 126301-65-3 2-(4-phenoxyphenoxy)-ethyl-tetrahydropyranyl-ether 
• 831-82-3 4-Phenoxyphenol 
• 540-51-2 2-bromoethanol 
• 107-07-3 2-chloro-ethanol 
• 131368-29-1 Ethyl (4-phenoxyphenoxy)acetate 

Downstream Products

• 87545-48-0 1-(4-(2-bromoethoxy)phenoxy)benzene 
• 88354-78-3 Acetaldehyde O-[2-(4-phenoxy-phenoxy)-ethyl]-oxime 
• 88354-82-9 Propan-2-one O-[2-(4-phenoxy-phenoxy)-ethyl]-oxime 
• 88354-83-0 Butan-2-one O-[2-(4-phenoxy-phenoxy)-ethyl]-oxime 
• 88354-91-0 N-[2-(4-Phenoxy-phenoxy)-ethoxy]-thioacetimidic acid methyl ester 
• 179019-84-2 C₂₂H₂₁FO₄S 
• 1303528-49-5 1-{[2-(4-phenoxyphenoxy)ethoxy]methyl}-3-aminocarbonylpyridinium chloride 
• 1303528-58-6 1-{[2-(4-phenoxyphenoxy)ethoxy]methyl}-6-aminocarbonylquinolinium chloride 
• 1303528-59-7 1-{[2-(4-phenoxyphenoxy)ethoxy]methyl}-3-aminocarbonyl-4-aminopyridinium chloride 

Relevant academic research and scientific papers

Synthetic and Mechanistic Studies on 2,3-Dihydrobenzo[ b ][1,4]-oxaselenines Formation from Selenocyanates

An expedient preparation of selenium-containing hetero-cycles via an m -chloroperbenzoic acid-mediated seleno-annulation starting from selenocyanate derivatives is described. In spite of its significance, this cyclization reaction is virtually understudied not only from the point of view of its scope, but also from the mechanistic aspects associated to this remarkable transformation. In this sense, several selenocyanate and thiocyanate derivatives bearing an aromatic ring were evaluated as substrates under different reaction conditions of this interesting cyclization yielding important insights on its scope as well as relevant information on the reaction mechanism.

Further insights of selenium-containing analogues of WC-9 against Trypanosoma cruzi

As a continuation of our project aimed at searching for new chemotherapeutic agents against American trypanosomiasis (Chagas disease), new selenocyanate derivatives were designed, synthesized and biologically evaluated against the clinically more relevant dividing form of Trypanosoma cruzi, the etiologic agent of this illness. In addition, in order to establish the role of each part of the selenocyanate moiety, different derivatives, in which the selenium atom or the cyano group were absent, were conceived, synthesized and biologically evaluated. In addition, in order to study the optimal position of the terminal phenoxy group, new regioisomers of WC-9 were synthesized and evaluated against T. cruzi. Finally, the resolution of a racemic mixture of a very potent conformationally rigid analogue of WC-9 was accomplished and further tested as growth inhibitors of T. cruzi proliferation. The results provide further insight into the role of the selenocyanate group in its antiparasitic activity.

Design, synthesis and biological characterization of novel inhibitors of CD38

Human CD38 is a novel multi-functional protein that acts not only as an antigen for B-lymphocyte activation, but also as an enzyme catalyzing the synthesis of a Ca2+ messenger molecule, cyclic ADP-ribose, from NAD+. It is well established that this novel Ca2+ signaling enzyme is responsible for regulating a wide range of physiological functions. Based on the crystal structure of the CD38/NAD+ complex, we synthesized a series of simplified N-substituted nicotinamide derivatives (Compound1-14). A number of these compounds exhibited moderate inhibition of the NAD+ utilizing activity of CD38, with Compound4 showing the highest potency. The crystal structure of CD38/Compound4 complex and computer simulation of Compound7 docking to CD38 show a significant role of the nicotinamide moiety and the distal aromatic group of the compounds for substrate recognition by the active site of CD38. Biologically, we showed that both Compounds4 and 7 effectively relaxed the agonist-induced contraction of muscle preparations from rats and guinea pigs. This study is a rational design of inhibitors for CD38 that exhibit important physiological effects, and can serve as a model for future drug development.

ARYL AMINO ACID DERIVATIVES AS INHIBITORS FOR TREATING INFLAMMATION

The present invention relates to a chemical genus of 3-(triaryl)-2-aminopropanol derivative inhibitors of LTA4H (leukotriene A4 hydrolase) useful for the treatment and prevention of inflammatory diseases and disorders. The compounds have general formula III: A particular embodiment is

LTA4 Hydrolase inhibitors

The present invention provides compounds of the formula Ar1-Q-Ar2-Y-R-Z and pharmaceutically acceptable salts thereof wherein Ar1 and Ar2 are optionally substituted aryl moieties, Z is an optionally substituted nitrogen-containing moiety which may be an acyclic, cyclic or bicyclic amine or an optionally substituted monocyclic or bicyclic nitrogen-containing heteroaromatic moiety; Q is a linking group capable of linking two aryl groups; R is an alkylene moiety; Y is a linking moiety capable of linking an aryl group to an alkylene moiety and wherein Z is bonded to R through a nitrogen atom. The compounds and pharmaceutical compositions of the present invention are useful in the treatment of inflammatory diseases which are mediated by LTB4 production, such as proriasis, ulcerative colitis, IBD and asthma.

Synthesis of analogs of juvenile hormons proceeding from phenol derivatives

New potential juvenoids, esters of alkenoic and alkadienoic acids with phenoxy-and phenoxy-phenoxyethanol were synthesized, and also esters of phenoxyacetic acid with alkenols amd alkadienols.

Studies on hydrolysis of chiral, achiral and racemic alcohol esters with Pseudomonas cepacia lipase: mechanism of stereospecificity of the enzyme

Steady-state kinetics of Pseudomonas cepacia lipase-catalysed hydrolysis of five analogues chiral and achiral substrates, i.e. (R)- and (S)-1-methyl-2-(4-phenoxyphenoxy)ethyl acetates (R)- and (S)-1a, (R)- and (S)-2-methyl-2-(4-phenoxyphenoxy)ethyl acetat

Cleavage of acetals promoted by copper (II) sulphate adsorbed on silica gel

Copper sulphate supported on silica gel promotes the easy removal of cyclic acetals and tetrahydropyranyl ethers to give the respective parent carbonyl and hydroxyl compounds.

Synthesis and Activity of Juvenile Hormone Analogues (JHA), Part II

Several derivatives of 4-phenoxyphenoxy-ethyl and 4-phenoxyphenylethyl bearing carbonate and thiolcarbonate as functional groups were synthesized.The products were tested for their respective juvenile hormone activity for Triatoma infestans.None of them showed an activity comparable to that of Fenoxycarb which was used as the standard control.The synthetic procedures and the biological results are discussed.Keywords: Juvenile Hormone Analogues, Activity, Synthesis

Oxime Ethers: New Potent Insect Growth Regulators

Oxime ethers containing a 4-phenoxyphenoxy group in the molecules were synthesized and their insect growth regulating (IGR) activities were studied.Of these new IGR's, propionaldehyde oxime O-2-(4-phenoxyphenoxy)ethyl ether and propionaldehyde oxime O-2-(phenoxyphenoxy)propyl ether were found to be most effective, having much higher activities than methoprene against larvae of Culex pipiens pallens and Musca domestica by the immersion method and medium method, respectively.In addition, the effects of steric isomerism of these compounds were examined; their IGR activities were found to have a close relationship to the juvenile hormone activity by the Galleria wax test.