94115-39-6

Upstream product

• 95207-31-1 O-3-phenylpropyl benzohydroxamate 
• 104-52-9 phenylpropyl chloride 
• 160725-45-1 2-(3-phenylpropoxy)isoindoline-1,3-dione 
• 14436-57-8 O-(3-phenylpropyl)carbethoxyhydroxamate 
• 122-97-4 3-Phenyl-1-propanol 
• 637-59-2 1-Bromo-3-phenylpropane 
• 4392-24-9 Cinnamyl bromide 
• 101283-40-3 Benzhydroxamsaeure-cinnamylether 

Downstream Products

• 5776-67-0 6β-(2-phenoxy-acetylamino)-penicillanic acid 3-phenyl-propoxyamide 
• 681146-43-0 2-[2-(3-phenyl-propoxyamino)-ethyl]-isoindole-1,3-dione 
• 292835-64-4 5-{(2S)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}amino)-3-oxo-3-[(3-phenylpropoxy)amino]propyl}-2-(carboxymethoxy)benzoic acid 
• 889666-51-7 C₄₄H₆₇N₃O₁₂ 
• 1207383-23-0 6-naphthalen-1-yl-4-[(3-phenylpropoxy)amino]-5,6-dihydro-2H-1,3-oxazin-2-one 
• 73941-30-7 O-(3-phenylpropyl)-hydroxylamine hydrochloride 
• 1542915-21-8 N¹-(adamant-2-yl)-N²-(3-phenylpropyloxy)oxalamide 

Relevant academic research and scientific papers

O-alkylhydroxylamines as rationally-designed mechanism-based inhibitors of indoleamine 2,3-dioxygenase-1

Indoleamine 2,3-dioxygenase-1 (IDO1) is a promising therapeutic target for the treatment of cancer, chronic viral infections, and other diseases characterized by pathological immune suppression. Recently important advances have been made in understanding IDO1's catalytic mechanism. Although much remains to be discovered, there is strong evidence that the mechanism proceeds through a heme-iron bound alkylperoxy transition or intermediate state. Accordingly, we explored stable structural mimics of the alkylperoxy species and provide evidence that such structures do mimic the alkylperoxy transition or intermediate state. We discovered that O-benzylhydroxylamine, a commercially available compound, is a potent sub-micromolar inhibitor of IDO1. Structure-activity studies of over forty derivatives of O-benzylhydroxylamine led to further improvement in inhibitor potency, particularly with the addition of halogen atoms to the meta position of the aromatic ring. The most potent derivatives and the lead, O-benzylhydroxylamine, have high ligand efficiency values, which are considered an important criterion for successful drug development. Notably, two of the most potent compounds demonstrated nanomolar-level cell-based potency and limited toxicity. The combination of the simplicity of the structures of these compounds and their excellent cellular activity makes them quite attractive for biological exploration of IDO1 function and antitumor therapeutic applications.

Structure-activity relationships of substituted oxyoxalamides as inhibitors of the human soluble epoxide hydrolase

We explored both structure-activity relationships among substituted oxyoxalamides used as the primary pharmacophore of inhibitors of the human sEH and as a secondary pharmacophore to improve water solubility of inhibitors When the oxyoxalamide function was modified with a variety of alkyls or substituted alkyls, compound 6 with a 2-adamantyl group and a benzyl group was found to be a potent sEH inhibitor, suggesting that the substituted oxyoxalamide function is a promising primary pharmacophore for the human sEH, and compound 6 can be a novel lead structure for the development of further improved oxyoxalamide or other related derivatives In addition, introduction of substituted oxyoxalamide to inhibitors with an amide or urea primary pharmacophore produced significant improvements in inhibition potency and water solubility In particular, the N,N,O-trimethyloxyoxalamide group in amide or urea inhibitors (26 and 31) was most effective among those tested for both inhibition and solubility The results indicate that substituted oxyoxalamide function incorporated into amide or urea inhibitors is a useful secondary pharmacophore, and the resulting structures will be an important basis for the development of bioavailable sEH inhibitors

Remote C-H functionalization: Using the N-O moiety as an atom-economical tether to obtain 1,5- and the rare 1,7-C-H insertions

(Chemical Equotion Present) Dr. N-O: Rhodium-catalyzed intramolecular C-H insertion with diazocompounds, which are tethered by alkoxyamines, afforded 1,5- and the rare 1,7-insertion products (see scheme; Bn = benzyl). The resulting N-O tether is unaffected under the C-H insertion reaction conditions and it can be readily cleaved or transformed into various functionalities. The reduction of the N-O moiety controls acyclic stereochemistry.

3,6-Bicyclolides

The present invention discloses compounds of formula (I) or pharmaceutically acceptable salts, esters, or prodrugs thereof: which exhibit antibacterial properties. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject in need of antibiotic treatment. The invention also relates to methods of treating a bacterial infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention. The invention further includes process by which to make the compounds of the present invention.

A new supported reagent for the parallel synthesis of primary and secondary O-alkyl hydroxylamines through a base-catalyzed Mitsunobu reaction

The growing field of applications of O-alkyl hydroxylamines in medicinal chemistry and chemical biology has motivated the search for a parallel synthesis. A solid-phase approach based on the alkylation by alcohols of a new supported N-hydroxyphthalimide reagent using a Mitsunobu reaction followed by methylaminolysis has been optimized. This study points out the importance of the linker and a specific base effect for the Mitsunobu reaction. A large variety of alcohols can be used to give with moderate to high yields diverse O-alkyl hydroxylamines in high purity.

1-Benzyloxy-4,5-dihydro-1H-imidazol-2-yl-amines, a novel class of NR1/2B subtype selective NMDA receptor antagonists

Screening of the Roche compound depository led to the identification of (1-benzyloxy-4,5-dihydro-1H-imidazol-2-yl)-butyl amine 4, a structurally novel NR1/2B subtype selective NMDA receptor antagonist. The structure-activity relationships developed in this series resulted in the discovery of a novel class of potent and selective NMDA receptor blockers displaying activity in vivo.

6-O-acyl ketolide antibacterials

6-O-Acyl ketolide antibacterials of the formula: wherein R1, R2, R3, R4, W, X, X′, Y, and Y′ are as described herein and in which the substituents have the meaning indicated in the description. These compounds are useful as antibacterial agents.

Capture-ROMP-release: application for the synthesis of O-alkylhydroxylamines.

[reaction: see text] A new capture-ROMP-release method for chromatography-free purification of N-hydroxysuccinimde Mitsunobu reactions is described. The Mitsunobu reaction captures a variety of alcohols onto a norbornenyl N-hydroxysuccinimide monomer. Subjection of the resulting crude reaction mixture to ROM-polymerization generates a polymer that can be precipitated with methanol and filtered from the Mitsunobu byproducts. Treatment of the polymer with hydrazine releases the substrate from the water-soluble polymer, producing a variety of O-alkylhydroxylamines with good purity.

Synthesis and opioid activities of some naltrexone oxime ethers

A series of alkyl, cycloalkyl, aryl, and aralkyl ethers of naltrexone oxime was prepared.The compounds were examined in binding assays for μ, δ, and κ opioid receptor affinity.In addition, the naltrexone oxime ethers were studied in animal models that measure opioid agonist and antagonist activity.These studies led to the discovery of several compounds, notably phenethyl 3e and phenylpropyl 3f ethers of naltrexone, which have a 10-fold increase in potency at the κ opioid receptor with potent μ and κ agonist properties in vivo.naltrexone / oxime ether / opioid receptor / analgesia / receptor binding / kappa