19790-63-7

Upstream product

• 50-00-0 formaldehyd 
• 16728-57-7 6-phenoxyhexanenitrile 
• 74972-56-8 (hex-5-en-1-yloxy)benzene 
• 85234-59-9 6-phenoxy-hex-1-ene oxide 
• 4286-55-9 1-bromo-6-hexanol 
• 16654-54-9 6-phenoxyhexan-1-ol 
• 108-95-2 phenol 
• 2695-47-8 6-Bromo-1-hexene 

Downstream Products

• 1234334-59-8 2-[2-hydroxy-7-phenoxyheptyl]-6-methoxy-3,5-dimethyl-4H-pyran-4-one 
• 1383151-98-1 (2R,3R,4R,5S)-2-(hydroxymethyl)-1-(6-phenoxyhexyl)piperidine-3,4,5-triol 

Relevant academic research and scientific papers

ALDEHYDE-SELECTIVE WACKER-TYPE OXIDATION OF UNBIASED ALKENES

This disclosure is directed to methods of preparing organic aldehydes, each method comprising contacting a terminal olefin with an oxidizing mixture comprising: (a) a dichloro-palladium complex; (b) a copper complex; (c) a source of nitrite; under aerobic reaction conditions sufficient to convert at least a portion of the terminal olefin to an aldehyde.

Design, synthesis, and biological evaluation of N-Alkylated deoxynojirimycin (DNJ) derivatives for the treatment of dengue virus infection

We recently described the discovery of oxygenated N-alkyl deoxynojirimycin (DNJ) derivative 7 (CM-10-18) with antiviral activity against dengue virus (DENV) infection both in vitro and in vivo. This imino sugar was promising but had an EC50 against DENV in BHK cells of 6.5 μM, which limited its use in in vivo. Compound 7 presented structural opportunities for activity relationship analysis, which we exploited and report here. These structure-activity relationship studies led to analogues 2h, 2l, 3j, 3l, 3v, and 4b-4c with nanomolar antiviral activity (EC50 = 0.3-0.5 μM) against DENV infection, while maintaining low cytotoxicity (CC50 > 500 μM, SI > 1000). In male Sprague-Dawley rats, compound 3l was well tolerated at a dose up to 200 mg/kg and displayed desirable PK profiles, with significantly improved bioavailability (F = 92 α 4%).

Synthesis and evaluation of verticipyrone analogues as mitochondrial complex I inhibitors

Verticipyrone has recently been isolated from the culture broth of Verticillium sp. and shown to inhibit NADH fumarate reductase, as well as NADH oxidoreductase (complex I) of the mitochondrial electron transport chain. In order to assess the structural elements in verticipyrone essential for complex I inhibitor, 15 structural analogues were prepared and analyzed for their effects on mitochondrial NADH oxidoreductase and NADH oxidase activities. Also measured were the abilities of several of the analogues to inhibit respiration as judged by a shift to glycolysis, and to inhibit the growth of several mammalian cell lines. The nature of the pyrone ring was shown to be important to potency of inhibition, as was the length and nature of substituents in the side chain of the analogues.

REGIOSELECTIVITY OF OLEFIN OXIDATION BY IODOSOBENZENE CATALYZED BY METALLOPORPHYRINS: CONTROL BY THE CATALYST

The regioselectivity of the oxidation of three monosubstituted olefins, 6-phenoxyhex-1-ene, hex-1-ene and styrene, by iodosobenzene in the presence of various Fe-, Mn- or Cr-tetraaryl-porphyrins, was studied.It was found that, besides epoxides, known products from such systems, allylic alcohols and aldehydes were formed, the latter not being derived from the corresponding epoxides.The relative importance of these reactions greatly depends upon both the metal and porphyrin constituents of the catalyst.More particularly, the competition between epoxidation and allylic hydroxylation can be efficiently controlled by non bonded interactions between the olefin and porphyrin substituents.No hydroxylation of the aromatic rings and no oxidative dealkylation of the ether function was detected.

MONOOXYGENASE-LIKE OXIDATIONS OF OLEFINS AND ALKANES CATALYZED BY MANGANESE PORPHYRINS : COMPARISON OF SYSTEMS INVOLVING EITHER O2 AND ASCORBATE OR IODOSYLBENZENE

A biphasic system using a manganese porphyrin as a catalyst and sodium ascorbate as a reducing agent is able to activate dioxygen and to oxidize olefins selectively into epoxides and alkanes into alcohols and ketones.Its properties and specifities are shown to be different from those of the manganese porphyrin-iodosylbenzene system, suggesting that a manganese -oxo complex is not involved in these O2-dependent oxidations.