143654-03-9Relevant articles and documents
Method for synthesizing eugenol
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Paragraph 0041; 0045, (2020/08/06)
A method for synthesizing eugenol comprises the steps that firstly, guaiacol, lithium chloride and a catalytic amount of copper chloride are dissolved in glacial acetic acid, bubbling is conducted, oxygen is introduced for a reaction, and 4-chloro-2-methoxyphenol is obtained; then, 4-chloro-2-methoxyphenol reacts with alkyl halide alkyl ether in the presence of alkali to obtain 4-chloro-2-methoxy-1-alkoxy alkylphenol; 4-chloro-2-methoxy-1-alkoxy alkylphenol reacts with allyl magnesium halide in an ether solution to obtain 4-allyl-2-methoxy-1-alkoxy alkylphenol; and finally, 4-allyl-2-methoxy-1-alkoxy alkylphenol and p-toluenesulfonic acid monohydrate react in an organic solvent, and after the organic solvent is removed, residues obtained are subjected to high vacuum distillation to obtainthe eugenol product. According to the method, the problems that in the prior art, guaiacol directly reacts with 3-chloropropene to easily generate ortho-isomers difficult to separate, and the yield ofthe para-product eugenol is low are successfully solved, the quality of the eugenol product is improved, and the yield of eugenol is increased to 70% or above.
Synthesis and Structure-Activity Relationship of Dehydrodieugenol B Neolignans against Trypanosoma cruzi
Sear, Claire E.,Pieper, Pauline,Amaral, Maiara,Romanelli, Maiara M.,Costa-Silva, Thais A.,Haugland, Marius M.,Tate, Joseph A.,Lago, Joa? H. G.,Tempone, Andre G.,Anderson, Edward A.
, p. 2872 - 2878 (2020/11/10)
Trypanosoma cruzi is the etiologic agent of Chagas disease, which affects over seven million people, especially in developing countries. Undesirable side effects are frequently associated with current therapies, which are typically ineffective in the treatment of all stages of the disease. Here, we report the first synthesis of the neolignan dehydrodieugenol B, a natural product recently shown to exhibit activity against T. cruzi. Using this strategy, a series of synthetic analogues were prepared to explore structure-activity relationships. The in vitro antiparasitic activities of these analogues revealed a wide tolerance of modifications and substituent deletions, with maintained or improved bioactivities against the amastigote forms of the parasite (50% inhibitory concentration (IC50) of 4-63 μM) and no mammalian toxicity (50% cytotoxic concentration (CC50) of >200 μM). Five of these analogues meet the Drugs for Neglected Disease Initiative (DNDi) "hit criteria"for Chagas disease. This work has enabled the identification of key structural features of the natural product and sites where scaffold modification is tolerated.
A rapid, solvent-free deprotection of methoxymethyl (MOM) ethers by pTSA; An eco-friendly approach
Pandurangan, Nanjan
, p. 231 - 235 (2017/07/15)
Background: Ease of preparation and alkaline stability of methoxymethyl (MOM) makes it an important hydroxyl protecting group. A number of methods are available for the deprotection of MOM. Though the methods are good in general, they use solvents, require prolonged reaction time and tedious work up. A solvent free, solid phase, fast deprotection of MOM has been developed and is the major theme of this paper. Methods: A mixture of MOM protected compounds and pTSA is triturated in a mortar (5 min) and left at room temperature for 30 min. On addition of water (4°C), pTSA, methanol and formaldehyde dissolved leaving the products as precipitates. Results: A series of different MOM ethers were deprotected by this method in good to excellent yield (85-98%). The compatibility of MOM in the presence of other protections such as methoxyl, benzyl, ester, amide, allyl and lactone was also established. Acetate protection is not stable under these conditions. Conclusion: An efficient, selective and high yielding deprotection MOM groups by pTSA under solvent free condition is described. The process is environment friendly since no solvent was used in the deprotection process. The reaction conditions are mild and should be useful for the deprotection of MOM derivatives of complex and labile molecules.
