501-92-8Relevant academic research and scientific papers
Synthesis of 3-Methylobovatol
Pilkington, Lisa I.,Barker, David
, p. 2425 - 2428 (2015)
Biphenyl lignans are rare compounds that exhibit a broad range of biological activities. The first total synthesis of natural biphenyl ether lignan, 3-methylobovatol, has been achieved in four steps. This synthesis allows for modification of the C-2 phenol and in doing so, will facilitate various structure-activity relationship studies into these bioactive compounds.
Magnolol derivative, honokiol derivative, hydrochloride of honokiol derivative, preparation method and application
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Paragraph 0073-0074; 0084-0087, (2021/02/06)
The invention discloses a magnolol derivative, a honokiol derivative, hydrochloride of honokiol derivative, a preparation method and application of the honokiol derivative and the hydrochloride. The magnolol derivative, the honokiol derivative and the hydrochloride of the honokiol derivative have the structure shown in the following formula (I), and by applying the technical scheme provided by theinvention, the magnolol derivative, the honokiol derivative and the hydrochloride of the honokiol derivative are modularly prepared by utilizing a chemical synthesis method, namely a C14 atom markerand a D atom marker, the two compounds can be used for drug metabolism research of magnolol derivatives, honokiol derivatives and hydrochloride thereof. The problems caused by low drug recovery rate in the traditional drug metabolism experiment can be well solved by using the C14 marker, and the processes related to in-vivo absorption, distribution, metabolism and excretion of the drug can be conveniently clarified.
Synthesis and Structural Revision of Glyphaeaside C
Byatt, Brendan J.,Kato, Atsushi,Pyne, Stephen G.
supporting information, p. 4029 - 4033 (2021/05/29)
The iminosugar core of natural glyphaeaside C, originally assigned as a derivative of the piperidine natural product 1-deoxynojirimycin (DNJ), has been revised as a derivative of 2,5-dideoxy-2,5-imino-l-mannitol (l-DMDP) by the total synthesis of its enantiomer. This revised l-DMDP-derived configuration is the first of its kind to be observed in nature. The prepared iminosugars displayed the nanomolar inhibition of bovine liver β-glucosidase and β-galactosidase.
Nickel-catalyzed reductive deoxygenation of diverse C-O bond-bearing functional groups
Cook, Adam,MacLean, Haydn,St. Onge, Piers,Newman, Stephen G.
, p. 13337 - 13347 (2021/11/20)
We report a catalytic method for the direct deoxygenation of various C-O bond-containing functional groups. Using a Ni(II) pre-catalyst and silane reducing agent, alcohols, epoxides, and ethers are reduced to the corresponding alkane. Unsaturated species including aldehydes and ketones are also deoxygenated via initial formation of an intermediate silylated alcohol. The reaction is chemoselective for C(sp3)-O bonds, leaving amines, anilines, aryl ethers, alkenes, and nitrogen-containing heterocycles untouched. Applications toward catalytic deuteration, benzyl ether deprotection, and the valorization of biomass-derived feedstocks demonstrate some of the practical aspects of this methodology.
Structure–Activity Relationship of Anti-malarial Allylpyrocatechol Isolated from Piper betle
Horii, Toshihiro,Itagaki, Sawako,Kawano, Tomikazu,Miyoshi, Akihito,Murakami, Nobutoshi,Tamura, Satoru
, p. 784 - 790 (2020/09/18)
Malaria disease remains a serious worldwide health problem. In South-East Asia, one of the malaria infection “hot-spots,” medicinal plants such as Piper betle have traditionally been used for the treatment of malaria, and allylpyrocatechol (1), a constituent of P. betle, has been shown to exhibit anti-malarial activities. In this study, we verified that 1 showed in vivo anti-malarial activity through not only intraperitoneal (i.p.) but also peroral (p.o.) administration. Additionally, some analogs of 1 were synthesized and the structure–activity relationship was analyzed to disclose the crucial sub-structures for the potent activity.
Chemoselective rearrangement reactions of sulfur ylide derived from diazoquinones and allyl/propargyl sulfides
Zhou, Cong-Ying,Yan, Sijia,Rao, Junxin
, p. 9091 - 9096 (2020/12/02)
Here, we describe three types of rearrangement reactions of sulfur ylide derived from diazoquinones and allyl/ propargyl sulfides. With Rh2(esp)2 as the catalyst, diazoquinones react with allyl/propargyl sulfides to form a sulfur ylide, which undergoes a chemoselective tautomerization/[2,3]-sigmatropic rearrangement reaction, a Doyle?Kirmse rearrangement/Cope rearrangement cascade reaction, or a Doyle?Kirmse rearrangement/elimination reaction, depending on the substituent of the sulfides. The protocol provides alkenyl and allenyl sulfides and multisubstituted phenols with moderate and high yields.
MIDA boronate allylation-synthesis of ibuprofen
Brodie, Glen,France, David J.,Memarzadeh, Sarah,Phillips, David,Tang, Gi Lum
, p. 30624 - 30630 (2020/09/11)
MIDA boronates are among the most useful reagents for the Suzuki-Miyaura reaction. This chemistry typically generates new bonds between two aromatic rings, thereby restricting access to important areas of chemical space. Here we demonstrate the coupling of MIDA boronates to allylic electrophiles, including a new synthesis of the well-known COX inhibitor ibuprofen. This journal is
Cleavage of Catechol Monoalkyl Ethers by Aluminum Triiodide-Dimethyl Sulfoxide
Sang, Dayong,Tian, Juan,Tu, Xiaodong,He, Zhoujun,Yao, Ming
, p. 704 - 712 (2019/01/23)
Using eugenol and vanillin as model substrates, a practical method is developed for the cleavage o -hydroxyphenyl alkyl ethers. Aluminum oxide iodide (O=AlI), generated in situ from aluminum triiodide and dimethyl sulfoxide, is the reactive ether cleaving species. The method is applicable to catechol monoalkyl ethers as well as normal phenyl alkyl ethers for the removal of methyl, ethyl, isopropyl, and benzyl groups. A variety of functional groups such as alkenyl, allyl, amide, cyano, formyl, keto, nitro, and halogen are well tolerated under the optimum conditions. Partial hydrodebromination was observed during the demethylation of 4-bromoguaiacol, and was resolved using excess DMSO as an acid scavenger. This convenient and efficient procedure would be a practical tool for the preparation of catechols.
Carbonylative Transformation of Allylarenes with CO Surrogates: Tunable Synthesis of 4-Arylbutanoic Acids, 2-Arylbutanoic Acids, and 4-Arylbutanals
Wu, Fu-Peng,Li, Da,Peng, Jin-Bao,Wu, Xiao-Feng
supporting information, p. 5699 - 5703 (2019/08/01)
In this Communication, procedures for the selective synthesis of 4-arylbutanoic acids, 2-arylbutanoic acids, and 4-arylbutanals from the same allylbenzenes have been developed. With formic acid or TFBen as the CO surrogate, reactions proceed selectively and effectively under carbon monoxide gas-free conditions.
Ether bond cracking method of phenylalkyl ether
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Paragraph 0169-0171, (2018/11/26)
The invention discloses an ether bond cracking method of phenylalkyl ether. The method comprises the following steps: performing ether bond breaking reaction on phenylalkyl ether at -20 to reflux temperature in the presence of aluminium triiodide and dimethyl sulfoxide, thereby generating phenol and derivatives thereof. The method disclosed by the invention is mild in condition, simple and convenient for operation, high in yield, and extensive in applicable phenylalkyl ether range.
