621-54-5Relevant academic research and scientific papers
Rhodium(III)-Catalyzed Meta-Selective C-H Alkenylation of Phenol Derivatives
Mi, Rui-Jie,Sun, Yong-Zhen,Wang, Jing-Yun,Sun, Jing,Xu, Zhaoqing,Zhou, Ming-Dong
supporting information, p. 5126 - 5129 (2018/09/12)
Rhodium(III)-catalyzed remote meta-selective-C-H alkenylation of phenol derivatives has been developed using a traceless organosilicon template as the directing group. This transformation proceeds smoothly with good yields and high meta-selectivities toward a series of phenol and alkene substrates. In addition, this protocol provides an effective strategy for late-stage transformations of various meta-alkenylated aromatic compounds.
Improved and large-scale synthesis of 10-methyl-aplog-1, a potential lead for an anticancer drug
Kikumori, Masayuki,Yanagita, Ryo C.,Irie, Kazuhiro
, p. 9776 - 9782 (2015/01/09)
10-Methyl-aplog-1 (1), a simplified analog of tumor-promoting aplysiatoxin, is a potential lead for cancer therapy that exhibits marked and selective growth inhibitory effects against several human cancer cell lines and negligible tumor-promoting activity in vivo. However, more detailed evaluations of its toxicity and anticancer activity in vivo are hampered by supply problems associated with a non-optimal synthetic method. We here addressed this issue through a more practical and reliable synthetic method that afforded several hundred milligrams of 1 with high purity (>98%) in 23 steps from commercially available m-hydroxycinnamic acid with an overall yield of 1.1%. The utilization of two key reactions, substrate-controlled epoxidation and the oxidative cleavage of alkene with a free hydroxyl group, successfully reduced the existing five synthetic steps and markedly improved the handling of large amounts of intermediates. We also demonstrated for the first time that such an analog was synthetically accessible in reliable quantities and also that this large supply could advance in vivo trials for the treatment of cancer.
A biocompatible alkene hydrogenation merges organic synthesis with microbial metabolism
Sirasani, Gopal,Tong, Liuchuan,Balskus, Emily P.
supporting information, p. 7785 - 7788 (2014/08/05)
Organic chemists and metabolic engineers use orthogonal technologies to construct essential small molecules such as pharmaceuticals and commodity chemicals. While chemists have leveraged the unique capabilities of biological catalysts for small-molecule production, metabolic engineers have not likewise integrated reactions from organic synthesis with the metabolism of living organisms. Reported herein is a method for alkene hydrogenation which utilizes a palladium catalyst and hydrogen gas generated directly by a living microorganism. This biocompatible transformation, which requires both catalyst and microbe, and can be used on a preparative scale, represents a new strategy for chemical synthesis that combines organic chemistry and metabolic engineering. Reduction to practice: A hydrogenation reaction has been developed that employs hydrogen generated in situ by a microorganism and a biocompatible palladium catalyst to reduce alkenes on a synthetically useful scale. This type of transformation, which directly combines tools from organic chemistry with the metabolism of a living organism for small-molecule production, represents a new strategy for chemical synthesis.
Synthesis and evaluation of dimeric 1,2,3,4-Tetrahydro-naphthalenylamine and Indan-1-ylamine derivatives with mast cell-stabilising and anti-allergic activity
Barlow, James W.,Walsh, John J.
scheme or table, p. 25 - 37 (2010/03/04)
In a continuation of our studies into 4-Amino-3,4-dihydro-2H-naphthalen-1-ones as novel modulators of allergic and inflammatory phenomena, we have extended our work to include dimeric analogues. Of these derivatives, the most promising activity was seen with tertiary amine 58a, which exhibited potent mast cell-stabilising activity in vitro against a variety of stimuli and also in vivo against passive cutaneous anaphylaxis.
First synthesis, characterization, and evidence for the presence of hydroxycinnamic acid sulfate and glucuronide conjugates in human biological fluids as a result of coffee consumption
Fumeaux, Rene,Menozzi-Smarrito, Candice,Stalmach, Angelique,Munari, Caroline,Kraehenbuehl, Karin,Steiling, Heike,Crozier, Alan,Williamson, Gary,Barron, Denis
supporting information; experimental part, p. 5199 - 5211 (2010/12/25)
A systematic investigation of the human metabolism of hydroxycinnamic acid conjugates was carried out. A set of 24 potential human metabolites of coffee polyphenols has been chemically prepared, and used as analytical standards for unequivocal identifications. These included glucuronide conjugates and sulfate esters of caffeic, ferulic, isoferulic, m-coumaric and p-coumaric acids as well as their dihydro derivatives. A particular focus has been made on caffeic and 3,4-dihydroxyphenylpropionic acid derivatives, especially the sulfate conjugates, for which regioselective preparation was particularly challenging, and have so far never been identified as human metabolites. Ten out of the 24 synthesized conjugates have been identified in human plasma and/or urine after coffee consumption. A number of these conjugates were synthesized, characterized and detected as hydroxycinnamic acid metabolites for the first time. This was the case of dihydroisoferulic acid 3′-O-glucuronide, caffeic acid 3′-sulfate, as well as the sulfate and glucuronide derivatives of 3,4-dihydroxyphenylpropionic acid.
Conversion of dehydrodiferulic acids by human intestinal microbiota
Braune, Annett,Bunzel, Mirko,Yonekura, Reiko,Blaut, Michael
experimental part, p. 3356 - 3362 (2010/06/16)
Plant cell wall associated dehydrodiferulic acids (DFA) are abundant components of cereal insoluble dietary fibers ingested by humans. The ability of human intestinal microbiota to convert DFA was studied in vitro by incubating 8-O-4- and 5-5-coupled DFA with fecal suspensions. 8-O-4-DFA was completely degraded by the intestinal microbiota of the majority of donors, yielding homovanillic acid, 3-(3,4-dihydroxyphenyl)propionic acid, and 3,4-dihydroxyphenylacetic acid as the main metabolites. The transient formation of ferulic acid and presumably 3-(3-hydroxy-4-methoxyphenyl)pyruvic acid suggests an initial cleavage of the ether bond. In contrast to 8-O-4-DFA, the 5-5-coupled DFA was not cleaved into monomers by any of the fecal suspensions. Only the side chains were hydrogenated and the methoxy groups were demethylated. The cleavage of DFA by human intestinal microbiota, which depended on their coupling type, may affect both the bioavailability of DFA and the degradability of DFA-coupled fiber in the gut.
Structure-antifungal activity relationship of cinnamic acid derivatives
Bisogno, Fabricio,Mascoti, Laura,Sanchez, Cecilia,Garibotto, Francisco,Giannini, Fernando,Kurina-Sanz, Marcela,Enriz, Ricardo
experimental part, p. 10635 - 10640 (2009/11/30)
A structure-antifungal activity relationship (SAR) study of 22 related cinnamic acid derivatives was carried out. Attention was focused on the antifungal activities exhibited against Aspergillus flavus, Aspergillus terreus, and Aspergillus niger. (E)-3-(4-Methoxy-3-(3-methylbut-2-enyl)phenyl)acrylic acid (16) exhibited antifungal activity against A. niger, comparable to that of miconazole and a significant antifungal effect against A. flavus and A. terreus as well. A structure-activity relationship (SAR) study of related cinnamic acid derivatives has allowed a model to be proposed for the recognition of the minimal structural requirements for the antifungal effect in this series.
Structural modification of phenylpropanoid-derived compounds and the effects on their participation in redox processes
Russell, Wendy R.,Scobbie, Lorraine,Chesson, Andrew
, p. 2537 - 2546 (2007/10/03)
Oxidation and reduction processes are fundamental to many of the proposed mechanisms by which dietary phytochemicals are thought to exert protective effects against cardiovascular disease and some cancers. An understanding of the redox chemistry of these compounds is essential in assessing their potential to participate in these processes. Phenylpropanoid-derived compounds were selected and synthesised where required to represent many of the structural features found in this important group of compounds. Using electron paramagnetic resonance spectroscopy and computational chemistry a structure-redox activity relationship was obtained. Good correlation of computational and experimental results was observed for the mono-hydroxylated compounds. This demonstrated the value of computational chemistry in obtaining information about compounds, not readily available and the effect of electron delocalisation on parent radical stability. For compounds containing more than one hydroxyl, the relationship was found to be more complex. The importance of quinone formation in compounds containing more than one hydroxyl substituent was highlighted, as this was found to have a significant effect on stabilisation and therefore, their participation in redox processes.
A Rapid and Efficient Microwave-Assisted Synthesis of Substituted 3-Phenylpropionic Acids from Benzaldehydes in Minutes
Sharma, Anuj,Joshi, Bhupendra P.,Sinha, Arun K.
, p. 1186 - 1187 (2007/10/03)
A convenient, inexpensive, and efficient synthesis of 3-phenylpropionic acids (1a-1f) by reacting benzaldehyde (2a-2f) and malonic acid in acetic acid and piperidine into cinnamic acid (3a-3f) in 77 to 89% followed by its reduction with PdCl2 in the biphase of formic acid and aqueous sodium hydroxide is reported under microwave irradiation which utilizes short reaction time ranging 5 to 7 min to provide 1a-1f in moderate to high yield (69-86%) depending upon methoxy, methylenedioxy, and hydroxy groups present at the phenyl ring.
The heterocyclic ring fission and dehydroxylation of catechins and related compounds by Eubacterium sp. strain SDG-2, a human intestinal bacterium
Wang, Li-Quan,Meselhy, Meselhy Raga,Li, Yan,Nakamura, Norio,Min, Byung-Sun,Qin, Guo-Wei,Hattori, Masao
, p. 1640 - 1643 (2007/10/03)
A human intestinal bacterium, Eubacterium (E.) sp. strain SDG-2, was tested for its ability to metabolize various (3R)- and (3S)-flavan-3-ols and their 3-O-gallates. This bacterium cleaved the C-ring of (3R)- and (3S)flavan-3-ols to give 1,3-diphenylpropan-2-ol derivatives, but not their 3-O-gallates. Furthermore, E. sp. strain SDG-2 had the ability of p-dehydroxylation in the B-ring of (3R)-flavan-3-ols, such as (-)-catechin, (-)-epicatechin, (-)-gallocatechin and (-)-epigallocatechin, but not of (3S)-flavan-3-ols, such as (+)-catechin and (+)-epicatechin.
