2107-69-9Relevant articles and documents
Efficient demethylation of aromatic methyl ethers with HCl in water
Bomon, Jeroen,Bal, Mathias,Achar, Tapas Kumar,Sergeyev, Sergey,Wu, Xian,Wambacq, Ben,Lemière, Filip,Sels, Bert F.,Maes, Bert U. W.
supporting information, p. 1995 - 2009 (2021/03/26)
A green, efficient and cheap demethylation reaction of aromatic methyl ethers with mineral acid (HCl or H2SO4) as a catalyst in high temperature pressurized water provided the corresponding aromatic alcohols (phenols, catechols, pyrogallols) in high yield. 4-Propylguaiacol was chosen as a model, given the various applications of the 4-propylcatechol reaction product. This demethylation reaction could be easily scaled and biorenewable 4-propylguaiacol from wood and clove oil could also be applied as a feedstock. Greenness of the developed methodversusstate-of-the-art demethylation reactions was assessed by performing a quantitative and qualitative Green Metrics analysis. Versatility of the method was shown on a variety of aromatic methyl ethers containing (biorenewable) substrates, yielding up to 99% of the corresponding aromatic alcohols, in most cases just requiring simple extraction as work-up.
A metal-free method for the facile synthesis of indanonesviathe intramolecular hydroacylation of 2-vinylbenzaldehyde
He, Guoxue,Ma, Jinyu,Zhou, Jianhui,Li, Chunpu,Liu, Hong,Zhou, Yu
, p. 1036 - 1040 (2021/02/09)
A facile method for the synthesis of indanones was developed under metal- and additive-free conditions, whereinl-proline served as an efficient and environmentally benign catalyst. Compared with previously synthesized indanones, synthesis by the transition-metal-catalyzed intramolecular hydroacylation of 2-vinylbenzaldehyde provided a more green synthetic pathway to indanone scaffolds with good to excellent yields. More importantly, it could be used to synthsize the anti-AD drug donepezil.
Trifluoroacetic Anhydride Mediated One-Pot Synthesis of 1-Aryl Isochroman-3-ones via the Carboxy-Pictet-Spengler Reaction
Chang, Meng-Yang,Chen, Shin-Mei,Hsiao, Yu-Ting
, p. 11687 - 11698 (2019/10/02)
In this paper, a novel and open-vessel route for the facile-operational synthesis of 1-aryl isochroman-3-ones is described via (CF3CO)2O (trifluoroacetic anhydride, TFAA)-mediated intermolecular (4 + 2) annulation of oxygenated arylacetic acids with arylaldehydes or ketones under mild reaction conditions. A plausible mechanism is proposed and discussed herein. Various reaction conditions are investigated for efficient transformation under an environmentally friendly one-pot carboxy-Pictet-Spengler reaction.
Synthesis of various arylated trifluoromethyl substituted indanes and indenes, and study of their biological activity
Iakovenko, Roman O.,Chicca, Andrea,Nieri, Daniela,Reynoso-Moreno, Ines,Gertsch, Jürg,Krasavin, Mikhail,Vasilyev, Aleksander V.
supporting information, p. 624 - 632 (2019/01/04)
A series of 1-trifluoromethyl substituted indanes and indenes bearing aryl groups in positions 1 and/or 3 of the indane core have been synthesized mainly by electrophilic cyclization and arylation of the corresponding trifluoromethylated allyl and propargyl alcohols. The distinctly lipophilic compounds thus obtained were tested against various components of human endocannabinoid system. None of the compounds displayed affinity toward CB1 or CB2 receptors. Two compounds inhibited monoacylglycerol lipase (MAGL) and three compounds showed inhibition of anandamide (AEA) uptake. The latter can be related to the low-micromolar inhibition of fatty acid amide hydrolase (FAAH) inhibition displayed by one of these compounds.
Rigidification of a macrocyclic tris-catecholate scaffold leads to electronic localisation of its mixed valent redox product
Greatorex, Sam,Vincent, Kevin B.,Baldansuren, Amgalanbaatar,McInnes, Eric J. L.,Patmore, Nathan J.,Sproules, Stephen,Halcrow, Malcolm A.
supporting information, p. 2281 - 2284 (2019/02/27)
The catecholate groups in [{Pt(L)}3(μ3-tctq)] (H6tctq = 2,3,6,7,10,11-hexahydroxy-4b,8b,12b,12d-tetramethyltribenzotriquinacene; L = a diphosphine chelate) undergo sequential oxidation to their semiquinonate forms by voltammetry, with ΔE1/2 = 160-170 mV. The monoradical [{Pt(dppb)}3(μ3-tctq)]+ is valence-localised, with no evidence for intervalence charge transfer in its near-IR spectrum. This contrasts with previously reported [{Pt(dppb)}3(μ3-ctc)]+ (H6ctc = cyclotricatechylene), based on the same macrocyclic tris-dioxolene scaffold, which exhibits partly delocalised (class II) mixed valency.
Synthesis and antitumor activity of aza-brazilan derivatives containing imidazolium salt pharmacophores
Huang, Mingqin,Duan, Shengzu,Ma, Xueqiong,Cai, Bicheng,Wu, Dongmei,Li, Yan,Li, Liang,Zhang, Hongbin,Yang, Xiaodong
, p. 1027 - 1036 (2019/06/27)
The synthesis of a series of novel aza-brazilan derivatives containing imidazolium salt pharmacophores is presented. The biological activity of such imidazolium salts was further evaluated in vitro against a panel of human tumor cell lines. The results suggest that the electron-withdrawing group on the aza-brazilan moiety, substituted 5,6-dimethyl-benzimidazole ring and substitution of the imidazolyl-3-position with a 4-methylbenzyl group were essential for modulating the cytotoxic activity. Compounds 55 and 39, bearing a 4-methylbenzyl substituent at position-3 of 5,6-dimethyl-benzimidazole, were found to be the most potent compounds with IC50 values of 0.52-1.30 μM and 0.56-1.51 μM against four human tumor cell lines investigated. Particularly, compound 57 exhibited inhibitory activity against the MCF-7 cell line with an IC50 value of 0.35 μM and was 56-fold more sensitive than DDP. Moreover, compound 55 inhibited cell proliferation through inducing G0/G1 cell cycle arrest and apoptosis in SMMC-7721 cells.
Two novel donepezil-lipoic acid hybrids: Synthesis, anticholinesterase and antioxidant activities and theoretical studies
Terra, Bruna S.,Da Silva, Pedro H. C.,Tramarin, Anna,Franco, Lucas L.,Da Cunha, Elaine F. F.,Macedo, Fernando,Ramalho, Teodorico C.,Bartolini, Manuela,Bolognesi, Maria L.,De Fátima, ?ngelo
, p. 738 - 747 (2018/02/07)
Alzheimer disease (AD) is a complex disease related to multiple pathogenic mechanisms. A strategy to develop effective drugs is based on the so-called multi-Target directed ligands (MTDL) by using hybrid compounds. So, in the present study, we have designed and synthesized two hybrids, containing the indanone-piperidine moiety of donepezil, a drug approved for the treatment of AD, and the lipoic acid scaffold, an antioxidant compound endowed with neuroprotective effects. One hybrid was synthesized in four steps with 42percent global yield, and the other hybrid in six steps with 19percent global yield. The latter hybrid displayed moderate inhibitory activity against human acetylcholinesterase (hAChE) and greater activity against human butyrylcholinesterases (hBuChE). The selectivity for hBuChE was further rationalized by theoretical study. Importantly, the second hybrid showed a good antioxidant activity, exhibiting better ability in scavenging 2,2-diphenyl- 1 picrylhydrazyl (DPPH) radicals than lipoic acid.
METHOD FOR PREPARING INDENOISOQUINOLINE DERIVATIVES
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Paragraph 0056, (2019/03/30)
A method for preparing indenoisoquinoline derivatives represented by the following formula (I) is disclosed, which comprises the following steps: (A) providing a first reactant represented by the following formula (II) and a second reactant represented by the following formula (III): wherein, R1, R3, A, X, Y, Z, m and n are defined in the specification; and (B) reacting the first reactant represented by the formula (II) and the second reactant represented by the formula (III) in a solvent and selectively adding R2NH2 therein, to obtain the indenoisoquinoline derivatives represented by the formula (I).
Design, synthesis, molecular docking, and in vitro antidiabetic activity of novel PPARγ agonist
Chaturvedi, Radha Nandan,Pendem, Krishnaiah,Patel, Vipul P.,Sharma, Mukta,Malhotra, Sunita
, p. 2069 - 2084 (2018/08/22)
Abstract: The present work describes the design, synthesis, molecular docking, biological evaluation, and assessment of structure–activity relationship of new derivatives based upon the molecular skeleton of the drug pioglitazone, a compound which is currently used for the management of type 2 diabetes mellitus. Pioglitazone has several side effects such as weight gain, edema, congestive heart failure, and bladder cancer. Therefore, there is a strong demand for identification of new lead candidates in the treatment of type 2 diabetes mellitus. A series of 24 compounds were prepared and evaluated for their peroxisome proliferator-activated receptor-γ (PPARγ) binding affinity assay and the IC50 values were determined. Among these compounds, six compounds exhibited promising IC50 values as compared to standard drugs pioglitazone and rosiglitazone. Furthermore, in order to confirm the target of these molecules, molecular docking study was carried out with peroxisome proliferator-activated receptor-γ (PPARγ) protein. Molecular modeling studies suggested that these compounds appropriately interact in the active sites of receptor. Graphical abstract: [Figure not available: see fulltext.].
Design, Synthesis, and Evaluation of Donepezil-Like Compounds as AChE and BACE-1 Inhibitors
Costanzo, Paola,Cariati, Luca,Desiderio, Doriana,Sgammato, Roberta,Lamberti, Anna,Arcone, Rosaria,Salerno, Raffaele,Nardi, Monica,Masullo, Mariorosario,Oliverio, Manuela
supporting information, p. 470 - 475 (2016/06/01)
An ecofriendly synthetic pathway for the synthesis of donepezil precursors is described. Alternative energy sources were used for the total synthesis in order to improve yields, regioselectively, and rate of each synthetic step and to reduce the coproduction of waste at the same time. For all products, characterized by an improved structural rigidity respect to donepezil, the inhibitor activity on AChE, the selectivity vs BuChE, the side-activity on BACE-1, and the effect on SHSY-5Y neuroblastoma cells viability were tested. Two potential new lead compounds for a dual therapeutic strategy against Alzheimers disease were envisaged.
