881-68-5Relevant articles and documents
Visible-Light-Promoted Biomimetic Reductive Functionalization of Quaternary Benzophenanthridine Alkaloids
Cheng, Pi,Liu, Wei,Liu, Yisong,Reiser, Oliver,Wang, Lin,Wang, Wei,Wang, Xinhao,Xie, Hongqi,Zeng, Jianguo
, p. 2390 - 2397 (2021/08/20)
Reduction of an iminium C=N double bond is the most important phase I metabolism process associated with the cytotoxic property of quaternary benzophenanthridine alkaloids (QBAs). Inspired by the light-mediated reduction of QBAs with nicotinamide adenine dinucleotide, a visible-light-promoted reductive functionalization reaction of QBAs is reported in this study. C4-Alkyl-1,4-dihydropyridines (DHPs) enable the direct reductive alkylation of QBA independently, serving as both single-electron-transfer reductant reagents under irradiation with 455 nm blue light in the absence of photocatalysts and additional additives. Our protocol can be further applied to the semisynthesis of natural 6-substituted dihydrobenzophenanthridine derivatives such as O-acetyl maclekarpine E.
Molecular dynamics simulation, synthesis and topoisomerase inhibitory actions of vanillin derivatives: a systematic computational structural integument
Dehury, Budheswar,Padhy, Rabindra Nath,Paidesetty, Sudhir Kumar,Sahoo, Chita Ranjan,Sarathbabu, Subbarayan,Senthil Kumar, Nachimuthu
, (2021/08/12)
A series of 4-hydroxy-3-methoxy benzaldehyde (vanillin) derivatives (3a–3r) was designed for the principle of Schiff base condensation with several individual sulfanilamide analogues. The inhibitory potencies of the designed compounds were evaluated through molecular docking simulation studies against the targets, breast cancer-topo isomerase-IIα and estrogen receptor-α; and the top scoring poses with higher binding energy were selected to assess the mode of binding and stability of each complex through molecular dynamics simulations. Compounds that remained stable in the active sites of the both target receptors through a number of strong H-bonds and hydrophobic contacts were selected. Based on the computational results, these selected compounds, 3b, 3e and 3f were synthesized and were followed up for structural elucidation attempts, by FT/ATR, 1H NMR and 13C NMR. From the experimental in vitro studies on 3b, 3e and 3f, the following remarkable activities against breast cancer cell line were done; IC50 values of 3b, 3e and 3f were noted, 6.7, 4.3 and 11 ng/mL, respectively. These newly synthesized compounds may be used as novel inhibitors of nuclear receptors with potential therapeutic applications in control of cancer. Communicated by Ramaswamy H. Sarma.
Synthesis of task-specific imidazolium ionic liquid as an efficient catalyst in acetylation of alcohols, phenols, and amines
Chaubey, Snehkrishn A.,Mishra, Roli
, p. 3259 - 3268 (2020/04/17)
Herein, we report the synthesis of task-specific amino-functionalized imidazolium ionic liquid, acetate1-(2-tert-butoxycarbonylamino-ethyl)-3-methyl-3H-imidazol-1-ium; (Boc-NH-EMIM.OAc), as an efficient catalyst for the acetylation of alcohols, phenols, and amines in the presence of acetic anhydride (acetylating reagent). Remarkably, acetic anhydride in the presence of 10?molpercent of catalyst (Boc-NH-EMIM.OAc) under solvent-free conditions showed excellent acetylation activity in shorter duration of time. On the basis of this, a general procedure for acetylation of alcohols, phenols, and amines has been developed. The ionic liquid (Boc-NH-EMIM.OAc) can be readily recovered and reused successfully up to four consecutive cycles without any significant loss of its catalytic activity. We have been able to show that this acetylating method has many advantages. It gives high yields, takes shorter time, and develops the possibility of benign environmental-friendly process.
A metal-free heterogeneous photocatalyst for the selective oxidative cleavage of CC bonds in aryl olefins: via harvesting direct solar energy
Das, Shoubhik,Hatami, Nareh,Jooss, Christian,Lange, Niklas Simon,Ronge, Emanuel,Schilling, Waldemar,Zhang, Yu
supporting information, p. 4516 - 4522 (2020/08/10)
Selective cleavage of CC bonds is highly important for the synthesis of carbonyl containing fine chemicals and pharmaceuticals. Novel methodologies such as ozonolysis reactions, Lemieux-Johnson oxidation reaction etc. already exist. Parallel to these, catalytic methods using homogeneous catalysts also have been discovered. Considering the various advantages of heterogeneous catalysts such as recyclability and stability, couple of transition metal-based heterogeneous catalysts have been applied for this reaction. However, the pharmaceutical industries prefer to use metal-free catalysts (especially transition metal-free) to avoid further leaching in the final products. This is for sure a big challenge to an organic chemist and to the pharmaceutical industries. To make this feasible, a mild and efficient protocol has been developed using polymeric carbon nitrides (PCN) as metal-free heterogeneous photocatalysts to convert various olefins into the corresponding carbonyls. Later, this catalyst has been applied in the gram scale synthesis of pharmaceutical drugs using direct solar energy. Detailed mechanistic studies revealed the actual role of oxygen, the catalyst, and the light source.
Improved Pd/Ru metal supported graphene oxide nano-catalysts for hydrodeoxygenation (HDO) of vanillyl alcohol, vanillin and lignin
Arora, Shalini,Gupta, Neeraj,Singh, Vasundhara
supporting information, p. 2018 - 2027 (2020/04/07)
Pd and Ru nanoparticles supported on graphene oxide (GO) [Pd?GO and Ru?GO] and bimetallic [Pd/Ru?GO] were prepared and well characterized by XRD, FT-IR, EDS, TEM, XPS and ICP-AES analyses. The prepared nano-catalysts were tested for hydrodeoxygenation (HDO) of lignin monomer molecules-vanillyl alcohol and vanillin. In comparison with previously reported methods, Ru?GO and bimetallic Pd/Ru?GO catalysts showed high activity and selectivity, under milder conditions, at room temperature and 145 psi H2 pressure, for the formation of p-creosol, a value added product, as a potential future biofuel with antibacterial and anti-insecticidal properties. The multifold advantages of both these catalysts are in terms of reduced catalyst loading with a lower metal content and ambient temperture conditions resulting in higher conversion of the starting material. Furthermore, the efficacy of the developed methodology using Ru?GO and bimetallic Pd/Ru?GO catalysts under the optimized conditions was tested on the phenolic components of commercial lignin obtained by photo-catalytic fragmentation using TiO2, to obtain a mixture after HDO which contained vanillyl alcohol and p-creosol among others, as indicated by HPLC-MS analysis.
Convergent First Total Synthesis of Melovinone: A Densely Substituted 3-Methoxy-4-quinolone Isolated from Melochia tomentosa L
Aguilar, Abel A. Arroyo,Kaufman, Teodoro S.,Larghi, Enrique L.,Ledesma, Gabriela N.,Tirloni, Bárbara
, p. 4253 - 4262 (2019/11/14)
The first total synthesis of melovinone, a nonrutaceous 3-methoxy-4-quinolone alkaloid isolated from Melochia tomentosa L., is reported. The target was acquired in a convergent fashion through the Suzuki-Miyaura cross-coupling reaction between an ortho-nitrobenzoic acid acetonyl ester derivative prepared from vanillin and potassium 5-phenyl-1-pentyltrifluoroborate, obtained from β-phenethyl bromide. The coupling was followed by a chemoselective reduction of the nitro group and a microwave-Assisted and AcOH-promoted cyclization with rearrangement of the resulting acetonyl anthranilate. This afforded a pseudane intermediate, which was selectively methylated on the 3-OH. The synthetic pathway enabled to reach the objective in 11 steps and 18% overall yield. The 1 H NMR spectra of the synthetic and natural product were in full agreement.
Unprecedented acetylation of phenols using a catalytic amount of magnesium powder
Bajracharya, Gan B.,Shrestha, Suryaman Sama
supporting information, p. 1688 - 1693 (2018/06/15)
The acetylation of phenols with acetic anhydride was achieved using a catalytic amount of magnesium metal powder under air and solvent-free conditions to afford corresponding phenyl acetates in excellent yield (up to 98%).
EASILY DECOMPOSABLE LIGNIN GENERATOR
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Paragraph 0080; 0084; 0085, (2018/02/22)
PROBLEM TO BE SOLVED: To provide an easily decomposable lignin generator containing a compound that can be introduced to a structure of lignin and can make lignin easily decomposable. SOLUTION: The easily decomposable lignin generator contains a compound represented by general formula (1), where R1 to R3 are identical or different and each represent a hydrogen atom, alkoxy group or alkyl group, R4 represents an organic group, and n represents an integer from 0 to 3. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPO&INPIT
Method for preparing aspirin vanillin ester
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Paragraph 0023; 0024; 0025, (2018/09/21)
The invention belongs to the field of medicine preparation and in particular relates to a method for preparing aspirin vanillin ester. The method comprises the following steps: dissolving aspirin andvanillin into a solvent of 0 DEG C, adding a catalyst, keeping the temperature of 0 DEG C, and uniformly stirring and mixing; adding dicyclohexyl carbodiimide to implement a reaction; after the reaction is completed, performing depressurized suction filtration on the reaction liquid, and performing depressurized concentration on the filtrate till the filtrate is dried so as to obtain a crude product of an aspirin derivative; purifying the crude product through column chromatography, thereby obtaining the aspirin vanillin ester. By adopting the method, combination principles are reasonably utilized, the aspirin and the vanillin are adopted as substrate, the aspirin vanillin ester is prepared through DCC (Deep Catalytic Cracking) dehydration condensation, and the method is simple and convenient and green and environmental-friendly.
BORON-CONTAINING SMALL MOLECULES
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Paragraph 0294, (2017/09/19)
Compounds, pharmaceutical formulations, and methods of treating bacterial infections are disclosed.
