97-51-8Relevant academic research and scientific papers
Synthesis, characterization, and photochromism study of two spiropyran molecules with a terminal alkynyl functional group and their new 1,2,3-triazoline-containing derivatives
Mahdavian, Ali Reza,Nasr-Isfahani, Hossein,Notash, Behrouz,Sepehr, Zeinalabedin
, (2021/10/19)
The spiropyran derivatives are known for their good photochromic properties. These photochromic compounds are isomerized between two forms; merocyanine is the open-ring form and spiropyran is the closed-ring form. In this work, two spiropyran derivatives (compounds 1 and 2) with the N-alkynyl functional group are prepared. The click reactions of these spiropyran derivatives with 1-azido-4-nitrobenzene and (azidomethyl)benzene are studied. For this purpose, 3,3-dimethyl-2-methylene-1-prop-2-ynyl-2,3-dihydro-1H-indole is synthesized, which is then reacted with 3- and 5-nitrosalicylaldehyde. The FT-IR, 1H-NMR, and 13C-NMR spectra of the reaction products are used for their characterization. The solutions of the products in methanol are prepared, and their UV–visible spectra are investigated. The darkening of the crystals of compound 1 upon exposure to the UV irradiation indicates that the spiro C–O bond in this compound is weaker than that in compound 2, which is due to the presence of the nitro group in the para position relative to this bond, and consequently, the stabilization of the open-ring form.
Phosphine-catalyzed sequential (2+3)/(2+4) annulation of γ-vinyl allenoates: Access to the synthesis of chromeno[4,3-: B] pyrroles
Huang, You,Li, Xiaohu
supporting information, p. 9934 - 9937 (2021/10/12)
A phosphine-catalyzed cascade (2+3)/(2+4) cyclization reaction of γ-vinyl allenoates with aldimine esters has been developed to provide a series of chromeno[4,3-b]pyrrole derivatives that contain three contiguous stereogenic centers. The method gives a good yield, excellent chemoselectivity and diastereoselectivity under mild conditions.
Method for synthesizing mesalazine
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Paragraph 0011; 0037-0040, (2020/08/25)
A method for synthesizing mesalazine is disclosed. The method comprises the following steps: 1) adding p-nitrophenol, p-toluenesulfonic acid, absolute ethyl alcohol and hexamethylenetetramine, stopping heating after the reaction is finished, heating to room temperature while stirring with ice water, separating out solids, filtering, washing and drying to obtain 5-nitrosalicylaldehyde; 2) adding the 5-nitrosalicylaldehyde, potassium tert-butoxide, copper salt and acetonitrile, adding tert-butyl hydroperoxide while stirring, after the reaction is finished, performing vacuum concentration to remove the solvent, pouring cold water into residues, stirring, performing suction filtration, adjusting the pH value of the filtrate with hydrochloric acid, performing suction filtration, and drying to obtain 5-nitrosalicylic acid; and 3) adding stannous chloride dihydrate, concentrated hydrochloric acid, the 5-nitrosalicylic acid and ethanol, carrying out vacuum concentration after the reaction is finished, dissolving residues in water, adjusting the pH value with a concentrated hydrochloric acid solution, standing for crystallization, carrying out suction filtration, washing filter cake with water, and drying to obtain mesalazine. No isomer is generated, and the yield is high; the method does not need high-temperature and high-pressure conditions; the reaction cost is low; and raw materialsand auxiliary materials with high toxicity and heavy environmental pollution are not used.
Method for synthesizing 5-nitrosalicylaldehyde
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Paragraph 0020; 0023-0039, (2020/10/04)
The invention discloses a method for synthesizing 5-nitrosalicylaldehyde. 5-nitrosalicylaldehyde is prepared by taking p-nitrophenol as a raw material and trifluoroacetic acid as a catalyst through animproved Duff reaction and hexamethylenetetramine reaction. Compared with a salicylaldehyde nitration method, the synthesis method provided by the invention effectively inhibits the generation of isomers in the synthesis process of 5-nitrosalicylaldehyde, and is convenient for separation and purification of a target product; the use of reaction raw materials with high toxicity and serious environmental pollution and high-temperature and high-pressure reaction conditions are avoided, the reaction conditions are mild, the post-treatment process is simple, the synthesis reaction efficiency is improved, and the yield of the 5-nitrosalicylaldehyde reaches 63% or above.
Catalytic oxidation of alcohols and alkyl benzenes to carbonyls using Fe3O4?SiO2?(TEMPO)-: Co -(Chlorophyll-CoIII) as a bi-functional, self-co-oxidant nanocatalyst
Hamah-Ameen, Baram Ahmed,Kazemnejadi, Milad,Mahmoudi, Boshra,Rostami, Amin
, p. 6600 - 6613 (2020/11/16)
Chlorophyll b was extracted from heliotropium europaeum plant, demetalated, allylated and grafted to acrylated TEMPO through a copolymerization protocol. Then, the chlorophyll monomers were coordinated to Co ions, immobilized on magnetic nanoparticles and the resulting hybrid was used as a powerful catalyst for a variety of oxidation reactions. By using the present method, oxidation of benzylic alcohols and alkyl benzenes to carbonyls was accomplished in water under aerobic conditions. Moreover, direct oxidation of alcohols to carboxylic acids was performed by adding NaOCl to the mixture. All entries were oxidized to the corresponding desired product with high to excellent yields and up to 97% selectivity. The catalyst was thoroughly characterized by CV, TGA, VSM, XRD, XPS, DLS, FE-SEM, TEM, UV-Vis, EDX, and BET analyses. The activity of the catalyst was investigated by applying various components of the catalyst to the oxidation model separately. The reasonable mechanisms are suggested based on the cooperation between the TEMPO groups and cobalt(iii) (or Co(iv)) sites on the catalyst. The catalyst could be recovered and reused for at least 7 consecutive recycles without any considerable reactivity loss. This journal is
Design, synthesis and preliminary biological evaluation of benzylsulfone coumarin derivatives as anti-cancer agents
Wang, Tao,Peng, Tao,We, Xiaoxue,Wang, Gang,Sun, Yunbo,Liu, Shuchen,Zhang, Shouguo,Wang, Lin
supporting information, (2019/11/20)
In this work, a series of benzylsulfone coumarin derivatives 5a-5o were synthesized and characterized. Kinase inhibitory activity assay indicated that most of the compounds showed considerable activity against PI3K. Anti-tumor activity studies of the active compounds were also carried out in vitro on the Hela, HepG2, H1299, HCT-116, and MCF-7 tumor cell lines by MTS assay. The structure-activity relationships (SARs) of these compounds were analyzed in detail. Compound 5h exhibited the most potent activities against the mentioned cell lines with IC50 values ranging from 18.12 to 32.60 μM, followed by 5m with IC50 values of 29.30-42.14 μM. Furthermore, 5h and 5m clearly retarded the migration of Hela cells in vitro. Next, an in silico molecular docking study was conducted to evaluate the binding models of 5h and 5m towards PI3Kαand PI3Kβ. Collectively, the above findings suggested that compounds 5h and 5m might be promising PI3K inhibitors deserving further investigation for cancer treatment.
Fe3O4@SiO2@Im[Cl]Mn(III)-complex as a highly efficient magnetically recoverable nanocatalyst for selective oxidation of alcohol to imine and oxime
Kazemnejadi, Milad,Alavi, Seyyedeh Ameneh,Rezazadeh, Zinat,Nasseri, Mohammad Ali,Allahresani, Ali,Esmaeilpour, Mohsen
, p. 230 - 249 (2019/03/28)
An efficient and environmentally friendly oxidation process for the one-pot preparation of oxime, imine and carbonyl compounds through alcohol oxidation in the presence of H2O2 and/or O2 have been developed by a melamine-Mn(III) Schiff base complex supported on Fe3O4@SiO2–Cl nanoparticles, named as Fe3O4@SiO2@Im[Cl]Mn(III)-complex nanocomposite, at room temperature. Direct oxidation of alcohol to carboxylic acid was performed using the catalyst in the presence of molecular O2 at room temperature in a different approach. The oxidation products were obtained with excellent yields and high TOFs. The properties of the catalyst were characterized by Fourier transform infrared spectroscopy (FTIR), elemental analysis (C, H, N), X-ray diffraction (XRD), field emission scanning electron microscopy (FE-SEM), dynamic light scattering (DLS), energy dispersive X-ray analysis (EDX), X-ray photoelectron spectroscopy (XPS), inductive coupled plasma (ICP), cyclic voltammetry (CV), nuclear magnetic resonance (1H & 13C NMR), vibration sample magnetometer (VSM), Brunauer– Emmett–Teller (BET) and differential pulse voltammetry (DPV) analyses. The mechanism of the oxidation processes was investigated for the both H2O2 and O2 oxidants. The role of the imidazolium moiety in the catalyst as a secondary functionality was investigated. Chemoselectivity behavior of the catalyst was studied by some combinations. The catalyst could be recycled from the reaction mixture by a simple external magnet and reused for several times without any considerable reactivity loss.
Light-activated cycle-reversible intramolecular charge transfer fluorescent probe: Monitoring of pHi trace change induced by UV light in programmed cell death
Jiang, Tao,Wang, Xin,Wang, Ge,Wang, Yafu,Wang, Kui,Xuan, Xiaopeng,Chen, Changpo,Jiang, Kai,Zhang, Hua
supporting information, p. 5279 - 5282 (2019/05/08)
Under the synergistic effects of protonation and deprotonation, a light-activated fluorescent probe (UV-SP) exhibited cycle-reversible intramolecular charge transfer (ICT) for different pH after activation by UV light, resulting in emission of multiple ratio fluorescent signals (FI563/FI595 and FI664/FI595). Based on these kinds of response signals, UV-SP can specifically monitor the cycle-reversible trace change of intracellular pH caused by UV radiation. More importantly, according to the stable and invariant multiple ratio fluorescent signals, UV-SP can sort cells entering programmed death.
Method of catalytically preparing 5-nitrosalicylaldehyde from heteropolyacid acidic ionic liquid
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Paragraph 0025; 0029-0034; 0038-0042, (2019/01/04)
The invention discloses a method of catalytically preparing 5-nitrosalicylaldehyde from a heteropolyacid acidic ionic liquid. According to the method, p-nitrophenol and hexamethylene tetramine are taken as the raw materials, a heteropolyacid acidic ionic liquid is taken as the catalyst to carry out reactions to prepare 5-nitrosalicylaldehyde; the yield of 5-nitrosalicylaldehyde can reach 90% or more, and the HPLC purity can reach 98.5%.
Co-immobilization of Laccase and TEMPO in the Compartments of Mesoporous Silica for a Green and One-Pot Cascade Synthesis of Coumarins by Knoevenagel Condensation
Mogharabi-Manzari, Mehdi,Amini, Mohsen,Abdollahi, Mohammad,Khoobi, Mehdi,Bagherzadeh, Ghodsieh,Faramarzi, Mohammad Ali
, p. 1542 - 1546 (2018/02/28)
Co-immobilization of bio- and chemocatalysts produces sustainable, recyclable hybrid systems that open new horizons for green cascade approaches in organic synthesis. Here, the co-immobilization of laccase and 2,2,6,6-tetramethylpiperidin-1-oxyl (TEMPO) in mesoporous silica was used for the one-pot aqueous synthesis of 30 coumarin-3-carboxylate derivatives under mild conditions through the condensation of in situ oxidized 2-hydroxybenzyl alcohols and malonate derivatives. A maximum yield was obtained after incubating at pH 6.0 and 45 °C for 24 h. An efficient organic synthesis was catalyzed by the hybrid catalyst in 10 % organic solvent. More than 95 % of the initial activity of the enzyme was preserved after 10 cycles, and no significant catalyst deactivation occurred after 10 runs. This new system efficiently catalyzed the in situ aerobic oxidation of salicyl alcohols, followed by Knoevenagel condensation, which confirmed the possibility of producing efficient hybrid catalysts by co-immobilization of catalytic species in mesoporous materials.
