20009-25-0Relevant academic research and scientific papers
Synthesis and biological evaluation of 7-deoxy analogues of the human rhinovirus 3c protease inhibitor thysanone
Schuenemann, Katrin,Furkert, Daniel P.,Connelly, Stephen,Fraser, John D.,Sperry, Jonathan,Brimble, Margaret A.
, p. 122 - 128 (2014)
The synthesis of (±)-7-deoxythysanone and three analogues has been developed. The key oxa-Pictet-Spengler reaction enabled the synthesis of the naphthopyran precursor, which could be readily converted to 7-deoxythysanone and three related analogues. The biological activity of these compounds was also evaluated against HRV 3C protease, the results of which suggest that inhibition of the enzyme requires the presence of the 7-oxa functionality. Several 7-deoxy analogues of the 3C protease inhibitor thysanone have been synthesised by using an oxa-Pictet-Spengler reaction as the key step. The biological activity of these compounds was also evaluated against human rhinovirus (HRV) 3C protease, the results of which suggest that inhibition of the enzyme requires the presence of the 7-oxa functionality. Copyright
Oxidative amidation in the naphthalene series
Jain, Nikita,Ciufolini, Marco A.
, p. 631 - 634 (2015)
The successful oxidative spirocyclization of 1- or 2-naphtholic sulfonamides extends oxidative amidation methods to the naphthalene series. A method to prepare N-unsubstituted spirolactam derivatives of 1-naphthol is also presented.
Design and synthesis of 2,3-dihydro- and 5-chloro-2,3-dihydro-naphtho-[1,2-b]furan-2-carboxylic acid N-(substitutedphenyl)amide analogs and their biological activities as inhibitors of NF-κB activity and anticancer agents
Choi, Minho,Jo, Hyeju,Kim, Dayoung,Yun, Jieun,Kang, Jong-Soon,Kim, Youngsoo,Jung, Jae-Kyung,Hong, Jin Tae,Cho, Jungsook,Kwak, Jae-Hwan,Lee, Heesoon
, p. 618 - 630 (2016)
A series of 2,3-dihydro- and 5-chloro-2,3-dihydro-naphtho-[1,2-b]furan-2-carboxylic acid N-(substitutedphenyl)amide analogs (1a–k and 2a–i) were designed and synthesized for developing novel naphthofuran scaffolds as anticancer agents and inhibitors of NF-κB activity. Compound 1d, which had a 4′-chloro group on the N-phenyl ring, exhibited inhibitory activity of NF-κB. Compound 2g, which had a 5′-chloro group on the naphthofuran ring and a 3′,5′-bistrifluoromethane group on the N-phenyl ring, had the best NF-κB inhibitory activity. In addition, the novel analogs exhibited potent cytotoxicity at low concentrations against HCT-116, NCI-H23, and PC-3 cell lines. The two electron-withdrawing groups, especially at the 3′,5′-position on the N-phenyl ring, increased anticancer activity and NF-κB inhibitory activity. However, only 5-chloro-2,3-dihydronaphtho[1,2-b]furan-2-carboxylic N-(3′,5′-bis(trifluoromethyl)phenyl)amide (2g) exhibited both outstanding cytotoxicity and NF-κB inhibitory activities. This novel lead scaffold may be helpful for investigation of new anticancer agents by inactivation of NF-κB.
Solid composite copper-copper chloride assisted alkylation of naphthols promoted by microwave irradiation
Zadmard,Aghapoor,Bolourtchian,Saidi
, p. 4495 - 4499 (1998)
Naphthyl ethers and naphthyl esters were synthesized in good yield by using mixture of copper metal powder and copper (II) chloride in conventional microwave oven in short time.
Bismuth triflate catalyzed Claisen rearrangement of allyl naphthyl ethers
Ollevier, Thierry,Mwene-Mbeja, Topwe M.
, p. 4051 - 4055 (2006)
Bismuth triflate was found to be an efficient catalyst for the Claisen rearrangement of allyl naphthyl ethers. The reaction proceeds smoothly with a catalytic amount of bismuth triflate (20 mol %) to afford the corresponding ortho-allyl naphthol in moderate to good yields in most cases.
Nickel-catalyzed deallylation of aryl allyl ethers with hydrosilanes
Ding, Guangni,Fan, Sijie,Wang, Jingyang,Wang, Yu,Wu, Xiaoyu,Xie, Xiaomin,Yang, Liqun,Zhang, Zhaoguo
supporting information, (2021/09/28)
An efficient and mild catalytic deallylation method of aryl allyl ethers is developed, with commercially available Ni(COD)2 as catalyst precursor, simple substituted bipyridine as ligand and air-stable hydrosilanes. The process is compatible with a variety of functional groups and the desired phenol products can be obtained with excellent yields and selectivity. Besides, by detection or isolation of key intermediates, mechanism studies confirm that the deallylation undergoes η3-allylnickel intermediate pathway.
Highly Deformed o-Carborane Functionalised Non-linear Polycyclic Aromatics with Exceptionally Long C?C Bonds
Marsh, Adam V.,Little, Mark,Cheetham, Nathan J.,Dyson, Matthew J.,Bidwell, Matthew,White, Andrew J. P.,Warriner, Colin N.,Swain, Anthony C.,McCulloch, Iain,Stavrinou, Paul N.,Heeney, Martin
supporting information, p. 1970 - 1975 (2020/12/25)
The effect of substituting o-carborane into the most sterically hindered positions of phenanthrene and benzo(k)tetraphene is reported. Synthesised via a Bull–Hutchings–Quayle benzannulation, the crystal structures of these non-linear acenes exhibited the highest aromatic deformation parameters observed for any reported carborane compound to date, and among the largest carboranyl C?C bond length of all organo-substituted o-carboranes. Photoluminescence studies of these compounds demonstrated efficient intramolecular charge-transfer, leading to aggregation induced emission properties. Additionally, an unusual low-energy excimer was observed for the phenanthryl compound. These are two new members of the family of carborane-functionalised non-linear acenes, notable for their peculiar structures and multi-luminescent properties.
Preparation method 3 - phenoxybromopropane or analogue thereof
-
Paragraph 0054-0056, (2021/11/26)
The invention discloses a preparation method of 3 -phenoxybromopropane or an analogue thereof, wherein 3 - phenoxybromopropane and an allyl compound thereof are obtained through substitution reaction and addition reaction so as to avoid the inconvenience of using gaseous hydrogen bromide, 2nd-step addition reaction is realized by using the brominated salt and the acid in situ, and the process is simple in operation. The condition is easy to control, the atom economy is good, the aspect of environmental impact is low pollution, zero emission accords with the current green chemical synthesis direction, and the cost is economic.
Investigating the microwave-accelerated Claisen rearrangement of allyl aryl ethers: Scope of the catalysts, solvents, temperatures, and substrates
Hui, Zi,Jiang, Songwei,Qi, Xiang,Ye, Xiang-Yang,Xie, Tian
supporting information, (2020/05/18)
The microwave-accelerated Claisen rearrangement of allyl aryl ethers was investigated, in order to gain insight into the scope of the catalysts, solvents, temperatures, and substrates. Among the catalysts examined, phosphomolybdic acid (PMA) was found to greatly accelerate the reaction in NMP, at temperatures ranging from 220 to 300 °C. This method was found to be useful for preparing several intermediates previously reported in the literature using precious metal catalysts such as Au(I), Ag(I), and Pt(II). Additionally, substrates bearing bromo and nitro groups on the aryl portion required careful tailoring of the reaction conditions to avoid complex product profiles.
Enantioselective Construction of Si-Stereogenic Center via Rhodium-Catalyzed Intermolecular Hydrosilylation of Alkene
He, Tao,Liu, Li-Chuan,Ma, Wen-Peng,Li, Bin,Zhang, Qing-Wei,He, Wei
supporting information, p. 17011 - 17015 (2020/11/30)
Catalytic, enantioselective synthesis of stereogenic silicon compounds remains a challenge. Herein, we report a rhodium-catalyzed regio- and enantio-selective intermolecular hydrosilylation of alkene with prochiral dihydrosilane. This new method features a simple catalytic system, mild reaction conditions and a wide functional group tolerance.
