- Ni-Catalyzed Cycloisomerization between 3-Phenoxy Acrylic Acid Derivatives and Alkynes via Intramolecular Cleavage and Formation of the C-O Bond to Give 2,3-Disubstituted Benzofurans
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Reactions based on transition-metal-catalyzed C-O bond cleavage have attracted much attention as a new synthetic method. Until now, several intermolecular reactions via C-O bond cleavage of aryl ethers, alkenyl ethers, esters, and others have been reported. Here we report an unprecedented C-O bond cleavage of 3-phenoxy acrylic acid derivatives, followed by intramolecular C-O bond formation with alkynes. This reaction gave 2,3-disubstituted benzofurans having useful functional groups-silyl substituents and acrylic acid derivatives- A t the 2- A nd 3-positions, respectively. This report also described theoretical (DFT) insights into the mechanism.
- Ohno, Shohei,Qiu, Jiawei,Miyazaki, Ray,Aoyama, Hiroshi,Murai, Kenichi,Hasegawa, Jun-Ya,Arisawa, Mitsuhiro
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supporting information
p. 8400 - 8403
(2019/10/14)
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- Expanding the Reactivity of Donor-Acceptor Cyclopropanes: Synthesis of Benzannulated Five-Membered Heterocycles via Intramolecular Attack of a Pendant Nucleophilic Group
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Lewis-acid-induced domino transformations of donor-acceptor cyclopropanes, possessing a nucleophilic center embedded in a donor group, into functionalized 2,3-dihydrobenzo[b]furans and 2,3-dihydrobenzo[b]thiophenes are reported herein. An unusual switch o
- Ivanova, Olga A.,Andronov, Vladimir A.,Vasin, Vladimir S.,Shumsky, Alexey N.,Rybakov, Victor B.,Voskressensky, Leonid G.,Trushkov, Igor V.
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supporting information
p. 7947 - 7952
(2019/01/04)
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- Benzofuran quinolone derivative and application of benzofuran quinolone derivative in preparation of medicine for treating Alzheimer's disease
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The invention discloses a benzofuran quinolone derivative and application of the benzofuran quinolone derivative in preparation of a medicine for treating Alzheimer's disease. The benzofuran quinolone derivative is a multiple target point active molecule for resisting the Alzheimer's disease, has inhibitory activity of phosphodiesterase 4D and also has functions of resisting oxidation, inhibiting A beta aggregation and depolymerizing; animal experimental results show that the benzofuran quinolone derivative disclosed by the invention has efficacies of improving cognitive ability and spatial memory of rats with the Alzheimer's disease, protecting brain hippocampal neuronal cells of the rats with the Alzheimer's disease, and inhibiting the loss and necrosis of neuronal cells.
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Paragraph 0035; 0036; 0046-0048
(2016/10/10)
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- Design, synthesis, and evaluation of orally available clioquinol-moracin M hybrids as multitarget-directed ligands for cognitive improvement in a rat model of neurodegeneration in Alzheimer's disease
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A novel series of clioquinol-moracin hybrids were designed and synthesized by fusing the pharmacophores of clioquinol and moracin M, and their activities as multitarget-directed ligands against Alzheimer's disease were evaluated. Biological activity results demonstrated that these hybrids possessed significant inhibitory activities against phosphodiesterase 4D (PDE4D) and Aβ aggregation as well as remarkable antioxidant effects and excellent blood-brain barrier permeability. The optimal compound, 18d (WBQ5187), exhibited excellent PDE4D inhibitory potency (IC50 = 0.32 μM), significant antioxidant effects, appropriate biometal chelating functions, and interesting properties that modulated self- and metal-induced Aβ aggregation. Two-dimensional NMR studies revealed that 18d had significant interactions with Aβ1-42 at the R5, H6, H14, Q15, and F20 residues. Furthermore, this typical hybrid possessed preeminent neuroprotective effects against inflammation in microglial cells. Most importantly, oral administration of 18d·HCl demonstrated marked improvements in cognitive and spatial memory in a rat model of Alzheimer's disease and protected hippocampal neurons from necrosis.
- Wang, Zhiren,Wang, Yali,Wang, Bo,Li, Wenrui,Huang, Ling,Li, Xingshu
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p. 8616 - 8637
(2015/11/25)
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- Multidimensional optimization of promising antitumor xanthone derivatives
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A promising antitumor xanthone derivative was optimized following a multidimensional approach that involved the synthesis of 17 analogues, the study of their lipophilicity and solubility, and the evaluation of their growth inhibitory activity on four human tumor cell lines. A new synthetic route for the hit xanthone derivative was also developed and applied for the synthesis of its analogues. Among the used cell lines, the HL-60 showed to be in general more sensitive to the compounds tested, with the most potent compound having a GI50 of 5.1 μM, lower than the hit compound. Lipophilicity was evaluated by the partition coefficient (Kp) of a solute between buffer and two membrane models, namely liposomes and micelles. The compounds showed a log Kp between 3 and 5 and the two membrane models showed a good correlation (r2 = 0.916) between each other. Studies concerning relationship between solubility and structure were developed for the hit compound and 5 of its analogues.
- Azevedo, Carlos M.G.,Afonso, Carlos M.M.,Sousa, Diana,Lima, Raquel T.,Helena Vasconcelos,Pedro, Madalena,Barbosa, Jo?o,Corrêa, Arlene G.,Reis, Salette,Pinto, Madalena M.M.
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p. 2941 - 2959
(2013/07/05)
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- Pt(IV)-catalyzed generation and [4+2]-cycloaddition reactions of o-quinone methides
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Novel intermolecular and intramolecular generations of ortho-quinone methides and their formal [4+2]-cycloaddition reactions with olefins catalyzed by PtCl4 and AuCl3 under mild conditions have been developed. Good to excellent yields (up to 99%) and diastereoselectivity (up to >99:1) of the chromans were obtained. PtCl4 was found to be effective and compatible with various functional groups present in the substrates. A mechanism accounting for its catalytic cycle is proposed and discussed.
- Radomkit, Suttipol,Sarnpitak, Pakornwit,Tummatorn, Jumreang,Batsomboon, Paratchata,Ruchirawat, Somsak,Ploypradith, Poonsakdi
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supporting information; experimental part
p. 3904 - 3914
(2011/06/22)
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- Zinc-chelating ratiometric fluorescent probes and related methods
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Benzoxazole fluorescent sensor compounds and related ratiometric imaging methods for zinc metal ion.
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Page/Page column 13
(2008/06/13)
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- Design, synthesis and biological evaluation of novel riccardiphenol analogs
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A novel, facile, high yield, and less cumbersome synthesis of riccardiphenol analogs is described. The synthesized compounds were characterized and assessed for its in vitro activity in a panel of human cancer cell lines of differing origin: HuCCT-1, BxPC3, Panc-1, Mia-Paca, A431, Hep2, and HN006. HuCCT-1 was derived from an intrahepatic cholangiocarcinoma; BxPC3, Mia-Paca, and Panc-1 were derived from pancreatic cancers; A431 was derived from a vulvar epithelial carcinoma; and Hep2 and HN006 were derived from squamous cell carcinomas of the head and neck. The cytotoxicity of a newly developed riccardiphenol analog against human cancer cell lines was assessed. The cancer cells exhibited varying sensitivities to the compound, with IC50 values from 30 to 50 μM. This susceptibility was particularly interesting in the case of lines such as Hep2 and BxPC3 that are resistant to classic cytotoxic drugs as well as some targeted agents. These results demonstrate that the novel riccardiphenol analog has effective action against human-derived cancer cell in vitro.
- Kumar, Srinivas K.,Amador, Maria,Hidalgo, Manuel,Bhat, Sujata V.,Khan, Saeed R.
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p. 2873 - 2880
(2007/10/03)
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- A new series of estrogen receptor modulators: Effect of alkyl substituents on receptor-binding affinity
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New types of selective estrogen receptor modulators (SERMs) were synthesized and evaluated for their binding affinity and biological effect on reproductive cells. A proposed lead structure (B) was derivatized to provide compounds 30 and 44, which showed g
- Kamada, Atsushi,Sasaki, Atsushi,Kitazawa, Noritaka,Okabe, Tadashi,Nara, Kazumasa,Hamaoka, Shinichi,Araki, Shin,Hagiwara, Hiroaki
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- The synthesis of bisanthraquinone derivatives as DNA bisintercalating agents
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The linked bisanthraquinone derivatives 4a-c were synthesized as DNA bisintercalating agents. Starting from the aldehyde 7, the linking chain was introduced via a Grignard reaction to afford the ethers 9a-c. Subsequent anodic oxidation of these products, followed by annelation with the anion of phthalide 5 afforded the linked anthraquinones 12. The target compounds were then obtained by selective esterification with the acid 14, followed by deprotection with anhydrous hydrogen chloride.
- Ge, Ping,Russell, Richard A.
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p. 17477 - 17488
(2007/10/03)
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