- Base-promoted 1,3-dipolar cycloaddition reaction of nitrile oxides with methyl 1,4-dioxo-1,4-dihydronaphthalene-2-carboxylate for the construction of naphtho[2,3-d]isoxazole-4,9(3aH,9aH)-diones
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A base mediated 1,3-dipolar cycloaddition reaction of methyl 1,4-dioxo-1,4-dihydronaphthalene-2-carboxylate with nitrile oxides in situ generated from N-hydroximoyl chlorides was achieved. With this developed protocol, a range of structurally diverse naphtho[2,3-d]isoxazole-4,9(3aH,9aH)-dione derivatives were smoothly obtained in high yields (up to 95%) with up to >20:1 regioselectivities and >20:1 diastereoselectivities under mild conditions. The promising applicability of the protocol was also demonstrated by the further transformations.
- You, Yong,Chen, Yong-Zheng,Zhang, Xiao-Mei,Xu, Xiao-Ying,Yuan, Wei-Cheng
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Read Online
- Copper nitrate-mediated synthesis of 3-aryl isoxazolines and isoxazoles from olefinic azlactones
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A copper nitrate-mediated [2 + 2 + 1] cycloaddition reaction was developed for the expedient synthesis of pharmacologically interesting 3-aryl substituted isoxazolines and isoxazoles through CC bond cleavage. Copper nitrate is employed as a reaction promoter and precursor of nitrile oxides. The given approach features a new mode of cycloaddition from olefinic azlactones, copper nitrate and unsaturated compounds with wide substrate scope, good functional group tolerance and operational simplicity.
- Lin, Yifan,Zhang, Ke,Gao, Mingchun,Jiang, Zheyi,Liu, Jiajie,Ma, Yurui,Wang, Haoyu,Tan, Qitao,Xiao, Junjie,Xu, Bin
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supporting information
p. 5509 - 5513
(2019/06/14)
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- Novel heat shock protein 90 inhibitors suppress P-glycoprotein activity and overcome multidrug resistance in cancer cells
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Heat Shock Protein 90 (Hsp90) chaperone interacts with a broad range of client proteins involved in cancerogenesis and cancer progression. However, Hsp90 inhibitors were unsuccessful as anticancer agents due to their high toxicity, lack of selectivity against cancer cells and extrusion by membrane transporters responsible for multidrug resistance (MDR) such as P-glycoprotein (P-gp). Recognizing the potential of new compounds to inhibit P-gp function and/or expression is essential in the search for effective anticancer drugs. Eleven Hsp90 inhibitors containing an isoxazolonaphtoquinone core were synthesized and evaluated in two MDR models comprised of sensitive and corresponding resistant cancer cells with P-gp overexpression (human non-small cell lung carcinoma and colorectal adenocarcinoma). We investigated the effect of Hsp90 inhibitors on cell growth inhibition, P-gp activity and P-gp expression. Structure-activity relationship analysis was performed in respect to cell growth and P-gp inhibition. Compounds 5, 7, and 9 directly interacted with P-gp and inhibited its ATPase activity. Their potential P-gp binding site was identified by molecular docking studies. In addition, these compounds downregulated P-gp expression in MDR colorectal carcinoma cells, showed good relative selectivity towards cancer cells, while compound 5 reversed resistance to doxorubicin and paclitaxel in concentration-dependent manner. Therefore, compounds 5, 7 and 9 could be promising candidates for treating cancers with P-gp overexpression.
- Dini?, Jelena,Podolski-Reni?, Ana,Jovanovi?, Mirna,Musso, Loana,Tsakovska, Ivanka,Pajeva, Ilza,Dallavalle, Sabrina,Pe?i?, Milica
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- Isoxazolo(aza)naphthoquinones: A new class of cytotoxic Hsp90 inhibitors
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A series of 3-aryl-naphtho[2,3-d]isoxazole-4,9-diones and some of their 6-aza analogues were synthesized and found to inhibit the heat shock protein 90 (Hsp90). The compounds were tested for their binding to Hsp90 and for their effects on Hsp90 client pro
- Bargiotti, Alberto,Musso, Loana,Dallavalle, Sabrina,Merlini, Lucio,Gallo, Grazia,Ciacci, Andrea,Giannini, Giuseppe,Cabri, Walter,Penco, Sergio,Vesci, Loredana,Castorina, Massimo,Milazzo, Ferdinando Maria,Cervoni, Maria Luisa,Barbarino, Marcella,Pisano, Claudio,Giommarelli, Chiara,Zuco, Valentina,De Cesare, Michelandrea,Zunino, Franco
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experimental part
p. 64 - 75
(2012/07/30)
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- Synthesis and evolution of new isoxazolo-1,4-quinones of biologic interest
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In the exploration of synthesis and chemistry of isoxazoles, we found that the reaction of aromatic nitrile oxides with the Quinone derivatives produced isoxazolo-1,4-quinones is of considerable biological interest. The reductive cleavage of the N-O bond
- Hamadi, Naoufel Ben,Msaddek, Moncef
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p. 457 - 462
(2008/02/12)
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- Synthesis of 3-arylnaphth-isoxazole-4,9-diones from Lawsone
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3-Arylnaphthisoxazole-4,9-diones have been obtained by the reaction of Lawsone (1) with aryl nitrile oxide.Their structures have been confirmed by converting them into the corresponding reductive acetates (3).
- Brahmeshwari, G.,Rao, V. Rajeswar,Rao, T. V. Padmanabha
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p. 139 - 140
(2007/10/02)
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- Quinone derivatives and compositions containing the same
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Novel quinone derivatives having plant-growth regulating activity and being prepared by light irradiation or catalylic reduction from isoxazole derivatives, and compositions containing the said quinone derivatives.
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