- Parietic acid aminophosphonic acid ester derivative and its synthetic method and application
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The invention discloses a series of rhein aminophosphonate derivatives, and a synthetic method and applications thereof. The synthetic method of the rhein aminophosphonate derivatives comprises: taking rhein and an alpha-aminophosphonate as raw materials,
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Paragraph 0058; 0059
(2016/10/08)
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- Diacetyl Rhein aminophosphonic acid ester derivative and its synthetic method and application
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The invention discloses a series of diacerhein aminophosphonate derivatives, and a synthetic method and applications thereof. The synthetic method of the diacerhein aminophosphonate derivatives comprises: taking diacerhein and an alpha-aminophosphonate as raw materials, dissolving in a polar solvent, in the presence of a catalyst HOBT and a condensing agent EDAC, reacting completely; and adding trichloromethane into the reaction liquid, washing with water, applying the organic layer to silica gel for column chromatography, eluting with a mixed solvent of ethyl acetate and petroleum ether with a volume ratio of 1:6-100 to obtain the corresponding derivative. The diacerhein aminophosphonate derivatives have the structural general formula (I) as shown in the description, wherein R is p-bromophenyl, o-bromophenyl, m-bromophenyl, p-fluorophenyl, o-fluorophenyl, p-chlorophenyl, m-chlorophenyl, o-chlorophenyl, m-methoxyphenyl, o-methoxyphenyl, phenyl, naphthyl, p-methoxyphenyl, m-methylphenyl, p-methylphenyl, m-fluorophenyl or anthryl.
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Paragraph 0059; 0060
(2017/01/26)
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- Novel coumarin-containing aminophosphonatesas antitumor agent: synthesis, cytotoxicity, DNA-Binding and apoptosis evaluation
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A series of novel coumarin-containing α-aminophosphonates were synthesized and evaluated for their antitumor activities against Human colorectal (HCT-116), human nasopharyngeal carcinoma (human KB) and human lung adenocarcinoma (MGC-803) cell lines in vit
- Li, Ya-Jun,Wang, Cai-Yi,Ye, Man-Yi,Yao, Gui-Yang,Wang, Heng-Shan
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p. 14791 - 14809
(2015/09/21)
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- Synthesis of derivatives of artesunate α-aminophosphonate and their antimicrobial activities
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Thirteen α-aminophosphonate derivatives with artesunate were synthesized by introducing bioactive α-aminophosphonate combination with artesunate in this work. The reaction were easily carried out at normal pressure, low temperature and without any catalys
- He, Sheng,Ouyang, Xilin,Huang, Xiaochao,Hu, Weisong,Dai, Weilong,Tian, Xiaoyan,Pan, Yingming,Huang, Shiwen,Wang, Hengshan
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p. 408 - 416
(2015/06/22)
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- Synthesis and antitumor activities of novel rhein α-aminophosphonates conjugates
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Several rhein α-aminophosphonates conjugates (5a-5q) were synthesized and evaluated for in vitro cytotoxicity against HepG-2, CNE, Spca-2, Hela and Hct-116 cell lines. Some compounds showed relatively high cytotoxicity. Especially, compound 5i exhibited t
- Yao, Gui-Yang,Ye, Man-Yi,Huang, Ri-Zhen,Li, Ya-Jun,Pan, Ying-Ming,Xu, Qing,Liao, Zhi-Xin,Wang, Heng-Shan
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supporting information
p. 501 - 507
(2014/01/23)
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- Coumarin-containing aminophosphonates bridged with chiral side chain: Synthesis and influence of chirality on cytotoxicity and DNA binding
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A series of novel coumarin-containing α-Aminophosphonates with two chiral centers were synthesized and a single-crystal structure of compound 8g (8g', (R)-diethyl ((S)-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)propanamido)(2- bromophenyl)methylphosphonate) was
- Li, Ya-Jun,Ye, Man-Yi,Huang, Ri-Zhen,Yao, Gui-Yang,Pan, Ying-Ming,Liao, Zhi-Xin,Wang, Heng-Shan
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p. 3144 - 3156
(2014/05/06)
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- Synthesis and antitumor activities of novel diacerein α-aminophosphonates conjugates
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Several diacerein α-aminophosphonates conjugates 4a-k have been synthesized, the structures of compounds have been characterized by IR, 1H NMR, 13C NMR, 31P NMR, ESI-MS spectra and elementary analysis. In vitro cytotoxicity against HepG-2, CNE, Spca-2 and Hct-116 cells are evaluated and employing standard MTT assay in comparing with commercial anticancer drug 5-fluorouracil (5-FU). Some compounds exhibit moderate to high levels of antitumor activity. Especially, compound 4i exhibit the strongest cytotoxicity against Hct-116 cells with IC50 9.83 μM. All the synthesized compounds exhibit low cytotoxicity against HUVEC cells. The mechanism of compound 4i has been preliminarily investigated by Hoechst 33258 staining, JC-1 mitochondrial membrane potential staining and flow cytometry, which indicate that the compound 4i induced apoptosis in Hct-116 cancer cells. Cell cycle analysis show that compound 4i mainly arrested Hct-116 cells in G1 stage. The effects of 4i on the activation of caspases expression indicate that 4i might induce apoptosis via the membrane death receptor pathways. In addition, the binding properties of a model analog 4i to DNA have been investigated by methods (UV-Vis, fluorescence, CD spectroscopy) in comparison with that of diacerein. Results indicate that 4i show moderate ability to interact ct-DNA.
- Qin, Jian-Mei,Li, Jian-Fei,Ye, Man-Yi,Huang, Ri-Zheng,Xu, Qing,Pan, Ying-Ming,Wang, Heng-Shan,Yao, Gui-Yang
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p. 1584 - 1595
(2015/02/02)
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- Synthesis and antitumor activities of novel α-aminophosphonates dehydroabietic acid derivatives
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A series of novel α-aminophosphonate derivatives containing DHA structure were designed and synthesized as antitumor agents. In vitro antitumor activities of these compounds against the NCI-H460 (human lung cancer cell), A549 (human lung adenocarcinoma ce
- Huang, Xiao-Chao,Wang, Meng,Pan, Ying-Ming,Tian, Xiao-Yan,Wang, Heng-Shan,Zhang, Ye
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p. 5283 - 5289
(2013/09/23)
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- Synthesis and herbicidal activity of novel pyrimidinyl derivatives containing an α-amino phosphonate moiety
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In order to find novel pyrimidinyl carboxylic acid analogs with high activity and low toxicity, a series of novel pyrimidinyl derivatives containing an -amino phosphonate moiety 5 was synthesized by the condensation of 4-(4,6-dimethoxypyrimidin-2-yloxy)phenoxyacetic 3a or propionic acids 3b with dialkyl -amino substitutedbenzyl phosphonates 4. Their structures were characterized by spectroscopic data (IR, 1H NMR, 31P NMR, MS) and elemental analyses. The results of preliminary herbicidal activities (in vitro) showed that most of these compounds exhibited higher herbicidal activities against dicotyledonous weeds (Brassica campestris L) than monocotyledonous weeds (Echinochloa crus-galli). Further bioassays (in vivo) indicated that some of compounds 5 possessed selective herbicidal activity against amaranth pigweed (A. retroflexus) in post-emergence treatment. Copyright Taylor & Francis Group, LLC.
- Yu, Zhi-Hua,Shi, De-Qing
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experimental part
p. 2316 - 2323
(2011/01/12)
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- Synthesis and herbicidal activity of O,O-diethyl N-{4-Methyl-[1,2,3] thiadiazole-5-carbonyl}- 1-amino-1-substitutedbenzyl phosphonates
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Target compounds 3 were synthesized by the condensation of O,O-diethyl α-amino substitutedbenzyl phosphonates 1 and 4-methyl-[1,2,3]thiadiazole- 5-carboxylic acid 2 in the presence of dicyclohexylcarbodiimide (DCC) as a dehydration reagent. Their structures were confirmed by spectroscopic data (IR, 1H NMR, 31P NMR, MS) and elemental analysis. The results of a preliminary bioassay (in vitro) indicated that some of the title compounds 3 possessed moderate to good herbicidal activities against dicotyledonous plants (Brassica campestris L) at the concentration of 100 mg/L, and most of these compounds exhibited higher herbicidal activities against dicotyledonous plants (Brassica campestris L) than monocotyledonous plants (Echinochloa crus-galli). Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. Copyright Taylor & Francis Group, LLC.
- Tang, Wu,Yu, Zhi-Hua,Shi, De-Qing
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scheme or table
p. 2024 - 2029
(2010/12/19)
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- One-pot synthesis of primary 1-aminophosphonates: Coupling reaction of carbonyl compounds, hexamethyldisilazane, and diethyl phosphite catalyzed by al(otf)3
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Al(OTf)3 has been utilized as a new and efficient catalyst for the selective synthesis of primary 1-aminophosphonates by a one-pot coupling reaction of various types of aldehydes/ketones, hexamethyldisilazane, and diethyl phosphite under solvent-free cond
- Sobhani, Sara,Tashrifi, Zahra
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experimental part
p. 109 - 115
(2009/09/29)
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- Al(OTf)3 as an efficient catalyst for one-pot synthesis of primary diethyl 1-aminophosphonates under solvent-free conditions
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A simple and general method has been developed for the one-pot, three-component synthesis of a variety of primary 1-aminophosphonates catalyzed by Al(OTf)3 under solvent-free conditions in good to high yields. Copyright Taylor & Francis Group, LLC.
- Sobhani, Sara,Tashrifi, Zahra
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body text
p. 120 - 131
(2009/04/06)
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- A simple and convenient procedure for the synthesis of 1-aminophosphonates from aromatic aldehydes
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A simple, efficient, possible industrial process has been developed for the synthesis of 1-aminophosphonic acids from simple starting materials. As described below, treatment of aromatic aldehydes with ammonia and reaction with diethyl phosphite gives die
- Kaboudin, Babak,Moradi, Khavar
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p. 2989 - 2991
(2007/10/03)
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- Synthesis of 1-phosphono-2-aza-1,3-dienes and scope of their aziridination
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Several 1-phosphono-2-aza-1,3-dienes 14 and 1-aryl-1-phosphono-2-aza-1,3- dienes 15-17 were prepared by 1,4-dehydrochlorination of the corresponding diethyl [(2-chloro-1-alkylidene)amino]methylphosphonates 10-13. 1-Phosphono-2-aza-1,3-dienes 14 react smoo
- Vanderhoydonck, Bart,Stevens, Christian V.
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p. 722 - 734
(2007/10/03)
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- A mild and highly efficient protocol for the one-pot synthesis of primary α-amino phosphonates under solvent-free conditions
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Under solvent-free reaction conditions and in the presence of solid LiClO4 a novel and mild protocol for the one-pot, three-component synthesis of primary α-amino phosphonates from an aldehyde, hexamethyldisilazane and a trialkyl phosphite is described giving high yields and having short reaction times. The same products are obtained in very low yields, when the three-component reaction is carried out under microwave irradiation and in the absence of solid LiClO4. Examples of some prepared 1-aryl-N,N′-bis(arylidene)methanediamines are also described.
- Azizi, Najmedin,Rajabi, Fatemeh,Saidi, Mohammad R.
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p. 9233 - 9236
(2007/10/03)
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- Silica-Supported Ammonium Hydrogen Carbonate as an Efficient Reagent for One-Pot Synthesis of 1-Aminophosphonates from Aldehydes
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Silica-supported ammonium hydrogen carbonate was found to be an efficient reagent for the synthesis of 1-aminophosphonates under microwave irradiation in solvent-free conditions. This method is an easy, rapid, one-pot, and good-yielding reaction for the s
- Kaboudin, Babak,Rahmani, Abbas
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p. 2705 - 2708
(2007/10/03)
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- A novel synthesis of diethyl 1-aminoarylmethylphosphonates on the surface of alumina
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A novel route has been devised for the preparation of a series of diethyl 1-aminoarylmethylphosphonates. The route involves facile reaction among aromatic aldehydes, diethyl hydrogen phosphite and HMDS on the surface of alumina.
- Sardarian,Kaboudin
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p. 2543 - 2546
(2007/10/03)
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- An efficient synthesis of diethyl 1-aminoalkylphosphonate hydrochlorides via the intermediate diethyl 1-azidoalkylphosphonates
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The title compounds 4 have been obtained in high yields in a one-step sequence by the Mitsunobu reaction of diethyl 1-hydroxyalkylphosphonates 1 with hydrazoic acid, and subsequence treatment of the intermediate azides 2 with triphenylphosphine, followed
- Gajda,Matusiak
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p. 2193 - 2203
(2007/10/02)
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