- 1-Aminoalkanephosphonates. Part II. A facile conversion of 1-aminoalkanephosphonic acids into O,O-diethyl 1-aminoalkanephosphonates
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1-(N-Trifluoroacetylamino)alkanephosphonate O,O-diethyl esters 2C, obtained from parent 1-aminoalkanephosphonic acids 1, have been selectively deprotected on the amino function affording O,O-diethyl 1-aminoalkanephosphonates 3. Protonation constants of all amino esters 3 synthesized have been determined by potentiometric titration.
- Kudzin, Zbigniew H.,?yzwa, Piotr,?uczak, Jerzy,Andrijewski, Grzegorz
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Read Online
- Design, synthesis of novel celastrol derivatives and study on their antitumor growth through HIF-1α pathway
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Four series of hypoxia-inducible factor-1 alpha (HIF-1α) functioning derivatives stemming from modifications to the C-29 carboxyl group of celastrol were designed and synthesized, and their anticancer activities were evaluated. To address the structure and activity relationship of each derivative, extensive structural changes were made. HRE luciferase reporter assay demonstrated that 12 modified compounds showed superior HIF-1α inhibitory activity. Among them, compound C6 exhibited the best features: firstly, the strongest HIF-1α inhibitory activity (IC50 = 0.05 μM, 5-fold higher than that of celastrol); secondly, lower cytotoxicity (22-fold lower, C6-16.85 μM vs celastrol-0.76 μM). Thus, the safety factor of C6 was about 112 times higher than that of celastrol. Western blot assay indicated that C6 may inhibit the expression of HIF-1α protein in cells. Additionally, C6 hindered tumor cell cloning, migration and induced cell apoptosis. It is worth mentioning that in the mouse tumor xenograft model, C6 (10 mg/kg) displayed good antitumor activity in vivo, showing a better inhibition rate (74.03%) than the reference compound 5-fluorouracil (inhibition rate, 59.58%). However, the celastrol treatment group experienced collective death after four doses of the drug. Moreover, C6 minimally affected the mouse weight, indicating that its application in vivo has little toxic effect. H&E staining experiments show that it could also exacerbate the degree of tumor cell damage. The results of water solubility experiment show that the solubility of C6 is increased by 1.36 times than that of celastrol. In conclusion, C6 is a promising antitumor agent through HIF-1α pathway.
- Shang, Fan-Fan,Wang, Jing Ying,Xu, Qian,Deng, Hao,Guo, Hong-Yan,Jin, Xuejun,Li, Xiaoting,Shen, Qing-Kun,Quan, Zhe-Shan
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- Carbon Dioxide-Mediated C(sp2)-H Arylation of Primary and Secondary Benzylamines
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C-C bond formation by transition metal-catalyzed C-H activation has become an important strategy to fabricate new bonds in a rapid fashion. Despite the pharmacological importance of ortho-arylbenzylamines, however, effective ortho-C-C bond formation of free primary and secondary benzylamines using PdII remains an outstanding challenge. Presented herein is a new strategy for constructing ortho-arylated primary and secondary benzylamines mediated by carbon dioxide (CO2). The use of CO2 with Pd is critical to allowing this transformation to proceed under relatively mild conditions, and mechanistic studies indicate that it (CO2) is directly involved in the rate-determining step. Furthermore, the milder temperatures furnish free amine products that can be directly used or elaborated without the need for deprotection. In cases where diarylation is possible, an interesting chelate effect is shown to facilitate selective monoarylation.
- Kapoor, Mohit,Chand-Thakuri, Pratibha,Young, Michael C.
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supporting information
p. 7980 - 7989
(2019/05/22)
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- Design and synthesis of C-19 isosteviol derivatives as potent and highly selective antiproliferative agents
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Six series of novel isosteviol derivatives; modified in the C-19 position; were synthesized; and their antiproliferative activity was evaluated against three human cancer cell lines (HCT-116; BEL-7402; HepG2) and the human L02 normal cell line in vitro. M
- Luan, Tian,Cao, Li-Hua,Deng, Hao,Shen, Qing-Kun,Tian, Yu-Shun,Quan, Zhe-Shan
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- Synthesis and Biological Evaluation of (+)-Usnic Acid Derivatives as Potential Anti- Toxoplasma gondii Agents
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Six series of (+)-usnic acid derivatives were synthesized. The IC50 values of these compounds were determined in T. gondii infected HeLa cells (μM) and in HeLa cells (μM), and their selectivity indexes (SI) were calculated. In vitro, most of th
- Guo, Hong-Yan,Jin, Chun-Mei,Jin, Chunmei,Quan, Zhe-Shan,Shen, Qing-Kun,Zhang, Hai-Ming
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- Nickel-Catalyzed Hydrophosphonylation and Hydrogenation of Aromatic Nitriles Assisted by Lewis Acid
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In this paper, we describe the catalytic hydrophosphonylation of several aromatic nitriles used to synthesize α-aminophosphonates (α-APs) using commercially available trialkyl phosphites (P(OR)3, R=Et, iPr, Bu,) and simple and inexpensive nickel chloride (NiCl2.6H2O) as the catalytic precursor. The use of triethylborane (Et3B) as a Lewis acid (LA) was mandatory in order to successfully perform H-phosphite moiety incorporation at the CN bond of non-activated benzonitriles (BN) derivatives. Interestingly, when a highly activated BN such as 2,3,4,5,6-pentafluorobenzonitrile (BN-g) was employed, it was possible to perform the reaction in the absence of an LA using milder reaction conditions. Also, we found that using HP(O)(OiPr)2 as a starting material afforded the aminobisphosphonate derivative with better selectivity than using the method involving P(OiPr)3 as the initial reagent. Remarkably, when using HP(O)(OiPr)2 with an excess of Et3B, the reaction's selectivity completely changed to yield N-benzyl- benzylimine (BBI) and 2,4,5-triphenylimidazole.
- Islas, Rosa E.,García, Juventino J.
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p. 1337 - 1345
(2019/02/01)
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- Novel α,β-unsaturated amide derivatives bearing α-amino phosphonate moiety as potential antiviral agents
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Based on flexible construction and broad bioactivity of ferulic acid, a series of novel α,β-unsaturated amide derivatives bearing α-aminophosphonate moiety were designed, synthesized and systematically evaluated for their antiviral activity. Bioassay results indicated that some compounds exhibited good antiviral activities against cucumber mosaic virus (CMV) and tobacco mosaic virus (TMV) in vivo. Especially, compound g18 showed excellent curative and protective activities against CMV, with half-maximal effective concentration (EC50) values of 284.67 μg/mL and 216.30 μg/mL, which were obviously superior to that of Ningnanmycin (352.08 μg/mL and 262.53 μg/mL). Preliminary structure-activity relationships (SARs) analysis revealed that the introduction of electron-withdrawing group at the 2-position or 4-position of the aromatic ring is favorable for antiviral activity. Present work provides a promising template for development of potential inhibitor of plant virus.
- Lan, Xianmin,Xie, Dandan,Yin, Limin,Wang, Zhenzhen,Chen, Jin,Zhang, Awei,Song, Baoan,Hu, Deyu
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p. 4270 - 4273
(2017/09/12)
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- Improved facile synthesis of α-amino phosphonates by the reaction of α-amido sulfones with dialkyl trimethyl silyl phosphites catalyzed by Fe(III) chloride
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An improved efficient synthesis of α-amino phosphonates has been discovered by the reaction of N-benzyloxycarbonylamino sulfones with dialkyl trimethyl silyl phosphites in the presence of FeCl3as a catalyst. The products were formed in high yie
- Veeranjaneyulu, Boyapati,Das, Biswanath
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supporting information
p. 449 - 456
(2017/02/24)
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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, photopolymerization, and adhesive properties of hydrolytically stable phosphonic acid-containing (meth)acrylamides
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Three novel dental monomers containing phosphonic acid groups (1a and 2a, based on diethyl amino(phenyl)methylphosphonate and 3a based on diethyl 1-aminoheptylphosphonate) were synthesized in two steps: the reaction of α-aminophosphonates with acryloyl ch
- Altin, Ayse,Akgun, Burcin,Sarayli Bilgici, Zeynep,Begum Turker, Sebnem,Avci, Duygu
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p. 511 - 522
(2014/01/23)
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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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- THIENOPYRIMIDINE INHIBITORS OF FARNESYL AND/OR GERANYLGERANYL PYROPHOSPHATE SYNTHASE
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The present invention relates to novel compounds, compositions containing same and methods for inhibiting human farnesyl pyrophosphate synthase or for the treatment or prevention of disease conditions using said compounds;
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- Multistage screening reveals chameleon ligands of the human farnesyl pyrophosphate synthase: Implications to drug discovery for neurodegenerative diseases
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Human farnesyl pyrophosphate synthase (hFPPS) is the gate-keeper of mammalian isoprenoids and the key target of bisphosphonate drugs. Bisphosphonates suffer from poor "drug-like" properties and are mainly effective in treating skeletal diseases. Recent investigations have implicated hFPPS in various nonskeletal diseases, including Alzheimer's disease (AD). Analysis of single nucleotide polymorphisms in the hFPPS gene and mRNA levels in autopsy-confirmed AD subjects was undertaken, and a genetic link between hFPPS and phosphorylated tau (P-Tau) levels in the human brain was identified. Elevated P-Tau levels are strongly implicated in AD progression. The development of nonbisphosphonate inhibitors can provide molecular tools for validating hFPPS as a therapeutic target for tauopathy-associated neurodegeneration. A multistage screening protocol led to the identification of a new monophosphonate chemotype that bind in an allosteric pocket of hFPPS. Optimization of these compounds could lead to human therapeutics that block tau metabolism and arrest the progression of neurodegeneration.
- De Schutter, Joris W.,Park, Jaeok,Leung, Chun Yuen,Gormley, Patrick,Lin, Yih-Shyan,Hu, Zheping,Berghuis, Albert M.,Poirier, Judes,Tsantrizos, Youla S.
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p. 5764 - 5776
(2014/08/05)
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- Synthesis and photopolymerization of novel, highly reactive phosphonated-urea-methacrylates for dental materials
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An urea methacrylate (1) and two phosphonated methacrylates (2-3) were synthesized from 2-isocyanatoethyl methacrylate (IEM) and benzyl amine (1), diethyl aminomethylphosphonate (2) and diethyl amino(phenyl)methylphosphonate (3). Their photopolymerization rates are notably higher than commercial monomers, despite the presence of only one double bond. Their polymerization rates follow the order 1 ~ 2 > 3 ~ triethylene glycol dimethacrylate (TEGDMA) > 2-hydroxyethyl methacrylate (HEMA). A tendency toward high crosslinking density during thermal bulk polymerizations, low oxygen sensitivity and high conversions with benzophenone during photopolymerization indicated the importance of hydrogen abstraction/chain transfer reactions. It was found that the addition of the monomers to HEMA significantly increased its polymerization rate, proving their utility as replacements for TEGDMA as reactive diluents for 2,2-bis[4-(2-hydroxy-3-methacryloyloxy propyloxy) phenyl] propane (Bis-GMA). Copolymer systems containing 2 and 3 showed improved Tg values compared to Bis-GMA/ TEGDMA systems.
- Altin, Ayse,Akgun, Burcin,Buyukgumus, Ozlem,Bilgici, Zeynep Sarayli,Agopcan, Sesil,Asik, Didar,Acar, Havva Yagci,Avci, Duygu
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p. 1319 - 1326
(2013/10/22)
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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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- Efficient one-pot synthesis of α-aminophosphonates from aldehydes and ketones catalyzed by ytterbium(III) triflate
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An efficient three component one-pot synthesis of N-silylated α-aminophosphonates and α,α-disubstituted α- aminophosphonates was developed using Yb(OTf)3 as a catalyst at room temperature under mild conditions.
- Heo, Yeon,Cho, Dae Hyan,Mishra, Mithilesh Kumar,Jang, Doo Ok
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experimental part
p. 3897 - 3899
(2012/09/08)
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- Synthesis and bioactivities of α-aminophosphonate derivatives containing benzothiazole and thiourea moieties
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The synthesis of a series of novel α-aminophosphonate derivatives containing benzothiazole and thiourea moieties from substituted 2-aminobenzothiazoles and synthetic intermediates O,O'-dialkylisothiocyanat- (phenyl)methylphosphonates under microwave irradiation has been demonstrated. Several salient features, such as good to excellent yields, shorter reaction times, milder reaction conditions, and simple purification procedures, make the present synthetic protocol highly attractive to access the title compounds. Bioassays indicated that most of the compounds possessed broad-spectrum insecticidal and antiviral activities against Tobacco Mosaic Virus (TMV) in vivo. Interestingly, in comparison with control insecticide Avermectin, two compounds displayed remarkably high in vitro insecticidal activities against Plutella xylostella. Furthermore, according to the results from preliminary bioassay, all were associated with moderate to good anti-TMV activities. [Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental resource: Tables S1-S4. Figures S1-S52.] Copyright Taylor and Francis Group, LLC.
- Liu, Jing-Zi,Song, Bao-An,Bhadury, Pinaki S.,Hu, De-Yu,Yang, Song
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- Synthesis and biological evaluation of novel phosphonates derivatives of as potential antitumor agents
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A series of dialkyl [2-(4,6-dimethoxypyrimidin-2-yloxy)benzamido](aryl) methylphosphonates derivatives were designed and synthesized. All the new compounds were identified by elemental analysis, IR, 1H NMR, 31P NMR, and MS. Their antitumor activity against KB and CNE1 cells was examined. Some of the compounds showed potential antitumor activity, which provided some hints for further study of structure modification. In particular, the compounds 6i and 6j displayed more potent cytotoxic activities against KB in comparison with 5-FU. Copyright Taylor & Francis Group, LLC.
- Jin, Chuanfei,Liang, Yong-Ju,He, Hongwu,Fu, Liwu
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experimental part
p. 2096 - 2103
(2011/12/01)
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- Synthesis and antiviral bioactivities of novel chiral bis-thiourea-type derivatives containing α-aminophosphonate moiety
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Starting from 1-((1R,2R)-2-aminocyclohexyl)-3-substituted thioureas (3a-c) and substituted isothiocyanates (9a-d), chiral bis-thiourea derivatives containing α-aminophosphonate moiety 10a-l were prepared and completely characterized by elemental analysis, physical and spectral (IR, 1H NMR, 13C NMR, 31P NMR) data. The results of bioassay revealed that compounds 10a and 10e possessed appreciable curative bioactivities on cucumber mosaic virus (CMV) at 0.5 mg/mL in vivo (inhibitory rate = 60.3%, 64.8% respectively) and tobacco mosaic virus (TMV) at 0.5 mg/mL in vivo (inhibitory rate = 50.3%, 50.8% respectively), which were comparable to the values shown by standard reference (58.7%) and commercial product Ningnanmycin (56.3%), respectively. Chiral compound 10e displayed more potent antiviral activity (EC50 = 0.149 mg/mL) than Ningnanmycin (EC50 = 0.201mg/mL) against CMV.
- Yang, Xuan,Song, Baoan,Jin, Linhong,Wei, Xue,Bhadury, S. Pinaki,Li, Xiangyang,Yang, Song,Hu, Deyu
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scheme or table
p. 103 - 109
(2011/12/21)
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- Synthesis and solution studies of Cu(II) complexes with pyridine derivatives of iminobisphosphonic acids
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New 2-pyridyl, 3-pyridyl and 4-pyridyl derivatives of iminobisphosphonic acid were prepared by addition of tris(trimethylsilyl)phosphite to the corresponding derivatives of pyridineimine-methylphosphonates 3 and subsequent methanolysis of the silylated pr
- Goldeman, Waldemar,Pyrkosz, Monika,Gumienna-Kontecka, Elbieta,Boduszek, Bogdan
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experimental part
p. 391 - 399
(2011/04/12)
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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 in vitro study of pseudo-peptide thioureas containing α-aminophosphonate moiety as potential antitumor agents
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Twenty pseudo-peptide thioureas IIa-l containing α-aminophosphonate moiety were synthesized from the reaction of chiral α-amino carboxamide derivatives Ia-c with O,O′-dialkylisothiocyanato(phenyl)methylphosphonate 5. The synthesized compounds were completely characterized by elemental analysis, physical and spectral (IR, 1H NMR, 13C NMR) data. According to the preliminary studies on antitumor activities, compounds IIa-l could inhibit tumor cells PC3, Bcap37 and BGC823. These compounds displayed low to high activity by MTT assays. Among them, L-IIk, D-IIa and D-IIe were identified as potent inhibitors, with IC50 values ranging from 4.7 to 11.2 μM according to in vitro assay.
- Liu, Jing-Zi,Song, Bao-An,Fan, Hui-Tao,Bhadury, Pinaki S.,Wan, Wen-Ting,Yang, Song,Xu, Weiming,Wu, Jian,Jin, Lin-Hong,Wei, Xue,Hu, De-Yu,Zeng, Song
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scheme or table
p. 5108 - 5112
(2011/01/04)
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- Synthesis and antiviral bioactivity of chiral thioureas containing leucine and phosphonate moieties
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A series of novel chiral thioureas 3a-n bearing leucine and phosphonate moieties were synthesized in excellent yields. The structures of the compounds were completely characterized by elemental analysis, IR, 1H-, 13C-, 31P- and 19F-NMR spectral data. A half-leaf method was used to determine the in vivo protective and curative efficacies of the title products against tobacco mosaic virus (V). The compounds 3l and 3n displayed good in vivo protection and curative effects against V with inhibitory rates of 60.1, 62.8% (protection) and 56.7, 53.6% (curative) at 0.5 mg/mL, respectively. To the best of our knowledge, this is the first report on the antiviral activity of chiral thioureas containing leucine and phosphonate moieties.
- Liu, Jingzi,Yang, Song,Li, Xiangyang,Fan, Huitao,Bhadury, Pinaki,Xu, Weiming,Wu, Jian,Wang, Zhencao
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scheme or table
p. 5112 - 5123
(2011/01/04)
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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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- Molecular iodine: An efficient catalyst for the one-pot synthesis of primary 1-aminophosphonates
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A new and convenient procedure has been developed for the one-pot synthesis of different types of primary 1-aminophosphonates from aldehydes/ketones, HMDS and diethyl phosphite using I2 as an inexpensive, non-toxic, non-metallic and readily available cata
- Sobhani,Vafaee
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experimental part
p. 227 - 236
(2010/10/21)
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- Solvent-and catalyst-free reaction of (aminomethyl)phosphonates with epoxides: Synthesis of novel {[(2-hydroxyethyl)amino]methyl}phosphonates
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Uncatalyzed reaction of epoxides with (aminomethyl)phosphonates for the synthesis of novel {[(2-hydroxyethyl)amino]methyl}phosphonates is described. Treatment of (aminomethyl)phosphonates with epoxides without any catalyst and under solvent-free condition
- Kaboudin, Babak,Sorbiun, Mina
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p. 284 - 289
(2011/04/12)
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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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- Synthesis and antiviral activities of chiral thiourea derivatives containing an α-aminophosphonate moiety
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Starting from benzaldehyde 1, the title compounds 8 were synthesized in six steps. Benzaldehyde1 was reacted with ammonium hydroxide, and the resulting imine was then treated with dialkyl phosphite 3 to give dialkyl N-(arylmethylene)-1-amino-1-aryl methylphosphonates 4. Phosphonates 4 were then easily hydrolyzed to give dialkyl 1-amino-1-aryl-methylphosphonates 6, which on treatment with triethylamine, carbon disulfide, and phosphorus oxychloride provided 7. Target compounds 8 were then prepared by the reaction of 7 with substituted chiral amine. The structures were clearly verified by spectroscopic data (IR, 1H, 13C, and 31P NMR, and elemental analysis). The bioassay of these compounds revealed them as antivirally active. It was found that title compounds 8g, 8e, 8k, and 8m had the same curative effects of TMV (inhibitory rate = 54.8, 50.5, 50.4, and 50.4%, respectively) as the commercial product Ningnanmycin (56.2%). This would appear to be the first report of the synthesis and antiviral activity of chiral thiourea derivatives containing an α-aminophosphonate moiety.
- Chen, Mei-Hang,Chen, Zhuo,Song, Bao-An,Bhadury, Pinaki S.,Yang, Song,Cai, Xue-Jian,Hu, De-Yu,Xue, Wei,Zeng, Song
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scheme or table
p. 1383 - 1388
(2010/05/18)
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- One-pot synthesis of α-aminophosphonates on silica under solvent-free conditions from aromatic aldehydes
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α-Aminophosphonates were synthesised under solvent-free conditions on an acidic silica gel support using aromatic aldehydes, diethyl phosphite and anhydrous ammonium acetate as starting materials in moderate yields.
- Wu, Ming Shu,Zhang, Xiang Zhu
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experimental part
p. 562 - 563
(2009/09/06)
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- Synthesis and antiviral activities of amide derivatives containing the &α-aminophosphonate moiety
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Starting from (substituted-)benzaldehydes, the title compounds 6 were synthesized through five step reactions. Benzaldehydes were treated with ammonium hydroxide, followed by dialkyl phosphite, to give dialkyl N-(arylmethylene)-1-amino-1-aryl methylphosphonates (3). Phosphonates 3 were then easily hydrolyzed to give dialkyl 1-amino-1-aryl-methylphosphonates 5. Target compounds 6 were then obtained by the reaction of 5 and substituted benzoic or cinnamic acid. Their structures were clearly verified by spectroscopic data (IR, 1H, 13C, and 31P NMR, and elemental analysis). These compounds were shown to be antivirally active in the bioassay. It was found that title compounds 6g, 6l, and 6n had the same inactivation effect of TMV (EC50 = 54.8, 60.0, and 65.2 μg/mL, respectively) as commercial product Ningnanmycin (EC50 = 55.6 μg/mL). To the best of our knowledge, this is the first report on the synthesis and antiviral activity of amide derivatives containing an α-aminophosphonate moiety.
- Hu, De-Yu,Wan, Qiong-Qiong,Yang, Song,Song, Bao-An,Bhadury, Pinaki S.,Jin, Lin-Hong,Yan, Kai,Liu, Fang,Chen, Zhuo,Xue, Wei
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supporting information; experimental part
p. 998 - 1001
(2009/05/07)
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- Synthesis and antiviral activities of cyanoacrylate derivatives containing an α-aminophosphonate moiety
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Target compounds 8 were obtained by the reaction of alkyl 2-cyano-3,3-dimethylthioacrylate or cyarylamide (7a-7e) and α- aminobenzylphosphonate (5a-5e) under reflux condition using ethanol as solvent. Their structures were clearly verified by spectroscopic data (IR and 1H, 13C, and 31P NMR) and elemental analysis. These compounds were shown to be antivirally active in the bioassay. It was found that title compounds 8d and 8e had the same inactivation effect against tobacco mosaic virus (EC50 = 55.5 and 55.3 μg/mL) as the commercial product ningnanmycin (EC50 = 50.9 μg/mL). To the best of our knowledge, this is the first report on the synthesis and antiviral activity of cyanoacrylate derivatives containing an α-aminophosphonate moiety.
- Long, Ning,Cai, Xue-Jian,Song, Bao-An,Yang, Song,Chen, Zhuo,Bhadury, Pinaki S.,Hu, De-Yu,Jin, Lin-Hong,Xue, Wei
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scheme or table
p. 5242 - 5246
(2010/04/06)
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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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- Microwave-assisted synthesis of 1-aminoalkyl phosphonates under solvent-free conditions
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A simple, efficient and general method has been developed for the synthesis of 1-aminoalkyl phosphonates through a one-pot reaction of aldehydes with amines in the presence of acidic alumina under solvent-free conditions using microwave irradiation. It wa
- Kaboudin, Babak,Nazari, Rahman
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p. 8211 - 8213
(2007/10/03)
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- Surface-mediated solid phase reactions: A simple and new method for the synthesis of α-aminophosphonates under solvent-free conditions
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Alumina-supported ammonium formate was found to be an efficient reagent for the synthesis of 1-aminophosphonates from aldehydes and diethyl phosphite. This method is an easy, rapid and high-yielding reaction for the synthesis of 1-aminophosphonates.
- Kaboudin, Babak
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p. 880 - 881
(2007/10/03)
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- The synthesis of N-(β-triphenylgermanyl)-propionyl-α-amino-benzylphosphonates
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A series of N-(β-triphenylgermanyl)propionyl-α-amino-benzylphosphonates was synthesized by reaction of β-triphenylgermanyl propionic acid with α-aminophosphonates under very mild conditions. The structures of products were determined by 1H NMR,
- Ye,Zeng,Liu
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p. 2373 - 2378
(2007/10/03)
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- Transformation of Arylmethylamines into α-Aminophosphonic Acids via Metalated Phosphoramidates: Rearrangement of Partly Configurationally Stable N-Phosphorylated α-Aminocarbanions
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N-Benzyl phosphoramidate was protected at nitrogen with a TMS, p-toluenesulfonyl, Boc, lithium carboxylate, or diethoxyphosphinyl group and metalated with s-BuLi or LDA at -78 °C at the benzylic carbon. For the latter three protecting groups, the intermediate α-amino(phenylmethyl)-lithiums isomerized to N-protected α-aminophosphonates (phosphoramidate-aminophosphonate rearrangement). (R)-N-[1-2H1]Phenylmethyl phosphoramidate in combination with Boc or (EtO)2P-(O) was used to demonstrate that metalation occurs with a high primary kinetic isotope effect (kH/kD 13-50) and migration of the diethoxyphosphinyl group with retention of configuration at carbon. Furthermore, the short-lived carbanion lithium pairs are partly configurationally stable as the aminophosphonates formed with the two protecting groups have enantiomeric excesses of 79 and 24%, respectively. When homochiral lithium amides derived from (R)-N-isopropyl-1-phenylethylamine and (R,R)-N,N-di(1-phenylethyl)amine were used to induce a phosphoramidate-aminophosphonate rearrangement, chiral nonracemic α-aminophosphonates were formed (ee 26-35%). Three racemic aminophosphonates were deprotected with hot 6 M HCl and purified by ion-exchange chromatography on Dowex 50W,H+ to exemplify the transformation of phenyl-, p-tolyl-, and (1′-naphthyl)methylamine into aminophosphonic acids via lithiated phosphoramidates.
- Hammerschmidt, Friedrich,Hanbauer, Martin
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p. 6121 - 6131
(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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- The facile synthesis of 1-aminophosphonates from 1-nitrophosphonate precursors
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1-Aminophosphonates may be generated in high yield and spectroscopic purity by the treatment of 1-nitrophosphonates with LiBH4/Me3SiCl in THF at room temperature.
- Green, Donovan,Elgendy, Said,Patel, Geeta,Baban, Jehan A.,Skordalakes, Emmanuel,Husman, Wahid,Kakkar, Vijay V.,Deadman, John
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p. 303 - 306
(2007/10/03)
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- A simple synthesis of 1-aminophosphonic acids from 1-hydroxyiminophosphonates with NaBH4 in the presence of transition metal compounds
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A new procedure has been developed for the synthesis of 1-aminophosphonic acids. Diethyl phosphonates are converted to hydroxyiminophosphonates when treated with hydroxylamine hydrochloride. Reduction of hydroiminophosphonates with NaBH4 in MeOH in the presence of MoO3 or NiCl2 and hydrolysis of 1-aminophosphonates gave 1-aminophosphonic acids in good yields.
- Demir, Ayhan S.,Tanyeli, Cihangir,Sesenoglu, Oezge,Demic, Serafettin,Evin, Oezden Oezel
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p. 407 - 410
(2007/10/02)
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- Substrate related O,O-dialkyldipeptidylaminophosphonates, a new type of thrombin inhibitor
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The facile reduction of O,O-dialkyl 1-hydroxyiminoalkanephosphonate precursors, using LiBH4/Me3SiCl in THF at ambient temperature, conveniently affords O,O-dialkyl 1-aminoalkanephosphonates in good yield and high state of purity. O,O
- Green, Donovan,Patel, Geeta,Elgendy, Said,Baban, Jehan A.,Skordalakes, Emmanuel,Husman, Wahid,Goodwin, Christopher A.,Scully, Michael F.,Kakkar, Vijay V.,Deadman, John
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p. 533 - 536
(2007/10/03)
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- Simple and improved preparation α-aminophosphonic acid derivatives, key building blocks of phosphonopeptides
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Strecker-type reaction of an aldehyde, ammonium acetate and diethyl phosphite in ethanol afforded the corresponding diethyl α-aminophosphonate, a key building block of the biologically interesting phosphonopeptides, in moderate to good yield.
- Takahashi,Yoshioka,Imai,Onimura,Kobayashi
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p. 763 - 764
(2007/10/02)
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- SYNTHESE DE PEPTIDES MODIFIES INCORPORANT UN MOTIF PHOSPHORE N OU C TERMINAL
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A general route to phosphopeptides with a 2-oxoalkylphosphonate moiety at the terminal N-amino group or with a 1-aminoalkylphosphonate moiety at the terminal C-carboxyl group is described.The method allows the preparation of various phosphopeptides with an α-alkylated carbon atom on the P-C bond from the very available dialkylpohosphonoalcanoic acids as starting products.
- Coutrot, Ph.,Grison, C.,Charbonnier-Gerardin, C.
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p. 9841 - 9868
(2007/10/02)
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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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- STUDIES ON ORGANOPHOSPHORUS COMPOUNDS. 65, A FACILE SYNTHETIC ROUTE TO PHOSPHONOPEPTIDES
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A direct procedure for the preparation of phosphonopeptides, containing either a N- or C-terminal phosphonic acid residue, is described.This method is based on a three component condensation reaction leading to diethyl 1-(N-carbobenzyloxyamino)-alkylphosp
- Yuan, Chengye,Wang, Guohong
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p. 207 - 212
(2007/10/02)
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