- Isoprenoid Biosynthesis Inhibitors Targeting Bacterial Cell Growth
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We synthesized potential inhibitors of farnesyl diphosphate synthase (FPPS), undecaprenyl diphosphate synthase (UPPS), or undecaprenyl diphosphate phosphatase (UPPP), and tested them in bacterial cell growth and enzyme inhibition assays. The most active compounds were found to be bisphosphonates with electron-withdrawing aryl-alkyl side chains which inhibited the growth of Gram-negative bacteria (Acinetobacter baumannii, Klebsiella pneumoniae, Escherichia coli, and Pseudomonas aeruginosa) at ~1–4 μg mL?1levels. They were found to be potent inhibitors of FPPS; cell growth was partially “rescued” by the addition of farnesol or overexpression of FPPS, and there was synergistic activity with known isoprenoid biosynthesis pathway inhibitors. Lipophilic hydroxyalkyl phosphonic acids inhibited UPPS and UPPP at micromolar levels; they were active (~2–6 μg mL?1) against Gram-positive but not Gram-negative organisms, and again exhibited synergistic activity with cell wall biosynthesis inhibitors, but only indifferent effects with other inhibitors. The results are of interest because they describe novel inhibitors of FPPS, UPPS, and UPPP with cell growth inhibitory activities as low as ~1–2 μg mL?1.
- Desai, Janish,Wang, Yang,Wang, Ke,Malwal, Satish R.,Oldfield, Eric
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p. 2205 - 2215
(2016/10/22)
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- Unusual reactivity of aryl aldehydes with triethyl phosphite and zinc bromide: A facile preparation of epoxides, benzisoxazoles, and α-hydroxy phosphonate esters
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Abstract A facile preparation of trans-epoxides was achieved by a (EtO)3P-ZnBr2-mediated deoxygenation reaction of the corresponding 2-nitrobenzaldehydes. The sterically hindered analogues of 2-nitrobenzaldehyde underwent a reaction
- Raju, Potharaju,Gobi Rajeshwaran, Ganesan,Nandakumar, Meganathan,Mohanakrishnan, Arasambattu K.
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p. 3513 - 3523
(2015/06/08)
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- Synthesis, structure, and catalytic activity of novel trinuclear rare-earth metal amido complexes incorporating μ-η5:η1 bonding indolyl and μ3-oxo groups
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The reactions of different pyrrolyl-functionalized indoles with rare-earth metal(iii) amides [(Me3Si)2N]3RE III(μ-Cl)Li(THF)3 (RE = Yb, Er, Dy, Eu, Y) produced different kinds of rare-earth metal amid
- Yang, Song,Zhu, Xiancui,Zhou, Shuangliu,Wang, Shaowu,Feng, Zhijun,Wei, Yun,Miao, Hui,Guo, Liping,Wang, Fenhua,Zhang, Guangchao,Gu, Xiaoxia,Mu, Xiaolong
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supporting information
p. 2521 - 2533
(2014/02/14)
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- Synthesis of α-oxycarbanilinophosphonates and their anticholinesterase activities: The most potent derivative is bound to the peripheral site of acetylcholinesterase
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A novel method has been developed for the synthesis of α-oxycarbanilino phosphonates through a reaction of α-hydroxyphosphonates with isocyanate under microwave irradiation. The synthesized compounds were evaluated for their acetylcholinesterase (AChE) inhibition potency through IC50determination. Molecular modelling studies suggest that the most potent inhibitor (compound 4h, IC50 = 6.36 μM) is bound to the peripheral site of AChE, which suggests that it decreases the catalytic activity not through binding to the active site but through blocking the entrance of the active site gorge. This puts forward the potential of compound 4h and its derivatives to be used in the design of dual inhibitors: inhibition of the catalytic activity of AChE and of amyloid β aggregation.
- Kaboudin, Babak,Emadi, Saeed,Faghihi, Mohammad Reza,Fallahi, Maryam,Sheikh-Hasani, Vahid
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p. 576 - 582
(2015/02/19)
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- Rare-earth metal amido complexes supported by bridged bis(β- diketiminato) ligand as efficient catalysts for hydrophosphonylation of aldehydes and ketones
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A series of rare-earth metal amides supported by a cyclohexyl-linked bis(β-diketiminato) ligand were synthesized, and their catalytic activities for hydrophosphonylation of aldehydes and ketones were developed. Reaction of [(Me3Si)2N
- Miao, Hui,Zhou, Shuang Liu,Wang, Shao Wu,Zhang, Li Jun,Wei, Yun,Yang, Song,Wang, Fen Hua,Chen, Zheng,Chen, Yue,Yuan, Qing Bing
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p. 329 - 336
(2013/07/26)
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- Synthesis of α-oxycarbanilinophosphonates and their anticholinesterase activities: the most potent derivative is bound to the peripheral site of acetylcholinesterase
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A novel method has been developed for the synthesis of α- oxycarbanilino phosphonates through a reaction of α-hydroxyphosphonates with isocyanate under microwave irradiation. The synthesized compounds were evaluated for their acetylcholinesterase (AChE) inhibition potency through IC50determination. Molecular modelling studies suggest that the most potent inhibitor (compound 4h, IC50 = 6.36 M) is bound to the peripheral site of AChE, which suggests that it decreases the catalytic activity not through binding to the active site but through blocking the entrance of the active site gorge. This puts forward the potential of compound 4h and its derivatives to be used in the design of dual inhibitors: inhibition of the catalytic activity of AChE and of amyloid β aggregation.
- Kaboudin, Babak,Emadi, Saeed,Faghihi, Mohammad Reza,Fallahi, Maryam,Sheikh-Hasani, Vahid
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p. 576 - 582
(2013/05/08)
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- Lanthanide amido complexes incorporating amino-coordinate-lithium bridged bis(indolyl) ligands: Synthesis, characterization, and catalysis for hydrophosphonylation of aldehydes and aldimines
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Two series of new lanthanide amido complexes supported by bis(indolyl) ligands with amino-coordinate-lithium as a bridge were synthesized and characterized. The interactions of [(Me3Si)2N] 3LnIII(μ-Cl)Li(THF)su
- Zhu, Xiancui,Wang, Shaowu,Zhou, Shuangliu,Wei, Yun,Zhang, Lijun,Wang, Fenhua,Feng, Zhijun,Guo, Liping,Mu, Xiaolong
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experimental part
p. 7134 - 7143
(2012/08/08)
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- Synthesis and characterization of organolanthanide complexes with a calix[4]-pyrrolyl ligand and their catalytic activities toward hydrophosphonylation of aldehydes and unactivated ketones
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The alkali metal salt free dinuclear trivalent lanthanide amido complexes (η5:η1:η5:η1-Et 8-calix[4]-pyrrolyl){LnN(SiMe3)2}2 (Ln = Nd (2), Sm (3), Gd (4)) were prepare
- Zhou, Shuangliu,Wang, Hengyu,Ping, Jian,Wang, Shaowu,Zhang, Lijun,Zhu, Xiancui,Wei, Yun,Wang, Fenhua,Feng, Zhijun,Gu, Xiaoxia,Yang, Song,Miao, Hui
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experimental part
p. 1696 - 1702
(2012/04/23)
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- Highly efficient hydrophosphonylation of aldehydes and unactivated ketones catalyzed by methylene-linked pyrrolyl rare earth metal amido complexes
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A series of rare earth metal amido complexes bearing methylene-linked pyrrolyl-amido ligands were prepared through silylamine elimination reactions and displayed high catalytic activities in hydrophosphonylations of aldehydes and unactivated ketones under
- Zhou, Shuangliu,Wu, Zhangshuan,Rong, Jiewei,Wang, Shaowu,Yang, Gaosheng,Zhu, Xiancui,Zhang, Lijun
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supporting information; experimental part
p. 2653 - 2659
(2012/04/04)
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- Ultrasound-assisted one-pot synthesis of α-oxycarbanilinophosphonates via a three-component condensation of an aldehyde, diethyl phosphite and an isocyanate under solvent-free conditions
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An efficient one-pot method has been developed for the synthesis of α-oxycarbanilinophosphonates via a one-pot reaction of an aldehyde with diethyl phosphite in the presence of magnesium oxide followed by reaction with an isocyanate under solvent-free conditions using ultrasonic irradiation. This method is simple, rapid and good yielding.
- Kaboudin, Babak,Fallahi, Maryam
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supporting information; experimental part
p. 4346 - 4348
(2011/08/22)
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- Lewis acid-mediated Michaelis-Arbuzov reaction at room temperature: A facile preparation of arylmethyl/heteroarylmethyl phosphonates
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A facile preparation of arylmethyl and heteroarylmethyl phosphonate esters was achieved involving a Lewis acid mediated Michaelis-Arbuzov reaction at room temperature. Interaction of arylmethyl halides/alcohols with triethyl phosphite in the presence of Lewis acid at room temperature afforded phosphonate esters in good yields.
- Rajeshwaran, Ganesan Gobi,Nandakumar, Meganathan,Sureshbabu, Radhakrishnan,Mohanakrishnan, Arasambattu K
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supporting information; experimental part
p. 1270 - 1273
(2011/04/23)
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- Iodine-catalyzed, efficient synthesis of α-hydroxy phosphonates in water
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An efficient and simple synthesis of α-hydroxy phosphonates from aldehydes and triethylphosphite in the presence of iodine in water has been developed. Environmentally benign reaction conditions, high yield, and easily available catalyst are important fea
- Wang, Hong-She,Zeng, Jun-E.
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experimental part
p. 1425 - 1428
(2010/09/17)
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- Tailoring the structure of aminobisphosphonates to target plant P5C reductase
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Using the structure of (3,5-dichlorophenyl)aminomethylenebisphosphonic acid as a lead compound, 25 new phosphonates were synthesized and evaluated as possible inhibitors of Arabidopsis thaliana δ1-pyrroline-5- carboxylate (P5C) reductase. Deriv
- Forlani, Giuseppe,Occhipinti, Andrea,Berlicki, Lukasz,Dziedziola, Gabriela,Wieczorek, Anna,Kafarski, Pawel
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p. 3193 - 3199
(2008/12/21)
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- 5-Fluorouracil derivatives containing α-hydroxy phosphonates
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In order to find high acitivity and low toxicity antitumor drug-lead compounds, 13 novel N1-(2-furanidyl)-N3-(O,O- dialkylphosphonyl aryl (alkyl)methoxy-carbonylmethyl)-5-fluorouracils were synthesized via phase-transferred catalytic reactions of chloroacetyloxyalkyl phosphonates 2 with N1-(2-furanidyl)-5-fluorouracil. The structures of the products were confirmed by 1H NMR, 31P NMR, IR, and MS spectra and elemental analyses. The results of preliminary bioassay showed that the new compounds possess some extent of inhibitory effect against HCT-8 and Bel-7402 cell lines and good fungicidal activities. Copyright Taylor & Francis Group, LLC.
- Shi, De-Qing,Li, Xiao-Ju,Wei, Jia
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p. 405 - 412
(2007/10/03)
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- The synthesis and herbicidal evaluation of fluorine-containing phenoxyacetoxyalkylphosphonate derivatives
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To investigate the influence of a fluorine moiety on the biological activity of phenoxyacetoxyalkylphosphonates, a series of fluorine-containing phenoxyacetoxyalkylphosphonates were synthesized and screened for herbicidal activity in a greenhouse. The majority of the title compounds showed better preemergence activity than postemergence activity against the test plants, especially on monocotyledon. Compound 5l exhibited notable activity. Results showed that by introducing a fluorine moiety to the parent structure of phenoxyacetoxyalkylphosphonates, a series of new compounds with satisfactory herbicidal activity could be synthesized. A reasonable combination of a fluorine moiety and other substituents on the benzene ring had a great influence on the herbicidal activity. Copyright Taylor & Francis Group, LLC.
- Chen, Ting,Shen, Ping,Li, Yanjun,He, Hongwu
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p. 2135 - 2145
(2007/10/03)
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- A convenient and mild procedure for the preparation of α-keto phosphonates of 1-hydroxyphosphonates under solvent-free conditions using microwave
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The Reactions of 1-hydroxyphosphonates on the alumina-supported CrO3 are accelerated by microwave irradiation under solvent-free conditions to afford a high yielding synthesis of α-keto phosphonates.
- Kaboudin,Nazari
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p. 2245 - 2250
(2007/10/03)
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- Surface-mediated solid-phase reactions: The preparation of acyl phosphonates by oxidation of 1-hydroxyphosphonates on the solid surface
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Alumina-supported CrO3, under solvent-free conditions, was found to be an efficient oxidizing reagent for the preparation of acyl phosphonates from 1-hydroxyphosphonates. This method is an easy, rapid, and high-yielding reaction for the prepara
- Kaboudin, Babak
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p. 3169 - 3171
(2007/10/03)
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- Surface-mediated solid phase reactions: Preparation of diethyl 1-hydroxyarylmethylphosphonates on the surface of magnesia
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Magnesia is found to be an effective catalyst for synthesis of diethyl 1-hydroxyarylmethylphosphonates from aromatic aldehydes and diethyl hydrogen phosphite.
- Sardarian,Kaboudin
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p. 543 - 551
(2007/10/03)
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