- Synthesis, structure and biological activity of pseudopeptidic macrolides based on an amino alcohol
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A series of new pseudopeptidic macrolides 2a-f based on an amino alcohol were synthesized and evaluated for in vitro antibacterial and antifungal activities. The structure-activity relationships of these compounds were studied and the results showed that compounds 2a and 2d exhibited moderate antibacterial activity against Staphylococcus aureus, Bacillus subtilis and Escherichia coli, whereas compound 2e showed potent antifungal activity against all the fungal species tested, showing a promising broad-spectrum antifungal activity. All the compounds have been studied in vitro for the hemolytic activity as a measure of their cytotoxicity, showing that these compounds have low lytic properties.
- Lv, Jian,Liu, Tingting,Wang, Yongmei
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Read Online
- Modulation of internuclear communication in multinuclear ruthenium(II) polypyridyl complexes
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The syntheses and characterisation of a series of mononuclear and dinuclear ruthenium polypyridyl complexes based on the bridging ligands 1,3-bis-[5-(2-pyridyl)-1H-1,2,4-triazol-3-yl]benzene, 1,4-bis-[5-(2-pyridyl)-1H-1,2,4-triazol-3-yl]benzene, 2,5-bis-[5-(2-pyridyl)-1H-1,2,4-triazol-3-yl]thiophene, 2,5-bis-[5-pyrazinyl-1H-1,2,4-triazol-3-yl]thiophene are reported. Electrochemical studies indicate that in these systems, the ground state interaction is critically dependent on the nature of the bridging ligand and its protonation state, with strong and weak interactions being observed for thiophene- and phenylene-bridged complexes, respectively.
- Browne, Wesley R.,Weldon, Frances,Guckian, Adrian,Vos, Johannes G.
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- Exploiting the chiral ligands of bis(Imidazolinyl)-and bis(oxazolinyl)thiophenes—Synthesis and application in Cu-catalyzed friedel–crafts asymmetric alkylation
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Five new C2-symmetric chiral ligands of 2,5-bis(imidazolinyl)thiophene (L1–L3) and 2,5-bis(oxazolinyl)thiophene (L4 and L5) were synthesized from thiophene-2,5-dicarboxylic acid (1) with enantiopure amino alcohols (4a–c) in excellent optical purity and chemical yield. The util-ity of these new chiral ligands for Friedel–Crafts asymmetric alkylation was explored. Subse-quently, the optimized tridentate ligand L5 and Cu(OTf)2 catalyst (15 mol%) in toluene for 48 h promoted Friedel–Crafts asymmetric alkylation in moderate to good yields (up to 76%) and with good enantioselectivity (up to 81% ee). The bis(oxazolinyl)thiophene ligands were more potent than bis(imidazolinyl)thiophene analogues for the asymmetric induction of the Friedel–Crafts asymmetric alkylation.
- Al-Majid, Abdullah Mohammed,Alammari, Abdullah Saleh,Alshahrani, Saeed,Barakat, Assem,Haukka, Matti,Islam, Mohammad Shahidul
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- Three multifunctional coordination polymers based on the amide-functionalized N2,N5-di(pyridin-3-yl)thiophene-2,5-dicarboxamide ligand (Nptp): Synthesis, magnetic properties and luminescent sensing for Pb2+, Cr2O72?
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Three three-dimensional (3D) transition metal coordination polymers (CPs), formulated as [Zn(Nptp)(HBTC)]n (1), [Mn(Nptp)(HBTC)]n (2) and [Co(Nptp)(HBTC)]n (3), have been designed and synthesized using the amide-functional
- Da, Xiao-Rong,Feng, Hua,Guo, Xiao-Feng,Hu, Dong-Cheng,Liu, Jia-Cheng,Tan, Jing-Jing
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- Synthesis of Novel C 2-Symmetric Sulfur-Based Catalysts: Asymmetric Formation of Halo- and Seleno-Functionalized Normal- and Medium-Sized Rings
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The synthesis of novel, highly functionalized, C 2 -symmetric sulfur-based catalysts is developed and their catalytic applications are explored in asymmetric bromo-, iodo- and seleno-functionalizations of alkenoic acids. This protocol provides
- Jana, Sadhan,Kumar, Sangit,Rathore, Vandana,Verma, Ajay
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supporting information
p. 1667 - 1672
(2019/08/28)
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- Optically probing the localized to delocalized transition in Mo2-Mo2 mixed-valence systems
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Four thienylene (C4H2S) bridged Mo2 dimers, [Mo2(DAniF)3]2(μ-OOCC4H2SCOO) (DAniF = N,N′-di(p-anisyl)formamidinate), [Mo2(DAniF)3]2(μ-N
- Wu, Yi Yang,Meng, Miao,Wang, Gang Yi,Feng, Pengju,Liu, Chun Y.
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supporting information
p. 3030 - 3033
(2017/03/17)
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- Synthesis and antibacterial activity of some novel piperazinophanes with an intraannular ester functionality
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1:1 and 2:2 oligomeric piperazinophanes with an intraannular ester functionality have been synthesized via Mannich reaction of various aromatic esters with piperazine by a one-pot reaction under benign conditions through the multicomponent reaction methodology. The newly synthesized piperazinophanes were characterized using spectral and analytical methods. The ester based 1:1 oligomeric piperazinophanes exhibit good target binding ability in molecular docking studies and also show better antibacterial activity against Escherichia coli, Klebsiella pneumoniae, Staphylococcus aureus and Streptococcus pyogenes bacteria than the 2:2 oligomeric piperazinophanes.
- Selvarani, Sivasamy,Rajakumar, Perumal
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p. 9494 - 9499
(2016/11/11)
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- Effect of Atomic-Scale Differences on the Self-Assembly of Thiophene-based Polycatenars in Liquid Crystalline and Organogel States
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Two series of polycatenars are reported that contain a central thiophene moiety connected to two substituted oxadiazole or thiadiazole units. The number, position, and length of the peripheral chains connected to these molecules were varied. The oxadiazol
- Pradhan, Balaram,Vaisakh,Nair, Geetha G.,Rao, D. S. Shankar,Prasad, S. Krishna,Sudhakar, Achalkumar Ammathnadu
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supporting information
p. 17843 - 17856
(2016/11/28)
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- Mesogenic heterocycles formed by bis-pyrazoles and bis-1,3,4-oxadiazoles
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Three new series of compounds 1a-c containing multiple heterocyclic 2,5-pyrazoles, 1,3,4-oxadiazole and thiophene exhibiting mesophases were reported. Crystallographic data showed that the crystal 1a (n=8) is a linear-shaped molecule with a molecular leng
- Lin, Kuan-Ting,Lee, Gene-Hsiang,Lai, Chung K.
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p. 4352 - 4361
(2015/06/08)
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- Monolayer to Interdigitated Partial Bilayer Smectic C Transition in Thiophene-Based Spacer Mesogens: X-ray Diffraction and 13C Nuclear Magnetic Resonance Studies
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Mesophase organization of molecules built with thiophene at the center and linked via flexible spacers to rigid side arm core units and terminal alkoxy chains has been investigated. Thirty homologues realized by varying the span of the spacers as well as the length of the terminal chains have been studied. In addition to the enantiotropic nematic phase observed for all the mesogens, the increase of the spacer as well as the terminal chain lengths resulted in the smectic C phase. The molecular organization in the smectic phase as investigated by temperature dependent X-ray diffraction measurements revealed an interesting behavior that depended on the length of the spacer vis-a-vis the length of the terminal chain. Thus, a tilted interdigitated partial bilayer organization was observed for molecules with a shorter spacer length, while a tilted monolayer arrangement was observed for those with a longer spacer length. High-resolution solid state 13C NMR studies carried out for representative mesogens indicated a U-shape for all the molecules, indicating that intermolecular interactions and molecular dynamics rather than molecular shape are responsible for the observed behavior. Models for the mesophase organization have been considered and the results understood in terms of segregation of incompatible parts of the mesogens combined with steric frustration leading to the observed lamellar order.
- Kesava Reddy,Varathan,Lobo, Nitin P.,Roy, Arun,Narasimhaswamy,Ramanathan
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p. 10831 - 10842
(2015/10/12)
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- Incorporating Pendent Fullerenes with High Refractive Index Backbones: A Conjunction Effect Method for High Refractive Index Polymers
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To achieve high refractive index polymers (HRIPs), we report here the design and synthesis of four fullerene polyesters (P1-P4), based on the conjunction effect from the high refractive index polyester backbones and pendent fullerene side chains. At sodiu
- Chen, Shuang,Chen, Dongxue,Lu, Min,Zhang, Xin,Li, He,Zhang, Xiaoyan,Yang, Xiaoming,Li, Xiaohong,Tu, Yingfeng,Li, Christopher Y.
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p. 8480 - 8488
(2015/12/12)
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- 2,5-Diamide-Substituted Five-Membered Heterocycles: Challenging Molecular Synthons
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We describe synthetic routes for preparing previously unknown 2,5-diamide-substituted five-membered heterocycles based on the thiophene, pyrrole, and furan ring systems by exploiting Curtius-like rearrangement reactions. Conformation analysis of the 2,5-diamidothiophene derivatives identified a "closed" conformation, in which the two carbonyl O atoms are in close contact with the thiophene S atom.
- Fabbro, Chiara,Armani, Simone,Carloni, Laure-Elie,De Leo, Federica,Wouters, Johan,Bonifazi, Davide
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p. 5487 - 5500
(2014/10/15)
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- Synthesis and two-photon absorption property of new π -conjugated donor-acceptor polymers carrying different heteroaromatics
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In this communication, we report the synthesis of three newly designed fluorescent polymers P1-P3, starting from simple thiophene derivatives through precursor polyhydrazide route. The new polymers, carrying donor and acceptor heterocyclic moieties with different spacer groups were found to be thermally stable and good of nonlinear optical (NLO) materials with two photon absorption property. The structures of newly synthesized monomers and polymers were confirmed by FTIR, NMR spectral and elemental analyses. Further, polymers were characterized by GPC and TGA studies. Their linear optical and electrochemical properties were evaluated by UV-vis, fluorescence spectroscopic and cyclic voltammetric (CV) studies, respectively, whereas their NLO properties were studied by Z-scan technique using Nd: YAG laser at 532 nm with 7 ns pulse. The electrochemical band gap of P1-P3 was determined to be 1.98, 1.91 and 2.05 eV, respectively. The NLO results reveal that polymers P1-P3 show good optical limiting property with TPA coefficient values 2.9 × 10 - 11 m/W, 8.0 × 10 - 11 m/W and 1.4 × 10 - 11 m/W, respectively.
- Sunitha,Vishnumurthy,Adhikari
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- Preparation and characterization of organic-functionalized mesoporous silica as heavy metal adsorbents
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Novel organic-inorganic hybrid mesoporous materials have attracted much attention because the functional organic groups can bring these materials special properties, such as selective absorption and new catalytic properties. In this paper, two kind of bis
- Zhao, Hongli,Hong, Tao,Lan, Minbo,Wang, Wenjuan,Zheng, Saijing,Liu, Baizhan
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p. 1295 - 1299
(2013/05/22)
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- Synthesis and Biological Evaluation of Oral Prodrugs Based on the Structure of Gemcitabine
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A series of oral prodrugs based on the structure of gemcitabine (2′,2′-difluorodeoxycytidine) were synthesised by introducing an amide group at the N4-position of the cytidine ring. A total of 16 compounds were obtained, and their chemical and biological characteristics were evaluated. The half-maximal inhibitory concentrations (IC50s) for most of these compounds were higher than that of gemcitabine in vitro. Compounds 5d and 5m, the representative compounds, were examined in terms of their physiological stabilities and pharmacokinetics. Compound 5d showed good stability in PBS and simulated intestinal fluid, and an analysis of its pharmacokinetics in mice suggested that the introduction of an amide group to gemcitabine could greatly improve its bioavailability. Further evaluation of compound 5din vivo showed that this compound possesses higher activity than gemcitabine against the growth of HepG2 human hepatocellular carcinoma cells and HCT-116 colon adenocarcinoma cells with less toxicity to animals. These results suggest that compound 5d could be further developed as a potential oral anticancer agent for clinical applications in which gemcitabine is currently used. A series of oral prodrugs based on the structure of gemcitabine were synthesized. Physiological and metabolic stabilities, pharmacokinetics and antitumor activities were evaluated for representative compounds.
- Zhao, Cuirong,Xue, Xiaoxia,Li, Gang,Sun, Cuicui,Sun, Changjun,Qu, Xianjun,Li, Wenbao
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experimental part
p. 479 - 488
(2012/10/07)
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- A palladium-catalyzed multicomponent coupling approach to π-conjugated oligomers: Assembling imidazole-based materials from imines and acyl chlorides
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Just like tinkertoys: An alternative approach to access imidazole-containing π-conjugated materials is presented. The imidazole core was assembled at the same time as the oligomer by the palladium-catalyzed multicomponent coupling of imines, diimines, and di(acyl chloride)s, thus providing access to families of new conjugated materials, each formed in a one-step, catalytic reaction (see scheme; Ts=4-toluenesulfonyl). Copyright
- Siamaki, Ali R.,Sakalauskas, Marc,Arndtsen, Bruce A.
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supporting information; experimental part
p. 6552 - 6556
(2011/09/13)
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- Novel diamidino-substituted derivatives of phenyl benzothiazolyl and dibenzothiazolyl furans and thiophenes: Synthesis, antiproliferative and DNA binding properties
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A series of new diamidino-, diisopropylamidino-, and diimidazolinyl- substituted derivatives of phenyl benzothiazolyl and dibenzothiazolyl furans and thiophenes were successfully prepared and evaluated for their antiproliferative activity on tumor cell lines in vitro, DNA binding propensity, and sequence selectivity as well as cellular distribution. A strong antiproliferative effect of the tested compounds was observed on all tested cell lines in a concentration-dependent response pattern. In general, imidazolinyl-substituted derivatives and/or the thiophene core were in correlation with increased antiproliferative activity. Two compounds (2b and 3b) were chosen for biological studies due to their differential antiproliferative properties. The DNA binding properties of this new series of compounds were assessed and evidenced their efficient minor groove binding properties with preferential interaction at AT-rich sites. Both compounds also present nuclear subcellular localization, suggesting that their cellular mode of action implies localization in the DNA compartment and direct inhibition of DNA replication and induction of apoptosis.
- Racané, Livio,Trali?-Kulenovi?, Vesna,Paveli?, Sandra Kraljevi?,Ratkaj, Ivana,Peixoto, Paul,Nhili, Raja,Depauw, Sabine,Hildebrand, Marie-Paule,David-Cordonnier, Marie-Hélène,Paveli?, Kre?imir,Karminski-Zamola, Grace
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experimental part
p. 2418 - 2432
(2010/09/03)
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- A simple and facile carboxylation method and its application for synthesis of liquid crystals
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Sonication of a mixture of magnesium powder, 1,2-dibromoethane, aryl bromide and diethyl dicarbonate in THF followed by treatment with BF 3·OEt2 at room temperature afforded aryl ester with reasonable yield. A series of aryl bromides were investigated and transformed to their corresponding aryl esters under the reaction conditions.
- Lee, Adam Shih-Yuan,Wu, Chih-Chiang,Lin, Li-Shin,Hsu, Hsiu-Fu
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p. 568 - 572
(2007/10/03)
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- Anion complexation properties of thiophene-2,4- and -2,5-biscarboxamides
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Thiophene-2,4- and -2,5-biscarboxamides have been synthesised and shown to act as anion receptors in DMSO-d6/water solution. The crystal structure of the fluoride complex of a N,N′-diphenylthiophene-2,5- biscarboxamide derivative has been solved and reveals the involvement of the thiophene CH protons in anion complexation in the solid state.
- Gale, Philip A.,Hursthouse, Michael B.,Light, Mark E.,Warriner, Colin N.
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p. 1301 - 1308
(2007/10/03)
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- Synthesis and structures of new chiral diamide-ester macrocycles
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A series of new hetero-macrocyclic diamide-ester compounds (4a - 4z, 6a - 6b) were synthesized using 4-(dimethylamino)pyridine as catalyst and characterization by infrared spectra, nuclear magnetic resonance spectra, mass spectra and elemental analyses. The structures of 4e and meso 4b were determined by X-ray crystallography. The association constants of the compounds with various metal ions were determined by UV-visible spectroscopic titration, and showed a selective recognition for certain metal ions.
- Gao, Ming Zhang,Reibenspies, Joseph H.,Wang, Bo,Xu, Zun Le,Zingaro, Ralph A.
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p. 899 - 908
(2007/10/03)
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- Novel structure-defined chiral bis(oxazolinyl)thiophenes for Ru-catalyzed asymmetric cyclopropanation
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The novel structures of sulfur-containing chiral bis(oxazoline) compounds which have been synthesized have been determined by X-ray crystal diffraction analyses. A high enantioselectivity (ee>99%) in the asymmetric cyclopropanation of diphenylethene with
- Gao, Ming Z.,Kong, Deyuan,Clearfield, Abraham,Zingaro, Ralph A.
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p. 5649 - 5652
(2007/10/03)
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- Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 16. Model studies for the construction of conjugated polymers
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Reaction of a range of bis(ylides) with acid chlorides has been used to prepare the bis(oxoylides) 11-15. Similarly a range of simple ylides react with bis(acid chlorides) to give bis(oxoylides) 19-27 with the isomeric structure. Flash vacuum pyrolysis (FVP) of one example of the first type results in extrusion of Ph3P rather than the expected Ph3PO while six examples of the second type do extrude Ph3PO upon FVP at 500 °C to afford the bis(alkynes) 28. Examples of the corresponding bis(tributylphosphonium ylides) have also been prepared but attempts to construct a tetrakis(oxoylide) 31 using a stepwise approach were unsuccessful. Fully assigned 13C NMR spectra are presented for six of the bis(oxoylides).
- Aitken, R. Alan,Drysdale, Martin J.,Hill, Lawrence,Lumbard, Keith W.,Maccallum, James R.,Seth, Shirley
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p. 11039 - 11050
(2007/10/03)
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- SYNTHESIS, STRUCTURE, AND SPECTRAL PROPERTIES OF SOME BIOXAZOLES
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Syntheses of systems containing two oxazole rings from aldehydes obtained by formylating 2-phenyl-, 2-(2-furyl)-, and 2-(2-thienyl)oxazole have been developed.Terephthalate and thiophen-2,5-dicarboxylate esters have been used to obtain 2,2'-(1,4-phenylene)- and 2,2'-(2,5-thienylene)bisoxazoles.The PMR, UV, and luminescence spectra of these systems have been examined, and quantum chemical calculations carried out in the PPP approximation.
- Belen'kii, L. I.,Cheskis, M. A.,Zvolinskii, V. P.,Obukhov, A. E.
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p. 654 - 663
(2007/10/02)
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- Liquid Crystalline Compounds in the Thiophene Series. 1. Liquid Crystalline Thiophene Carboxylic Esters
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Carboxylic esters have been prepared from 5-alkyl-2-thiophenecarboxylic acid and hydrochinone, biphenol, respectively cholesterol as well as one ester from 2,5-thiophene dicarboxylic acid and p-ethylphenol.Only the esters from biphenol respectively cholesterol have liquid crystalline phases. - Keywords: Liquid Crystalline Thiophene Derivatives, Thiophene Carboxylic Esters
- Kossmehl, Gerhard,Budwill, Detlev
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p. 1669 - 1677
(2007/10/02)
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- Eine einfache Methode zur Herstellung von Benzoxazolen
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The preparation of benzoxazoles by a facile one-pot reaction is reported.The reaction of carboxylic acids with 2-chloro-N-methyl-Δ1-pyrrolinium chloride in an excess of N-methyl-2-pyrrolidone afforded carboxylic acid chlorides which were converted subsequently to their 2-hydroxyanilides by addition of 2-aminophenols.Cyclization of the 2-hydroxy-anilides at elevated temperatures furnished the benzoxazoles in high yield and purity.
- Seha, Zdenek,Weis, Claus D
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p. 413 - 419
(2007/10/02)
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- Pyridine esters of cyclopropane-carboxylic acid
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Heterocyclic organic esters and thioesters characterized by the presence of one or two cyclopropane moieties, synthesis thereof, and compositions thereof for the control of mites and ticks.
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