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Hydrophilic Quaternary Ammonium Ionenes—Is There an Influence of Backbone Flexibility and Topology on Antibacterial Properties?
The antimicrobial properties of polycations are strongly affected by the structural features such as the backbone flexibility and topology (isomerism) through the polymer ability to attain proper conformation in interaction with the cell membrane. In this paper, a synthesis and biocidal properties evaluation of ionenes characterized by different backbone topology (isomerism) and flexibility are presented. The findings reveal influence of variation in topology on activity against different microorganisms, and general positive effect of improved flexibility. Furthermore, one of the obtained ionenes displays degradable properties in near physiological environment (phosphate-buffered saline pH 7.4, 37 °C). The degradation proceeds via Hofmann elimination reaction and the products are not of acidic character. For the first time a new class of degradable ionenes with a high antimicrobial potential is presented.
Kopiasz, Rafa? Jerzy,Tomaszewski, Waldemar,Ku?mińska, Aleksandra,Chreptowicz, Karolina,Mierzejewska, Jolanta,Ciach, Tomasz,Jańczewski, Dominik
(2020)
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1,2-Bis(1′,3′-dimethylimidazolin-2′-iminato)ethane - A novel chelating ligand [1]
The reaction of 2-imino-1,3-dimethylimidazoline (10, ImNH) with X-CH2CH2-X (11, X = p-CH3C6H4SO3) gives the diimine adduct ImN-CH2CH2-NIm · 2 HX (12) from which the diimine ImN-CH2CH2-NIm (13) is obtained on treatment with KH. 13 reacts with (C6H5CN)2PdCl2 (15) to give the chelate complex (ImN-CH2CH2-NIm)PdCl2 (16). The X-ray structures of 12 and 16 are reported.
Kuhn, Norbert,Grathwohl, Martin,Steimann, Manfred,Henkel, Gerald
p. 997 - 1003
(1998)
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Synthesis and characterization of novel triarylmethane-based dyes for thermally stable blue color filters
Two new triarylmethane-based dye molecules with a dimeric structure, TAM-1 and TAM-2, were designed and synthesized as potential blue color filter materials for liquid-crystal displays. The dimeric structure of TAM-1 was designed to improve the thermal stability of a well-known blue dye, Victoria Blue BO. TAM-2 was designed to further improve the solubility of TAM-1 by introducing long alkyl ester groups. The synthesized dyes TAM-1 and TAM-2 were transmissive in the wavelength range of 410-460 nm and showed good thermal stability with 5% weight degradation temperatures (T5d) of 259 °C and 289 °C, respectively, and less than 1% of weight loss at 230 °C. Moreover, TAM-2 showed excellent solubility (20.1 wt%) as opposed to Victoria Blue BO (0.03 wt%) and TAM-1 (3.5 wt%) in PGMEA.
Lee, Chan Gyu,Park, Jeong Yong,Park, Young Il,Jung, Seo-Hyun,Lee, Gyu Sung,Park, Jong Mok,Hwang, Do-Hoon,Kong, Hoyoul
p. 4782 - 4786
(2019)
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5,8-Bis(4-methoxy-2,3,6-trimethylbenzene-sulfonyl)-1,4-dioxa-5,8-diazocane
The molecular shape of the title compound, C24H34N2-O8S2, in the crystalline state is characterized by internal twofold symmetry, with the eight-membered ring adopting a crown conformation.
Van Meervelt, Luc,Lin, Paul Kong Thoo
p. 1131 - 1133
(1997)
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Revisiting complexation between DNA and polyethylenimine: Does the disulfide linkage play a critical role in promoting gene delivery?
Despite its cytotoxicity, polyethylenimine (PEI) is still used as a golden reference in gene transfection. Long PEI chains are more effective but also more cytotoxic. To solve this problem, an alternative strategy is to link short PEI chains into a longer PEI with disulfide bonds because they are degradable in the cell. However, how PEI promotes gene transfection is still unclear. Also, the chain length of PEI is also increased as disulfide bonds are formed. Therefore, it is important to investigate whether the increase in transfection efficiency is attributable to the disulfide linkage, chain size, or both. To distinguish between such factors, a novel method is developed here tomake longer linear PEI with disulfide bonds (lPEIs-s) by linking the mercapto groups of short linear PEI (lPEIi). By comparing the physiochemical properties and the transfection efficiencies of short lPEIi, long lPEIs-s, and un-degradable long PEI, it is found that introducing disulfide bonds instead of directly using longer PEI chains has less effect on gene transfection, and it is the chain length that plays a key role in promoting gene transfection.
Ma, Yongzheng,Chen, Baizhu,He, Ning,Chen, Gaojian,Li, Lianwei,Wu, Chi
p. 1807 - 1815
(2014)
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White-light emitting dye micelles in aqueous solution
Biscarbazole-loaded perylene bisimide (PBI) dye micelles in water afforded a fluorescence resonance energy transfer (FRET)-based white-light emitting nano luminary system with biscarbazoles as energy donors and PBI micelles as acceptors.
Zhang, Xin,Goerl, Daniel,Wuerthner, Frank
p. 8178 - 8180
(2013)
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Synthesis and biological evaluation of PET tracers designed for imaging of calcium activated potassium channel 3.1 (KCa3.1) channels: In vivo
Expression of the Ca2+ activated potassium channel 3.1 (KCa3.1) channel (also known as the Gàrdos channel) is dysregulated in many tumor entities and has predictive power with respect to patient survival. Therefore, a positron emission tomography (PET) tracer targeting this ion channel could serve as a potential diagnostic tool by imaging the KCa3.1 channel in vivo. It was envisaged to synthesize [18F]senicapoc ([18F]1) since senicapoc (1) shows high affinity and excellent selectivity towards the KCa3.1 channels. Because problems occurred during 18F-fluorination, the [18F]fluoroethoxy senicapoc derivative [18F]28 was synthesized to generate an alternative PET tracer targeting the KCa3.1 channel. Inhibition of the KCa3.1 channel by 28 was confirmed by patch clamp experiments. In vitro stability in mouse and human serum was shown for 28. Furthermore, biodistribution experiments in wild type mice were performed. Since [18F]fluoride was detected in vivo after application of [18F]28, an in vitro metabolism study was conducted. A potential degradation route of fluoroethoxy derivatives in vivo was found which in general should be taken into account when designing new PET tracers for different targets with a [18F]fluoroethoxy moiety as well as when using the popular prosthetic group [18F]fluoroethyl tosylate for the alkylation of phenols.
B?rgel, Frederik,Br?mmel, Kathrin,Budde, Thomas,Bulk, Etmar,Konken, Christian Paul,Obeng-Darko, Henry,Sch?fers, Michael,Schelhaas, Sonja,Schwab, Albrecht,Wünsch, Bernhard
p. 30295 - 30304
(2021/10/25)

DINUCLEATING LIGAND OR DINUCLEAR METAL COMPLEX
To provide a dinuclear metal complex that can be synthesized simply and easily and has a proper anticancer action.SOLUTION: The present disclosure provides a dinucleating ligand represented by the following formula (I) and a dinuclear metal complex thereof (where X is H or a substituted carbamoyl group, R1, R2, R3, and R4 independently represent H or a C1-8 linear or branched alkyl group).SELECTED DRAWING: None
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(2021/03/19)

Second-Sphere Interaction Promoted Turn-On Fluorescence for Selective Sensing of Organic Amines in a TbIII-based Macrocyclic Framework
Guided by a second-sphere interaction strategy, we fabricated a Tb(III)-based metal—organic framework (MMCF-4) for turn-on sensing of methyl amine with ultra-low detection limit and high turn-on efficiency. MMCF-4 features lanthanide nodes shielded in a nonacoordinate geometry along with secondary coordination spheres that are densely populated with H-bond interacting sites. Nonradiative routes were inhibited by binding-induced rigidification of the ligand on the second coordination sphere, resulting in luminescence amplification. Such remote interacting mechanism involved in the turn-on sensing event was confirmed by single-crystal X-ray diffraction and molecular dynamic simulation studies. The design of both primary and secondary coordination spheres of Tb(III) enabled the first turn-on sensing of organic amines in aqueous conditions. Our work suggests a promising strategy for high-performance turn-on sensing for Ln-MOFs and luminous materials driven by other metal chromophores.
Huang, Xianqiang,Liu, Qingzhi,Liu, Shixi,Ma, Shengqian,Nafady, Ayman,Niu, Zheng,Ren, Junyu,Tsai, Chen-Yen,Ye, Yingxiang
supporting information
p. 23705 - 23712
(2021/09/22)

Synthesis and characterization of novel biological tetracoumarin derivatives bearing ether moieties
A series of novel tetracoumarin derivatives (3a-f) were prepared using the reaction of ether functionalized dibenzaldehyde with 4-hydroxycoumarin in the presence of sodium acetate. The structure of compounds was validated by IR, NMR, and CHN analyzes. Antimicrobial (antibacterial and antifungal) activity was studied on the basis of the minimum bactericidal concentration, minimum inhibitory concentration and inhibitory zone diameter. Favorable biological activity was found in compound 3f.
Behzadi, Soheila Asadpour,Sheikhhosseini, Enayatollah,Ahmadi, Sayed Ali,Ghazanfari, Dadkhoda,Akhgar, Mohammadreza
p. 60 - 67
(2020/06/08)

Novel derivatives of anaplastic lymphoma kinase inhibitors: Synthesis, radiolabeling, and preliminary biological studies of fluoroethyl analogues of crizotinib, alectinib, and ceritinib
Anaplastic lymphoma kinase (ALK), an oncogenic receptor tyrosine kinase, is a therapeutic target in various cancers, including non-small cell lung cancer. Although several ALK inhibitors, including crizotinib, ceritinib, and alectinib, are approved for cancer treatment, their long-term benefit is often limited by the cancer's acquisition of resistance owing to secondary point mutations in ALK. Importantly, some ALK inhibitors cannot cross the blood-brain barrier (BBB) and thus have little or no efficacy against brain metastases. The introduction of a lipophilic moiety, such as a fluoroethyl group may improve the drug's BBB penetration. Herein, we report the synthesis of fluoroethyl analogues of crizotinib 1, alectinib 4, and ceritinib 9, and their radiolabeling with 18F for pharmacokinetic studies. The fluoroethyl derivatives and their radioactive analogues were obtained in good yields with high purity and good molar activity. A cytotoxicity screen in ALK-expressing H2228 lung cancer cells showed that the analogues had up to nanomolar potency and the addition of the fluorinated moiety had minimal impact overall on the potency of the original drugs. Positron emission tomography in healthy mice showed that the analogues had enhanced BBB penetration, suggesting that they have therapeutic potential against central nervous system metastases.
Radaram, Bhasker,Pisaneschi, Federica,Rao, Yi,Yang, Ping,Piwnica-Worms, David,Alauddin, Mian M.
(2019/08/20)

METHOD FOR PREPARING NOTA DERIVATIVE
A method for preparing a NOTA derivative is revealed. The method includes a plurality of steps. First take 4-toluenesulfonyl chloride and diethylenetriamine to carry out tosylation reaction and obtain a first product. Then the first substitution reaction takes place upon addition of the first product with sodium methoxide to get the second product. Next take 4-toluenesulfonyl chloride to react with ethylene glycol for preparing a third product by tosylation reaction therebewteen. Then a coupling reaction between the third product and the second product is carried out to produce a fourth product. The second substitution reaction occurs involving the fourth product in the presence of sulfuric acid. Lastly take the reaction product and hydrochloric acid to have bonding reaction and obtain a final product. The method solves the water-absorption problem of the cyclic organic compound TACN, a NOTA derivative.
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(2019/09/20)

A Bis-Triazacyclononane Tris-Pyridyl N9-Azacryptand “Beer Can” Receptor for Complexation of Alkali Metal and Lead(II) Cations
A new bis-triazacyclononane tris-pyridyl N9-azacryptand ligand is prepared via a convenient one-pot [2+3] condensation reaction between triazacyclononane and 2,6-bis(bromomethyl) pyridine in the presence of M2CO3 (M=Li, Na, K). The proton, lithium, sodium, potassium and lead(II) complexes of the ligand are characterised in the solid state. Preliminary solution-phase competition experiments indicate that the cryptand ligand preferentially binds lead(II) in the presence of sodium, calcium, potassium and zinc cations in methanol solution.
Brown, Asha,Bunchuay, Thanthapatra,Crane, Christopher G.,White, Nicholas G.,Thompson, Amber L.,Beer, Paul D.
supporting information
p. 10434 - 10442
(2018/07/31)

Ionic liquid brush as an efficient and reusable heterogeneous catalytic assembly for the tosylation of phenols and alcohols in neat water
A very efficient and reusable heterogeneous ionic liquid brush assembly was developed. The catalyst exhibits high catalytic activity for the tosylation of phenols and alcohols in neat water. Moreover, the catalyst shows outstanding stability and reusability, and it can be simply and effectively recovered and reused five times without noticeable loss of catalytic activity.
Feng, Simin,Li, Jing,Wei, Junfa
supporting information
p. 4743 - 4746
(2017/07/12)

NOVEL COMPOUND, BLUE RESIN COMPOSITION FOR COLOR FILTER INCLUDING THE SAME, AND COLOR FILTER USING THE SAME
The present invention relates to a compound in a form of a dimer, a blue resin composition for a color filter comprising the same, and a color filter using the same, wherein the compound is a triarylmethane based compound having excellent solubility and thermal stability, and a wide transmittance, so as to provide a blue resin composition for a color filter excellent in heat resistance.(AA) Comparative example(BB) Example 1(CC) Example 3(DD) Example 5(EE) Example 7COPYRIGHT KIPO 2017
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(2017/12/13)

A high-nuclearity metal-cyanide cluster [Mo6Cu14] with photomagnetic properties
A high-nuclearity metal-cyanide cluster [Mo6Cu14] has been prepared and its photomagnetic properties investigated. The photoswitchable magnetic phenomenon observed is thermally reversible (T ≈ 230 K). In the field of photomagnetism, [Mo6Cu14] represents a unique example of a nanocage and the highest nuclearity observed so far.
Bridonneau,Chamoreau,Gontard,Cantin,Von Bardeleben,Marvaud
supporting information
p. 9412 - 9418
(2016/07/06)

α-Glucosidase inhibition and antihyperglycemic activity of flavonoids from Ampelopsis grossedentata and the flavonoid derivatives
The dried leaves and stems of Ampelopsis grossedentata have been used as a health tea and herbal medicine for hundreds of years in China. The study was aimed at searching for novel α-glucosidase inhibitors among the richest components of A. grossedentata and their derivatives. Three known major components (1-3) were isolated by recrystallization process and six new derivatives (4-9) were obtained by etherification of the bioactive flavonoid. All compounds were evaluated for their inhibitory activities against α-glucosidase (from Saccharomyces cerevisiae). As a result, compound 9 showed a significant α-glucosidase inhibitory activity with IC50 value of 9.3 μM and acted as a competitive inhibitor with the value of the inhibition constant (Ki) being 10.3 μM. The oral administration of compound 9 at a dose of 50 mg/kg significantly reduced the post prandial blood glucose levels of normal and streptozotocin (STZ)-induced diabetic mice. Furthermore, compound 9 significantly decreased the fasting blood glucose levels in STZ-induced diabetic mice.
Chen, Jia,Wu, Yuechan,Zou, Jianwei,Gao, Kun
p. 1488 - 1494
(2016/03/16)

Tetranuclear ruthenium(ii) complexes with oligo-oxyethylene linkers as one- and two-photon luminescent tracking non-viral gene vectors
To prolong the observation time, increase the penetration depth and decrease self-absorption and phototoxicity, two-photon luminescent vectors have emerged as promising tools for tracking gene delivery in living cells. Herein, we report four new tetranuclear Ru(ii) complexes based on oligo-oxyethylene and polybenzimidazole as one- and two- photon luminescent tracking non-viral gene vectors. In such a molecular design, the oligo-oxyethylene, polybenzimidazole and Ru(ii) polypyridyl complexes were expected to render the vectors with increased cell permeability, biocompatibility, proton buffering capacity and one- and two-photon luminescence. Corresponding DNA interaction studies showed that the ability of the complexes to condense DNA decreased with increasing oligo-oxyethylene lengths. Additionally, all complexes protected DNA. The complexes were investigated as one- and two-photon tracking non-viral gene vectors in living cells and showed proper cellular uptake, good luciferase expression and low cytotoxicity. This journal is
Qiu, Kangqiang,Yu, Bole,Huang, Huaiyi,Zhang, Pingyu,Ji, Liangnian,Chao, Hui
supporting information
p. 7058 - 7065
(2015/04/14)

Synthesis of a new 18F labeled porphyrin for potential application in positron emission tomography. in vivo imaging and cellular uptake
Herein we report, for the first time, the development, labeling optimization and preliminary biodistribution studies of an [18F] radiolabeled meso-tetraphenylporphyrin. After synthesis and characterization of the "cold" fluorinated porphyrin, the conditions have been transferred to an automated radiochemistry module and the desired 5-(2-[18F]fluoroethoxyphenyl)-10,15,20-triphenylporphyrin was prepared in a radiochemical purity >95%. Moreover, data regarding the uptake into human bladder tumor cells and the radiotracer biodistribution after C57BL/6 mice injection are also presented. The maximum cellular uptake was reached at 45 min and was of 2.5%.
Sim?es, Ana V. C.,Pinto, Sara M. A.,Calvete, Mário J. F.,Gomes, Célia M. F.,Ferreira, Nuno C.,Castelo-Branco, Miguel,Llop, Jordi,Pereira, Mariette M.,Abrunhosa, Antero J.
p. 99540 - 99546
(2015/12/04)

Efficient synthesis of novel benzylidene barbituric and thiobarbituric acid derivatives containing ethyleneglycol spacers
Knoevenagel condensation reaction of ethylene glycol-based aromatic aldehyde with barbituric acid derivatives in ethanol produced novel benzylidene barbituric and thiobarbituric acid derivatives which contain good yields of ethylene glycol spacers. Structures of the products were deduced from their IR, 1H-NMR, and 13C-NMR spectroscopy and mass spectra.
Faryabi, Malihe,Sheikhhosseini, Enayatollah
p. 427 - 432
(2015/02/05)

Highly efficient synthesis of tetra benzo spiro bis-crown ether
Novel spiro bis-crown ethers derivatives with four benzo units connected via one carbon bridges have been prepared. These compounds represent well preorganized cavities with interesting complexation abilities towards cations. These macrocyclic were prepared by a four-step via template method by utilizing simple precursors catechol, oliethylen glycol and penta erythritol tetra bromide in good yield. Additionally, cesium carbonate could be used as an excellent base for these reactions.
Moradgholi, Fatemeh,Vahedi, Hooshang,Lari, Jalil
p. 85 - 90
(2015/06/23)

Synthesis and characterization of a novel series of agonist compounds as potential radiopharmaceuticals for imaging dopamine D2/3 receptors in their high-affinity state
Imaging of dopamine D2/3 receptors (D2/3R) can shed light on the nature of several neuropsychiatric disorders in which dysregulation of D2/3R signaling is involved. Agonist D2/3 tracers for PET/SPECT imaging are considered to be superior to antagonists because they are more sensitive to dopamine concentrations and may selectively label the high-affinity receptor state. Carbon-11-labeled D2/3R agonists have been developed, but these short-lived tracers can be used only in centers with a cyclotron. Here, we report the development of a series of novel D2R agonist compounds based on the 2-aminomethylchromane (AMC) scaffold that provides ample opportunities for the introduction of longer-lived [ 18F] or [123I]. Binding experiments showed that several AMC compounds have a high affinity and selectivity for D2/3R and act as agonists. Two fluorine-containing compounds were [18F]-labeled, and both displayed specific binding to striatal D2/3R in rat brain slices in vitro. These findings encourage further in vivo evaluations.
Van Wieringen, Jan-Peter,Shalgunov, Vladimir,Janssen, Henk M.,Fransen, P. Michel,Janssen, Anton G. M.,Michel, Martin C.,Booij, Jan,Elsinga, Philip H.
p. 391 - 410
(2014/02/14)

Development of a new thiol site-specific prosthetic group and its conjugation with [Cys40]-exendin-4 for in vivo targeting of insulinomas
A new tracer, N-5-[18F]fluoropentylmaleimide ([ 18F]FPenM), for site-specific labeling of free thiol group in proteins and peptides was developed. The tracer was synthesized in three steps (18F displacement of the aliphatic tosylate, di-Boc removal by TFA to expose free amine, and incorporation of the free amine into a maleimide). The radiosynthesis was completed in 110 min with 11-17% radiochemical yield (uncorrected), and specific activity of 20-49 GBq/μmol. [18F]FPenM showed comparable labeling efficiency with N-[2-(4-[18F] fluorobenzamido)ethyl]maleimide ([18F]FBEM). Its application was demonstrated by conjugation with glucagon-like peptide type 1 (GLP-1) analogue [cys40]-exendin-4. The cell uptake, binding affinity, imaging properties, biodistribution, and metabolic stability of the radiolabeled [ 18F]FPenM-[cys40]-exendin-4 were studied using INS-1 tumor cells and INS-1 xenograft model. Positron emission tomography (PET) results showed that the new thiol-specific tracer, [18F]FPenM-[cys 40]-exendin-4, had high tumor uptake (20.32 ± 4.36%ID/g at 60 min postinjection) and rapid liver and kidney clearance, which was comparable to the imaging results with [18F]FBEM-[cys40]-exendin-4 reported by our group.
Yue, Xuyi,Kiesewetter, Dale O.,Guo, Jinxia,Sun, Zhongchan,Zhang, Xiaoxiang,Zhu, Lei,Niu, Gang,Ma, Ying,Lang, Lixin,Chen, Xiaoyuan
p. 1191 - 1200
(2013/08/23)

Synthesis and evaluation of novel 18F-labeled spirocyclic piperidine derivatives as σ1 receptor ligands for positron emission tomography imaging
A series of spirocyclic piperidine derivatives were designed and synthesized as σ1 receptor ligands. In vitro competition binding assays showed that 1′-(4-(2-fluoroethoxy)benzyl)-3H-spiro[2- benzofuran-1,4′-piperidine] (19) possessed high σ1 receptor affinity (Ki = 0.79 nM) and excellent σ1/ σ2 subtype selectivity (350-fold) as well as high σ1/VAChT selectivity (799-fold). The radiolabeled compound [18F]19 was synthesized by substitution of the tosylate precursor 24 with [18F]fluoride, with an isolated radiochemical yield of 35-60%, a radiochemical purity of >99%, and a specific activity of 30-55 GBq/μmol. Biodistribution studies in imprinting control region mice indicated that [ 18F]19 displayed excellent initial brain uptake and slow washout. Ex vivo autoradiography in Sprague-Dawley rats demonstrated high accumulation of the radiotracer in brain areas known to express high levels of σ1 receptors. Micro positron emission tomography imaging and blocking studies confirmed the specific binding of [18F]19 to σ1 receptors in vivo.
Li, Yan,Wang, Xia,Zhang, Jinming,Deuther-Conrad, Winnie,Xie, Fang,Zhang, Xiaojun,Liu, Jian,Qiao, Jinping,Cui, Mengchao,Steinbach, J?rg,Brust, Peter,Liu, Boli,Jia, Hongmei
p. 3478 - 3491
(2013/06/27)

Synthesis and preliminary evaluation steroidal antiestrogen-geldanamycin conjugates
Three novel steroidal antiestrogen-geldanamycin conjugates were prepared using a convergent strategy. The antiestrogenic component utilized the 11β-(4-functionalized-oxyphenyl) estradiol scaffold, while the geldanamycin component was derived by replacement of the 17-methoxy group with an appropriately functionalized amine. Ligation was achieved in high yield using azide alkyne cyclization reactions. Evaluation of the products against two breast cancer cell lines indicated that the conjugates retained significant antiproliferative activity.
Adam Hendricks,Hanson, Robert N.,Amolins, Michael,Mihelcic, John M.,Blagg, Brian S.
supporting information
p. 3635 - 3639
(2013/07/19)

Design and synthesis of polymeric chiral bicyclo[3.3.0] diene as reusable ligand for rhodium-catalyzed asymmetric 1,4-addition
A series of A-B type sterically regular bicyclio[3.3.0] diene-based polymers were designed and synthesized as immobilized chiral diene ligands for asymmetric catalysis. With polymeric diene 6b, good to excellent enantioselectivities can be achieved in Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated ketones. A series of A-B type sterically regular bicyclio[3.3.0] diene-based polymers were designed and synthesized as immobilized chiral diene ligands for asymmetric catalysis. By using polymeric diene, good to excellent enantioselectivities can be achieved in Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated ketones. Copyright
Yang, Hongyu,Xu, Minghua
supporting information
p. 119 - 122
(2013/08/24)

Synthesis of a spin-labeled anti-estrogen as a dynamic motion probe for the estrogen receptor ligand binding domain
The preparation and characterization of a novel nitroxide spin probe based on a steroidal anti-estrogen is described. The probe 5 demonstrated very high binding affinity for both the alpha and beta isoforms of the estrogen receptor-ligand binding domain. EPR spectrometric studies demonstrate conformational constraints for the ligand, consistent with the nitroxyl moiety occupying a position just beyond the receptor-solvent interface.
Hendricks, J. Adam,Gullà, Stefano V.,Budil, David E.,Hanson, Robert N.
supporting information; experimental part
p. 1743 - 1746
(2012/04/10)

Effects of alkyl substitution on the physical properties and gas transport behavior in selected poly(R-phenoxyphosphazenes)
A systematic preparation of alkyl substituted phenoxyphosphazene polymers was performed and their gas transport properties determined. In this study, phosphazenes substituted with 4-methylphenol, 4-ethylphenol, and 4-isopropylphenol are reported. An additional polymer substituted with 4-tert-butylphenoxy-1-ethanol also was synthesized in this work. Data derived for these materials, including chemical, thermal and gas transport characterization, were compared to previous reports discussing poly[bis-phenoxyphosphazene] and its analog with tert-butyl substitution: poly[bis-(4-tert-butylphenoxy)phosphazene]. The tert-butyl moiety influences orderly chain packing, presumably through steric hindrance that can influence aromatic π-stacking. For the new poly[(alkylphenoxy)phosphazenes], semicrystallinity is maintained and the added steric bulk serves to decrease the polymer glass transition temperature (Tg) and increase both permeability and selectivity for the gas pairs: O2/N2 and CO 2/CH4. Removal of the tert-butyl moiety from the immediate vicinity of the backbone through a flexible spacer serves to depress the Tg as compared to poly[bis-(4-tert-butylphenoxy)phosphazene], but provides no performance enhancement for gas transport.
Ogden, Mark D.,Orme, Christopher J.,Stewart, Frederick F.
experimental part
p. 3879 - 3886
(2012/04/23)

Design and synthesis of new cryptophanes with intermediate cavity sizes
Chemical equations presented. The development of molecular imaging using hyperpolarized xenon MRI needs highly optimized biosensors. Cryptophane-111 and cryptophane-222 are promising candidates that show complementary encapsulation properties although they only differ by the length of the three alkane linkers joining two cyclotriphenolene units. Cryptophanes containing both methoxy and ethoxy linkers have never been synthesized. Here we synthesize two new cages with intermediate internal volumes, in two steps from cyclotriphenolene.
Kotera, Naoko,Delacour, Lea,Traore, Tenin,Tassali, Nawal,Berthault, Patrick,Buisson, David-Alexandre,Dognon, Jean-Pierre,Rousseau, Bernard
supporting information; experimental part
p. 2153 - 2155
(2011/07/08)

The interesting DNA-binding properties of three novel dinuclear Ru(II) complexes with varied lengths of flexible bridges
Three binuclear Ru(II) complexes with two [Ru(bpy)2(pip)] 2+-based subunits {where bpy = 2,2′-bipyridine and pip = 2-phenylimidazo[4,5-f][1,10]phenanthroline} being linked by varied lengths of flexible bridges, were synthesized and characterized by 1H NMR, elemental analysis, UV-visible (UV-vis) and photoluminescence spectroscopy. The structures of the three complexes were optimized by density functional theory calculations. The interaction of the complexes with calf thymus DNA was investigated by UV-vis and luminescence titrations, steady-state emission quenching by [Fe(CN)6]4-, DNA competitive binding with ethidium bromide, DNA melting experiments, and viscosity measurements. The experimental results indicated that the three complexes bound to the DNA most probably in a threading intercalation binding mode with high DNA binding constant values three orders of magnitude greater than the DNA binding constant value reported for proven DNA intercalator, mononuclear counterpart [Ru(bpy)2(p-mopip)]2+ {p-mopip = 2-(4-methoxylphenyl) imidazo[4,5-f][1,10]phenanthroline}.
Ju, Chuan-Chuan,Zhang, An-Guo,Yuan, Chui-Li,Zhao, Xiao-Long,Wang, Ke-Zhi
experimental part
p. 435 - 443
(2012/02/14)

Synthesis of new bis-BINOL-2,2′-ethers and bis-H8BINOL-2,2′-ethers evaluation of their Titanium complexes in the asymmetric ethylation of benzaldehyde
The preparation by means of different synthetic paths of a series of bis-BINOL and bis-H8BINOL ligands is described. The ligands consist of two BINOL or H8BINOL fragments, joined by diverse linkages through the oxygen at the 2′-position of the arylic fragments. These ligands were applied to the Ti(OiPr)4 catalyzed asymmetric alkylation of benzaldehyde with Et2Zn. The performance of these catalysts is very sensitive to the nature of the ether linkage. The ligand with a propylene link shows better enantioselectivity (ca. 70%) than those with two or four carbon atoms joining the BINOL fragments. Furthermore, using the propylene link, but replacing (R)-BINOL by (R)-H8BINOL, a significant improvement in the stereoselectivity of the catalysts was achieved (ca. 80% ee in (R)-1-phenylpropan-1-ol). A cooperative effect was observed between the chirality at the BINOL fragment and that of a (S,S)-4,5-bis(methylene)-2,2-dimethyl-1,3-dioxolane link, derived from tartaric acid. When this chiral link combines with two (S)-BINOL fragments, the alkylation of benzaldehyde in toluene produces 70% ee of (S)-1-phenylpropan-1-ol, while the (R)-BINOL derivative ligand with the same link, in identical conditions, yields only 40% ee of the (R)-alcohol.
Abreu, Artur R.,Pereira, Mariette M.,Bayón, J. Carles
experimental part
p. 743 - 749
(2010/09/14)

Tripodal tris-tacn and tris-dpa platforms for assembling phosphate-templated trimetallic centers
Multidentate tripodal ligands, N(CH2-m-C6H 4-CH2tacn)3 (L1) and N(CH2-o-C 6H4-CH2N(CH2py)2) 3 (L2), have been devised for assembling high-nuclearity metal clusters. By using the same tripodal platform with different ligand appendages, either triazacyclononanes or dipicolylamines, and functionalizing either the ortho or the meta positions on the tris(xylyl) linker arms, discrete trimetal phosphate units of relevance to phosphate-metabolizing trimetallic centers in biology were prepared. Four such compounds, [(CuIICl) 3(HPO4)L1](PF6) (1), [(CuIICl) 3(HAsO4)L1](PF6) (2), Na2[Mn III6MnII2(H2O) 2(HPO4)6(PO4)4(L1) 2] (3), and [CoII3(H2PO 4)Cl2(MeCN)L2](PF6)3 (4), all containing three metal centers bound to a central phosphate or arsenate unit bridging oxygen atoms, have been synthesized and structurally characterized. These results demonstrate the propensity of this novel tripodal ligand platform, in the presence of phosphate or arsenate, to assemble {M3(EO 4)} units and thus structurally mimic trimetallic active sites of proteins involved in phosphate metabolism. Reactivity studies reveal that the tricopper complex 1 is more efficient than monocopper analogues in catalyzing the hydrolysis of 4-nitrophenyl phosphate.
Cao, Rui,Mueller, Peter,Lippard, Stephen J.
supporting information; experimental part
p. 17366 - 17369
(2011/02/23)

A heterogeneous, selective oxidation catalyst based on Mn triazacyclononane grafted under reaction conditions
A unique method has been developed to synthesize an active heterogeneous oxidation catalyst by the in situ grafting of a 1,4,7-trimethyl-1,4,7- triazacyclononane manganese complex on carboxylic acid-functionalized supports serving dual roles as surface tether and necessary co-catalyst, massively increasing total turnovers as compared to the homogeneous analog.
Schoenfeldt, Nicholas J.,Korinda, Andrew W.,Notestein, Justin M.
supporting information; experimental part
p. 1640 - 1642
(2010/07/03)

New atropisomeric N-N ligands for CO/vinyl arene copolymerization reaction
New atropisomeric bidentate bipyridine-based ligands (3,3′- (ethylenedioxy)-2,2′-bipyridine 3; 3,3′-(propylenedioxy)-2,2′- bipyridine 4; 3,3′-(butylenedioxy)-2,2′-bipyridine 5) containing a bridge between the 3,3′ positions of the aromatic rings have been prepared. Together with the previously reported analogous ligands ((R)-3,3′-(1-methylethylenedioxy)-2,2′-bipyridine) 1 and ((S,S)-3,3′-(1,2-dimethylethylenedioxy)-2,2′-bipyridine) 2, they were used to synthesize the corresponding bis-chelated dicationic complexes [Pd(N-N)2][PF6]2. Crystal structures and comparison of the data obtained by X-ray analysis on four of these complexes is reported. These palladium compounds were used as precatalysts in the CO/styrene and CO/4-Me-styrene copolymerization reactions, where they showed that small variations in the ligand backbone remarkably affects the productivity of the catalytic system. The Royal Society of Chemistry 2008.
Durand, Jerome,Zangrando, Ennio,Carfagna, Carla,Milani, Barbara
p. 2171 - 2182
(2008/09/20)

Contrast Agents for Magnetic Resonance Imaging
The invention relates to contrast agents for magnetic resonance imaging comprising a chelating ligand and a transition metal ion, said ligand carrying a substituent capable of reacting chemically or biochemically with a target substance while bringing about a change in the spin state.
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Page/Page column 19

(2008/06/13)

A convenient method for the preparation of no-carrier-added O-(2-[18F]fluoroethyl)-L-Tyrosine)
This is a novel method for production of no-carrier-added O-(2-[18F]fluoroethyl)-L-Tyrosine which has been proved a suitable PET (position emission tomography) probe for tumor diagnosis imaging. The preparation of the title compound starts from precursors with the chemical structures as in Formula 1, wherein R1 is a protective group for the carboxyl functional group, R2 is a protective group for the amino group, and R3 acts as a leaving group. R1 represents an arylalkyl group, R2 represents a carboxyl group, and R3 represents a p-tosyloxy, methane sulfonyloxy or trifluoromethane sulfonyloxy or bromine. The final purification of the product is using a separation column, which is very convenient for automated synthesis. The invention uses the precursor with the chemical structures as in Formula 1. Formula 1 : Synthesis precursors for O-(2-C18F]fluoroethyl)-L-Tyrosine.
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Page/Page column 4-5

(2008/06/13)

The synthesis of tethered ligand dimers for PPARγ-RXR protein heterodimers
The synthesis of heterodimeric compounds based on tethering the peroxisome proliferator-activated receptors (PPAR)γ agonist, Rosiglitazone and the RXR ligand Targetin is investigated. The synthesis of these compounds was accomplished via a convergent strategy, employed for preparing the appropriately-functionalized subunits of Rosiglitazone and Targetin and then attaching them to opposite ends of the tether. It was observed that a Mitsunobu reaction between the alcohol 5 and 4-hydroxy-benzaldehyde produced the ether 6 in a yield of 80%. It was concluded that the convergent strategy for the synthesis of these compounds could be easily adaptable to a larger and more diverse set of compounds as ligands for the PPARγ-RXR protein heterodimer.
Mohler, Debra L.,Shen, Gang
p. 2082 - 2087
(2008/02/03)

Convenient method for the preparation of new precursor of no-carrier-added O-(2-[18F]fluoroethyl)-L-Tyrosine)
This is a new precursor and new method for the synthesis of no-carrier-added O-(2-[18F]fluoroethyl)-L-Tyrosine which has been proved a suitable PET (position emission tomography) probe for tumor diagnosis imaging, the preparation of the title compound starts from precursors with the chemical structures as in Formula 1, wherein R1 is a protective group for the carboxyl functional group, R2 is a protective group for the amino group, and R3 acts as a leaving group. R1 represents an arylalkyl group, R2 represents a carboxyl group, and R3 represents a p-tosyloxy, methane sulfonyloxy or trifluoromethane sulfonyloxy or bromine, the invention includes a method for the syntheses of new precursors with the chemical structures as in Formula 1.
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Page/Page column 2

(2008/06/13)

Convenient method for the preparation of no-carrier-added O-(2-[18F]fluoroethyl)-L-tyrosine)
This is a novel method for production of no-carrier-added O-(2-[18F]fluoroethyl)-L-Tyrosine, which has been proved a suitable PET (position emission tomography) probe for tumor diagnosis imaging, and the preparation of the title compound starts from precursors with the chemical structures as in Formula 1, wherein R1 is a protective group for the carboxyl functional group, R2 is a protective group for the amino group, and R3 acts as a leaving group, R1 represents an arylalkyl group, R2 represents a carboxyl group, and R3 represents a p-tosyloxy, methane sulfonyloxy or trifluoromethane sulfonyloxy or bromine, and the final purification of the product is using a separation column, which is very convenient for automated synthesis, and the invention uses the precursor with the chemical structures as in Formula 1.
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Page/Page column 4

(2008/06/13)

Contrast agents for myocardial perfusion imaging
The present disclosure is directed, in part, to compounds and methods for imaging myocardial perfusion, comprising administering to a patient a contrast agent which comprises a compound that binds MC-1, and an imaging moiety, and scanning the patient using diagnostic imaging.
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Page/Page column 37

(2010/02/13)

DNA hydrolysis catalyzed by tris(diisopropyl-1,4,7-triazacyclononanes) ethane metal complexes
Novel trinuclear coordinated ligands were designed using three of 1,4,7-triazacyclononane moieties with a tribromo linker. These ligands show greater capability and potency in association with various metal ions. Tris(diisopropyl-1,4,7-triazacyclononanes)ethane (2) associated with Cu 2+ and Ce4+ ions shows better reactivity to achieve DNA hydrolysis at 37 °C at pH 8 for 5 hr. Using high resolution of polyacrylamide gel electrophoresis, DNA cleavage reaction in Tris-HCl buffer causes a nicking site at the single-stranded region. Alternatively, the reaction in HEPES buffer shows a random DNA cleavage included the double-stranded region. Hydrolysis of phosphodiester bond mediated by trinuclear metal complex is capable of performing at the physiological temperature 37 °C, but it has a lower reactivity compared to mono- and di-nuclear metal complexes. The result suggests that trinuclear metal complexes have a bulky environment to prevent from going toward the phosphodiester bond. The design of an efficient chemical hydrolyase will be a challenge in order to construct a coordinate ligand with the enhancement of hydrolytic activity and the reduction of the steric environment.
Cheng, Chien-Chung,Huang, Yan-Chen,Liu, Ming-Chan
p. 1201 - 1208
(2007/10/03)

Efficient and mild Ytterbium(III)-catalyzed tosylation of alcohols
Ytterbium(III) trifluoromethanesulfonate efficiently catalyzes the reaction of primary and secondary alcohols with toluenesulfonic acid anhydride to yield the alkyl tosylates in high yields. The reactions were carried out under neutral and mild conditions and product purification was easily achieved by means of short column chromatography.
Comagic, Slobodan,Schirrmacher, Ralf
p. 885 - 888
(2007/10/03)

Periphery-modified crown ethers. Synthesis of bis-5,8-dimethoxy-1,4- methanonaphthalene-fused crown ethers
The easily accessible and multi-functionalized 5,8-dimethoxy-6,7-dihydroxy methyl-1,4-dihydro-1,4-methanonaphthalene (1) has been utilized as the basic building material to synthesize the symmetric bis-methanonaphthalene-fused crown ethers 14a-d (BMN-16-crown-4, BMN-22-crown-6, BMN-28-crown-8, and BMN-34-crown-10), that are constructed based on the connection between the α,β-bis-benzylic carbon atoms of diol 1 and oligoethylene glycols (9a-d) via two synthetic routes keyed upon the method of Williamson ether synthesis.
Chou, Teh-Chang,Chen, Shing-Yi,Chen, Yie-Hsung
p. 9939 - 9950
(2007/10/03)

Silver(I) oxide mediated highly selective monotosylation of symmetrical diols. Application to the synthesis of polysubstituted cyclic ethers
(Matrix Presented) The reaction of symmetrical diols and oligo(ethylene glycol)s with a stoichiometric amount of p-toluenesulfonyl chloride in the presence of silver(I) oxide and a catalytic amount of potassium iodide led selectively to the monotosylate derivatives in high yields. Polysubstituted cyclic ethers were obtained readily upon treatment of the corresponding diols with an excess of silver oxide. The high selectivity was explained on the basis of the difference in acidity between the two hydroxy groups, which undergo an intramolecular hydrogen bonding.
Bouzide, Abderrahim,Sauve, Gilles
p. 2329 - 2332
(2007/10/03)

Synthesis of a series of triaza-macrocyclicanes
Condensation of the N, N′, N″-tris(p-toluenesulfonyl)diethylenetrimine-N,N″-disodium with bissulphonate esters of two-, three-, four- and six-carbon diols gives the corresponding 9-, 10-,11-, 13-membered triamine macrocycles containing N-ptoluenesulfonyl group, respectively. The p-tuluenesulfonyl groups are removed with concentrated sulfuric acid, acetic acidhydrobromic acid or LiAlH4 which give the ammonium salts of 1,4,7-triazacyclononane, 1,4,7-triazacyclodecane, 1,4,7-triazacycloundecane, 1,4,7-triazacyclotridecane, respectively. Comparison and details of the different synthetic procedures of the triamine macrocycles are described as well.
Gao, Jinzhang,He, Hui,Zhang, Xuan,Lu, Xiaoquan,Kang, Jingwan
p. 372 - 375
(2007/10/03)

Silver(I) oxide-mediated facile and practical sulfonylation of alcohols
Primary and secondary alcohols were efficiently sulfonylated in the presence of silver(I) oxide and potassium iodide in dichloromethane. The sulfonylation occurs under mild, neutral reaction conditions. The ease of isolation of the final product presents a marked advantage over the known methodologies.
Bouzide, Abderrahim,LeBerre, Nicolas,Sauvé, Gilles
p. 8781 - 8783
(2007/10/03)

Synthesis and Properties of a New Series of Troegerophanes
A new series of macrocyclic compounds with one or two Troeger base skeletons has been synthesized by condensing mono-, di-, tri-, and teraethyleneglycol bis(p-aminophenoxy) ethers with formalin in the presence of concentrated hydrochloric acid in ethanol at room temperature for 13 days. This simple one-step cyclization provided 19 in remarkably high yield (46%) and 17, 18, and 20 in yields reflecting the strain of the rings and statistical factors. Complexation with lithium thiocyanate was observed for 20, the structure of which was elucidated by X-ray crystallography.
Ibrahim, Alhussein A.,Matsumoto, Mutsumi,Miyahara, Yuji,Izumi, Kenji,Suenaga, Masahiko,Shimizu, Nobujiro,Inazu, Takahiko
p. 209 - 215
(2007/10/03)

Phosphoric triamides. 31Phosphorus NMR chemical shift as a function of the P-N bond characteristics
Six phosphoric triamides in which amide nitrogens are incorporated into an increasing number (from 0 to 3) of the 1,3,2-diazaphospholidin-2-one rings have been prepared and their crystal structures have been determined. The structural changes from the non-cyclic to the mono-, di- and tri-cyclic systems result in the decrease of the N-P-N bond angles and the increase of the P-N bond distance. These changes are paralleled by a strong deshielding of the 31P nucleus, leading to an exceptionally high δp value for the tricyclic derivative. The δp-structural parameters relationship is discussed in terms of the changes in hybridization of phosphorus and the variation in the P-N bond order.
Bourne, Susan A.,Mbianda, Xavier Y.,Modro, Tomasz A.,Nassimbeni, Luigi R.,Wan, Huijie
p. 83 - 88
(2007/10/03)

Synthesis of N,N',N'-tri(3,5-dinitro benzenesulfonyl)-1,4,7- triazacyclononane and N,N',N'-tri(3,5-diamino benzenesulfonyl)-1,4,7- triazacyclononane
An easy three step synthesis of N, N', N'-tribenzenesulfonyl-1,4,7- triazacyclononane (I) was carried out in good yields and short reaction times starting from diethylenetriamine, 1,2-ethandiol and benzene sulfochloride. The first synthesis of nitro and amino derivatives of I was reported in detail.
Gao, Jinzhang,Feng, Yafei,Kang, Jingwan
p. 3219 - 3225
(2007/10/03)

Direct facile tetrahydrofuranylation of alcohols in p-TsCl/NaH/THF system
Several alcohols were converted in excellent yields into their 2-tetrahydrofuranyl-ethers in the presence of p-TsCl and NaH in THF under mild conditions. A radical process was proposed.
Yu,Hui
p. 2037 - 2042
(2007/10/02)