- Two-component assembly of recognition-encoded oligomers that form stable H-bonded duplexes
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A new family of recognition-encoded oligomers that form stable duplexes in chloroform have been prepared. Monomer building blocks composed of dialdehydes functionalised with either a trifluoromethylphenol or phosphine oxide H-bond recognition unit were prepared. The dialdehydes were coupled with diamines by imine formation and then reduction to give homo-oligomers between one and three recognition units in length. Duplex formation was characterised by 19F and 1H NMR titration experiments in toluene and in chloroform. For duplexes formed between length complementary H-bond donor and acceptor homo-oligomers, an order of magnitude increase in stability was observed for every base-pair added to the duplex in chloroform. The effective molarity for the intramolecular H-bonds responsible for zipping up the duplex is 30 mM, which results in the fully assembled duplex in all cases. The uniform increase in duplex stability with oligomer length suggests that the backbone structure and geometry is likely to be compatible with the formation of extended duplexes in longer oligomers.
- Gabrielli, Luca,Nú?ez-Villanueva, Diego,Hunter, Christopher A.
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- Antioxidant, DNA interaction, molecular docking and cytotoxicity studies of aminoethylpiperazine-containing macrocyclic binuclear copper(II) complexes
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A series of new macrocyclic binuclear copper(II) complexes of the type [Cu2L1–5(ClO4)](ClO4) (1–5) were synthesized by template condensation between precursor compounds 2,6-bis(4-aminoethylpiperazin-1-ylmethyl)-
- Karthick,Karthikeyan,Korrapati, Purna Sai,Rahiman, A. Kalilur
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- Bimetallic Bis-anion Cascade Complexes of Magnesium in Nonaqueous Solution
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Bimetallic magnesium(II) complexes are gaining significant interest in catalysis, yet their fundamental formation and behavior in organic media remain surprisingly unexplored relative to other divalent cations. To understand key principles of their formation, we investigate symmetric ditopic ligands bearing a phenolic backbone and characterize their ability to form dinuclear magnesium(II) cascade complexes with two bridging anions. High-fidelity production of bimetallic magnesium complexes relative to the monometallic complexes is indicative of positive cooperativity. Binding and recognition of analytes or substrates is a key characteristic of metal cascade complexes and relies on anion exchange, but this is also rarely studied with bimetallic magnesium complexes. Investigations with acetate, phosphate, and pyrophosphate reveal exchange of bridging nitrates using the bis-dipicolylamine complex. Rare seven-coordinate magnesium centers are found for the ester complex. The findings in this study provide formative steps to establish design principles for future generations of bimetallic magnesium(II) complexes.
- Carta, Veronica,Flood, Amar H.,Flynn, Ian G.,Van Craen, David
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- Readily prepared inclusion forming chiral calixsalens
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Calixsalens, chiral triangular hexaimines are readily synthesized by [3 + 3] cyclocondensation of trans-(R,R)-1,2-diaminocyclohexane with 2-hydroxyisophthalaldehyde derivatives. The usually rigid calixsalen ring is able to invert its conformation as a consequence of steric repulsion between bulky substituents at the C5 positions of the aromatic rings. The steric and electronic nature of the substituents does not affect only the conformation of the macrocycle. Small polar substituents enforce dimeric self-association to form an apohost where each of the monomers simultaneously serves as the host and the guest of its partner. Non-associating calixsalens form assemblies in which two symmetry-related molecules are arranged in a head-to-head fashion to form a capsule, or unimolecular cages that are able to entrap solvent molecules in their intrinsic voids.
- Janiak, Agnieszka,Petryk, Ma?gorzata,Barbour, Leonard J.,Kwit, Marcin
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- One-pot Synthesis of a Truncated Cone-shaped Porphyrin Macrocycle and Its Self-assembly into Permanent Porous Material
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Here, we report the synthesis of a truncated cone-shaped triangular porphyrinic macrocycle, P3L3, via a single step imine condensation of a cis-diaminophenylporphyrin and a bent dialdehyde-based linker as building units. X-ray diffra
- Kim, Ikjin,Dhamija, Avinash,Hwang, In-Chul,Lee, Hochan,Ko, Young Ho,Kim, Kimoon
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- Selective mono- and bis-oxidation of 2,6-bis(hydroxy methyl) phenols with active manganese dioxide
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Selective mono- and bis-oxidations of 2, 6-bis (hydroxy methyl) phenols with active M(n)O2 were realized, giving 2-hydroxy-3- hydroxymethyl benzaldehydes and 2-hydroxyisophthalaldehydes in good yields. The influence of oxidant activity, reaction solvent and temperature on the selectivity were investigated, and favorable conditions developed.
- Xie,Zhang,Yan,Yuan
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- A simple but highly efficient multi-formyl phenol-amine system for fluorescence detection of peroxide explosive vapour
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A simple, highly stable, sensitive and selective fluorescent system for peroxide explosives was developed via an aromatic aldehyde oxidation reaction. The high efficiency arises from its higher HOMO level and multiple H-bonding. The sensitivity is obtaine
- Xu, Wei,Fu, Yanyan,Gao, Yixun,Yao, Junjun,Fan, Tianchi,Zhu, Defeng,He, Qingguo,Cao, Huimin,Cheng, Jiangong
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- Mono- and diformylation of 4-substituted phenols: A new application of the duff reaction
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Careful control of the reaction conditions in a modified Duff reaction using anhydrous trifluoroacetic acid as the solvent enables the selective synthesis of either 4-substituted 2-formylphenols (5-substituted salicylaldehydes) or 4-substituted 2,6-diformylphenols in one step starting from commercially available 4-substituted phenols in moderate to good yield.
- Lindoy, Leonard F.,Meehan, George V.,Svenstrup, Niels
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- Carboxylic Acid Functionalized Clathrochelate Complexes: Large, Robust, and Easy-to-Access Metalloligands
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Polycarboxylate ligands are among the most important building blocks for the synthesis of metal-organic frameworks (MOFs). The ability to access these ligands in an efficient way is of key importance for future applications of MOFs. Here, we demonstrate that mono- and dinuclear clathrochelate complexes are versatile scaffolds for the preparation of polytopic carboxylate ligands. The largely inert clathrochelate complexes have a trigonal-bipyramidal shape. The synthesis of functionalized clathrochelates with two, three, four, or five carboxylic acid groups in the ligand periphery can be achieved in a few steps from simple starting materials. Apart from being easily accessible, the metalloligands display interesting characteristics for applications in metallasupramolecular chemistry and materials science: they are rigid, large (up to 2.2 nm), and robust and they can show additional functions (e.g., fluorescence or extra charge) depending on the metal ion that is present in the clathrochelate core. The utility of these new metalloligands in MOF chemistry is demonstrated by the synthesis of zinc- and zirconium-based coordination polymers. The combination of Zn(NO3)2 with clathrochelates having two or three carboxylic acid groups gives MOFs in which the clathrochelate ligands are connected by Zn4O clusters or zinc paddlewheel links. The structures of the resulting two- and three-dimensional networks could be established by single-crystal X-ray crystallography. The reaction of carboxylic acid functionalized clathrochelates with ZrCl4 gives amorphous powders that display permanent porosity after solvent removal.
- Marmier, Mathieu,Wise, Matthew D.,Holstein, Julian J.,Pattison, Philip,Schenk, Kurt,Solari, Euro,Scopelliti, Rosario,Severin, Kay
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- Racemic Porous Organic Cage Crystal with Selective Gas Adsorption Behaviors
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A mixture containing the reactions solution between 3,3′′,5,5′′-tetraformyl-4,4′′-[1,1′:4′,1′′-terphenyl]diol (TTD) and two enantiomers of cyclohexanediamine, respectively, affords porous racemic molecular crystal (1). Two kinds of homochiral [3+6] porous organic cage molecules 1 have been clearly disclosed by single crystal X-ray diffraction analysis, forming one-dimensional porous supramolecular channels with the narrowest size of 3.5 ?. The intercrossing channels of 1 enable the permanent porosity as well as the selective gas adsorption of acetylene and carbon dioxide over methane.
- Yang, Wei,Sun, Nana,Wang, Xinxin,Yu, Baoqiu,Wang, Hailong
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supporting information
(2022/01/22)
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- Multi-group compound with fluorescence specific response to different anions as well as preparation method and application of multi-group compound
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The invention discloses a multi-group compound with fluorescence specific response to different anions as well as a preparation method and application thereof, and relates to the field of compounds. The multi-group compound has a structure shown in the sp
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Paragraph 0017-0023
(2021/05/12)
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- Examination of structure-activity relationship of new n-acylhydrazones
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In this study we describe synthesis and characterization of new substituted hydroxy-bis-N-acylhydrazones in order to investigate influence of their switching emission properties, according to the nature of the substituent. The fluorescence of the compounds depended on the solvent used (organic or aqueous). The different emission colors observed could be explained by conformation modifications.
- Coman, Anca G.,Paun, Anca,Popescu, Codru?a C.,Hadade, Niculina D.,Hanganu, Anamaria,M?d?lan, Augustin M.,Matache, Mihaela
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p. 109 - 114
(2021/02/05)
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- Preparation method of a special impurity of febuxostat
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The invention provides a preparation method of a special impurity of febuxostat. The preparation method is as follows: (1): first, two aldehyde groups are introduced on a benzene ring through a reaction of N1 and HMTA to form N2, and the yield is up to 90% due to reduction of steric resistance; (2): a coupling reaction of N2 and N3 is carried out to produce A, and the yield is up to 70%; (3): A reacts with hydroxylamine hydrochloride to form B, and the yield is about 80%; and (4): B is subjected to hydrolysis to obtain C, and the yield is about 90%. According to the preparation method of the specific impurity of febuxostat, the total yield of synthesizing C is about 45%. Compared with the prior art, the yield is greatly improved, and the starting raw materials N1 and N3 of the new synthetic route are cheap and easy to obtain, the method is suitable for large-scale synthesis, and the disadvantages that amount accumulation and purification are relatively difficult when A is synthesized from M3 in the prior art are avoided.
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Paragraph 0024; 0025; 0026; 0030; 0031; 0035; 0036
(2020/01/12)
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- Examination of structure-activity relationship of new n-acylhydrazones
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In this study we describe synthesis and characterization of new substituted hydroxy-bis-N-acylhydrazones in order to investigate influence of their switching emission properties, according to the nature of the substituent. The fluorescence of the compounds depended on the solvent used (organic or aqueous). The different emission colors observed could be explained by conformation modifications.
- Coman, Anca G.,Hadade, Niculina D.,Hanganu, Anamaria,Mǎdǎlan, Augustin M.,Matache, Mihaela,Paun, Anca,Popescu, Codru?a C.
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p. 109 - 114
(2020/07/23)
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- Novel small molecular compound ae-848 potently induces human multiple myeloma cell apoptosis by modulating the nf-κb and pi3k/ akt/mtor signaling pathways
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Background: We aimed to investigate the anti-multiple myeloma (MM) activity of the new small molecular compound AE-848 (5-bromo-2-hydroxyisophthalaldehyde bis[(1-methyl-1H-benzimidazol-2-yl)hydrazone]) and its underlying anti-MM mechanism. Methods: Cell viability and apoptosis were detected and quantified by using MTT and flow cytometry, respectively. JC-1 dye-related techniques were used to assess mitochondrial membrane potential (MMP). Western blotting was applied to detect the expression of NF-κB and PI3K/Akt/mTOR pathway-associated proteins. The in vivo activity of AE-848 against MM was evaluated in a MM mouse model. Results: Application of AE-848 into the in vitro cell culture system significantly reduced the viability and induced apoptosis of the MM cell lines, RPMI-8226 and U266, in a dose-and time-dependent manner, respectively. JC-1 dye and Western blotting analysis revealed that AE-848 induced the cleavage of caspase-8, caspase-3, and poly ADP-ribose polymerase (PARP), resulting in loss of mitochondrial membrane potential (MMP). Both the NF-κB and PI3K/AKT/mTOR signaling pathways were involved in AE-848-induced apoptosis of U266 and RPMI8226 cells. Moreover, AE-848 leads to cell cycle arrest of MM cells. Its anti-MM efficacy was further confirmed in a xenograft model of MM. AE-848 administration significantly inhibited MM tumor progression and prolonged the survival of MM-bearing mice. More importantly, our results demonstrated that AE-848 markedly induced primary MM cell apoptosis. Conclusion: Our results for the first time showed that the small compound AE-848 had potent in vitro and in vivo anti-myeloma activity, indicating that AE-848 may have great potential to be developed as a drug for MM treatment.
- Xu, Yaqi,Feng, Xiaoli,Zhou, Qian,Jiang, Wen,Dai, Yibo,Jiang, Yang,Liu, Xiaoli,Li, Shuo,Wang, Yongjing,Wang, Fang,Li, Ai,Zheng, Chengyun
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p. 13063 - 13075
(2021/01/11)
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- Antitumor compound, method for synthesizing same and application of antitumor compound
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The invention provides an antitumor compound. A chemical name of the antitumor compound is 5-bromine-2-hydroxyl isophthalaldehyde di-[(1-methyl-1H-benzimidazole-2-group) hydrazone]. The antitumor compound which is an antitumor medicine can be used for pre
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Paragraph 0018
(2018/10/19)
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- Synthesis of Monofunctionalized Calix[5]arenes
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Seven OH-free and O -permethylated monofunctionalized calix[5]arenes carrying either additional methyl or tert -butyl groups are prepared following fragment condensation protocols. This strategy proves to be superior to previous approaches. Calix[5]arenes with free OH groups all adopt a cone conformation stabilized by a seam of hydrogen bonds at the lower rim. Post-condensation modifications, i.e., methylation of phenolic OH groups or functional group interconversions can also be achieved. Bulky tert -butyl groups are also found to stabilize the cone conformations of O -methylated compounds. These compounds offer versatile functional groups that make these concave molecules interesting building blocks for the synthesis of more sophisticated molecular architectures.
- Ingenfeld, Bj?rn,Straub, Steffen,Fr?mbgen, Christopher,Lützen, Arne
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p. 676 - 684
(2017/11/16)
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- Surface functionalization of dinuclear clathrochelates: Via Pd-catalyzed cross-coupling reactions: Facile synthesis of polypyridyl metalloligands
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Dinuclear clathrochelate complexes are easily accessible by reaction of zinc(ii) triflate or cobalt(ii) nitrate with arylboronic acids and phenoldioximes. The utilization of brominated arylboronic acids and/or brominated phenoldioximes allows preparing clathrochelates with two, three, five or seven bromine atoms on the outside. These clathrochelates can undergo Pd-catalyzed cross-coupling reactions with 3- and 4-pyridylboronic acid to give new metalloligands featuring up to seven pyridyl groups. The pyridyl-capped clathrochelates display characteristics which make them interesting building blocks for structural supramolecular chemistry: they are rigid, large (up to 2.7 nm), luminescent (for M = Zn), and anionic. The pentatopic pyridyl ligands display an unusual trigonal bipyramidal geometry.
- Marmier, Mathieu,Cecot, Giacomo,Curchod, Basile F.E.,Pattison, Philip,Solari, Euro,Scopelliti, Rosario,Severin, Kay
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supporting information
p. 8422 - 8427
(2016/06/01)
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- Facile synthesis of bis-thiosemicarbazone derivatives as key precursors for the preparation of functionalised bis-thiazoles
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A new class of bis-thiosemicarbazones was designed and synthesised by the condensation of 2,6-diformylphenol derivatives and thiosemicarbazide using either ultrasound or conventional methods. Both thiosemicarbazone groups of these derivatives underwent a heterocyclisation process to give a series of novel bis-thiazole derivatives as major products. The structures of all the synthesised compounds were characterised by multinuclear NMR (1H and 13C), IR, HRMS and elemental analyses.
- Arafa, Wael A.A.,Badry, Mohamed G.
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p. 385 - 392
(2016/07/21)
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- Synthesis of para-aryl-substituted salicyldialdehydes
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para-Substituted salicyldialdehydes are versatile molecular building blocks for porous organic cages, fluorescent dyes, spirobenzopyrans, homooxacalixarenes, dinuclear metal complexes, macrocycles, and cryptands. To date, no procedures for the synthesis of para-aryl-substituted salicyldialdehydes have been reported, which would broaden the scope of the above-mentioned topics, especially in the field of sensors and dyes, because the aromatic π systems can be enlarged and absorption or fluorescent events can be fine-tuned by various substituents. Herein, two synthetic routes to para-aryl-substituted salicyldialdehydes with both electron-withdrawing and -donating aromatic units are reported.
- Reinhard, Dennis,Sch?ttner, Ludger,Brosius, Victor,Rominger, Frank,Mastalerz, Michael
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p. 3274 - 3285
(2015/05/20)
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- BILATERALLY-SUBSTITUTED TRICYCLIC COMPOUNDS FOR THE TREATMENT OF HUMAN IMMUNODEFICIENCY VIRUS TYPE-1 (HIV-1) INFECTION AND OTHER DISEASES
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The invention relates to bilaterally-substituted tricyclic compounds and pharmaceutical compositions containing them, for use as medicaments. Due to their ability to interact with an internal RNA loop and to mimic a protein a-helix these compounds are effective in the treatment and/or prevention of HIV-1 (Human Immunodeficiency Virus-1) infection and other diseases such as those caused by other RNA viruses and by gram-positive and gram-negative bacteria, or infectious or chronic diseases responsive to inhibition of DNA transcription, or infectious or chronic diseases where these compounds can be used to modulate the function of RNA internal loops, or infectious or chronic diseases where these compounds can be used as agonists or inhibitors of a-helical proteins in interaction with other biomolecules.
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Page/Page column 46-47
(2014/09/03)
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- Structure-based design of an RNA-binding p-terphenylene scaffold that inhibits HIV-1 rev protein function
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Rev(ersing) RNA binding: RNA-binding inhibitors based on a bilaterally substituted p-terphenylene scaffold (green) project their substituents in a broad spatial angle and reproduce the interactions of a protein α-helix (red) embedded in its RNA receptor.
- Gonzalez-Bulnes, Luis,Ibanez, Ignacio,Bedoya, Luis M.,Beltran, Manuela,Catalan, Silvia,Alcami, Jose,Fustero, Santos,Gallego, Jose
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supporting information
p. 13405 - 13409
(2014/01/06)
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- Ratiometric pH responsive fluorescent probes operative on ESIPT
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A series of C-8′-oxime-appended spirobenzopyrans 4a-4d were synthesized and developed as fluorescent pH ratiometric probes operative in HEPES/ACN (8:2, v/v) buffer solutions. Acidochromic conversion of spirobenzopyran to merocyanine open form can facilita
- Chan, Yim-Pan,Fan, Li,You, Qihua,Chan, Wing-Hong,Lee, Albert W.M.,Shuang, Shaomin
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p. 5874 - 5879
(2013/07/27)
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- Solid-state photochromism of 5-tert-butyl-2-hydroxyisophthalaldehyde
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Colorless crystals of 5-tert-butyl-2-hydroxyisophthalaldehyde change to an orange-red color upon brief exposure to UV-vis radiation (λ> 300 nm). The colored crystals revert to colorless in the dark. X-ray diffraction revealed different packing patterns for the crystals of nonphotochromic and photochromic compounds.
- Tanaka, Koichi,Watanabe, Yuta,Kalicki, Przemyslaw,Urbanczyk-Lipkowska, Zofia
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experimental part
p. 727 - 729
(2012/08/08)
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- BRIDGED MACROCYCLIC MODULE COMPOSITIONS
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This invention is related to the fields of organic chemistry and nanotechnology. In particular, it relates to materials and methods for the preparation of organic synthons and bridged macrocyclic module compounds. The bridged macrocyclic module compounds may be used to prepare macrocyclic compositions such as nanofilms, which may be useful for filtration.
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Page/Page column 113
(2010/02/11)
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- Nanofilm and membrane compositions
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Nanofilms useful for filtration are prepared from oriented amphiphilic molecules and oriented macrocyclic modules. The amphiphilic species may be oriented on an interface or surface. The nanofilm may be prepared by depositing or attaching an oriented layer to a substrate. A nanofilm may also be prepared by coupling the oriented macrocyclic modules to provide a membrane.
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- Macrocyclic module compositions
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Macrocyclic module compositions are made from cyclic synthons. The macrocyclic module structures are prepared by stepwise or concerted schemes which couple synthons in a closed ring. The macrocyclic module structures may have a pore of nanometer dimensions.
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Page/Page column 29
(2008/06/13)
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- A novel selective oxidation of 5-substituted 2-hydroxy-3-hydroxymethylbenzaldehydes
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5-Substituted 2-hydroxy-1,3-benzenedicarbaldehydes 3 and 5-substituted 3-formyl-2-hydroxbenzoic acids 4 were prepared by selective oxidation of 5-substituted 2-hydroxy-3-(hydroxymethyl)-benzaldehydes 1 in a one-pot reaction. Compounds 1 were reacted with ethylenediamine and copper acetate to produce the complexes 2 as intermediates, in which formyl and phenolic hydroxy groups were protected in the subsequent oxidation step.
- Hu,Hu
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p. 325 - 326
(2007/10/02)
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