- Silica-Mediated Monohydrolysis of Dicarboxylic Esters
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A new method for the monohydrolysis of dicarboxylic esters is presented, involving as key step a silanolysis at elevated temperatures at the silica gel surface. In the second step, the surface bound silyl esters are cleaved off under mild conditions, giving a straightforward and fast access to half esters. Based on recovered starting material generally yields well above 70 % are achieved, both, with stiff aromatic as well as flexible aliphatic substrates, as long as the ester groups involved are remote enough from each other. Otherwise competing reactions are becoming determinative, anhydride formation in the case of phthalates and decarbonylative fragmentation in the case of malonates. The new method was also successfully tested on a multigram scale with a minimalistic apparatus setup.
- Dyker, Gerald
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supporting information
p. 6773 - 6776
(2021/12/31)
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- Benzene tricarboxamide derivatives with lipid and ethylene glycol chains self-assemble into distinct nanostructures driven by molecular packing
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The self-assembly in aqueous solution of benzene-1,3,5-tricarboxamide (BTA) bearing one alkyl chain and two PEG (polyethylene glycol) chains or two alkyl chains and one PEG chain yields completely distinct nanostructures. Two series of derivatives were sy
- Aljuaid, Nada,Hamley, Ian W.,Ruokolainen, Janne,Seitsonen, Jani,Tully, Mark
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supporting information
p. 8360 - 8363
(2021/08/25)
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- Efficient cycling utilization of solar-thermal energy for thermochromic displays with controllable heat output
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Use of solar energy as a source of heat is an important method of storing and providing clean energy for thermal management. However, the difficulties associated with combining the high-energy storage and high-rate heat release of solar thermal storage (S
- Yang, Weixiang,Feng, Yiyu,Si, Qianyu,Yan, Qinghai,Long, Peng,Dong, Liqi,Fu, Linxia,Feng, Wei
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supporting information
p. 97 - 106
(2019/01/03)
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- Optimized reaction pair of the Cyshis tag and Ni(II)-Nta probe for highly selective chemical labeling of membrane proteins
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Chemical labeling of proteins with synthetic molecular probes offers the possibility to probe the functions of proteins of interest in living cells. However, the methods for covalently labeling targeted proteins using complementary peptide tag-probe pairs are still limited, irrespective of the versatility of such pairs in biological research. Herein, we report the new CysHis tag-Ni(II) probe pair for the specific covalent labeling of proteins. A broad-range evaluation of the reactivity profiles of the probe and the CysHis peptide tag afforded a tag-probe pair with an optimized and high labeling selectivity and reactivity. In particular, the labeling specificity of this pair was notably improved compared to the previously reported one. This pair was successfully utilized for the fluorescence imaging of membrane proteins on the surfaces of living cells, demonstrating its potential utility in biological research.
- Zenmyo, Naoki,Tokumaru, Hiroki,Uchinomiya, Shohei,Fuchida, Hirokazu,Tabata, Shigekazu,Hamachi, Itaru,Shigemoto, Ryuichi,Ojida, Akio
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supporting information
p. 995 - 1000
(2019/07/18)
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- Tri-Orthogonal Scaffolds for the Solid-Phase Synthesis of Peptides
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Multi-orthogonal scaffolds can be useful for the attachment of several different compounds to the same central skeleton. Such compounds can find applications in the development of protein mimics because of their potential to mimic several distant epitopes
- Pícha, Jan,Fabre, Benjamin,Budě?ínsky, Milo?,Hajduch, Jan,Abdellaoui, Mehdi,Jirá?ek, Ji?í
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p. 5180 - 5192
(2018/08/01)
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- Tubular and lamellar hydrogen-bonding molecular assemblies of isophthalic acid derivatives bearing a -CONHCnH2 n +1 chain
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Isophthalic acid derivatives (CnIP), bearing alkylamide chains (-CONHCnH2n+1: n = 6, 10, 14, and 18) at the 5-position that can participate in hydrogen bonding, were prepared and evaluated for their hydrogen-bonding molecular assembl
- Lv, Chao,Takeda, Takashi,Hoshino, Norihisa,Akutagawa, Tomoyuki
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p. 22250 - 22258
(2018/06/26)
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- A highly porous acylamide decorated MOF-505 analogue exhibiting high and selective CO2 gas uptake capability
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Porous metal-organic frameworks (MOFs) constructed from organic linkers and metal ions/clusters can provide special pore environments for selective CO2 capture. In this work, we designed and synthesized a highly porous acylamide-functionalized
- Zheng, Baishu,Huang, Lu,Cao, Xiyang,Shen, Shaohua,Cao, Haifei,Hang, Cheng,Zeng, Wenjiang,Wang, Zhaoxu
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p. 1874 - 1881
(2018/04/03)
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- Azo phenyl photo-thermal energy storing molecule as well as preparation method and application thereof
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The invention provides an azo phenyl photo-thermal energy storing molecule which has the structure shown in the formula I. A single molecule contains two kinds of azobenzene molecules: two dicarboxylazobenzene units and one monoamino azobenzene unit, by u
- -
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Paragraph 0046-0048; 0061-0062; 0069-0070
(2018/09/11)
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- Metal-induced supramolecular chirality inversion of small self-assembled molecules in solution
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A non-covalent self-assembled chiral alanyl aminopyridine ligand exhibits supramolecular chirality in solution, independent of the organic solvent used. The supramolecular chirality of the assemblies is completely inverted by complexation to zinc ions. To date, such a supramolecular metal-ligand system has not been reported in the literature.
- Kokan, Zoran,Peri?, Berislav,Vazdar, Mario,Marini?, ?eljko,Viki?-Topi?, Dra?en,Me?trovi?, Ernest,Kirin, Sre?ko I.
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supporting information
p. 1945 - 1948
(2017/02/15)
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- Radiolabeled Dibenzodiazepinone-Type Antagonists Give Evidence of Dualsteric Binding at the M2 Muscarinic Acetylcholine Receptor
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The dualsteric ligand approach, aiming at ligands with improved subtype selectivity, has been increasingly applied to muscarinic receptors (MRs). In this article, we present the synthesis and characterization of a M2R subtype-preferring radiola
- Pegoli, Andrea,She, Xueke,Wifling, David,Hübner, Harald,Bernhardt, Günther,Gmeiner, Peter,Keller, Max
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supporting information
p. 3314 - 3334
(2017/05/05)
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- Self-assembly of homochiral porous supramolecular organic frameworks with significant CO2 capture and CO2/N2 selectivity
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A pair of homochiral porous supramolecular organic frameworks (JLU-SOF1-R and JLU-SOF1-S) has been assembled from brand-new enantiopure blocks via hydrogen bonding and π-π interactions. The frameworks not only maintain crystallinity well until 250 °C but
- Zhou, Yue,Liu, Bing,Sun, Xiaodong,Li, Jiantang,Li, Guanghua,Huo, Qisheng,Liu, Yunling
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p. 6653 - 6659
(2018/05/31)
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- POTENT AND SELECTIVE INHIBITORS OF NAV1.7
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Disclosed is a composition of matter comprising an isolated polypeptide, which is a peripherally-restricted NaV1.7 inhibitor. In some disclosed embodiments, the isolated polypeptide is an inhibitor of NaV1.7. Other embodiments are co
- -
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Paragraph 1043-1044
(2016/02/18)
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- Functionalized defects through solvent-assisted linker exchange: Synthesis, characterization, and partial postsynthesis elaboration of a metal-organic framework containing free carboxylic acid moieties
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Intentional incorporation of defect sites functionalized with free carboxylic acid groups was achieved in a paddlewheel-based metal-organic framework (MOF) of rht topology, NU-125. Solvent-assisted linker exchange (SALE) performed on a mixed-linker deriva
- Karagiaridi, Olga,Vermeulen, Nicolaas A.,Klet, Rachel C.,Wang, Timothy C.,Moghadam, Peyman Z.,Al-Juaid, Salih S.,Stoddart, J. Fraser.,Hupp, Joseph T.,Farha, Omar K.
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supporting information
p. 1785 - 1790
(2015/06/16)
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- Rationally designed non-enzymatic fluorogenic 'turn-on' probe for uric acid
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Abstract The simple and cost-effective detection of uric acid in serum or urine is highly desirable as uric acid acts as a biomarker for various diseases. Herein, we report a rationally designed, non-enzymatic probe for the detection of uric acid in serum samples over a wide range of concentrations (lower: ~60 μM, higher: ~700 μM and normal: ~120-380 μM) with 'turn-on' fluorogenic behaviour.
- Pradhan, Tuhin,Maiti, Sukhendu,Kumar, Rajesh,Lee, Yun Hak,Kim, Jong Wan,Lee, Joung Hae,Kim, Jong Seung
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- Peptide dendrimers with designer core for directed self-assembly
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A series of designer peptide dendrimers with urea and urea-triazole cores were synthesized. Urea cored dendrimers assembled into fibrillar morphology, while dendrimers with urea-triazole core assembled into vesicular morphology. The core-dependent self-as
- Verma, Ram P.,Shandilya, Ashutosh,Haridas
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supporting information
p. 8758 - 8765
(2015/10/20)
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- Robust Ordered Bundles of Porous Helical Nanotubes Assembled from Fully Rigid Ionic Benzene-1,3,5-tricarboxamides
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Size-controlled and ordered assemblies of artificial nanotubes are promising for practical applications; however, the supramolecular assembly of such systems remains challenging. A novel strategy is proposed that can be used to reinforce intermolecular no
- Wu, Xibo,Wang, Daoliang,Chen, Mingming,Wei, Chengsha,Wei, Shenghui,Huang, Ningdong,Li, Liangbin,Zhang, Guobing
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supporting information
p. 15388 - 15394
(2015/11/02)
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- Homochiral metal-organic frameworks with enantiopure proline units for the catalytic synthesis of -lactams
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Two enantiopure organic ligands integrating flexible proline units and rigid isophthalate units have been rationally designed and employed for the construction of four homochiral porous metal-organic frameworks (MOFs), respectively. One pair of these MOFs
- Xu, Zhong-Xuan,Tan, Yan-Xi,Fu, Hong-Ru,Liu, Juan,Zhang, Jian
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p. 12199 - 12204
(2015/01/09)
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- Lyotropic supramolecular helical columnar phases formed by C 3-symmetric and unsymmetric rigid molecules
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Unlike thermotropic liquid-crystalline C3-symmetric molecules with flexible chains, the herein-designed fully rigid three-armed molecules (C3-symmetric and unsymmetric) create a fancy architecture for the formation of lyotropic liqui
- Wang, Daoliang,Huang, Youju,Li, Junjun,Xu, Lu,Chen, Mingming,Tao, Jiaojiao,Li, Liangbin
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p. 685 - 690
(2013/04/10)
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- NOVEL BEXAROTENE ANALOGS
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The present invention relates to analogs of bexarotene and methods of use thereof.
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Page/Page column 20-21
(2011/09/19)
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- Modeling, synthesis and biological evaluation of potential Retinoid X Receptor (RXR) selective agonists: Novel analogues of 4-[1-(3,5,5,8,8- pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethynyl]benzoic acid (bexarotene)
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This report describes the synthesis of analogues of 4-[1-(3,5,5,8,8- pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethynyl]benzoic acid (1), commonly known as bexarotene, and their analysis in acting as retinoid X receptor (RXR)-specific agonists. Compound 1 has FDA approval to treat cutaneous T-cell lymphoma (CTCL); however, its use can cause side effects such as hypothyroidism and increased triglyceride concentrations, presumably by disruption of RXR heterodimerization with other nuclear receptors. The novel analogues in the present study have been evaluated forRXR activation in an RXR mammalian-2-hybrid assay as well as an RXRE-mediated transcriptional assay and for their ability to induce apoptosis as well as for their mutagenicity and cytotoxicity. Analysis of 11 novel compounds revealed the discovery of three analogues that best induce RXR-mediated transcriptional activity, stimulate apoptosis, have comparable Ki and EC50 values to 1, and are selective RXR agonists. Our experimental approach suggests that rational drug design can develop new rexinoids with improved biological properties. 2009 American Chemical Society.
- Wagner, Carl E.,Jurutka, Peter W.,Marshall, Pamela A.,Groy, Thomas L.,Van Der Vaart, Arjan,Ziller, Joseph W.,Furmick, Julie K.,Graeber, Mark E.,Matro, Erik,Miguel, Belinda V.,Tran, Ivy T.,Kwon, Jungeun,Tedeschi, Jamie N.,Moosavi, Shahram,Danishyar, Amina,Philp, Joshua S.,Khamees, Reina O.,Jackson, Jevon N.,Grupe, Darci K.,Badshah, Syed L.,Hart, Justin W.
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experimental part
p. 5950 - 5966
(2010/02/28)
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- Multi-tier dendrimers with an aromatic core
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We report various multi-tier designer dendritic molecules that incorporate an aromatic core and heterocyclic and peptide units. The 5-(azidomethyl)benzene- 1,3-dicarbonyl unit was chosen as the scaffold as this unit allows two identical units and a reacti
- Haridas,Sharma, Yogesti K.,Naik, Sarala
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body text
p. 1570 - 1577
(2009/07/11)
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- Supramolecular materials from benzene-1,3,5-tricarboxamide-based nanorods
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Telechelic polymers end-capped or copolymerized with the benzene-1,3,5-tricarboxamide (BTA) moiety lead to supramolecular materials. The intrinsic phase segregation of BTA nanorods with an amorphous polymer such as poly(ethylene butylene) results in therm
- Roosma, Jorg,Mes, Tristan,Leclere, Philippe,Palmans, Anja R. A.,Meijer
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p. 1120 - 1121
(2008/10/09)
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- Amplification of chirality in benzene tricarboxamide helical supramolecular polymers
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The chirality of benzene tricarboxamides is expressed and amplified into the helicity of self-assembled columnar aggregates according to 'sergeants and soldiers' and 'majority rules' principles; the strength of the amplification is analysed quantitatively
- Wilson, Andrew J.,Van Gestel, Jeroen,Sijbesma, Rint P.,Meijer
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p. 4404 - 4406
(2007/10/03)
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- Synthesis of an amide cyclophane building block of shape-persistent triangular molecular wedges
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The synthesis of an amide cyclophane, which can be considered as the first generation of a family of triangular shape-persistent molecular wedges is described.
- Amma, Achim,Mallouk, Thomas E.
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p. 1151 - 1153
(2007/10/03)
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- Photoinitiated Polymerization of Columnar Stacks of Self-Assembled Trialkyl-1,3,5-benzenetricarboxamide Derivatives
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A disk-shaped molecule, N-(5-sorbyl-pentyl)-N′,N″ -di(n-octyl)benzene-1,3,5-tricarboxamide (1), has been synthesized and assembled into a columnar stack in cyclohexane. Using a photoinitiated process, we polymerized monomer 1 in its self-assembled state a
- Masuda, Mitsutoshi,Jonkheijm, Pascal,Sijbesma, Rint P.,Meijer
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p. 15935 - 15940
(2007/10/03)
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- Refinement and evaluation of a pharmacophore model for flavone derivatives binding to the benzodiazepine site of the GABAA receptor
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To further develop and evaluate a pharmacophore model previously proposed by Cook and co-workers (Drug Des. Discovery 1995, 12, 193-248) for ligands binding to the benzodiazepine site of the GABAA receptor, 40 new flavone derivatives have been synthesized and their affinities for the benzodiazepine site have been determined. Two new regions of steric repulsive interactions between ligand and receptor have been characterized, and the receptor region in the vicinity of 6- and 3′-substituents has been mapped out. 2′-Hydroxy substitution is shown to give a significant increase in affinity, which is interpreted in terms of a novel hydrogen bond interaction with the previously proposed hydrogen bond-accepting site A2. On the basis of the results of these studies and the refined pharmacophore model, 5′-bromo-2′-hydroxy-6-methylflavone, the highest affinity flavone derivative reported so far (Ki = 0.9 nM), was successfully designed. A comparison of the pharmacophore model with a recently proposed alternative model (Marder; et al. Bioorg. Med. Chem., 2001, 9, 323-335) has been made.
- Kahnberg, Pia,Lager, Erik,Rosenberg, Celia,Schougaard, Jette,Camet, Linda,Sterner, Olov,Nielsen, Elsebet ?stergaard,Nielsen, Mogens,Liljefors, Tommy
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p. 4188 - 4201
(2007/10/03)
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- On the meaning of affinity: Cluster glycoside effects and concanavalin a
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The inhibition of protein - carbohydrate interaction provides a powerful therapeutic strategy for the treatment of myriad human diseases. To date, application of such approaches have been frustrated by the inherent low affinity of carbohydrate ligands for
- Dimick, Sarah M.,Powell, Steven C.,McMahon, Stephen A.,Moothoo, Davina N.,Naismith, James H.,Toone, Eric J.
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p. 10286 - 10296
(2007/10/03)
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- Synthesis of 3,5-bis(phosphonomethyl)benzoic acid and its application as a metal oxide surface bivalent anchor
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A protected form of 3,5-bis(phosphonomethyl)benzoic acid (Bpb-OH), a metal oxide surface bivalent anchor, has been synthesized, coupled to an amine functionality, deprotected, and shown to bind to metal oxide surfaces. The protected anchor, 3,5-bis(dimethoxyphosphinylmethyl)benzoic acid (Me4Bpb-OH) was synthesized in 23% yield over four steps, coupled to a proline-chromophore, deprotected with a solution of iodotrimethylsilane (TMSI) in acetonitrile and adsorbed to Tin(IV)-doped indium oxide and nanocrystalline TiO2 electrodes at surface coverages of 1.5 x 10-10 mol cm-2 and 4.9 x 10-11 mol cm-2, respectively. Finally, Me4Bpb-OH was converted to an amino derivative by attaching a diamino butane linker.
- Nakhle, Bassam M.,Trammell, Scott A.,Sigel, Keith M.,Meyer, Thomas J.,Erickson, Bruce W.
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p. 2835 - 2846
(2007/10/03)
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- Fmoc protected peptide mimetic based on a cyclohexane framework and incorporation into angiotensin II
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1,3,5-syn substituted cyclohexane based amino acids have been prepared and incorporated into synthetic peptides to serve as scaffold mimicking the Val-Tyr-Ile sequence of angiotensin II. The conformationally constrained tripeptide mimetic holds potential
- Kuehn, Christian,Lindeberg, Gunnar,Gogoll, Adolf,Hallberg, Anders,Schmidt, Boris
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p. 12497 - 12504
(2007/10/03)
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- Regiospecific synthesis of 3,5-bis(bromomethyl)benzoic acid, a cysteine crosslinking agent
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Bridging two molecules of an organic thiol with the 3,5-dimethylenebenzoic acid (Dmb) group produces a rigid five-carbon Dmb crosslink that is stable to disulfide reducing agents. Radical bromination of 3,5-dimethylbenzoic acid or its succinimido ester gave four α-brominated products. So NMR-pure 3,5-bis(bromomethyl)benzoic acid (Br2Dmb) was regiospecifically synthesized in 38% overall yield by a four-step route from 1,3,5-benzenetricarboxylic acid. S-Alkylation of cysteine methyl ester, a model thiol, with Br2Dmb provided the 2:1 adduct (Cys-OCH3)2Dmb in 79% yield. Subsequent N-protection with di(tert-butyl) dicarbonate gave (Boc-Cys-OCH3)2Dmb in 60% overall yield from cysteine methyl ester. This protected diamino acid is suitable for assembly of two Dmb-crosslinked peptide chains.
- Engel,Burris,Slate,Erickson
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p. 8761 - 8770
(2007/10/02)
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