- Synthesis of an exo-ditopic receptor based on calix[4]arene and catechol
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The synthesis of a calix[4]arene derivative immobilised in 1,3- alternate conformation by alkylation at the lower rim and bearing four catechoylamide units at the upper rim was achieved. The chelating coordination sites were by construction oriented, in a
- Mislin, Gilles,Graf, Ernest,Hosseini, Mir Wais
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Read Online
- Design of a Functional Chromene-Type Kobayashi Precursor: Gram-Scale Total Synthesis of Natural Xanthones by Highly Regioselective Aryne Annulation
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The 2,2-dimethyl-2H-chromene motif is widely found in many bioactive molecules, and is a privileged structure in the pharmaceutical arena. We have developed a concise and regioselective approach to chromenes and chromanes through an aryne-based synthetic
- Xu, Yuan-Ze,Sha, Feng,Wu, Xin-Yan
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p. 1066 - 1071
(2020/12/18)
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- Synthesis of catechol derived rosamine dyes and their reactivity toward biogenic amines
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Functional organic dyes play a key role in many fields, namely in biotechnology and medical diagnosis. Herein, we report two novel 2,3-and 3,4-dihydroxyphenyl substituted rosamines (3 and 4, respectively) that were successfully synthesized through a microwave-assisted protocol. The best reaction yields were obtained for rosamine 4, which also showed the most interesting photophysical properties, specially toward biogenic amines (BAs). Several amines including n-and t-butylamine, cadaverine, and putrescine cause spectral changes of 4, in UV–Vis and fluorescence spectra, which are indicative of their potential application as an effective tool to detect amines in acetonitrile solutions. In the gas phase, the probe response is more expressive for spermine and putrescine. Additionally, we found that methanolic solutions of rosamine 4 and n-butylamine undergo a pink to yellow color change over time, which has been attributed to the formation of a new compound. The latter was isolated and identified as 5 (9?aminopyronin), whose solutions exhibit a remarkable increase in fluorescence intensity together with a shift toward more energetic wavelengths. Other 9-aminopyronins 6a, 6b, 7a, and 7b were obtained from methanolic solutions of 4 with putrescine and cadaverine, demonstrating the potential of this new xanthene entity to react with primary amines.
- Leite, Andreia,Martins, Rui C.,Monteiro-Silva, Filipe,Queirós, Carla,Rangel, Maria,Rodríguez, María T.,Rojo, María J.,Silva, Ana M. G.,Torroba, Tomás
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- CONJUGATES AND CONJUGATES FOR USE IN PREVENTING OR TREATING OF BRAIN DAMAGE AND NEURODEGENERATIVE DISEASES
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The present invention relates to conjugates comprising one or more compounds selected from of (i) an anti-inflammatory compound, and/or (ii) an antioxidant compound, and/or (iii) and antibiotic compound and/or, (iv) a metal chelating compound and at least
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Page/Page column 49; 50; 51
(2021/03/05)
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- Potent human dihydroorotate dehydrogenase inhibitory activity of new quinoline-4-carboxylic acids derived from phenolic aldehydes: Synthesis, cytotoxicity, lipophilicity and molecular docking studies
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A series of novel 2-substituted quinoline-4-carboxylic acids was synthesized by Doebner reaction starting from freely available protocatechuic aldehyde and vanillin precursors. Human dihydroorotate dehydrogenase (hDHODH) was recognised as a clear molecular target for these heterocycles. All compounds were also tested for their antiproliferative potential against three cancer cells (MCF-7, A549, A375) and one normal cell line (HaCaT) to evaluate the selective cytotoxicity. Quinoline derivatives 3f and 3g were identified as potent hDHODH inhibitors while 3k and 3l demonstrated high cytotoxic activity against MCF-7 and A375 cells and good selectivity. In addition, the logD7.4 values obtained by the experimental method were found to be in the range from ?1.15 to 1.69. The chemical structures of all compounds were confirmed by IR, NMR and elemental analysis. The compounds pharmacology on the molecular level was revealed by means of molecular docking, highlighting the structural differences that distinguish highly active from medium and low active hDHODH inhibitors.
- Petrovi?, Milena M.,Roschger, Cornelia,Chaudary, Sidrah,Zierer, Andreas,Mladenovi?, Milan,Jakovljevi?, Katarina,Markovi?, Violeta,Botta, Bruno,Joksovi?, Milan D.
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- Compositions for prevention/prophylactic treatment of poison ivy dermatitis
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The present invention, in one or more embodiments, comprises water-soluble derivatives of 3-n-pentadecylcatechol (poison ivy urushiol saturated congener) and/or 3-n-heptadecylcatechol (poison oak urushiol saturated congener) as compositions for the prevention and/or prophylactic treatment of contact dermatitis caused by poison ivy and poison oak. The present invention is also directed towards processes for making such compounds. Disclosed are compounds which are effective for tolerizing and desensitizing a subject against allergens contained in plants of the Anacardiaceae and Ginkgoaceae families comprising water soluble urushiol esters of general formula (I) tolerizing and desensitizing mammals, including humans, to allergens contained in plants of the Anacardiaceae and Ginkgoaceae families is attained by administering a composition containing at least one water soluble urushiol ester compound.
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Page/Page column 15
(2016/09/12)
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- Bi-Aromatic And Tri-Aromatic Compounds As NADPH Oxidase 2 (Nox2) Inhibitors
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Bi- and tri-aromatic compounds of the formula (I) wherein R1 to RIO and X are as defined, are Nox2 inhibitors that are useful as medicaments for the treatment of a disease or condition selected from: cardiovascular diseases, respiratory diseases, inflamma
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Paragraph 0156; 0160
(2015/02/25)
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- Designing new analogs for streamlining the structure of cytotoxic lamellarin natural products
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Despite the therapeutic potential of marine-derived lamellarin natural products, their preclinical development has been hampered by their lipophilic nature, causing very poor aqueous solubility. In order to develop more drug-like analogs, their structure was streamlined in this study from both the cytotoxic activity and lipophilicity standpoints. First, a modified total synthetic route was successfully devised to construct a library of 59 systematically designed lamellarin analogs, which were then subjected to cytotoxicity and log P determinations. Along with the 25 first-generation lamellarins previously synthesized in our laboratory, the structure-activity and structure-lipophilicity relationships were extensively evaluated. Our results clearly indicated the additional structural requirements around the lamellarin skeleton which, when combined with those reported previously, can provide invaluable guidance for further modifications to increase the aqueous solubility of these compounds.
- Tangdenpaisal, Kassrin,Worayuthakarn, Rattana,Karnkla, Supatra,Ploypradith, Poonsakdi,Intachote, Pakamas,Sengsai, Suchada,Saimanee, Busakorn,Ruchirawat, Somsak,Chittchang, Montakarn
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p. 925 - 937
(2015/03/31)
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- BI-AROMATIC AND TRI-AROMATIC COMPOUNDS AS NADPH OXIDASE 2 (Nox2) INHIBITORS
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Bi- and tri-aromatic compounds of the formula (I) wherein R1 to RIO and X are as defined, are Nox2 inhibitors that are useful as medicaments for the treatment of a disease or condition selected from: cardiovascular diseases, respiratory diseases, inflamma
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Page/Page column 37; 39
(2013/03/28)
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- A novel fluorescein-based dye containing a catechol chelating unit to sense iron(III)
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In the present work we report the synthesis and characterization of a novel fluorescein-based dye containing a catechol chelating unit designed to act as a chemosensor for iron(III). The compound was prepared using conventional and microwave-assisted amid
- Queirós, Carla,Silva, Ana M.G.,Lopes, Sílvia C.,Ivanova, Galya,Gameiro, Paula,Rangel, Maria
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experimental part
p. 1447 - 1455
(2012/03/26)
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- Design, synthesis and SAR study of hydroxychalcone inhibitors of human β-secretase (BACE1)
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According to the structural characteristics of isoliquiritigenin from Glycyrrhiza uralensis, a series of hydroxychalcones has been designed, synthesized and evaluated for their in vitro inhibitory activities of β-secretase (BACE1). Structure-activity relationship study suggested that inhibitory activity against BACE1 was governed to a greater extent by the hydroxyl substituent on A-and B-ring of the chalcone, and the most active compound was substituted with four hydroxyl group (17, IC50=0.27 μM).
- Ma, Lei,Yang, Zhengyi,Li, Chenjing,Zhu, Zhiyuan,Shen, Xu,Hu, Lihong
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experimental part
p. 643 - 648
(2012/04/10)
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- Synthesis and evaluation of C-ring aromatized analogues of phenanthridone alkaloids
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Phenanthridone alkaloids are envisaged as an attractive lead for the development of anticancer agents. We have prepared a series of aromatized analogues on the basis of the structure of this class of alkaloids with the hope of finding the simplified compounds with comparable activities. The obtained analogues were evaluated for their cytotoxic effect against several cancer cell lines and found to be virtually inactive. These observations together with molecular modeling studies strongly suggest that the stereochemistries of hydroxyl groups in C-ring of phenanthridone alkaloids are crucial to biological effects.
- Lee, Seokwoo,Hwang, Soonho,Yu, Shuai,Jang, Wonyoung,Lee, Yun Mi,Kim, Sanghee
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scheme or table
p. 1065 - 1070
(2012/07/14)
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- COMPOUNDS AND METHODS FOR KINASE MODULATION, AND INDICATIONS THEREFOR
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Compounds active on protein kinases are described, as well as methods of using such compounds to treat diseases and conditions associated with aberrant activity of protein kinases.
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Page/Page column 86-87
(2008/12/07)
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- Ortho-substituted catechol derivatives: The effect of intramolecular hydrogen-bonding pathways on chloride anion recognition
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(Chemical Equation Presented) This paper reports a series of chloride anion receptors containing two catechol head groups connected through their ortho-positions via a spacer chain. The linking group chosen to attach the spacer chain to the catechol units has a major impact on the anion-binding potential of the receptor. Linking groups that are capable of forming stable six-membered intramolecular hydrogen-bonded rings with the catechol O-H groups significantly inhibit the ability of the catechol units to hydrogen bond to chloride anions. However, where the linking groups are only capable of forming five- or seven-membered intramolecular hydrogen-bonded rings, then anion binding via hydrogen bonding through the catechol O-H groups becomes a possibility. This process is solvent dependent; the presence of competitive solvent (e.g., DMSO-d6) disrupts the intramolecular hydrogen-bonding pattern and enhances anion binding relative to simple unfunctionalized catechol. The most effective receptor is that in which the hydrogen-bonding linker (-CH 2CONH-) is most distant from the catechol units and can only form a seven-membered intramolecular hydrogen-bonded ring. In this case, the receptor, which contains two catechol units, is a more effective chloride anion binder than simple unfunctionalized catechol, demonstrating that the two head groups, in combination with the N-H groups in the linker, act cooperatively and enhance the degree of anion binding. In summary, this paper provides insight into the hydrogen-bonding patterns in orthofunctionalized catechols and the impact these have on the potential of the catechol O-H groups to hydrogen bond to a chloride anion.
- Winstanley, Keith J.,Smith, David K.
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p. 2803 - 2815
(2008/02/01)
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- Deuterium labelled borocryptands: Synthesis, structural analysis and binding studies
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High yield syntheses of two new deuterium labelled compound 2 and 3 based on the [22] macrocyclic backbone bearing two catechol units was achieved. The solid state structure of the tetradeuterated compound 3 was elucidated by X-ray diffraction methods. Th
- Graf, Ernest,Hosseini, Mir Wais,De Cian, Andre,Fischer, Jean
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p. 3501 - 3504
(2007/10/03)
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- Borocryptands: Synthesis and structural analysis of a lithium borocryptate
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A new lithium receptor based on the combination of the [11] macrocyclic core and two catechol units was designed and prepared. The binding ability of the ligand towards boron and lithium was demonstrated in solution by NMR and in the solid state by an X-r
- Bockstahl, Frederic,Graf, Ernest,Hosseini, Mir Wais,Suhr, Dominique,De Cian, Andre,Fischer, Jean
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p. 7539 - 7542
(2007/10/03)
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- Synthesis of C3-cyclotriveratrylene ligands for iron(II) and iron(III) coordination
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The design and synthesis of a new family of siderophores based on cyclotriveratrylene is described. The ligands consist of a C3-cyclotriveratrylene unit provided with three arms (spacers) ending with hydroxamate, catecholate, bipyridine, or iminopyridine units suitable for the octahedral coordination of transition metals and particularly for the complexation of iron(II) and iron(III).
- Veriot, Gilles,Dutasta, Jean-Pierre,Matouzenko, Galina,Collet, Andre
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p. 389 - 400
(2007/10/02)
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- Synthesis of Enterochelin
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Enterochelin (enterobactin), the cyclic trilactone of N-(2,3-dihydroxybenzoyl)-L-serine 6, an important enterobacterial iron-transporting compound, has been synthesised from N,N-dibenzyl-L-serine 2 in four steps.The protected amino acid was oligomerised using N,N-dicyclohexylcarbodiimide in a high-dilution procedure yielding a mixture of di-, tri- and tetra-lactones.The trilactone 3b was deprotected by hydrogenolysis and the resultant amine 4 was acylated with 2,3-dibenzyloxybenzoyl chloride to yield hexa-O-benzylenterochelin 5.This upon hydrogenolysis gave enterochelin in moderate yield.
- Rogers, Henry J.
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p. 3073 - 3076
(2007/10/03)
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- Synthesis of macrocyclic ditopic receptors designed for simulataneous binding of alkaline and transition metal cations
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The synthesis of diazatetraoxacyclooctadecane derivatives bearing two catechol groups was achieved in good yield. The binucleating ligands were designed to bind both soft and hard cations simultaneously.
- Graf, Ernest,Hosseini, Mir Wais,Ruppert, Romain
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p. 7779 - 7782
(2007/10/02)
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- The Synthesis of Hallachrome Leucotriacetate (2,7,8-Triacetoxy-1-methoxy-3-methylanthracene)
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The synthesis of 2,7,8,-triacetoxy-1-methoxy-3-methylanthracene (30), a derivative of hallachrome (7-hydroxy-8-methoxy-6-methylanthracene-1,2-quinone) (1), the red pigment of the marine worm Halla parthenopeia (Delle Chiaje), is described.The key step in
- Comber, Mark F.,Sargent, Melvyn V.
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p. 1481 - 1489
(2007/10/02)
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- Regioselective Mono-O-alkylation of some Pyrocatechoxide Dianions
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In dimethyl sulphoxide the dianions derived from 2,3- or 3,4-dihydroxybenzaldehydes and 4-methylesculetin afford products corresponding to alkylation at the less acidic site while the monoanions give the isomeric phenols.
- Kessar, Satinder V.,Gupta, Yash P.,Mohammad, Taj,Goyal, Manju,Sawal, Kewal K.
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p. 400 - 401
(2007/10/02)
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