- α-Glucosidase inhibition and antihyperglycemic activity of flavonoids from Ampelopsis grossedentata and the flavonoid derivatives
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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
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Read Online
- New Macrocyclic Ligands. VI. 20- to 22-Membered Dibenzo-Substituted Rings Incorporating Mixed Nitrogen, Oxygen and/or Sulfur Donor Atoms
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The syntheses and characterization of 10 dibenzo-substituted macrocycles incorporating mixed nitrogen, oxygen and/or sulfur donor sets are reported.The new systems, which incorporate six potential donor sites, extend the range of related (potentially tetr
- Davis, Carol A.,Duckworth, Paul A.,Lindoy, Leonard F.,Moody, Wayne E.
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Read Online
- Impact of N-substituents on crystal packing of N-alkyl-N′-tosylpiperazines and development of new polymorph of tosylbis(2-(tosyloxy)ethyl)amine: Synthesis, DFT, photophysical, cytotoxic property
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Diethanol amine (DEA) was selected as a lead compound to prepare N-tosyldiethanol amine 1, N-tosylbis(2-(tosyloxy)ethyl)amine 2 and disubstituted piperazines ca N-alkyl-N′-tosylpiperazines 3–5 in high yield. The new compounds were characterized by using relevant techniques viz. MS, IR, 1H, 13C, DEPT 135 NMR, UV–vis. absorption and fluorescence spectral studies. Single crystal X-ray diffraction technique was used to detect a new polymorphic form of 2 and to measure the influence of various N-substituents on the association of molecules of 3–5 in the solid state. Evidently, the introduction of N-cyclohexyl substituent in 3 successfully switches off all the synthons ca CH…O and CH…N seen in compound 4 and 5. Compounds 4 and 5 holding N-furfuryl and N-benzyl substituents, respectively, adopt other packing strategies based on CH…O, CH…N (4) and CH…O (5) interactions. The antitumor activity of 1–5 was evaluated in vitro against Hep 3B and IMR 32 by the MTT assay and the results were compared with cisplatin. Remarkably, some compounds were found extremely active against both the cell lines and proved to be more potent as cytotoxic agents than cisplatin. Density functional theory and molecular docking studies have been performed to rationalize the experimental results.
- Kadu, Rahul,Savani, Chirag,Roy, Hetal,Soni,Singh, Atresh Kumar,Vennapu, Dushyanth R.,Singh, Vinay K.
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Read Online
- DINUCLEATING LIGAND OR DINUCLEAR METAL COMPLEX
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To provide a metal complex that has high cancer cell toxicity and has DNA target and cyclen.SOLUTION: The present disclosure provides a dinuclear metal complex represented by the following formula (IV).SELECTED DRAWING: None
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Paragraph 0052-0053
(2021/03/19)
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- Preparation method of (by machine translation)
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The benzothiazole derivatives are dissociated into o-aminophenylsulfated phenol under the catalysis of copper (II) or copper salt and react under the catalysis of copper or (III), copper salt to give a protected V-oxiracetaine, 2,4 - and the protected V 2 - (2,4 -cetine compound can) be (V) obtained 2 - (2,4 - under the action of) a (V) compound under (2 - the action) - 4 - of a reaction (VI) rate of Ts (dvcetine) (VII): Ts (dvcetine) (VII) (Mg STR9 (I) # STR9#). The synthesis method is easy to obtain, simple in process, low in cost, high in purity and suitable for industrial production. (by machine translation)
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Paragraph 0099-0103
(2019/11/28)
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- BINUCLEATING LIGAND OR BINUCLEAR METAL COMPLEX
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PROBLEM TO BE SOLVED: To provide a binuclear metal complex that can be easily synthesized and has a proper anticancer action. SOLUTION: The present invention provides a binuclear metal complex represented by the following chemical formula (IV). SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2018,JPOandINPIT
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Paragraph 0035; 0036
(2018/09/25)
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- METAL COMPLEX INCLUDING TRIDENTATE AMINODICARBENE LIGAND AND HYDROGENATION REDUCTION METHOD USING SAME
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The use of a metal complex containing a ruthenium ion or an osmium ion, and a tridentate aminodicarbene ligand, the tridentate aminodicarbene ligand having one secondary amino group and two specific heterocyclic carbene groups sandwiching the amino group, enables hydrogenation reduction of carbonyl compounds, such as ketones, carboxylic acid esters, lactones, carboxylic acid amides, and lactams, and imine compounds under relatively mild conditions to produce corresponding alcohols, amines, and the like in a high yield with high catalytic efficiency. The metal complex is obtained by a method comprising steps of reacting a specific metal compound with a specific aminodicarbene precursor and subsequently reacting a specific compound. Reduction of a carbonyl compound or an imine compound in the presence of this metal complex using a hydrogen donor makes it possible to reduce the carbonyl compound or imine compound by hydrogenation.
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Paragraph 0166
(2016/06/13)
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- Pyruvate kinase activators for use in therapy
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Described herein are methods for using compounds that activate pyruvate kinase.
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Page/Page column 92-93
(2016/08/29)
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- DERIVATIVES OF DOLASTATIN 10 AND USES THEREOF
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Derivatives of dolastatin 10 and uses thereof, the structures of which are shown as formula I, II, III and IV are provided.
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Page/Page column 24; 25
(2016/12/22)
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- Highly efficient synthesis of tetra benzo spiro bis-crown ether
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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
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- Bis-imidazolium and benzimidazolium based gemini-type ionic liquids structure: synthesis and antibacterial evaluation
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Based on bis-imidazolium and benzimidazolium, new sets of geminal dicationic ionic liquids containing a sulphonamide moiety were successfully synthesized with good yields. Their structures were confirmed by 1H-NMR, 13C-NMR, FT-IR, an
- Al-Mohammed, Nassir N.,Alias, Yatimah,Abdullah, Zanariah
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p. 92602 - 92617
(2015/11/16)
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- Synthesis and antibacterial evaluation of some novel imidazole and benzimidazole sulfonamides
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Several new substituted sulfonamide compounds were synthesized and their structures were confirmed by 1H-NMR, 13C-NMR, FT-IR, and mass spectroscopy. The antibacterial activities of the synthesized compounds were screened against stan
- Al-Mohammed, Nassir N.,Alias, Yatimah,Abdullah, Zanariah,Shakir, Raied M.,Taha, Ekhlass M.,Hamid, Aidil Abdul
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p. 11978 - 11995
(2013/11/06)
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- Synthesis and spectroscopic properties of new bis-tetrazoles
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Syntheses of N,N′-phenyltetrazole podands link with aliphatic chains containing oxygen, nitrogen and sulphur atoms, are described. The complexing properties of these compounds towards metal cations (Fe2+, Cu 2+, Zn2+, Co2+, Ni2+) were investigated by absorption and infrared spectroscopy. The UV-Vis titrations were performed to estimate the stability constant values of the respective complexes with Cu2+ ion. Changes in UV-Vis absorption spectra and IR spectra of compound 6 under various concentrations of Cu2+ ion in methanol suggest formation of very unstable complex. The structure of ligand 2 has been deduced by X-ray crystallography. The Author(s) 2012.
- Pazik, Agnieszka,Skwierawska, Anna
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- Straightforward approach to efficient oxidative DNA cleaving agents based on Cu(ii) complexes of heterosubstituted cyclens
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The Cu(ii) complexes of cyclen and two of its heterosubstituted analogues were shown to be efficient oxidative DNA cleavers. The reactivity strongly depends on the heteroatom inserted into the macrocycle (O > S > N). The Royal Society of Chemistry 2013.
- Hormann, Jan,Perera, Chrischani,Deibel, Naina,Lentz, Dieter,Sarkar, Biprajit,Kulak, Nora
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supporting information
p. 4357 - 4360
(2013/04/24)
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- Synthesis, biological evaluation and study of the effect of various N-substituents on the thermal stabilities of some new diethanolamine derivatives
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Diethanolamine and its derivatives are of considerable interest in medicinal and other industrial products. A series of new diethanolamine derivatives has been synthesized and characterized by 1H NMR, 13C NMR, FTIR and mass spectrometry. All synthesized compounds have been tested for their in vitro antibacterial activity against pathogenic microorganisms Escherichia coli, Staphylococcus aureus, Micrococcus luteus, Pseudomonas aeruginosa, Bacillus subtilis, Pasteurrella mutocida, Rhizopus oryzae and Salmonella typhi. Among the tested compounds, compounds 2a, 2b, 2c, 3a and 4b have been found to be most potent members, which inhibited most of the pathogens used in the assay. Diethanolamine must posses tosyl or trifluoro groups in order to have good antimicrobial activities. All synthesized derivatives exhibited average FRAP activity and considerably good metal chelating activity and compound 2c showed excellent ABTS radical scavanging among all tested derivatives. Thermal stability and the effect of various N-protected groups on the thermal stability and degradation of selected diethanolamine derivatives (free flowing oils at room temperature and solid derivative 2a) has been studied by TGA and DSC analysis.
- Yar, Muhammad,Mushtaq, Nafeesa,Afzal, Sadia,Khan, Abdul Samad,Khan, Islam Ullah,Akhter, Muhammad Nadeem,Zareen, Seema,Shahzad, Sohail Anjum,Khan, Zulfiqar Ali,Raza Naqvi, Syed Ali,Mahmood, Nasir,Tahir, Lubna,Saleem, Muhammad
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p. 7297 - 7304
(2013/08/23)
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- One-step cyclization: Synthesis of N -heteroalkyl-N′-tosylpiperazines
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Piperazine derivatives are important intermediates in organic synthesis and useful building blocks in pharmaceutical and fine chemical industries. Currently available synthetic routes for these heterocyclic compounds have limited scope owing to the harsh reaction conditions, low yields, and multistep process. Herein, we reported a practical method for synthesis of alkyl-, alcohol-, amine-, and ester-extended tosylpiperazines under mild conditions with moderate to high yields. This protocol exhibits potential applicability in the synthesis of pharmaceuticals and natural products because of the operational simplicity and the conveniently available reactants. On the basis of the experimental and theoretical results, a plausible mechanism of aliphatic nucleophilic substitution (SN) in the cyclization has been postulated and evidence for the formation of a six-membered ring has also been confirmed by means of density functional theory (DFT) calculations.
- Huang, Jianying,Xu, Weiyuan,Xie, Hujun,Li, Shijun
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p. 7506 - 7511
(2012/10/29)
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- THERAPEUTIC COMPOUNDS AND COMPOSITIONS
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Compounds and compositions comprising compounds that modulate pyruvate kinase M2 (PKM2) are described herein. Also described herein are methods of using the compounds that modulate PKM2 in the treatment of cancer.
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Page/Page column 22
(2012/07/14)
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- An improved synthesis of 1,4,7-triazacyclononanes (tacns) and 1,4,7,10-tetraazacyclododecanes (cyclens)
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Reaction of tosylbis[2-(tosyloxy)ethyl]amine with ethylenediamine gives 1-tosyl-1,4,7-triazacyclononane in good yield. A similar reaction of tosylbis[2-(tosyloxy)ethyl]amine with diethylenetriamine gives 1-tosyl-1,4,7,10-tetraazacyclododecane. These tosyl
- Huang, Jianying,Zhou, Zhongyuan,Tak, Hang Chan
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experimental part
p. 2341 - 2344
(2010/02/28)
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- Synthesis, characterisation and anti-protozoal activity of carbamate-derived polyazamacrocycles
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A short, highly efficient approach for the synthesis of a novel class of polyazamacrocycles containing N-functionalised carbamate side-chains has been developed. The key steps involved a phase-transfer mediated macrocyclisation to form the ring system as well as a tin-catalysed reaction with isocyanates to introduce the carbamate side-chains. X-Ray crystallography confirmed successful formation of the 1,4,7,10-tetraazacyclododecane ring and N-functionalisation of all the amine centres. Preliminary testing of the biological activity of the compounds revealed significant anti-parasitic activity against bloodstream form African trypanosomes. The Royal Society of Chemistry.
- Wilson, Jennifer M.,Giordani, Federica,Farrugia, Louis J.,Barrett, Michael P.,Robins, David J.,Sutherland, Andrew
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p. 3651 - 3656
(2008/09/21)
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- The synthesis and characterization of the pendant-armed ligand N,N′-bis(2′-pyridylmethyl)-1,7-dithia-4,11-diazacyclotetradecane (L4) and crystal structures of L4 and the copper(II) complex [Cu(L4)](ClO4)2
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The synthesis and characterization of the mixed donor ligand N,N′-bis(2′-pyridylmethyl)-1,7-dithia-4,11-diazacyclotetradecane (L4) containing two pendant pyridine arms is described. The macrocycle formation involves reaction of N-tosylbis(2-bro
- Chak,McAuley
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p. 187 - 195
(2007/10/03)
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- Synthesis and metal-ion binding properties of monoazathiacrown ethers
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Synthetic procedures for monoazathiacrown ethers were explored, and monoazatrithia-12-crown-4, monoazatetrathia-15-crown-5, and monoazapentathia-18-crown-6 were obtained in moderate yields by the reaction of bis(2-chloroethyl)amine with the appropriate dithiols in the presence of lithium hydroxide in THF. To evaluate metal-ion binding properties of the monoazathiacrown ethers by solvent extraction, lipophilic dodecyl and dodecanoyl groups were incorporated onto the monoazathiacrown ethers. The solvent extraction experiments suggested that monoazathiacrown ethers have Ag+ and Hg2+ selectivities and that the relative selectivity between Ag+ and Hg2+ depends on their nitrogen atom properties and numbers of sulfur atoms reflecting the respective affinities of nitrogen and sulfur atoms to Hg2+ and Ag+. An interesting ability to bind Mg2+ was observed in the case of N-dodecyl monoazatrithia-12-crown-4.
- Tanaka,Nakamura,Ikeda,Ikeda,Ando,Shibutani,Yajima,Kimura
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p. 7008 - 7012
(2007/10/03)
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- Synthesis of dicarboxymethyl tetraazacyclododecane derivatives for polycondensation
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Three different routes to synthesize selectively protected tetraaza macrocycles bifunctionalized with carboxymethyl acid groups have been developed in order to obtain monomers for polycondensation. The first way has been carried out from cyclen, whose synthesis has been improved, requires 6 steps. The second way allowed to obtain the bifunctional protected macrocycle from ethylenediamine and diethyl iminodiacetate in 2 steps. The last way has consisted in synthesizing directly a monomer by cyclization from ethylenediaminetetraacetic acid bisanhydride and ethylenediamine.
- Montembault,Mouaziz,Blondeau,Touchard,Soutif,Brosse
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p. 4279 - 4294
(2007/10/03)
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- Synthesis and some octahedral complexes of a chiral triaza macrocycle
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The chiral and bulky tacn (1,4,7-triazacyclononane, L1) analogue chtacn (2,5,8-triazabicyclo[7.4.01,9]tridecane, L2), which has a cyclohexane ring fused to the tacn framework, has been synthesized commencing with (±), (+)-
- Golding, Simon W.,Hambley, Trevor W.,Lawrance, Geoffrey A.,Luther, Stephan M.,Maeder, Marcel,Turner, Peter
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p. 1975 - 1980
(2007/10/03)
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- The synthesis and characterization of a new family of polyamide dendrimers
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A new family of dendrimers has been constructed with 5-hydroxy-isophthalic acid and diethanolamine as the sources of the branching units. The design of a second-generation building block in the form of an orthogonally-protected aminotetraacid (a single diethylphosphoramide-protected amine and four methyl-ester-protected carboxylic acid groups) has been established by a series of logical developments involving the synthesis of various dendrimer prototypes. This building block has been utilized in both convergent and divergent methods in the synthesis of monodisperse dendrimers up to the fourth generation and subsequently polydisperse sixth-generation dendrimers at the level of a mixture. One-, two-, and three-directional dendrimers of the second and fourth generation were synthesized in order to carry out detailed comparisons by GPC and by 1H NMR spectroscopy. The GPC results suggest that the fourth-generation dendrimers adopt globular shapes, while the variable-temperature NMR spectroscopic investigations demonstrate that the periphery of the fourth-generation dendrimer is less mobile than either of its internal regions or the analogous portions of the second-generation dendrimer. Molecular modeling suggests highly globular shapes for the larger dendrimers and gives values for molecular radii in very close agreement with those obtained from analysis of the GPC results.
- Ashton, Peter R.,Anderson, Derek W.,Brown, Christopher L.,Shipway, Andrew N.,Stoddart, J. Fraser,Tolley, Malcolm S.
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p. 781 - 795
(2007/10/03)
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- Synthesis and complexation of nickel(II) and copper(II) by pendant-arm alcohol derivatives of [9]aneNS2 (7-aza-1,4-dithiacyclononane)
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A simplified procedure for the preparation of [9]aneNS2 (7-aza-1,4-dithiacyclononane) is described. The structure of the complex [Cu([9]aneNS2)2]2+ confirms that the CU(II) centre is in a distorted octahedral environment, Cu-S(1) 2.5469(14), Cu-S(4) 2.5386(13), Cu-N(7) 2.016(4) A. Reaction of [9]aneNS2 with isobutylene oxide or 2,2-diphenyl-oxirane gives the alcohol derivatives, HL1 and HL2, respectively. The 1:1 metal:ligand complex [Cu2(L1)2]2+ was found to be binuclear with the alcohol functions deprotonated to form alkoxide bridges between two CU(II) centres, Cu-N(1) 2.042(4), Cu-S(4) 2.452(2), Cu-S(7) 2.430(2), Cu-O(14) 1.927(4), Cu-O(14′) 1.922(4), Cu-Cu′ 3.0063(9) A, Cu-O-Cu′ 102.7(2)°. Magnetochemical data for this complex confirm antiferromagnetic coupling between the two Cu(II) centres with 2J = -417 ± 2 cm-1. With Ni(II) the complex [Ni(HL1)(CH3CO2)]+ can be isolated, the structure of which shows it to be a monomer with the ligand HL1 acting as a tetradentate ligand to the metal centre, Ni-N(1) 2.064(3), Ni-S(4) 2.3658(12), Ni-S(7) 2.3875(13), Ni-O(14) 2.061(3) A. A chelating acetate ligand completes the distorted octahedral geometry, Ni-O(16) 2.098(3), Ni-O(17) 2.102(3) A.
- Blake, Alexander J.,Danks, Jonathan P.,Fallis, Ian A.,Harrison, Andrew,Li, Wan-Sheung,Parsons, Simon,Ross, Steven A.,Whittaker, Gavin,Schroeder, Martin
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p. 3969 - 3976
(2007/10/03)
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- Enantiomers of 1-[(4-chlorophenyl)phenylmethyl]-4-[(4-methylphenyl) sulfonyl]piperazine
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Levorotatory and dextrorotatory enantiomers of 1-[(4-chlorophenyl)phenylmethyl]-4-[(4-methylphenyl)sulfonyl]piperazine of the formula STR1 their preparation and use for the preparation of substantially optically pure enantiomers of 1-[(4-chlorophenyl)phenylmethyl]piperazine, which are themselves valuable intermediate products for the preparation of optically active therapeutic compounds having a very high degree of optical purity.
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- Chromogenic and fluorogenic crown ether compounds for the selective extraction and determination of Hg(II)
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Two novel crown ether compounds, N,N′-bis(2-hydroxy-5-nitrobenzyl)-4,13-diazadibenzo-18-crown-6 (CCE) and N,N′-bis(7-hydroxy-4-methylcoumarin-8-methylene)-4,13-diazadibenzo-18- crown-6 (FCE), have been synthesized as potential reagents for the selective e
- Vaidya, Bikas,Zak, Jerzy,Bastiaans, Glenn J.,Porter, Marc D.,Hallman, Johnny L.,Nabulsi, Nabeel A. R.,Utterback, Marty D.,Strzelbicka, Bozena,Bartsch, Richard A.
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p. 4101 - 4111
(2007/10/02)
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- Synthesis of Selectively Protected Polyaza Macrocycles
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A general route to selectively protected polyaza macrocycles has been developed using a mixture of diethylphosphoryl and tosyl groups for protection of linear chain polyamines.Condensation of N-(diethoxyphosphoryl)-N',N''-ditosyldiethylenetriamine (1a), N
- Qian, Ligang,Sun, Zhong,Mertes, Mathias P.,Mertes, Kristin Bowman
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p. 4904 - 4907
(2007/10/02)
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- Nitrogen-containing cyclic ligands
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The subject of the invention is nitrogen-containing cyclic ligands and metal complexes formed by these ligands, the uses of these complexes as magnetic resonance imaging (MRI) agents, as X-ray contrast agents and as chemical shift reagents in vivo.
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- Improved synthesis and application of lanthanide 1,4,7,10-tetrakis(phosphonomethyl)-1,4,7,10-tetraazacyclododecane complexes Ln(DOTP)
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Complexes of lanthanides with 1,4,7,10-tetrakis(phosphonomethyl)-1,4,7,10-tetraazacyclododecane (DOTP) were synthesized for use as shift reagents in a study on the three-dimensional structure of the gene-5 protein encoded by Coli-phage M13.The
- Swinkels, Dorine W.,Duynhoven, John P. M. van,Hilbers, Cornelis W.,Tesser, Godefridus I.
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p. 124 - 128
(2007/10/02)
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- Synthesis of 1,10-Dithia-4,7,13,16-tetra-azacyclo-octadecane, 1-aza-4,7-dithiacyclononane, and N,N'-1,2-Bis(1-aza-4,7-dithia-cyclononyl)ethane. Structural and Solution Studies of their Silver Complexes
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The synthesis of the ligands 1-aza-4,7-dithiacyclononane, N,N'-1,2-bis(1-aza-4,7-dithiacyclononyl)ethane, and 1,10-dithia-4,7,13,16-tetra-azacyclo-octadecane and their silver(I) complexes are reported.Stability constants in water and methanol have been de
- Craig, Andrew S.,Kataky, Ritu,Matthews, Robert C.,Parker, David,Ferguson, George,et al.
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p. 1523 - 1531
(2007/10/02)
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- MACROHETEROCYCLES. 15.* SYNTHESIS OF MACROCYCLIC POLYAMINES IN A BIPHASIC SYSTEM
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Macrocyclic polyamines are conveniently synthesized by condensation of bissulfonamides with ditosylates or dibromides of glycols in the biphasic system toluene(xylene)-aqueous sodium hydroxide.
- Luk'yanenko, N. G.,Basok, S. S.,Filonova, L. K.,Kulikov, N. V.,Pastushok, V. N.
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p. 346 - 349
(2007/10/02)
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- Twelve-ring Azacrowns with 2-Alkoxyethyl Side Arms
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The hydrophilic azacrown ligand 1,4,7,10-tetrakis(2-hydroxyethyl)-1,4,7,10-tetraazacyclododecane can be easily tetramethylated and tetraethylated.Complexation with sodium salts remains strong for both derivatives in chloroform, but extraction with water removes NaI from its complex with the tetraethylated ligand.Pyrolysis of complexes of the tetramethylated ligand liberates the ligand if pure, but results in degradation to 1,4-bis(2-methoxyethyl)piperazine if traces of alkylation reagent are present.The methylated derivative is also obtained by cyclooligomerization of N-(2-methoxyethyl)aziridine, which is hovewer difficult to prepare.The direct reaction between ethyleneglycol ditosylate and 2-methoxyethaneamine (1:1) gives mainly the piperazine, but with excess of amine a series of acyclic oligoamines are obtained.Attempts to prepare 12-azacrowns by reacting the triamine with tosylated diethylamine or diethylamine glycol led instead to six-ring compounds.
- Buoen, Solfrid,Dale, Johannes
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p. 278 - 282
(2007/10/02)
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- Improved Richman-Atkins Syntheses of Cyclic Polyamines Particularly 1,4,7-Triazacyclononane (tacn) and 1,4,7-Triazacyclodecane (tacd), with the Aid of Cation-Exchange in Purification and Isolation
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Richman-Atkins cyclization syntheses for the cyclic triamines 1,4,7-triazacyclononane (tacn) and 1,4,7-triazacyclodecane (tacd) with the alternative possible sets of reagents asd tosyl derivatives have been examined in detail and compared.The cyclizations from the tritosyl derivative of diethylenetriamine (dientt) and the appropriate diols as ditosylates proceeded relatively cleanly, although there were small amounts of higher products and some carry through of dientt for tacn.The alternative cyclizations, from 2,2'-(tosylimino)bisethyl ditosylate and a ditosyl diamine, gave little reaction to form tacn as the tritosyl derivative.The reaction to form tritosyl tacd proceeded further, but was accompanied by significant formation of higher condensation products, particularly the hexamines 1,4,7,11,14,17-hexaazacycloeicosane (2:2 cyclic dimer) and 3,7,10,13-tetraazahexadecane-1,16-diamine.A cation-exchange procedure, applied after the detosylation stage, is described for obtaining the required pure 1 : 1 cyclic polyamines as their hydrochloride salts with high recovery.This is an effective method for removing higher co-products.These may be recovered, and by this means the above hexamines were isolated in admixture.
- Searle, Graeme H.,Geue, Rodney J.
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p. 959 - 970
(2007/10/02)
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- Synthesis of some 4-hydroxypiperazine and N.N.-dibenzylhydroxylamine esters with potential local anaesthetic activity.
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In the synthetic approach to some new local anaesthetics, it was desirable to prepare esters of N1-methyl-N4-hydroxypiperazine and N.N-dibenzylhydroxylamine. Their local anaesthetic activity testing is in progress.
- Rida,Issa,Beltagy
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p. 711 - 713
(2007/10/05)
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- Asymmetric macrocycles containing oxygen and binaphthyl ring members
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Chiral, hinged and functionalized host multiheteromacrocycles of the oxygen, nitrogen and sulfur-containing type are disclosed possessing holes sized to afford selective complexation of specific guest substances and shapes to recognize chirally guest molecules by virtue of the chiral steric barrier of the 2,2'-diheteroatom-1,1'-binaphthyl grouping, the naphthyl-naphthyl dihedral angle, and the provision of ortho positioned side chain substituents (arms) bearing terminal functional groups which act as counterions or additional complexing sites, and the provision of remote position side chain substituents used to control solubility and volatility properties or to bond the multiheteromacrocycles to solid supports.
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