- Probing the effect of arm length and inter- and intramolecular interactions in the formation of Cu(II) complexes of Schiff base ligands derived from some unsymmetrical tripodal amines
-
The syntheses of two previously known, 2-((2-aminoethyl)(pyridin-2-ylmethyl)amino)ethanol (1) and 2-((3-aminopropyl)(pyridin-2-ylmethyl)amino)ethanol (2), and four new unsymmetrical N-capped tripodal amines, 2-((4-aminobutyl)(pyridin-2-ylmethyl)amino)ethanol (3), 3-((2-aminoethyl)(pyridin-2-ylmethyl)amino)propan-1-ol (4), 3-((3-aminopropyl)(pyridin-2-ylmethyl)amino)propan-1-ol (5) and 3-((4-aminobutyl)(pyridin-2-ylmethyl)amino)propan-1-ol (6), are reported. The ligands (3-4) feature a longer arm, 3-hydroxypropyl or butylamino, than in the analogues previously employed (2-hydroxyethyl arm, ethylamino-arm or propylamino-arm in 1 and 2). All six tripodal amines, 1-6, are equipped with a 2-methylpyridyl-arm and either an ethylamino-arm (1 and 4), propylamino-arm (2 and 5) or butylamino-arm (3 and 6). The new amines, 3-6, have been employed in one pot condensation reactions with 2-hydroxy-1-naphthaldehyde and salicylaldehyde (and its derivatives) in the presence of Cu(II) metal ions to generate a series of new mononuclear complexes, [MIILaldi](ClO4) as well as new dinuclear complexes [CuIILaldi]2(ClO4)2 of new ligands Laldi. Four monomeric complexes and one dimeric complex have been characterised by single crystal X-ray diffraction, revealing a distorted square-pyramidal copper(II) ion. A general comparison between these structures shows that the number and types of chelate ring sequences around the metal ions are important in the formation of structures. Theoretical studies show that the 3-hydroxypropyl arm in these complexes is a weak coordinating group and it can readily be removed from the coordination sphere of metal ions, resulting in a dimerised four coordinate complex. Calculations show that the interaction between the two monomeric fragments is very weak.
- Keypour, Hassan,Shayesteh, Maryam,Salehzadeh, Sadegh,Dhers, Sébastien,Maleki, Farahnaz,ünver, Hüseyin,Dilek, Nefise
-
-
Read Online
- A highly selective CHEF-type chemosensor for monitoring Zn2+ in aqueous solution and living cells
-
A new simple quinolone-based chemosensor 1 was synthesized for Zn2+. 1 exhibited selective fluorescence enhancement in the presence of Zn2+ with a 1:1 stoichiometry in aqueous solution, which was reversible with the addition of ethylenediaminetetraacetic acid (EDTA). The detection limit (0.019 μM) of 1 for Zn2+ is far lower than the World Health Organization guideline (76 μM) in drinking water. 1 was successfully applied to quantify and image Zn2+ in water samples and living cells. The sensing mechanism of Zn2+ by 1via the chelation-enhanced fluorescence (CHEF) effect was supported by theoretical calculations. Therefore, 1 could be used in a practical system for monitoring Zn2+ in aqueous solution.
- Lee, Jae Jun,Lee, Seul Ah,Kim, Hyun,Nguyen, Letuyen,Noh, Insup,Kim, Cheal
-
-
Read Online
- Compound for detecting brassicaceous vegetable sclerotinia sclerotiorum and application thereof
-
The invention discloses a compound for detecting brassicaceous vegetable sclerotinia sclerotiorum, wherein the structure of the compound is shown in the specification, wherein in the formula, R1 is selected from hydrogen and halogen; R2 is selected from hydrogen and halogen; R3 is selected from hydrogen and halogen; R4 is selected from hydrogen and halogen; and R5 is selected from hydrogen and halogen. The compound provided by the invention can realize rapid detection of brassicaceous vegetable sclerotinia sclerotiorum, has the characteristics of high accuracy, low operation difficulty, short time consumption and the like, and is worthy of popularization and application.
- -
-
Paragraph 0063-0066
(2021/08/07)
-
- Excellent synergistic activity of a designed membrane acting pyridinium containing antimicrobial cationicN-acylethanolamine with isoniazid against mycobacterium
-
The emergence of drug-resistant microorganisms and the failure of conventional antibiotics demand extensive research efforts to develop more effective antimicrobial therapies. A new series of cationicN-acylethanolamines was synthesized through introducing a (2-methylene-1-methylpyridinium iodide) moiety, and their antimicrobial activity was evaluated againstMycobacterium smegmatis. The minimum inhibitory concentration (MIC) of cNAEs follows a fourfold decrement when theN-acyl chain length increases by two methylene units. Inspiringly, the lowest MIC of 15.63 μM was observed with 2-((N-(2-hydroxyethyl)palmitamido)methyl)-1-methylpyridin-1-ium iodide, suggesting the necessity of a hydrophilic-lipophilic balance for better antimicrobial activity. cNAEs are unique, because they do not produce reactive oxygen species as most antibiotics do, but exert antimicrobial activity through loss of membrane integrity and membrane depolarization. Further, cNAEs and their combination with a standard drug, isoniazid, exhibit synergistic activity at lower concentrations (cN16E/INH - 3.91/1.95 μM) in comparison to the MIC of the individual drug. Strikingly, the combination showed a bactericidal effect through bacterial membrane disruption, ROS generation and membrane depolarization. Notably, a hemolytic study showed that cN16E is nontoxic to human red blood cells, even above 100 fold higher MIC. The result signifies that cN16E can be used as a potential drug against mycobacteria, as well as in combination with other antimycobacterial drugs.
- Subramaniyan, Siva Bala,Sengan, Megarajan,Subburethinam, Ramesh,Veerappan, Anbazhagan
-
p. 11937 - 11945
(2021/07/19)
-
- A selective and sensitive near-infrared fluorescent probe for real-time detection of Cu(i)
-
The disruption of copper homeostasis (Cu+/Cu2+) may cause neurodegenerative disorders. Thus, the need for understanding the role of Cu+ in physiological and pathological processes prompted the development of improved methods of Cu+ analysis. Herein, a new near-infrared (NIR) fluorescent turn-on probe (NPCu) for the detection of Cu+ was developed based on a Cu+-mediated benzylic ether bond cleavage mechanism. The probe showed high selectivity and sensitivity toward Cu+, and was successfully applied for bioimaging of Cu+ in living cells. This journal is
- Liu, Yiqing,Kang, Ting,He, Qian,Hu, Yuefu,Zuo, Zeping,Cao, Zhihua,Ke, Bowen,Zhang, Weiyi,Qi, Qingrong
-
p. 14824 - 14828
(2021/05/17)
-
- Dinuclear copper(II) complexes of “end-off” bicompartmental ligands: Alteration of the chelating arms on ligands to regulate the reactivity of the complexes towards DNA
-
Two phenol-based “end-off” biscompartmental heptadentate ligands were designed by introduction of substituents with different electronic and steric properties to the chelating arms, i.e. 2,6-bis{[(2-pyridylmethyl)(2-hydroxyethyl)amino]methyl}-4-methylphen
- Cao, Shuhong,Cheng, Run,Wang, Dandan,Zhao, Yunfeng,Tang, Ruiren,Yang, Xiuli,Chen, Jingwen
-
p. 126 - 139
(2019/01/24)
-
- Zinc-Catalyzed Esterification of N-β-Hydroxyethylamides: Removal of Directing Groups under Mild Conditions
-
Amide transformations involving C–N bond cleavage are recognized as difficult reactions owing to the inert nature of amides resulting from resonance. Accordingly, a strong inductive effect and geometrical distortion reasonably decrease the resonance stabilization to attenuate the C–N linkage. Although the conversion of such activated amides has been studied intensively, reaction systems for “unactivated” amides are underdeveloped. We herein report that a zinc(II) trifluoromethanesulfonate [Zn(OTf)2] catalyst achieves the esterification of a wide range of unactivated tertiary amides with the assistance of intramolecular acyl rearrangement. The reaction was applied to the one-pot removal of various amide-based directing groups under mild reaction conditions to afford the corresponding esters in high yields.
- Nishii, Yuji,Hirai, Takahiro,Fernandez, Sarah,Knochel, Paul,Mashima, Kazushi
-
supporting information
p. 5010 - 5014
(2017/09/21)
-
- Dinuclear Cu(II) complexes of compartmental Schiff base ligands formed from unsymmetrical tripodal amines of varying arm lengths: Crystal structure of [Cu2L1](ClO4)2 and theoretical studies
-
Three new dinuclear copper complexes were synthesized via condensation reaction of three new unsymmetrical N-capped tripodal amines and 2,6-diformyl-4-methylphenol, in the presence of copper(II) perchlorate. The solid-state structure of the dinuclear complex, [Cu2L1](ClO4)2, has been determined by X-ray crystallography, showing that the CuII centers have distorted square-pyramidal geometry with N3O2 coordination. The copper (II) ions are bridged by phenolic and hydroxyalkyl groups when in both cases, deprotonation of the hydrogen atoms of the OH groups occurs. The distance between the copper atoms is 3.062 ?. This compound consists of the dication [Cu2L1]2+ and two ClO4- anions in which one of ClO4- groups has a week interaction with one of the Cu atoms. All complexes were characterized by a variety of physico-chemical techniques such as elemental analyses, IR, mass spectra, conductivity measurements and electronic spectral studies. Computational investigation of mentioned binuclear Cu(II) complexes was done by using M062X method with LANL2DZ basis set in vacuo.
- Keypour, Hassan,Shayesteh, Maryam,Rezaeivala, Majid,Sayin, Koray
-
p. 110 - 118
(2016/02/19)
-
- A Novel Quinolin Based Compounds, Agent Selecting Zinc Ion Using The Same, Detecting Method And Detecting Device Thereof
-
The present invention relates to a novel quinolin-based compound, to an agent for detecting a zinc ion (Zn^2+), to a detection method, and to a detection device using the same. More specifically, the present invention relates to a quinolin-based compound having the selectivity specific to the zinc ion (Zn^2+), to an agent for detecting a zinc ion (Zn^2+), to a detection method, and to a detection device using the same. The novel quinolin-based compound of the present invention can be manufactured at room temperature to be manufactured in an easy manner.COPYRIGHT KIPO 2016
- -
-
Paragraph 0045-0048; 0051-0052
(2017/05/06)
-
- Structure and properties of metal complexes of a pyridine based oxazolidinone synthesized by atmospheric CO2 fixation
-
We present here the synthesis of a pyridine containing oxazolidinone, 3-(pyridin-2-ylmethyl)oxazolidin-2-one (L) through the fixation of atmospheric CO2 and without any added base. L has been used to generate three metal complexes [Cu(L)2
- Sarkar, Amrita,Bhattacharyya, Sudipta,Dey, Suman Kr,Karmakar, Subhendu,Mukherjee, Arindam
-
p. 817 - 826
(2014/02/14)
-
- COMPLEX CATALYSTS BASED ON AMINO-PHOSPHINE LIGANDS FOR HYDROGENATION AND DEHYDROGENATION PROCESSES
-
The present application discloses novel PWNN and PWNWP metal catalysts for organic chemical syntheses including hydrogenation (reduction) of unsaturated compounds or dehydrogenation of substrates. The range of hydrogenation substrate compounds includes esters, lactones, enals, enones, enolates, oils and fats, resulting in alcohols, enols, diols, and triols as reaction products. The catalysts of current application can be used to catalyze a hydrogenation reaction under solvent free conditions. The present catalysts also allow the hydrogenation to proceed without added base, and it can be used in place of the conventional reduction methods employing hydrides of the main-group elements. Furthermore, the catalysts of the present application can catalyze a dehydrogenation reaction under homogenous and/or acceptorless conditions. As such, the catalysts provided herein can be useful in substantially reducing cost and improving the environmental profile of manufacturing processes for a variety of chemicals.
- -
-
Page/Page column 30; 31
(2014/09/29)
-
- Synthesis and characterization of mononuclear and dimeric Ni(II), Cu(II) and Cd(II) Schiff base complexes with two new asymmetrical tripodal amines. Crystal structures of Ni(II) and Cd(II) complexes and their antibacterial studies
-
Two new tripodal amines, 2-[(2-aminoethyl)-pyridin-2-ylmethyl-amino]ethanol (1) and 2-[(3-aminopropyl)-pyridin-2-ylmethyl-amino]ethanol (2) have been prepared. These have been used to synthesis some new Schiff base complexes by template condensation with various aldehydes in the presence of Ni(II) and Cd(II) metal ions in methanol. Five new mononuclear complexes [NiL 1](ClO4), [ZnL1](ClO4), [CuL 1](ClO4), [NiL2](ClO4), [NiL 3](ClO4), and four new dimeric complexes [NiL 4]2(ClO4)2·1.5H 2O·0.5CH3CN, [NiL5]2(ClO 4)2, [NiL6]2(ClO4) 2 and [CdL6]2(ClO4)2 have been synthesized. All the complexes have been characterized using spectroscopic methods and the crystal structure of [NiL1](ClO4), [NiL4]2(ClO4)2·1.5H 2O·0.5CH3CN and [CdL6] 2(ClO4)2 were confirmed by single crystal X-ray diffraction studies. It is worth mentioning that as the chain length increases, dimeric complexes are obtained instead of mononuclear ones. Single crystal X-ray structure analysis showed that in the mononuclear Ni(II) complex, [NiL1](ClO4), the Ni(II) ion is in a distorted tetrahedral environment whilst in [NiL4]2(ClO4) 2·1.5H2O·0.5CH3CN and [CdL 6]2(ClO4)2, two distorted octahedral Ni(II) or Cd(II) ions are bridged asymmetrically by a pair of phenoxido groups. Also, the antibacterial activity of the synthesized Ni(II) complexes against Escherichia coli (Lio), Serratia marcescens (PTCC 1330), Staphylococcous aureus (ATCC 6633), and Proteus vulgaris (Lio) was screened. All Ni(II) complexes showed antibacterial effects and [NiL1](ClO4), [NiL 4]2(ClO4)2·1.5H 2O·0.5CH3CN and [NiL6] 2(ClO4)2 are more effective against E. coli.
- Keypour, Hassan,Jamshidi, Amir Hossein,Rezaeivala, Majid,Valencia, Laura
-
p. 872 - 878
(2013/06/04)
-
- Cadmium(II) complexes: Mimics of organophosphate pesticide degrading enzymes and metallo-β-lactamases
-
Figure Persented: Cadmium(II) complexes of ethyl 4-hydroxy-3,5-bis(((2- hydroxyethyl)(pyridin-2-ylmethyl)amino)methyl)benzoate (CO2EtH 3L1) and ethyl 4-hydroxy-3,5-bis(((2-methoxyethyl)(pyridin-2- ylmethyl)amino)methyl)benzoate (COs
- Daumann, Lena J.,Gahan, Lawrence R.,Comba, Peter,Schenk, Gerhard
-
experimental part
p. 7669 - 7681
(2012/09/05)
-
- Biomimetic iron(iii) complexes of N3O and N3O 2 donor ligands: Protonation of coordinated ethanolate donor enhances dioxygenase activity
-
A series of iron(iii) complexes 1-4 of the tripodal tetradentate ligands N,N-bis(pyrid-2-ylmethyl)-N-(2-hydroxyethyl)amine H(L1), N,N-bis(pyrid-2- ylmethyl)-N-(2-hydroxy- propyl)amine H(L2), N,N-bis(pyrid-2-ylmethyl)-N- ethoxyethanolamine H(L3), and N-((pyrid-2-ylmethyl)(1-methylimidazol-2-ylmethyl) )-N-(2-hydroxyethyl)amine H(L4), have been isolated, characterized and studied as functional models for intradiol-cleaving catechol dioxygenases. In the X-ray crystal structure of [Fe(L1)Cl2] 1, the tertiary amine nitrogen and two pyridine nitrogen atoms of H(L1) are coordinated meridionally to iron(iii) and the deprotonated ethanolate oxygen is coordinated axially. In contrast, [Fe(HL3)Cl3] 3 contains the tertiary amine nitrogen and two pyridine nitrogen atoms coordinated facially to iron(iii) with the ligand ethoxyethanol moiety remaining uncoordinated. The X-ray structure of the bis(μ-alkoxo) dimer [{Fe(L5)Cl}2](ClO4)25, where HL is the tetradentate N3O donor ligand N,N-bis(1-methylimidazol-2-ylmethyl)-N- (2-hydroxyethyl)amine H(L5), contains the ethanolate oxygen donors coordinated to iron(iii). Interestingly, the [Fe(HL)(DBC)]+ and [Fe(HL3)(HDBC)X] adducts, generated by adding ~1 equivalent of piperidine to solutions containing equimolar quantities of iron(iii) complexes 1-5 and H2DBC (3,5-di-tert-butylcatechol), display two DBC2- → iron(iii) LMCT bands (λmax: 1, 577, 905; 2, 575,915; 3, 586, 920; 4, 563, 870; 5, 557, 856 nm; Δλmax, 299-340 nm); however, the bands are blue-shifted (λmax: 1, 443, 700; 2, 425, 702; 3, 424, 684; 4, 431, 687; 5, 434, 685 nm; Δλmax, 251-277 nm) on adding 1 more equivalent of piperidine to form the adducts [Fe(L)(DBC)] and [Fe(HL3)(HDBC)X]. Electronic spectral and pH-metric titration studies in methanol disclose that the ligand in [Fe(HL)(DBC)]+ is protonated. The [Fe(L)(DBC)] adducts of iron(iii) complexes of bis(pyridyl)-based ligands (1,2) afford higher amounts of intradiol-cleavage products, whereas those of mono/bis(imidazole)-based ligands (4,5) yield mainly the auto-oxidation product benzoquinone. It is remarkable that the adducts [Fe(HL)(DBC)] +/[Fe(HL3)(DBC)X] exhibit higher rates of oxygenation affording larger amounts of intradiol-cleavage products and lower amounts of benzoquinone. The Royal Society of Chemistry 2011.
- Sundaravel, Karuppasamy,Sankaralingam, Muniyandi,Suresh, Eringathodi,Palaniandavar, Mallayan
-
experimental part
p. 8444 - 8458
(2011/10/10)
-
- NOVEL SULFONAMIDE COMPOUNDS
-
The invention relates to novel sulfonamide compounds and their use as orexin receptor antagonists.
- -
-
Page/Page column 11; 13
(2009/12/02)
-
- Synthesis, herbicidal activity, and structure-bioactivity relationship of pyridyl-containing 2-phenyliminothiazolidines
-
A series of novel 2-phenyliminothiazolidine derivatives were designed and synthesized. All title compounds were characterized by 1H NMR and, in some cases, by 13C NMR, IR, and HRMS. Their agricultural bioactivities were evaluated and some of these compounds exhibited efficient herbicidal activities against Echinochloa crusgalli, Sorghum vulgare, Digitaria sanguinalis, Eclipta prostrasta, Cucumis sativus, and Brassica campestris at 50∈μg/cm3. Analysis of the quantitative structure-activity relationship (QSAR) showed that the electronic parameter was the main factor to affect herbicidal activities.
- Li, Gangyue,Qian, Xuhong,Yan, Shenggang,Cui, Jingnan,Zhang, Rong,Xiao, Yi
-
p. 169 - 178
(2008/12/22)
-
- NOVEL SULFONAMIDE COMPOUNDS
-
The invention relates to sulfonamide compounds of formula (I), where A, B, R3 and R4 are as defined in the claims, and their use as orexin receptor antagonists in the prevention and treatment of eating and drinking disorders, all types of sleep disorders, all kinds of cognitive dysfunctions in the healthy population and psychiatric and neurologic disorders. Formula (I).
- -
-
Page/Page column 32
(2008/06/13)
-
- Phenylpropanoic acid derivatives bearing a benzothiazole ring as PPARδ-selective agonists
-
To find novel PPARδ-selective agonists, we designed and synthesized phenylpropanoic acid derivatives bearing 6-substituted benzothiazoles. Optimization of this series led to the identification of a potent and selective PPARδ agonist 17. Molecular modeling suggested that compound 17 occupies the Y-shaped pocket of PPARδ appropriately.
- Fujieda, Hiroki,Usui, Shinya,Suzuki, Takayoshi,Nakagawa, Hidehiko,Ogura, Michitaka,Makishima, Makoto,Miyata, Naoki
-
p. 4351 - 4357
(2008/02/12)
-
- SULFONYLAMINO-ACETIC ACID DERIVATIVES
-
The invention relates to novel sulfonylamino-acetic acid derivatives and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of such compounds, pharmaceutical compositions containing one or more of those compounds and especially their use as orexin receptor antagonists.
- -
-
-
- Chemokine receptor binding heterocyclic compounds
-
This invention relates to a novel class of heterocyclic compounds that bind chemokine receptors, inhibiting the binding of their natural ligands thereby. These compounds result in protective effects against infection by HIV through binding to chemokine receptors, including CXCR4 and CCR5, thus inhibiting the subsequent binding by these chemokines. The present invention provides a compound of Formula I wherein, W is a nitrogen atom and Y is absent or, W is a carbon atom and Y═H; R1to R7may be the same or different and are independently selected from hydrogen or straight, branched or cyclic C1-6alkyl; R8is a substituted heterocyclic group or a substituted aromatic group Ar is an aromatic or heteroaromatic ring each optionally substituted at single or multiple, non-linking positions with electron-donating or withdrawing groups; n and n′ are independently, 0-2; X is a group of the formula: Wherein, Ring A is an optionally substituted, saturated or unsaturated 5 or 6-membered ring, and P is an optionally substituted carbon atom, an optionally substituted nitrogen atom, sulfur or oxygen atom. Ring B is an optionally substituted 5 to 7-membered ring. Ring A and Ring B in the above formula can be connected to the group W from any position via the group V, wherein V is a chemical bond, a (CH2)n″group (where n″=0-2) or a C═O group. Z is, (1) a hydrogen atom, (2) an optionally substituted C1-6alkyl group, (3) a C0-6alkyl group substituted with an optionally substituted aromatic or heterocyclic group, (4) an optionally substituted C0-6alkylamino or C3-7cycloalkylamino group, (5) an optionally substituted carbonyl group or sulfonyl. These compounds further include any pharmaceutically acceptable acid addition salts and metal complexes thereof and any stereoisomeric forms and mixtures of stereoisomeric forms thereof.
- -
-
Page column 64
(2008/06/13)
-