1007-54-1Relevant academic research and scientific papers
Synthesis, silver (I) extraction and silver (I) binding studies of novel N 1,N 3-bis(2-(benzylthio)ethyl)propanediamide derivatives
Aderibigbe, Abiodun D.,Clark, Andrew J.
, p. 397 - 410 (2021)
Abstract: Solvent or liquid–liquid extraction represents a highly valuable technique for the selective recovery of metals from the aqueous phase due to the ease of operation and short turnaround times. Ligands bearing soft donor atoms including nitrogen and sulfur are ideal candidates for selective silver recovery due to their preference for silver binding. Herein, novel N1,N3-bis(2-(benzylthio)ethyl)propanediamide derivatives bearing sulfur and nitrogen donor atoms were prepared in low to high yields and tested for Ag+ extraction from ternary aqueous solutions also containing Cu2+ and Pb2+ following a well-established solvent extraction protocol. It was observed that electronics effects at the 4-aryl position in the propanediamide (or malondiamide) derivatives had a significant effect on the selectivity, but little effect on the efficiency of Ag+ extraction with the 4-methoxy analogue proving the most selective. Steric hindrance provided by dimethyl substitutions at the α-positions to the sulfur atoms had negative effects on Ag+ extraction efficiency and selectivity, while diethyl steric hindrance at the methylene center lowered selectivity but increased extraction efficiency for Ag+. Detailed binding studies reveal that one of the malondiamide derivatives which lacked the electronic and steric hindrance groups studied coordinated Ag+ in a 1:1 fashion suggesting a tetrahedral complex geometry. Overall, the results show that simple modification of the electronics and sterics of the N1,N3-bis(2-(benzylthio)ethyl)propanediamides, can improve their selectivity for Ag+ recovery from the aqueous phase. Graphic abstract: [Figure not available: see fulltext.].
Synthesis and structural characterization of a dinuclear copper(II) complex with a (N,S) donor ligand: Catecholase and phenoxazinone synthase activities
Mondal, Debalina,Ghosh, Ayon Kanti,Chatterjee, Arnab,Ghosh, Rajarshi
, p. 719 - 723 (2019)
[CuII2(L)2Cl4] (1) [L = 2-(benzylthio)ethanamine] has been synthesized and characterized using spectroscopic and X-ray crystallographic results. Structural analyses reveal bidentate chelation behaviour of the neutral L having a distorted square pyramidal coordination environment around each copper(II) with one L, one chloride and two bridging chloro. 1 behaves as an effective catalyst towards oxidation of 3,5-di-tert-butylcatechol to its corresponding quinone with molecular oxygen and also the coupling of o-aminophenol to its phenoxazinone chromophore in methanolic solutions with turnover numbers 2.18 × 102 h?1 (catecholase activity, MeOH), and 3.60 × 102 h?1 (phenoxazinone synthase activity, MeOH) and 2.36 × 102 h?1 (Phenoxazinone synthase activity, MeCN).
A Schiff base fluorescence probe for highly selective turn-on recognition of Zn2+
Zhu, Jinli,Zhang, Yuhuan,Chen, Yihan,Sun, Tongming,Tang, Yanfeng,Huang, Yang,Yang, Qingqing,Ma, Danyang,Wang, Yipu,Wang, Miao
, p. 365 - 370 (2017)
A simple Schiff base CTS, synthesized between 2-hydroxy-1-naphthaldehyde and 2-benzylthio-ethanamine, was found to be a good turn-on fluorescence probe for the detection of Zn2+, due to the restriction of the rotation of the bond between C[dbnd]N and naphthalene ring and/or the blocking of the photo-induced electron transfer (PET) mechanism of the nitrogen atom to naphthalene ring. Excellent selectivity for Zn2+was evidenced, over many other competing ions, including Fe3+, Cr3+, Ni2+, Co2+, Fe2+,Mn2+, Ca2+, Hg2+, Pb2+, Cu2+, Mg2+, Ba2+, Cd2+, Ag+, Li+, K+, and Na+, in EtOH/HEPES buffer (95:5, v/v, pH?=?7.4). It was noteworthy that Cd2+had no interference with Zn2+. The stoichiometric complex of CTS-Zn2+was determined to be 2:1 for CTS and Zn2+in molar, based on the Job plot and single crystal X-ray diffraction data. The binding constant of the complex was 85.7?M?2with a detection limit of 5.03?×?10?7?M. The fluorescence bio-imaging capability of CTS to detect Zn2+in live cells was also studied. These results indicated that CTS could serve as a favorable probe for Zn2+.
Synthesis, structural and magnetic characterizations of a dinuclear copper(II) complex with an (N,S,O) donor ligand: Catecholase and phenoxazinone synthase activities
Ghosh, Ayon Kanti,Ali, Anzar,Singh, Yogesh,Purohit, Chandra Shekhar,Ghosh, Rajarshi
, p. 156 - 163 (2018)
A new dinuclear Cu(II) complex (1) was synthesized and crystallographically characterized. Each of the Cu(II) centres has penta coordination and been found to adopt square pyramidal geometry. Variable temperature magnetic measurements showed that there is weak ferromagnetic interaction between the Cu(II) centres in 1. 1 shows catecholase as well as phenoxazinone synthase activities in different solvents. The turn over numbers for the catecholase activity were 4.02 × 103 h?1 (MeOH) and 9.57 × 103 h?1 (MeCN), and that of phenoxazinone synthase activity were 1.065 × 103 h?1 (MeOH), 2.13 × 102 h?1 (MeCN) and 2.844 × 103 h?1 (DCM).
Importance of the azole moiety of cimetidine derivatives for the inhibition of human multidrug and toxin extrusion transporter 1 (hmate1)
Shinya, Susumu,Kawai, Kentaro,Tarui, Atsushi,Karuo, Yukiko,Sato, Kazuyuki,Matsuda, Masaya,Kitatani, Kazuyuki,Kobayashi, Naoki,Nabe, Takeshi,Otsuka, Masato,Omote, Masaaki
, p. 905 - 912 (2021/09/06)
Herein, we describe the design and synthesis of cimetidine analogs, as well as their inhibitory activity toward the human multidrug and toxin extrusion transporter 1 (hMATE1), which is related to nephrotoxicity of drugs. Cimetidine is the histamine H2-receptor antagonist, but also inhibits hMATE1, which is known to cause renal impairment. We designed and synthesized cimetidine analogs to evaluate hMATE1 inhibitory activity to reveal whether the analogs could reduce the inhibition of hMATE1. The results showed that all analogs with an unsubstituted guanidino group exhibited hMATE1 inhibitory activity. On the other hand, there was a clear difference in the hMATE1 inhibitory activity for the other compounds. That is, compounds with a methylimidazole ring exhibited hMATE1 inhibition, while compounds with a phenyl ring did not. The results suggest that the ability to form hydrogen bonds at the azole moiety is strongly involved in the hMATE1 inhibition.
Synthesis and biological activities of novel trifluoromethylpyridine amide derivatives containing sulfur moieties
Chen, S. H.,Dai, A. L.,Guo, S. X.,He, F.,Wu, J.,Zhang, R. F.
, p. 35658 - 35670 (2020/10/27)
A series of trifluoromethylpyridine amide derivatives containing sulfur moieties (thioether, sulfone and sulfoxide) was designed and synthesized. Their antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo), Ralstonia solanacearum (R. solana
Reversible redox inter-conversion of biologically active NAD+/NADH derivatives bound to a gold electrode: ToF-SIMS evidence
Qian, Ruo-Can,Zhao, Li-Jun,Lv, Jian,Hua, Xin,Long, Yi-Tao
supporting information, p. 13945 - 13948 (2019/01/03)
The realization of the reversible inter-conversion between NADH and NAD+ is a long-term challenge in biological and energy-related chemistry. Here, we achieve the electrochemical reversible redox of NAD+/NADH derivatives by the funct
Enantioselective Synthesis of N,S-Acetals by an Oxidative Pummerer-Type Transformation using Phase-Transfer Catalysis
Biswas, Souvagya,Kubota, Koji,Orlandi, Manuel,Turberg, Mathias,Miles, Dillon H.,Sigman, Matthew S.,Toste, F. Dean
supporting information, p. 589 - 593 (2018/02/21)
Reported is the first enantioselective oxidative Pummerer-type transformation using phase-transfer catalysis to deliver enantioenriched sulfur-bearing heterocycles. This reaction includes the direct oxidation of sulfides to a thionium intermediate, followed by an asymmetric intramolecular nucleophilic addition to form chiral cyclic N,S-acetals with moderate to high enantioselectivites. Deuterium-labelling experiments were performed to identify the stereodiscrimination step of this process. Further analysis of the reaction transition states, by means of multidimensional correlations and DFT calculations, highlight the existence of a set of weak noncovalent interactions between the catalyst and substrate that govern the enantioselectivity of the reaction.
Homo- and Heterodinuclear Rh and Ir Complexes Supported by SNnMixed-Donor Ligands (n = 2–4): Stereochemistry and Coordination-Site-Exchange Reactions of Cp*M (M = Rh, Ir) Units
Nakajima, Takayuki,Kawasaki, Yuki,Kure, Bunsho,Tanase, Tomoaki
, p. 4701 - 4710 (2016/10/11)
A series of SNnmixed-donor ligands [n = 2: H2NC2H4SCH2-2-pyridyl (2-NSpy) (1a), H2NC2H4SCH2-4-pyridyl (4-NSpy) (1b), n = 3: 2-pyridylCH2NHC2H4SCH2-2-pyridyl (2-pyNSpy) (2), n = 4: (2-pyridylCH2)2NC2H4SCH2-2-pyridyl (2-py2NSpy) (3)] was utilized to support homo- and heterodinuclear complexes including Cp*MIIIunits (M = Rh, Ir; Cp* = pentamethylcyclopentadienyl). Reactions of [Cp*MCl2]2with 2-pyNSpy (2), 2-py2NSpy (3), and 4-NSpy (1b) afforded homodinulear complexes, [(Cp*MCl)(2-pyNSpy)(Cp*MCl)](PF6)2[M = Rh (5a), Ir (5b)], [(Cp*M)(2-py2NSpy)(Cp*MCl)](PF6)3[M = Rh (6a), Ir (6b)], [(Cp*MCl)(4-NSpy)(Cp*MCl2)]Cl [M = Rh (8a), Ir (8b)]. Heterodinuclear complexes [(Cp*MCl)(4-NSpy)(Cp*M′Cl2)]Cl [M, M′ = Rh, Ir (8c), Ir, Rh (8d)] were prepared using mononuclear complexes [(Cp*MCl)(4-NSpy)]Cl [M = Rh (7a), Ir (7b)] reacted with [Cp*MCl2]2(M = Ir, Rh), respectively. Complexes 5–8 were characterized by X-ray crystallography to determine the configurations around the M, M′, S, and N centers. The solid-state structures of 6 are retained in acetonitrile solution whereas four diastereomers are generated in the case of 5 due to low stereoselectivity around the coordinated amine nitrogen atom, in contrast to the sulfur atom. Heterodinuclear complexes 8c,d are unstable in solution at 55 °C, readily affording mixtures of 8a–d via intra- and intermolecular coordination-site-exchange reactions of Cp*M fragments between the SN moiety and the py site. In order to evaluate the selectivity of Cp*M fragments for the SN and py coordination sites, several competitive reactions of [Cp*MCl2]2(M = Rh, Ir) with H2NC2H4SCH2C6H5(NSph) (4) and/or 4-methylpyridine (4-Mepy) were carried out to demonstrate predominant formation of iridium complexes 9b and 10b among [(Cp*MCl)(NSph)]Cl [M = Rh (9a), Ir (9b)] and [(Cp*MCl)(4-Mepy)]Cl [M = Rh (10a), Ir (10b)]. These reactions indicated higher affinity of the Cp*Ir fragment to both the NS and py sites relative to the rhodium analogue.
Copper(I) complexes of N-centered aliphatic tripodal trithioether ligands - Adjustment of complex geometry by variation of spacer lengths
Blomenkemper, Marc,Schr?der, Henning,Pape, Tania,Hahn, F. Ekkehardt
experimental part, p. 76 - 80 (2011/03/22)
A series of novel aliphatic tripodal trithioether ligands 4-6 differing in the lengths of the alkyl chains between central nitrogen atom and sulfur donor function has been synthesized. The neutral ligands 4-6 react with copper(I) under formation of the mo
