- Synthesis and fluorescent properties of a novel dansyl-based fluorescent probe for Hg2+
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A novel turn-off fluorescent probe containing a dansyl fluorophore has been synthesised. Its recognition properties towards various metal ions have been studied by fluorescence spectrometry. The compound showed a high sensitivity and selectivity to Hg2+ ion and a complexation ratio towards Hg 2+ of 2 : 1. Its fluorescence intensity varied almost linearly versus the concentration of Hg2+ (0.8-8.4 μmol L-1), and the detection limit of Hg2+ was estimated to be 0.88 μmol L -1.
- Zuo-An, Xiao,Dan, Zhan,Xiao, Yang
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Read Online
- Novel piperazine based compounds as potential inhibitors for SARS-CoV-2 Protease Enzyme: Synthesis and molecular docking study
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Structurally diverse piperazine-based compounds hybrid with thiadiazole, isatin or with sulfur/nitrogen, functionalities were synthesized. The structures of the new compounds were established based on their spectral data and elemental analysis. The physicochemical, bioactivity scores and pharmacokinetic behavior of all the prepared ligands were evaluated using in silico computational tools. The new piperazine ligands have been screened for their inhibition activity against SARS-CoV-2 protease enzyme using molecular docking analysis. The docking studies showed that all the ligands have been docked with negative dock energy onto the target protease protein. Moreover, Molecular interaction studies revealed that SARS-CoV-2 protease enzyme had strong hydrogen bonding interactions with piperazine ligands. The present in silico study thus, provided some guidance to facilitate drug design targeting the SARS-CoV-2 main protease.
- El-atawy, Mohamed,El-sadany, Samer K.,Hamed, Ezzat A.,Mosa, Tawfik M.,Omar, Alaa Z.
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- Synthesis, in vitro cytotoxicity and biological evaluation of twenty novel 1,3-benzenedisulfonyl piperazines as antiplatelet agents
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In order to discover antiplatelet drug with novel structure and expand our research scope, total twenty 1,3-benzenedisulfonyl piperazines, were designed and synthesized. These target compounds were divided into two series, namely 4-methoxy-1,3-benzenedisulfonyl piperazines of series 1 and 4-ethoxy-1,3-benzenedisulfonyl piperazines of series 2. With adenosine diphosphate (ADP), arachidonic acid (AA) and collagen as inducers, respectively, the Born turbidimetric method was used to screen the antiplatelet activity in vitro of all target compounds at a concentration of 1.3 μM, with aspirin and picotamide as positive control drugs. And of which, the activities of five compounds for collagen were higher than both picotamide and aspirin. In ADP or AA channel, compounds with an inhibition rate greater than 33% were selected, and their corresponding IC50 values were obtained. According to the IC50, the in vitro activity of one compound for ADP was higher than picotamide, and for AA, two compounds were higher than two positive control drugs and other two compounds only higher than or equal to aspirin. The preliminary analysis of the structure-activity relationship of the target compounds involved in this study was completed. Further, eight compounds exhibiting higher activity in one or two test channels, were subjected to cytotoxicity test on mouse fibroblasts (L929) by CCK-8 method. The in vitro cytotoxicity of most test compounds showed less than or same to control drug picotamide at 10 μM, but at the higher concentration of 100 μM, merely two compounds exhibited higher cell survival rate than that of picotamide. In addition, compound N1,N3-di(4-ethoxy-1,3-phenylenedisulfonyl)bis(1-(m-tolyl)piperazine), which is delivery activity in the three test channels, and another compound N1,N3–di(4-methoxy-1,3-phenylenedisulfonyl)bis(1-(m-tolyl)piperazine), which has the lowest cytotoxic in vitro compound among series 1 and series 2, respectively, are found and selected for simulation analysis as two most likely to dock with the receptor P2Y12. Each of synthesized compounds in silico molecular property and ADME (absorption, distribution, metabolism and excretion) are predicted by using Molinspiration property engine v2018.10 and PreADMET online servers, respectively. Compared with other series of compounds in the previous stage, the two series compounds obtained after the introduction of piperazinyl have a similar in vitro activity.
- Liu, Xiu-jie,Wang, Yan,Wang, Xiao,Zhang, Zhi-hao
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- Dynamic Kinetic Resolution of Alcohols by Enantioselective Silylation Enabled by Two Orthogonal Transition-Metal Catalysts
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A nonenzymatic dynamic kinetic resolution of acyclic and cyclic benzylic alcohols is reported. The approach merges rapid transition-metal-catalyzed alcohol racemization and enantioselective Cu-H-catalyzed dehydrogenative Si-O coupling of alcohols and hydrosilanes. The catalytic processes are orthogonal, and the racemization catalyst does not promote any background reactions such as the racemization of the silyl ether and its unselective formation. Often-used ruthenium half-sandwich complexes are not suitable but a bifunctional ruthenium pincer complex perfectly fulfills this purpose. By this, enantioselective silylation of racemic alcohol mixtures is achieved in high yields and with good levels of enantioselection.
- Oestreich, Martin,Seliger, Jan
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supporting information
p. 247 - 251
(2020/10/29)
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- Surface active SNS-based dicationic ionic liquids containing amphiphilic anions: Experimental and theoretical studies of their structures and organization in solution
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Surface active ionic liquids (SAILs) have been reported as new media that collectively offer the advantages of the aqueous and oily phases. In particular, dicationic ionic liquids (DILs) have attracted much interests because their tunable physicochemical properties allow them to act as sustainable active catalysts in chemical reactions (CO2 conversion, esterification) and also as extraction media to remove drugs/pollutants from aqueous systems. In order to better understand this class of ILs, this work describes new strategies for the synthesis of SNS-based dicationic ILs containing amphiphilic anions ([C12SO4]-, [C12ESO4]-, [C12BSO3]- and [C12SAR]-) and the evaluation of their structural organization and aggregation level in solution. The results obtained by experimental techniques (FTIR, TGA, DSC, POM, ESI-MS, DLS and NMR) combined with those achieved by theoretical DFT calculations revealed that the anion has an important function to modulate the properties of the SNS-based ILs in solution, while the presence of a methyl group at the C2 position of the imidazolium ring seems to be not sufficient to change such physicochemical properties. The ILs containing the anion [C12BSO3]- showed a superior ionic organization in solution due to the cationic aggregates observed in the ESI(+) mode and the large size of aggregates observed by DLS. This behavior may be assigned to a close proximity of the cationic imidazolium ring and the aromatic ring in the anion (π-π interaction), and by NMR analysis (ROESY and DOSY) it was possible to confirm interactions between cation and anion. Therefore, the theoretical and experimental results obtained for the SNS-based dicationic ILs containing amphiphilic anions indicate that these ILs can be applied as media in both pure and/or solution systems for many sustainable applications.
- Domingos, Josiel B.,Dupont, Jairton,Ferreira, Thuany M.,Monteiro, Wesley F.,Scholten, Jackson D.,Vieira, Michele O.,dos Santos, Francisco P.
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- RECYCLABLE CLEAN FRACTURING FLUID THICKENER, PREPARATION METHOD AND RECOVERY METHOD THEREOF, AND HIGH-TEMPERATURE RESISTANT CLEAN FRACTURING FLUID
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Disclosed are a recyclable clean fracturing fluid thickener, a preparation method and a recovery method thereof, and a high-temperature resistant clean fracturing fluid, which relate to the stimulation treatment of oil and gas fields. Diethanolamine and thionyl chloride are used as raw materials and reacted to obtain an intermediate, which is then reacted with an unsaturated fatty acid amidopropyl dimethylamine to produce the recyclable clean fracturing fluid thickener. The clean fracturing fluid can be used in the fracturing stimulation treatment of low and medium permeability reservoirs.
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Paragraph 0051-0052
(2020/12/04)
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- Preparation method of 1-(2,3-dichlorophenyl)piperazine hydrochloride
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The invention belongs to the field of preparation of chemical intermediates, and particularly relates to a preparation method of 1-(2,3-dichlorophenyl)piperazine hydrochloride. The preparation methodcomprises the following steps of using diethanol amine as the initial raw material, and performing chlorination reaction, so as to obtain beta,beta'-dichlorodiethylamine hydrochloride; performing cyclization reaction with 2,3-dichloroaniline in a water solution under the condition of no catalyst, so as to synthesize a target compound, namely the 1-(2,3-dichlorophenyl)piperazine hydrochloride. Thepreparation method of the 1-(2,3-dichlorophenyl)piperazine hydrochloride has the advantages that the reaction rate is obviously accelerated, the yield rate is increased, and the cost is reduced.
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Paragraph 0011; 0012
(2019/06/08)
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- Synthesis and Antitumor Effect of Sophoridine Derivatives Bearing an Acyclic Aryloxy Phosphoramidate Mustard Functionality
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To elevate the potency of sophoridine, phosphoramidate mustard motif was incorporated to D-ring opened sophoridine scaffold. A series of acyclic aryloxy phosphoramidate mustard functionalized sophoridine derivatives were synthesized and screened for cytostatic activity in a range of different tumor cell lines (S180, H22, K562, MCF-7, SMMC-7721, and LoVo). All these compounds were shown to be more sensitive to S180 and H22 cells with IC50 values ranging from 2.10 to 7.21?μM. In addition, all targeted derivatives distinctly are more cytotoxic to cancer cells than normal cell L929. Compounds 8b, 8c, 8d, and 8e displayed moderate tumor suppression without apparent organ toxicity in vivo against mice bearing H22 liver tumors. Their potential binding modes with DNA topoisomerase I complex have also been investigated.
- Dai, Lin-Lin,Li, Dong-Dong,Zhao, Xiu-Mei,Zhi, Shuang,Shen, Hong-Sheng,Yang, Zi-Bo
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p. 417 - 425
(2018/12/05)
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- Design, synthesis, and biological evaluation of structurally constrained hybrid analogues containing ropinirole moiety as a novel class of potent and selective dopamine D3 receptor ligands
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Two series of hybrid analogues were designed, synthesized, and evaluated as a novel class of selective ligands for the dopamine D3 receptor. Binding affinities of target compounds were determined (using the method of radioligand binding assay). Compared to comparator agent BP897, compounds 2a and 2c were found to demonstrate a considerable binding affinity and selectivity for D3 receptor, and especially compound 2h was similarly potent and more selective D3R ligand than BP897, a positive reference. Thus, they may provide valuable information for the discovery and development of highly potent dopamine D3 receptor ligands with outstanding selectivity.
- Zhou, Benhua,Hong, Kwon Ho,Ji, Min,Cai, Jin
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p. 1597 - 1609
(2018/07/31)
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- Synthesis of novel perfluoroalkyl ether derivatives
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A series of novel fluoroether-containing monomers has been designed and prepared based on the commercially available perfluoroalkyl ether acid fluoride. Treating acid fluoride with allyl alcohol, 2-hydroxyethyl methacrylate or N-allylmethylamine allowed for the direct formation of corresponding vinyl-containing fluorinated monomers. High yields of the fluorinated epoxy monomers could be obtained from acid chloride with glycidol; meanwhile, fluorinated diol was prepared from diethanolamine or 3-amino-1,2-propanediol. Moreover, fluorinated monoamine, fluorinated monoalcohol and fluorinated dichloride were also obtained. Most of these fluorinated monomers were liquid at room temperature and exhibited good solubility in common organic solvents.
- Shi, Xiang,Shi, Hongxin,Wu, Hongke,Shen, HaiMin
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p. 5091 - 5105
(2018/04/05)
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- Novel sophoridine derivatives bearing phosphoramide mustard moiety exhibit potent antitumor activities in vitro and in vivo
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Novel mustard functionalized sophoridine derivatives were synthesized and evaluated for their cytotoxicity against of a panel of various cancer cell lines. They were shown to be more sensitive to S180 and H22 tumor cells with IC50 values ranging from 1.01–3.65 μM, and distinctly were more cytotoxic to cancer cells than normal cell L929. In addition, compounds 7a, 7c, and 7e displayed moderate tumor suppression without apparent organ toxicity in vivo against mice bearing H22 liver tumors. Furthermore, they arrested tumor cells in the G1 phase and induced cellular apoptosis. Their potential binding modes with DNA-Top I complex have also been investigated.
- Li, Dongdong,Dai, Linlin,Zhao, Xiumei,Zhi, Shuang,Shen, Hongsheng,Yang, Zibo
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- Synthesis of the novel crown and lariat ethers with integrated 1,2,3-triazole ring
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Crown ethers possessing an external chain are called lariat ethers. Huisgen cycloaddition is the 1,3-dipolar cycloaddition occurs between a suitable azide and terminal alkyne to give a stable 1,2,3-triazole system. It is the most common reaction of the so called philosophy of “click chemistry,” introduced by Nobel prize laureate Sharpless.
- Romański, Jaros?aw,Jaworski, Przemys?aw
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p. 231 - 234
(2017/01/22)
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- Preparation method of thiomorpholine-1,1-dioxide hydrochloride and preparation method of thiomorpholine-1,1-dioxide
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The invention discloses a preparation method of thiomorpholine-1,1-dioxide hydrochloride and a preparation method of thiomorpholine-1,1-dioxide. The preparation method of thiomorpholine-1,1-dioxide hydrochloride includes the following steps that firstly, a thiomorpholine amino protection compound and potassium permanganate which is added into a reaction system in batches are subjected to an oxidation reaction to generate a thiomorpholine-1,1-dioxide amino protection compound; secondly, the thiomorpholine-1,1-dioxide amino protection compound obtained in the first step is hydrolyzed under the hydrochloric acid condition, and thiomorpholine-1,1-dioxide hydrochloride is obtained. When the thiomorpholine amino protection compound and potassium permanganate are subjected to the oxidation reaction in the preparation method, a batch-wise addition mode is used, the oxidation effect is good, and the reaction is sufficient. Meanwhile, the situation that a lot of heat is dissipated in a short time in the oxidation reaction can be avoided, the reaction process is smooth and easy to control, and operation is safer.
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Paragraph 0045; 0060; 0066; 0074; 0082; 0090; 0098
(2017/05/18)
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- Hexahydropyrazine-quinoline D3 receptor ligand and preparation method and use
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The present invention discloses a hexahydropyrazino-quinoline D3 receptor ligand, which is a compound shown as formula I or a pharmaceutically acceptable salt thereof, wherein n = 2,3 or 4; R is H, 4-Cl, 2,3-diCl, 4-CH3, 2,3-diCH3, 4-OCF3, 4-OCH3, 2-OCF3, 2,6-di CH3, 3,4-di CH3, 3-CF3, 4-Cl, 3-OCH3, 2-C2H5 or 2-CH3. Compared with the prior art, the compound has strong activity to a dopamine D3 receptor, and can be used for effective treatment of Parkinson's disease, schizophrenia, drug dependence and other central nervous and mental diseases.
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Paragraph 0047; 0048
(2016/10/08)
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- Synthesis and sensing applications of a new fluorescent derivative of cholesterol
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A fluorescent 4-chloro-7-nitro-1,2,3-benzoxadiazole (NBD) derivative of cholesterol (CTN) was designed and synthesized. The compound forms a 1: 1 non-fluorescent complex with Hg2+ in a solvent mixture of water and ethanol. Based on this discovery, a detection method with a detection limit (DL) of ～0.08 μM for Hg2+ was developed. The presence of other commonly found metal ions has little effect on the detection. Though Fe2+ and Cu2+ have some interference, it could be avoided by a simple oxidation or reduction procedure. Further studies revealed that the complex can be used for the turn-on detection of some organophosphorus pesticides (OPs), such as DDVP, glyphosate, chlorpyrifos, diazinon and phoxim, either in solution or film state. The DLs for the five OPs are 0.015, 0.018, 0.087, 0.098 and 0.113 μg mL-1 in solution, respectively. In addition, the compound as developed is interesting and attractive because it can sense the heavy metal ion and the OPs in a fast and sensitive manner. It is therefore believed that the developed method possesses the potential to be used for rapid on-site detection of hazardous chemicals.
- Lü, Yanchao,Sun, Qingqing,Hu, Baolong,Chen, Xiangli,Miao, Rong,Fang, Yu
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supporting information
p. 1817 - 1824
(2016/02/19)
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- Matrine derivative having antitumor performance
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The invention relates to a matrine derivative, and provides a matrine derivative with characteristics of high activity, low toxicity and good antitumor performance, and uses of the matrine derivative in preparation of antitumor drugs.
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Paragraph 0059; 0060; 0061
(2016/10/08)
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- Synthesis and biological evaluation of novel 3-substituted amino-4-hydroxylcoumarin derivatives as chitin synthase inhibitors and antifungal agents
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A series of novel 3-substituted amino-4-hydroxycoumarin derivatives have been designed and synthesized as chitin synthase (CHS) inhibitors. All the synthesized compounds have been screened for their CHS inhibition activity and antimicrobial activity in vitro. The enzymatic assay indicated that most of the compounds have good inhibitory activity against CHS, in which compound 6o with IC50 of 0.10 mmol/L had stronger activity than that of polyoxins B, which acts as control drug with IC50 of 0.18 mmol/L. As far as the antifungal activity is concerned, most of the compounds possessed moderate to excellent activity against some representative pathogenic fungi. Especially, compound 6b was found to be the most potent agent against Cryptococcus neoformans with minimal inhibitory concentration (MIC) of 4 g/mL. Moreover, the results of antibacterial screening showed that these compounds have negligible actions to some tested bacteria. Therefore, these compounds would be promising to develop selective antifungal agents.
- Ge, Zhiqiang,Ji, Qinggang,Chen, Chunyan,Liao, Qin,Wu, Hualong,Liu, Xiaofei,Huang, Yanrong,Yuan, Lvjiang,Liao, Fei
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p. 219 - 228
(2016/02/03)
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- Discovery of novel N,N-3-phenyl-3-benzylaminopropionanilides as potent inhibitors of cholesteryl ester transfer protein in vivo
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Epidemiological studies have identified that the risk of cardiovascular events increases due to the decreased levels of high density lipoprotein-cholesterol and the elevated levels of low density lipoprotein-cholesterol. Herein, we report a novel series of N,N-3-phenyl-3-benzylaminopropionanilide derivatives, which were identified as potent cholesteryl ester transfer protein (CETP) inhibitor. The initial lead compound L10 (IC50 8.06 μM) was found by pharmacophore-based virtual screening (Dong-Mei Zhao et al., Chin. Chem. Lett. 2014, 25, 299). After systematic structure variation and biological testing against CETP, two different series were identified as scaffolds for potent CETP inhibitors. One is N,N-3-phenyl-3-benzylaminopropanamide derivatives, which were investigated in our previous paper (Bioorg. Med. Chem. 2015, doi: http://dx.doi.org/10.1016/j.bmc.2015.12.010). The most potent compound HL16 in that series has the IC50 of 0.69 μM. The other series is N,N-3-phenyl-3-benzylaminopropionanilide derivatives, which was investigated in current study. Further optimization of the structure-activity relationship (SAR) resulted in H16 (IC50 0.15 μM), which was discovered as a potent CETP inhibitor in vitro by BODIPY-CE fluorescence assay. In addition, the results of pharmacodynamics studies showed that H16 exhibited both favorable HDL-C enhancement and LDL-C reduction in vivo by hamster. It also has an excellent stability in rat liver microsomal.
- Xie, Honglei,Li, Yiqun,Bai, Changlin,Wang, Ruifeng,Liu, Chunchi,Hao, Chenzhou,Lin, Bin,Cheng, Maosheng,Zhao, Dongmei
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p. 1811 - 1818
(2016/04/05)
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- Design, synthesis and biological evaluation of N,N-3-phenyl-3-benzylaminopropanamide derivatives as novel cholesteryl ester transfer protein inhibitor
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A series of N,N-3-phenyl-3-benzylaminopropanamide derivatives were identified as novel CETP (cholesteryl ester transfer protein) inhibitors. In our previous study, lead compound L10 was discovered by pharmacophore-based virtual screening (Dong-Mei Zhao et al., 2014). Based on L10 (IC50 8.06 μM), compound HL6 (IC50 10.7 μM) was discovered following systematic structure variation and biological tests. Further optimization of the structure-activity relationship (SAR) resulted in N,N-3-phenyl-3-benzylaminopro panamides derivatives as novel CETP inhibitors. They were synthesized and evaluated against CETP by BODIPY-CE fluorescence assay. Among them, HL16 (IC50 0.69 μM) was a highly potent CETP inhibitor in vitro. In addition, HL16 exhibited favorable HDL-C enhancement and LDL-C reduction in vivo by hamster. The molecular docking of HL16 into the CETP was performed. The binding mode demonstrated that HL16 occupied the CETP binding site and formed interactions with the key amino acid residues.
- Zhao, Dongmei,Xie, Honglei,Bai, Changlin,Liu, Chunchi,Hao, Chenzhou,Zhao, Shizhen,Yuan, Hongli,Luo, Changqun,Wang, Jian,Lin, Bin,Zheng, Jiang,Cheng, Maosheng
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p. 1589 - 1597
(2016/04/05)
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- Cyclic process for the production of taurine from alkali isethionate and alkali vinyl sulfonate
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The present invention discloses a cyclic process for the production of taurine from alkali isethionate and alkali vinyl sulfonate in a high overall yield of greater than 95% by continuously converting the byproducts of the ammonolysis reaction, sodium ditaurinate and sodium tritaurinate, to sodium taurinate. Pure sodium ditaurinate and sodium tritaurinate are prepared from diethanolamine and triethanolamine as starting materials, respectively, and are subjected to the ammonolysis reaction to yield a mixture of sodium taurinate, sodium ditaurinate, and sodium tritaurinate.
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Paragraph 0043
(2015/11/23)
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- Evaluation of alkylating and intercalating properties of mannich bases for cytotoxic activity
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A series of new "hybrid compounds", Mannich base derivatives of planar polycyclic/heterocyclic starting materials, was designed and synthesized. The structures of the compounds were confirmed by spectroscopic methods and elemental analysis. Cytotoxicity of compounds was investigated in three cancer cell lines (PC3, HeLa, and MCF7) and one non-tumoral cell line (293 HEK). We tested the DNA-intercalating capability of the molecules by ethidium bromide (EtBr) fluorescence displacement experiment. Compounds' alkylation potency was investigated via in vitro incubation test using 2-mercaptoethanol, a biomimetic nucleophile. The five of the compounds (7s, 9d, 10b, 11b, 12c) are reported for first time in the literature. Our results suggest that compound 9d has a biological activity close to the reference compound doxorubicin, an intercalating agent in clinical use.
- Istanbullu, Huseyin,Erzurumlu, Yalcin,Kirmizibayrak, Petek Ballar,Erciyas, Ercin
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p. 1096 - 1106
(2015/04/14)
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- 2-AMINOTHIAZOLE DERIVATIVE, PREPARATION METHOD, AND USE
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The present invention relates to the preparation of a 2-aminothiazole derivative having a structure as formula (I) and a therapeutic effect thereof for Alzheimer's disease (AD), and a therapeutic effect thereof against transplant rejection, autoimmune diseases, ischemia-reperfusion injury, chronic inflammation response, endotoxemia, and other diseases.
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Paragraph 0018; 0080
(2014/01/18)
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- Synthesis and characterization of divalent manganese, iron, and cobalt complexes in tripodal phenolate/N-heterocyclic carbene ligand environments
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Two novel tripodal ligands, (BIMPNMes,Ad,Me)- and (MIMPNMes,Ad,Me)2-, combining two types of donor atoms, namely, NHC and phenolate donors, were synthesized to complete the series of N-anchored ligands, ranging from chelating species with tris(carbene) to tris(phenolate) chelating arms. The complete ligand series offers a convenient way of tuning the electronic and steric environment around the metal center, thus, allowing for control of the complex's reactivity. This series of divalent complexes of Mn, Fe, and Co was synthesized and characterized by 1H NMR, IR, and UV/vis spectroscopy as well as by single-crystal X-ray diffraction studies. Variable-temperature SQUID magnetization measurements in the range from 2 to 300 K confirmed high-spin ground states for all divalent complexes and revealed a trend of increasing zero-field splitting |D| from Mn(II), to Fe(II), to Co(II) complexes. Zero-field 57Fe Moessbauer spectroscopy of the Fe(II) complexes 3, 4, 8, and 11 shows isomer shifts δ that increase gradually as carbenes are substituted for phenolates in the series of ligands. From the single-crystal structure determinations of the complexes, the different steric demand of the ligands is evident. Particularly, the molecular structure of 1 - in which a pyridine molecule is situated next to the Mn-Cl bond - and those of azide complexes 2, 4, and 6 demonstrate the flexibility of these mixed-ligand derivatives, which, in contrast to the corresponding symmetrical TIMENR ligands, allow for side access of, e.g., organic substrates, to the reactive metal center.
- Kaess, Martina,Hohenberger, Johannes,Adelhardt, Mario,Zolnhofer, Eva M.,Mossin, Susanne,Heinemann, Frank W.,Sutter, Joerg,Meyer, Karsten
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supporting information
p. 2460 - 2470
(2014/03/21)
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- A highly selective and sensitive fluorescent sensor for copper(ii) ion characterized by one dichlorofluorescein moiety and two azathia-crown ether
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A new fluorescent sensor 1, which functionalized with one dichlorofluorescein moiety as fluorogenic signaling subunit and two azathiacrown ether macrocyclic as binding site was designed, synthesized and characterized. It was found that sensor 1 can selectively recognize Cu2+ by a remarkable emission quenching in DMSO-H2O (1:1, v/v), which was attributed to the 1:2 complex formation between 1 and Cu2+, while other ion including K+, Na+, Mg2+, Zn 2+, Ba2+, Co2+, Ca2+, Fe 2+, Fe3+, Pb2+, Pb2+, Ni 2+ and Ag+ induced no or much small fluorescence changes. In addition, the sensor 1 exihibited a rapid, stable and linear response to Cu2+ in the concentration range from 5 × 10-7 to 1 × 10-5 mol L-1 with a detection limit as low as 8.7 × 10-8 mol L-1. Furthermore, the sensor 1 was applied to practical determination of Cu2+ in different water samples with satisfactory results.
- Jiang, Y,Huang, Zhong,Dai, Huajun,Wang, Lihua,Ying, Liu,Kou, Xingming
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p. 8292 - 8296
(2013/11/06)
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- A selective and sensitive fluorescence probe for imaging endogenous zinc in living cells
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A carboxamidoquinoline-based fluorescent Zn2+ probe 1 containing N/S/S heteroatoms as a receptor was designed and readily synthesized, which was featured by the Zn2+-induced red-shift of emission (45 nm) based on internal charge transfer (ICT) in an aqueous HEPES buffer (pH=7.4). Moreover, spectroscopic studies indicated that the composition of the complex 1-Zn 2+ was 1:1, which was also confirmed by X-ray crystallography. In addition, 1H NMR titration experiment suggested that probe 1 transformed from the amide tautomer to imidic acid tautomer after binding with Zn2+. The binding of zinc with 1 was easily reversed by addition of N,N,N′,N′-tetrakis(2-picolyl)ethylenediamine (TPEN) or EDTA. Furthermore, probe 1 was successfully applied to image both exogenous and endogenous zinc in living HeLa cells.
- Zhang, Liangwei,Duan, Dongzhu,Cui, Xuemei,Sun, Jinyu,Fang, Jianguo
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- Design, synthesis and evaluation of aminobenzophenone derivatives containing nitrogen mustard moiety as potential central nervous system antitumor agent
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A series of novel substituted aminobenzophenone derivatives containing nitrogen mustard moiety (5a-f) were synthesized and characterized on the basis of their IR, 1H NMR, 13C NMR, CHN, and mass spectral data. All the compounds when evaluated for chemical 4-(4-nitrobenzyl) pyridine alkylating activity proved to be active alkylating agents. All the synthesized compounds were subjected to physicochemical parameters determination required for central nervous system (CNS) activity through computational, online software, and QikProp 3.2. The log P values and other in silico ADME physicochemical descriptors analyzed lay between the ranges those are required for good BBB penetration. The in vitro antiproliferative activity against human cancer cell lines viz. A 549 (lung), COLO 205 (colon), U 87 (glioblastoma), and IMR-32 (neuroblastoma) was investigated. Most of the test compounds showed potent antitumor activity, especially compound (5f) which displayed the highest activity against CNS cancer cell line comparable to that of chlorambucil and docetaxel. The preliminary structure-activity relationship (SAR) revealed that 5-chloroaminobenzophenone-mustard series (5a-c) exhibited better antitumor activity than 5-nitroaminobenzophenone-mustard series (5d-f).
- Singh, Rajesh K.,Prasad,Bhardwaj
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p. 5901 - 5911
(2013/11/06)
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- Synthesis and characterization of thiophene-derived amido bis-nitrogen mustard and its antimicrobial and anticancer activities
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The thiophene-derived amido bis-nitrogen mustard N2,N 2,N5,N5-tetrakis(2-chloroethyl)-3,4- dimethylthiophene-2,5-dicarboxamide was designed and synthesized via five-step reactions from commercially available 2-chloroacetonitrile. This target compound was confirmed by 1H NMR, 13C NMR, MS, IR spectra and elemental analyses, and its structure was further characterized by X-ray single-crystal analysis. The biological activities for the title compound and some intermediates were evaluated in vitro for their antibacterial, antifungal and cytotoxic activities. The preliminary results showed that the title compound could inhibit efficiently the growth of the tested microorganisms including drug-resistant bacteria MRSA to some extent. Moreover, the target compound was found to be effective against prostatic carcinoma cell line (PC-3), breast carcinoma cell line (MCF-7), colon carcinoma (LoVo) and lung cancer (A549). Especially, it gave selective antitumor efficacy against prostatic carcinoma cell line (PC-3) at a low dose.
- Tang, Yidan,Zhang, Jingqing,Zhang, Shaolin,Geng, Rongxia,Zhou, Chenghe
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p. 1831 - 1840
(2012/10/30)
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- Synthesis and biological evaluation of novel N-[3-(4-phenylpip-erazin-1-yl) -propyl]-carboxamide derivatives
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A series of novel N-[3-(4-phenylpiperazin-1-yl)-propyl]-carboxamide derivatives were synthesised and studied for the potential treatment of HIV. These compounds were obtained through the efficient synthetic route that involved microwave assisted synthesis. These new compounds have been characterised by IR,1H NMR, MS and elemental analysis. The cell-cell fusion inhibitory activities of the compounds have also been evaluated.
- Weng, Zhiyong,Gao, Yanping,Zhang, Jiankang,Dong, Xiaowu,Liu, Tao
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experimental part
p. 43 - 46
(2011/05/04)
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- A highly selective fluorescent sensor for mercury ion (II) based on azathia-crown ether possessing a dansyl moiety
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An intramolecular charge transfer (ICT) fluorescent sensor 1 using a dansyl moiety as the fluorophore and an azathia-crown ether as the receptor was designed, synthesized and characterized. The ions-selective signaling behaviors of the sensor 1 were investigated in CH3CN-H2O (1:1, v/v) by fluorescence spectroscopy. It exhibited remarkable fluorescence quenching upon addition of Hg2+, which was attributed to the 1:1 complex formation between 1 and Hg2+, while other selected metal ions induced basically no spectral changes. The sensor 1 showed a rapid and linear response towards Hg2+ in the concentration range from 5.0 × 10 -7 to 1.0 × 10-5 mol L-1 with the detection limit of 1.0 × 10-7 mol L-1. Furthermore, the whole process could be carried out in a wide pH range of 2.0-8.0 and was not disturbed by other metal ions. Thus, the sensor 1 was used for practical determination of Hg2+ in different water samples with satisfactory results. Copyright
- Dai, Huajun,Liu, Fei,Gao, Qianqian,Fu, Tianhua,Kou, Xingming
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experimental part
p. 523 - 530
(2012/06/01)
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- A simple and efficient asymmetric synthesis of anxiolytic drug enciprazine
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A straightforward and efficient asymmetric synthesis of (S)-1-[4-(2-methoxyphenyl)piperazin-1-yl]-3-(3,4,5-trimethoxyphenoxy) propan-2-ol is described. The key intermediate, (S)-2-[(3,4,5-trimethoxyphenoxy) methyl]oxirane, was obtained by a hydrolytic kinetic resolution method using the catalyst (R,R)-salen-cobalt(III) complex. Georg Thieme Verlag Stuttgart.
- Narsaiah, A. Venkat,Nagaiah
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experimental part
p. 2705 - 2707
(2010/10/18)
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- Synthesis of some nitrogen mustrads (Quinazoline series)
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Several nitrogen mustards with quinazoline moiety have been synthesised by condensation of 4-chloroquinazoline and 4,6- dichloroquinazoline with ethanol amine, diethanolamine and N-bis (2-chloroethyl) amine hydrochloride respectively.
- Sinha, Girish Kumar,Pandey, Bibhishan,Sinha, Alka
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experimental part
p. 1401 - 1406
(2011/10/13)
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- Linear cationic click polymer for gene delivery: Synthesis, biocompatibility, and in Vitro Transfection
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Sixteen novel cationic click polymers (CPs) were parallelly synthesized via the conjugation of four alkyne- functionalized monomers to four azide-functionalized monomers by "click chemistry". The biocompatibility of CPs was evaluated by in vitro cytotoxicity (MTT assay, Hoechst/PI apoptosis/necrosis assay, and cell cycle analysis) and blood compatibility tests (hemolysis and erythrocyte aggregation). The experimental results showed that the kind of amine groups, charge density, and number of methylene or ethylene glycol groups brought about the effect on toxicity of CPs. Among all polymers, two polymers (B1 and B2) showed good biocompatibility, inducing neither apoptosis nor necrosis at the test concentration and low hemolysis ratio and erythrocyte aggregation. In particular, B1 and B2 exhibited the comparable transfection efficiency compared with PEI (25 kDa) but much lower cytotoxicity. These results suggested that the novel cationic CPs could be promising carriers for gene delivery.
- Gao, Yu,Chen, Lingli,Zhang, Zhiwen,Gu, Wangwen,Li, Yaping
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experimental part
p. 3102 - 3111
(2011/10/08)
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- Photo-control of peptide conformation on a timescale of seconds with a conformationally constrained, blue-absorbing, photo-switchable linker
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Azobenzene derivatives can be used to reversibly photo-regulate conformation and activity when introduced as intramolecular bridges in peptides and proteins. Here we report the design, synthesis, and characterization of an azobenzene derivative that absorbs between 400-450 nm in aqueous solution to produce the cis isomer, and relaxes back to the trans isomer with a half-life of a few seconds at room temperature. In the trans form, the linker can span a distance of approximately 25 A, so that it can bridge Cys residues spaced i, i + 15 in an α-helix. Switching of the azobenzene cross-linker from trans to cis causes a decrease in the helix content of peptides where the linker is attached via Cys residues spaced at i, i + 15 and i, i + 14 positions, no change in helix content with Cys residues spaced i, i + 11 and an increase in helix content in a peptide with Cys residues spaced at i, i + 7. In the presence of 10 mM reduced glutathione, the azobenzene cross-linker continued to photo-switch after 24 hours. This cross-linker design thus expands the possibilities for fast photo-control of peptide and protein structure in biochemical systems.
- Beharry, Andrew A.,Sadovski, Oleg,Woolley, G. Andrew
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supporting information; experimental part
p. 4323 - 4332
(2009/02/07)
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- Hydrolytic kinetic resolution of α-naphthyl glycidyl ether: A practical access to highly enantioselective β-adrenergic blocking agents
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Kinetic resolution of (±)-naphthyl glycidyl ether using 0.5 mol% (R,R)-salen Co(III)OAc and water (0.55 equiv) provided enantiomerically pure naphthyl glycidyl ether and 1-naphthylglycerol derivatives with high enantiomeric excess. Application of this approach to highly enantioenriched (S)-naftopidil and (S)-propranolol is described. Georg Thieme Verlag Stuttgart.
- Subhas Bose,Narsimha Reddy,Chavhan, Sanjay W.
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p. 2345 - 2348
(2007/10/03)
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- The first enantiomerically pure synthesis of (S)- And (R)-naftopidil utilizing hydrolytic kinetic resolution of (±)-(α-Naphthyl) glycidyl ether
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Hydrolytic Kinetic Resolution (HKR) of (±)-(α-Naphthyl) glycidyl ether with (R,R)-salen Co(III) OAc complex provided enatiomerically pure (S)-naphthyl glycidyl ether and (R)-1-naphthyl glycerol; opening of the corresponding pure terminal epoxide with 1-(2-methoxyphenyl)piperizine gave the enantiomerically pure (S)- and (R)-Naftopidil.
- Kothakonda, Kiran Kumar,Bose, D. Subhas
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p. 1212 - 1213
(2007/10/03)
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- New heteroditopic, linked macrocyclic systems derived from selectively protected N2S2-, N3O2- and N4-donor macrocycles
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The use of selectively tert-butoxycarbonyl protected derivatives of 1,9-dithia-5,13-diazacyclohexadecane 1, 1,7-dithia-4,11-diazacyclotetradecane 2, 1,4,8,11-tetraazacyclotetradecane 3 and 2,5-dioxa-8,11,14-triaza-1,6(1,2)dibenzenacyclopentadecaphane 4 has enabled the efficient synthesis of new linked heteroditopic macrocyclic systems incorporating combinations of N2S2- and N4- or N3O2-donor sites. Incorporation of two types of binding sites in the respective products makes them suitable candidates for the synthesis of a range of mixed-metal, di- and oligo-nuclear metal complexes.
- Chartres, Jy D.,Groth, Andrew M.,Lindoy, Leonard F.,Lowe, Mark P.,Meehan, George V.
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p. 3444 - 3450
(2007/10/03)
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- Synthesis of heterocycles. Construction of the 1-azabicyclo[2.2.1]heptyl system by sequential ring-closure of acylic β-ammonio substituted radicals
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Treatment of an irradiated solution of 1-methyl-1-(2-propynyl)-1-bis(2-phenylselenylethyl)ammonium iodide in tert-amyl alcohol with tributyltin hydride is found to be an effective procedure for the synthesis of 1,4-dimethyl-1-azoniabicyclo[2.2.1]heptane iodide. Attachment of a trimethylsilyl or phenyl substituent to the terminal carbon of the triple bond in the alkynyl salt leads to bridgehead-substituted bicylic heterocyclic salts.
- Della, Ernest W.,Knill, Andrew M.
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p. 5805 - 5808
(2007/10/03)
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- Degradation products of cyclophosphamide synthesis and structural studies
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The degradation of cyclophosphamide in neutral or slightly acidic aqueous solution starts with an intramolecular alkylation leading to an intermediary bicyclic compound which hydrolyses immediately and exclusively to a nine-membered heterocycle. Subsequent acid-catalyzed hydrolysis of the P-N-bond leads to a phosphoric acid monoester. In strongly acidic solutions (1 N HCl) cyclophosphamide decomposes exclusively to bis(2-chloroethyl)-amine and to the corresponding phosphoric acid monoester H2N(CH2)3OP(O)(OH)2. In solid samples of cyclophosphamide, heated up to its melting point, the first pathway predominates over the second one. The structures of the phosphorus compounds were established by 1H and 31p NMR spectroscopy, and synthesis. The structure of the bicyclic compound 2 is confirmed by a single crystal X-ray diffraction study which allows an explanation for the selective and immediate hydrolysis with formation of a nine-membered heterocycle and for the absence of the isomer with a six-membered ring.
- Niemeyer, Ulf,Kutscher, Bernhard,Engel, Juergen,Neda, Ion,Fischer, Axel,Schmutzler, Reinhard,Jones, Peter G.,Malet-Martino, Marie-C.,Gilard, Veronique,Martino, Robert
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p. 473 - 476
(2007/10/03)
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