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1.
Discovery,Structure Elucidation,and Biological Characterization of Nannocystin A,a Macrocyclic Myxobacterial Metabolite with Potent Antiproliferative Properties
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Dr. Holger Hoffmann Priv.‐Doz. Dr. Herbert Kogler Dipl.‐Ing. Winfried Heyse Dr. Hans Matter Dr. Michael Caspers Prof. Dr. Dietmar Schummer Dr. Christine Klemke‐Jahn Dr. Armin Bauer Dr. Geraldine Penarier Dr. Laurent Debussche Prof. Dr. Mark Brönstrup 《Angewandte Chemie (International ed. in English)》2015,54(35):10145-10148
2.
Near‐Infrared Fluorescent Probe with New Recognition Moiety for Specific Detection of Tyrosinase Activity: Design,Synthesis, and Application in Living Cells and Zebrafish
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Xiaofeng Wu Dr. Lihong Li Prof. Dr. Wen Shi Dr. Qiuyu Gong Prof. Dr. Huimin Ma 《Angewandte Chemie (International ed. in English)》2016,55(47):14728-14732
Fluorescence imaging of tyrosinase (a cancer biomarker) in living organisms is of great importance for biological studies. However, selective detection of tyrosinase remains a great challenge because current fluorescent probes that contain the 4‐hydroxyphenyl moiety show similar fluorescence responses to both tyrosinase and some reactive oxygen species (ROS), thereby suffering from ROS interference. Herein, a new tyrosinase‐recognition 3‐hydroxybenzyloxy moiety, which exhibits distinct fluorescence responses for tyrosinase and ROS, is proposed. Using the recognition moiety, we develop a near‐infrared fluorescence probe for tyrosinase activity, which effectively eliminates the interference from ROS. The high specificity of the probe was demonstrated by imaging and detecting endogenous tyrosinase activity in live cells and zebrafish and further validated by an enzyme‐linked immunosorbent assay. The probe is expected to be useful for the accurate detection of tyrosinase in complex biosystems. 相似文献
3.
Xiaofeng Wu Lihong Li Wen Shi Qiuyu Gong Huimin Ma 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2016,128(47):14948-14952
Fluorescence imaging of tyrosinase (a cancer biomarker) in living organisms is of great importance for biological studies. However, selective detection of tyrosinase remains a great challenge because current fluorescent probes that contain the 4‐hydroxyphenyl moiety show similar fluorescence responses to both tyrosinase and some reactive oxygen species (ROS), thereby suffering from ROS interference. Herein, a new tyrosinase‐recognition 3‐hydroxybenzyloxy moiety, which exhibits distinct fluorescence responses for tyrosinase and ROS, is proposed. Using the recognition moiety, we develop a near‐infrared fluorescence probe for tyrosinase activity, which effectively eliminates the interference from ROS. The high specificity of the probe was demonstrated by imaging and detecting endogenous tyrosinase activity in live cells and zebrafish and further validated by an enzyme‐linked immunosorbent assay. The probe is expected to be useful for the accurate detection of tyrosinase in complex biosystems. 相似文献
4.
Haiyin He HuiY. Yang ScottW. Luckman ValerieS. Bernan Gordon Tsai DeborahM. Roll GuyT. Carter 《Helvetica chimica acta》2004,87(6):1385-1391
Echinosporamicin ( 1 ), a novel antibiotic containing an aromatic polycyclic system and a piperazinone moiety, was isolated from the fermentation broth of a new strain of Micromonospora echinospora subspecies echinospora, LL‐P175. The structure of this compound was determined by spectroscopic analysis by using variable‐temperature NMR techniques. Compound 1 exhibited potent activity against methicillin‐resistant Staphylococci and vancomycin‐resistant Enterococci strains. The methyl, ethyl, and benzyl esters showed improved antibacterial activity against Streptococci. 相似文献
5.
《Journal of heterocyclic chemistry》2017,54(4):2417-2425
The reaction of 4‐thiochromane thiocarbohydrazone with a series of hydrazonoyl halides in dioxane in the presence of triethylamine afforded novel thiochromane derivatives incorporating 1,3‐thiazole moiety. The structure of the latter compounds was established by elemental analysis and spectral technique and by their chemical transformation. Moreover, the antimicrobial activity of the newly synthesized compounds was screened and the results showed that some compounds have higher activity than the applied fungicide and bactericide. The antimicrobial activity of the most active compounds was interpreted by molecular docking study. 相似文献
6.
Synthesis and Antimicrobial Activity of Some Novel Hydrazide,Pyrazole, Triazine,Isoxazole, and Pyrimidine Derivatives
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In continuation of our efforts to find a new class of antimicrobial agents, a series of pyrazole, 1,2,4‐triazine, isoxazole, pyrimidine, and other related products containing a hydrazide moiety were prepared via the reaction of 2‐cyano‐N‐((2‐methoxynaphthalen‐1‐yl)methylene) acetohydrazide ( 1 ) with appropriate chemical reagents. These compounds were evaluated for their antimicrobial activities, and also their minimum inhibitory concentration against most of test organisms was performed. Among the tested compounds 4 , 5 , 6 , and 16 displayed excellent antimicrobial activity. All the synthesized products were confirmed by elemental analysis, IR, 1H‐NMR, 13C‐NMR, and mass spectral data. 相似文献
7.
Pedro Morales‐Bonilla Andrea Prez‐Cardea Esther Quintero‐Mrmol Jos Luis Arias‐Tllez Gonzalo J. Mena‐Rejn 《Heteroatom Chemistry》2006,17(4):254-260
Seven 2‐amino‐4‐aryl‐1,3‐thiazoles ( 1a–g ) and their corresponding 2‐aminoacetyl ( 2a–g ) and 2‐aminoacetyl‐5‐bromo ( 3a–g ) derivatives were synthesized and tested in vitro against 11 reference strains, three Gram‐positive and four Gram‐negative bacteria, two yeasts, and two moulds. Toxicity of the compounds was also evaluated using the brine shrimp test. Compounds 1a, 1b, 1e–g , and 3b showed moderate antimicrobial activity at different concentrations. The results indicated that acetylation of the amino group and bromination at position 5 of the thiazole moiety cause lost of activity. Compounds 1a, 1e , and 1f showed toxicity to brine shrimp nauplii below 10 ppm. Most other compounds showed moderate toxicity, LD50 above 100 ppm. Structures of all compounds were confirmed by NMR and MS data. © 2006 Wiley Periodicals, Inc. Heteroatom Chem 17:254–260, 2006; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20182 相似文献
8.
Ruthenium Complexes with Dendritic Ferrocenyl Phosphanes: Synthesis,Characterization, and Application in the Catalytic Redox Isomerization of Allylic Alcohols
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Paul Neumann Dr. Hanna Dib Dr. Alix Sournia‐Saquet Toni Grell Dr. Marcel Handke Prof. Dr. Anne‐Marie Caminade Prof. Dr. Evamarie Hey‐Hawkins 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(17):6590-6604
An efficient system for the catalytic redox isomerization of the allylic alcohol 1‐octen‐3‐ol to 3‐octanone is presented. The homogeneous ruthenium(II) catalyst contains a monodentate phosphane ligand with a ferrocene moiety in the backbone and provides 3‐octanone in quantitative yields. The activity is increased by nearly 90 % with respect to the corresponding triphenyl phosphane ruthenium(II) complex. By grafting the catalyst at the surface of a dendrimer, the catalytic activity is further increased. By introducing different spacers between ferrocene and phosphorus, the influence on the electronic properties of the complexes is shown by evaluating the electrochemical behavior of the compounds. 相似文献
9.
《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2017,129(41):12666-12671
The uridyl peptide antibiotics (UPAs), of which pacidamycin is a member, have a clinically unexploited mode of action and an unusual assembly. Perhaps the most striking feature of these molecules is the biosynthetically unique 3′‐deoxyuridine that they share. This moiety is generated by an unusual, small and monomeric dehydratase, Pac13, which catalyses the dehydration of uridine‐5′‐aldehyde. Here we report the structural characterisation of Pac13 with a series of ligands, and gain insight into the enzyme's mechanism demonstrating that H42 is critical to the enzyme's activity and that the reaction is likely to proceed via an E1cB mechanism. The resemblance of the 3′‐deoxy pacidamycin moiety with the synthetic anti‐retrovirals, presents a potential opportunity for the utilisation of Pac13 in the biocatalytic generation of antiviral compounds. 相似文献
10.
A ruthenium(II) functionalized pyrrole, Ruthenium‐bis‐N,N′‐(2,2′‐bipyridyl)‐N‐(pyridine‐4‐ylmethyl‐(8‐pyrrole‐1‐yl‐octyl)amine)chloride, 1 , has been synthesized and characterized by spectroscopic (UV/vis, 1H NMR) techniques and cyclic voltammetry. In solution 1 gave a redox couple associated with the Ru3+/2+ redox system and an irreversible wave associated with the oxidation of the covalently linked pyrrole moiety. What is believed to be homopolymerization, redox active surface films of 1 have been prepared by electrooxidation of the monomeric solution. The resulting polymeric film exhibited clear redox activity associated with the incorporated Ru2+ redox centre, which is covalently linked ruthenium centre to the pyrrole moiety in 1. The effect of surface coverage upon the electrochemical behavior of the deposited films has been undertaken. Preliminary investigations into the homogeneous charge transport dynamics of the polymeric film deposited onto platinum microelectrodes has been undertaken. Copolymerization with 3‐methylthiophene was carried out and a clear ruthenium response was seen. Films were formed by both cyclic voltammetry and chronocoulometry and studied. Various ratios were attempted but the ideal was found to be 52 : 5 mmol (3‐methylthiophene: 1 ). 相似文献
11.
Silvija Mara
i Jasmina Lapi Senka Djakovi Teuta Opa
ak‐Bernardi Ljubica Glava‐Obrovac Valerije Vr
ek Silvana Rai‐Mali 《应用有机金属化学》2019,33(1)
Novel O‐alkylated quinoline and N‐alkylated 4‐quinolone derivatives attached to the ferrocene moiety through 4,1‐ ( 7a–d , 8a–d and 12a–d ) and 1,4‐disubstituted ( 9a , 9b , 10a and 10b ) 1,2,3‐triazole moiety were synthesized. The observed regioselectivity of O‐ vs. N‐alkylation was explored by the use of NMR and computational techniques. Among the N‐alkylated derivatives, the quinolone‐ferrocene conjugate 9a displayed marked activities against chronic myeloid leukemia in blast crisis (K562) and Burkitt lymphoma (Raji). The 6‐chloroquinolone‐ferrocene conjugate 12c , with selective inhibitory activity on Raji cells and no cytostatic effect on normal MDCK1 cells was highlighted as the most promising anticancer organometallic complex in a group of O‐alkylated quinolines. 相似文献
12.
《Angewandte Chemie (International ed. in English)》2017,56(41):12492-12497
The uridyl peptide antibiotics (UPAs), of which pacidamycin is a member, have a clinically unexploited mode of action and an unusual assembly. Perhaps the most striking feature of these molecules is the biosynthetically unique 3′‐deoxyuridine that they share. This moiety is generated by an unusual, small and monomeric dehydratase, Pac13, which catalyses the dehydration of uridine‐5′‐aldehyde. Here we report the structural characterisation of Pac13 with a series of ligands, and gain insight into the enzyme's mechanism demonstrating that H42 is critical to the enzyme's activity and that the reaction is likely to proceed via an E1cB mechanism. The resemblance of the 3′‐deoxy pacidamycin moiety with the synthetic anti‐retrovirals, presents a potential opportunity for the utilisation of Pac13 in the biocatalytic generation of antiviral compounds. 相似文献
13.
Total Synthesis and Functional Evaluation of Fourteen Derivatives of Lysocin E: Importance of Cationic,Hydrophobic, and Aromatic Moieties for Antibacterial Activity
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Takuya Kaji Dr. Motoki Murai Dr. Hiroaki Itoh Dr. Jyunichiro Yasukawa Dr. Hiroshi Hamamoto Prof. Dr. Kazuhisa Sekimizu Prof. Dr. Masayuki Inoue 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(47):16912-16919
Lysocin E ( 1 ) is a structurally complex 37‐membered depsipeptide comprising 12 amino‐acid residues with an N‐methylated amide and an ester linkage. Compound 1 binds to menaquinone (MK) in the bacterial membrane to exert its potent bactericidal activity. To decipher the biologically important functionalities within this unique antibiotic, we performed a comprehensive structure‐activity relationship (SAR) study by systematically changing the side‐chain structures of l ‐Thr‐1, d ‐Arg‐2, N‐Me‐d ‐Phe‐5, d ‐Arg‐7, l ‐Glu‐8, and d ‐Trp‐10. First, we achieved total synthesis of the 14 new side‐chain analogues of 1 by employing a solid‐phase strategy. We then evaluated the MK‐dependent liposomal disruption and antimicrobial activity against Staphylococcus aureus by 1 and its analogues. Correlating data between the liposome and bacteria experiments revealed that membrane lysis was mainly responsible for the antibacterial functions. Altering the cationic guanidine moiety of d ‐Arg‐2/7 to a neutral amide, and the C7‐acyl group of l ‐Thr‐1 to the C2 or C11 counterpart decreased the antimicrobial activities four‐ or eight‐fold. More drastically, chemical mutation of d ‐Trp‐10 to d ‐Ala‐10 totally abolished the bioactivities. These important findings led us to propose the biological roles of the side‐chain functionalities. 相似文献
14.
Synthesis,Characterization, Molecular Structure,and Electrochemistry of a New Ferrocenoyl Derivative
Ana I. Matesanz Isabel Cuadrado Jadra Mosa Irene García Pilar Souza 《无机化学与普通化学杂志》2005,631(11):1979-1981
A new organometallic compound containing a heterocyclic amine linked to the ferrocenoyl moiety was synthesized and characterized by elemental analysis (C, H, N), mass spectrometry, IR and 1HNMR spectroscopy. Its crystal and molecular structure was determined by X‐ray diffraction methods. This compound crystallizes in the monoclinic P21 space group, a = 5.80260(10), b = 9.24160(10), c = 12.3510(2) Å, β = 92.8200(10)° and Z = 2. An interesting feature of the crystal structure is the presence of an intermolecular non‐classical hydrogen bonding interaction between a cyclopentadienyl hydrogen atom and a carbonyl oxygen group. The electrochemical behaviour of this compound is characterized by the reversible one‐electron oxidation of the ferrocene moiety. 相似文献
15.
Quinoline‐based benzimidazole compounds have been successfully synthesized and characterized by various spectroscopic techniques like FT‐IR, 1H NMR, 13C NMR, and mass spectral analysis, and the structures have been authenticated by single crystal X‐ray diffraction method. Here, we report an economical, mild, and efficient procedure that involves condensation of 8‐hydroxyquinoline‐2‐carbaldehyde with various diamines as substrates to give bis‐imines. A systematic study towards both aliphatic and aromatic bis‐imines has been conducted to investigate the ring‐closure reaction that generates the benzimidazole moiety in the heterocyclic compounds discussed in this study. Aliphatic bis‐imines does not undergo cyclization; however, the bis‐imines derived from o‐phenylenediamine and derivatives generates heterocyclic compounds with benzimidazole moiety. In contrast to synthetic procedures reported earlier for benzimidazoles, the reaction conditions herein reported are simpler. Path for reactions holds initial condensation with one equivalent of 8‐hydroxyquinoline‐2‐carbaldehyde to form mono‐imine followed by immediate intramolecular ring closure. The subsequent nupleophilic attack to another equivalent of 8‐hydroxyquinoline‐2‐carbaldehyde and migration of hydride generates the benzimidazole moiety and the active methylene group. The ─CH2 group was confirmed from 1H and 13C NMR, wherein the two hydrogens appeared at around 6.40–6.52 ppm and the carbon center appeared at 51.54–51.77 ppm. The single crystal X‐ray diffraction also confirmed the formation of benzimidazole moiety and the active methylene group in the heterocyclic compounds discussed in this study. 相似文献
16.
Shuji Ioka Dr. Tsuyoshi Saitoh Dr. Satoshi Iwano Prof. Dr. Koji Suzuki Dr. Shojiro A. Maki Prof. Dr. Atsushi Miyawaki Prof. Dr. Masaya Imoto Prof. Dr. Shigeru Nishiyama 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(27):9330-9337
Five new firefly luciferin ( 1 ) analogues were synthesized and their light emission properties were examined. Modifications of the thiazoline moiety in 1 were employed to produce analogues containing acyclic amino acid side chains ( 2 – 4 ) and heterocyclic rings derived from amino acids ( 5 and 6 ) linked to the benzothiazole moiety. Although methyl esters of all of the synthetic derivatives exhibited chemiluminescence activity, only carboluciferin ( 6 ), possessing a pyrroline‐substituted benzothiazole structure, had bioluminescence (BL) activity (λmax=547 nm). Results of bioluminescence studies with AMP‐carboluciferin (AMP=adenosine monophosphate) and AMP‐firefly luciferin showed that the nature of the thiazoline mimicking moiety affected the adenylation step of the luciferin–luciferase reaction required for production of potent BL. In addition, BL of 6 in living mice differed from that of 1 in that its luminescence decay rate was slower. 相似文献
17.
Swetha Yagnam Eda Rami Reddy Rajiv Trivedi Narra Vamshi Krishna Lingamallu Giribabu Balaji Rathod Reddy Shetty Prakasham Balasubramanian Sridhar 《应用有机金属化学》2019,33(4)
A series of bioactive, triazole‐linked benzyl, aryl, sugar and aliphatic conjugates of 3‐ferrocenylidene‐oxindole have been synthesized. A facile 1,3‐dipolar‐Huisgen coupling reaction of the respective azides with the 3‐ferrocenylidene‐oxindole N‐propargyl moiety ( 3 ) gave the corresponding conjugates ( 5a–n ). All the newly synthesized compounds ( 5a–n ) were characterized by 1H‐NMR, 13C‐NMR, HRMS, Fourier transform‐infrared spectroscopy and elemental analysis. The UV–Vis and electrochemical studies of these compounds were performed in dimethylsulfoxide solutions. The structure of compound ( 3 ) was determined by single crystal X‐ray diffraction study. These compounds exhibited moderate to good antimicrobial activity against Gram‐positive and Gram‐negative strains. 相似文献
18.
Zhi‐Dong Xu Min Wang Su‐Long Xiao Yan‐Juan Zhang Ming Yang 《Helvetica chimica acta》2004,87(11):2834-2841
The novel analogues 11 – 16 of bleomycin A6 ( 3 ) were obtained by selective protection of the primary‐amine function of the β‐aminoalaninamide moiety of 3 by means of coordination with CuII ions, condensation with an aliphatic or aromatic acid R′COOH in the presence of dicyclohexylcarbodiimide, and demetalization (Scheme). The antitumor activity against HeLa and BGC‐823 in vitro, binding property with CT‐DNA, and cleavage potency towards pBR322 DNA were also studied (Tables 1–3). All the compounds 11 – 16 displayed significant antitumor activity, which was enhanced as the hydrophobicity of the C‐terminus substituent R′ increased, but decreased as the DNA‐binding affinity increased. There was a negative relationship between DNA‐cleavage potency and binding affinity to DNA in this series of compounds. 相似文献
19.
Wang Kang Xingqiong Du Lanzhi Wang Lijuan HU Yuhuan Dong Yanqing Bian Yuan Li 《中国化学》2013,31(10):1305-1314
Our studies examined the structural features responsible for the antifungal activity of 2-ethoxycarbonyl-1,5- benzothiazepine (7a). Three series of 1,5-benzothiazepine derivatives were synthesized and screened for their antifungal activity. The results suggested that the ethoxycarbonyl group at the 2 position and the imine moiety on the seven-membered ring are essential for activity. The most potent of the synthesized analogues (7a, 7b) were further studied by evaluating their cytotoxicity and mode of action (for 7a). The results showed that compounds 7a and 7b were relatively safe for BV2 cells, but compound 7a interfered with Cryptococcus neoformans cell wall integrity by increasing the chitinase activity. Therefore, compound 7a was considered safe as an antifungal agent for animal cells. 相似文献
20.
Sobhi M. Gomha Hassan M. Abdel-aziz Mohamed G. Badrey Mohamed M. Abdulla 《Journal of heterocyclic chemistry》2019,56(4):1275-1282
The current study in this article concerned with construction of five‐membered heterocycles with multiple heteroatoms as nitrogen and sulfur from readily available starting materials and reagents. Treatment of 1‐(2‐oxo‐2H‐chromene‐3‐carbonyl)‐3‐phenyl‐1H‐pyrazol‐5(4H)‐one with each of phenylisothiocyanate in alcoholic potassium hydroxide and carbon disulfide in basic medium gave rise to a thioanilide and methylthio derivatives, respectively. Treatment of the latter compounds with a variety of hydrazonoyl halides resulted in construction of thiadiazole moiety linked to pyrazole ring. Furthermore, triazole derivatives were synthesized from the thioanilide derivative through its reaction with methyl iodide followed by reaction with hydrazonoyl halides. 5α‐Reductase inhibition activity for the prepared compounds was investigated against the reference drug anastrozole, and the results showed that the inhibition activity of compounds 5g and 11g is more potent than anastrozole. Also compounds bearing triazole moiety is more potent than compounds bearing thiadiazole one. Moreover, the anti‐prostate cancer screening anti‐androgenic bioassay in human prostate cancer cells for the tested compounds was evaluated, and the results showed great inhibition growth and potential antiandrogens. 相似文献