- Synthesis of styryl substituted semicarbazides under microwave irradiation
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A series of styryl substituted semicarbazides were synthesised by reaction of trans-styryl isocyanate, prepared by Curtius rearrangement of cinnamoyl azide, with acid hydrazides under microwave irradiation using a one-pot procedure. The effects of microwa
- Chai, Lan-Qin,Zhang, Hong-Song,Liu, Gang,Huang, Jiao-Jiao,Cheng, Qiao-Qiao
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- Synthesis and evaluation of α-glucosidase inhibitory activity of sulfonylurea derivatives
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Two series of sulfonylureas derivatives including 24 compounds (4, 7, 5a-5o, 8a-8h), among them 17 new derivatives, have been synthesized and evaluated for their α-glucosidase inhibitory activity. Compounds 5c, 5h and 8e showed significant in vitro α-glucosidase inhibition with IC50 values of 5.58, 79.85 and 213.36 μm, respectively, comparing with the standard compounds acarbose (IC50 = 268.29 μm) and glipizide (IC50 = 300.47 μm). The preliminary structure-activity relationships (SARs) of the synthesized compounds were also investigated.
- Bui, Thi Thoi,Tran, Van Loc,Ngo, Dai Quang,Tran, Van Chien,Tran, Van Sung,Tran, Thi Phuong Thao
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p. 163 - 171
(2021/03/16)
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- Benzoic hydroxamate-based iron complexes as model compounds for humic substances: Synthesis, characterization and algal growth experiments
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A series of monomeric and dimeric FeIII complexes bearing benzoic hydroxamates as O,O-chelates has been prepared and characterized by elemental analysis, IR spectroscopy, UV-Vis spectroscopy, electrospray ionization mass spectrometry (ESI-MS), cyclic voltammetry, EPR spectroscopy and for some examples by X-ray diffraction analysis. The stability of the synthesized complexes in pure water and seawater was monitored over 24 h by means of UV-Vis spectrometry. The ability to release iron from the synthesized model complexes has been investigated with algae growth experiments.
- Orlowska, Ewelina,Roller, Alexander,Wiesinger, Hubert,Pignitter, Marc,Jirsa, Franz,Krachler, Regina,Kandioller, Wolfgang,Keppler, Bernhard K.
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p. 40238 - 40249
(2016/05/24)
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- New Umami Amides: Structure-Taste Relationship Studies of Cinnamic Acid Derived Amides and the Natural Occurrence of an Intense Umami Amide in Zanthoxylum piperitum
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A series of aromatic amides were synthesized from various acids and amines selected from naturally occurring structural frameworks. These synthetic amides were evaluated for umami taste in comparison with monosodium glutamate. The effect of the substituti
- Frerot, Eric,Neirynck, Nathalie,Cayeux, Isabelle,Yuan, Yoyo Hui-Juan,Yuan, Yong-Ming
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p. 7161 - 7168
(2015/09/01)
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- The Synthesis and Characterization of Aromatic Hybrid Anderson-Evans POMs and their Serum Albumin Interactions: The Shift from Polar to Hydrophobic Interactions
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Four aromatic hybrid Anderson polyoxomolybdates with Fe3+ or Mn3+ as the central heteroatom have been synthesized by using a pre-functionalization protocol and characterized by using single-crystal X-ray diffraction, FTIR, ESI-MS, s
- Al-Sayed, Emir,Blazevic, Amir,Roller, Alexander,Rompel, Annette
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supporting information
p. 17800 - 17807
(2015/12/08)
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- Cobalt-catalyzed, aminoquinoline-directed C(sp2)-H bond alkenylation by alkynes
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A method for cobalt-catalyzed, aminoquinoline- and picolinamide-directed C(sp2)-H bond alkenylation by alkynes was developed. The method shows excellent functional-group tolerance and both internal and terminal alkynes are competent substrates for the coupling. The reaction employs a Co(OAc)2·4 H2O catalyst, Mn(OAc)2 co-catalyst, and oxygen (from air) as a terminal oxidant.
- Grigorjeva, Liene,Daugulis, Olafs
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supporting information
p. 10209 - 10212
(2015/03/31)
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- Screening and Engineering the Synthetic Potential of Carboxylating Reductases from Central Metabolism and Polyketide Biosynthesis
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Carboxylating enoyl-thioester reductases (ECRs) are a recently discovered class of enzymes. They catalyze the highly efficient addition of CO2 to the double bond of α,β-unsaturated CoA-thioesters and serve two biological functions. In primary metabolism of many bacteria they produce ethylmalonyl-CoA during assimilation of the central metabolite acetyl-CoA. In secondary metabolism they provide distinct α-carboxyl-acyl-thioesters to vary the backbone of numerous polyketide natural products. Different ECRs were systematically assessed with a diverse library of potential substrates. We identified three active site residues that distinguish ECRs restricted to C4 and C5-enoyl-CoAs from highly promiscuous ECRs and successfully engineered a selected ECR as proof-of-principle. This study defines the molecular basis of ECR reactivity, allowing for predicting and manipulating a key reaction in natural product diversification.
- Peter, Dominik M.,Schada Von Borzyskowski, Lennart,Kiefer, Patrick,Christen, Philipp,Vorholt, Julia A.,Erb, Tobias J.
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supporting information
p. 13457 - 13461
(2015/11/09)
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- Structure-Activity Relationships of Glycogen Phosphorylase Inhibitor FR258900 and Its Analogues: A Combined Synthetic, Enzyme Kinetics, and Computational Study
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A series of O- or N-cinnamoylated, p-coumaroylated, feruloylated, phenyl, and substituted phenylpropiolated derivatives of L-malic, 3-hydroxypentanedioic, and L-glutamic acids were synthesized as analogues of the natural product glycogen phosphorylase (GP) inhibitor FR258900 (2,3-bis(4-hydroxycinnamoyloxy)glutaric acid). These compounds proved practically inactive against rabbit muscle glycogen phosphorylase b. A structure-activity study involving previously synthesized tartaric acid analogues of FR258900 revealed that two acyl moieties must be present in the compounds to make a good inhibitor. Molecular modeling methods (docking and quantitative structure-activity relationship (QSAR) calculations) were used to understand the nature of the binding affinities of these GP inhibitors. The generated 3D models for GP-inhibitor complexes showed that both the polar allosteric site pocket and the hydrophobic pocket at the interface of the homodimeric units of GP were important for effective binding of the acyl and aromatic moieties of the inhibitors. The predictive QSAR models consist of empirical and quantum mechanics descriptors and provide good explanatory and predictive abilities (prediction coefficient Q2=0.7-0.9 when cross-validation procedures were performed).
- Juhsz, Lszl,Varga, Gergely,Sztankovics, Andrea,Bke, Ferenc,Docsa, Tibor,Kiss-Szikszai, Attila,Gergely, Pl,Ka, Juraj,Tvaroka, Igor,Somsk, Lszl
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p. 1558 - 1568
(2015/08/24)
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- Synthesis and biological activity of novel deoxynojirimycin derivatives as potent α-glucosidase inhibitors
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Thirteen 1-deoxynojirimycin (DNJ) derivatives of five different skeletal structures were designed and synthesized. The newly synthesized compounds were evaluated using an in vitro α-glucosidase assay, and kinetic parameters (Ki, IC50) were measured. Some DNJ derivatives showed weak α-glucosidase inhibitory activities, and the compounds 1-(3-benzyloxy-2-hydroxypropyl)- 2-hydroxymethyl-piperidine-3,4,5-triol (2a) and 1-{3-[1-(4-fluorophenyl)-1H-[1,2,3]triazol-4-ylmethoxy]- 2-hydroxypropyl}-2- hydroxymethyl-piperidine-3,4,5-triol (13d) showed activities comparable to that of DNJ. While 2a was found to be a reversible, non-competitive inhibitor of a-glucosidase with a Ki value of 1.56×10-4 M and an IC 50 value of 3.07×10-4 M, 13d was a reversible, competitive inhibitor of α-glucosidase with a Ki value of 2.08×10-4 M and an IC50 value of 3.31×10 -4 M.
- Yu, Dan,Hu, Fangfang,Zhang, Yu.,Zheng, Xiaorui,Kuang, Chunxiang,Yang, Qing
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p. 383 - 390
(2013/06/05)
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- Convenient preparation of primary amides via activation of carboxylic acids with ethyl chloroformate and triethylamine under mild conditions
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Primary amides were easily prepared in 22-99% yields from the corresponding carboxylic acids 1 or 5 with NH4Cl via activation with ClCO 2Et and Et3N. The enantiomers of the corresponding primary amides of Cbz-, Boc-, or Fmoc-α-amino acids can be separated by using a chiral column.
- Noguchi, Takuya,Sekine, Masahiro,Yokoo, Yuki,Jung, Seunghee,Imai, Nobuyuki
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p. 580 - 582
(2013/07/05)
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- Microwave-assisted synthesis of 2-styryl-1,3,4-oxadiazoles from cinnamic acid hydrazide and triethyl orthoesters
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A novel and efficient synthesis of 2-styryl-1,3,4-oxadiazoles by cyclocondensation of cinnamic acid hydrazide and triethyl orthoesters under microwave irradiation is reported.
- Kudelko, Agnieszka,Zieliński, Wojciech
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supporting information; experimental part
p. 76 - 77
(2012/01/05)
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- Synthesis, characterization and potential application of monoacyl-cyclodextrins
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Although the preparation of cyclodextrin (CD) monoesters with a variety of carboxylic acids has been already described in the literature, the direct regioselective CD acylation has proved to be critical, often requiring to be replaced with a more elaborat
- Martina, Katia,Puntambekar, Devendra Sharad,Barge, Alessandro,Gallarate, Marina,Chirio, Daniela,Cravotto, Giancarlo
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body text
p. 191 - 198
(2010/03/23)
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- Selective reduction of mixed anhydrides of carboxylic acids to alcohols using borohydride exchange resin (BER)-nickel acetate
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Mixed anhydrides of carboxylic acids have been selectively reduced to alcohols with borohydride exchange resin-nickel acetate under mild conditions and in good yields.
- Bandgar,Modhave,Wadgaonkar,Sande
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p. 1993 - 1994
(2007/10/03)
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- 3,6-Bis(2-arylethenyl)-1,2,4,5-tetrazines - Synthesis, LC Properties and Photochemistry
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The (E,E)-3,6-bis(2-arylethenyl)-1,2,4,5-tetrazines 8 were prepared in a synthetic sequencve starting with aromatic aldehydes 1 and cinnamic acids 2, respectively (Scheme 1).The rod-like conjugated molecules represent clamitic mesogens as well as extended chromophores.Hence, we investigated the formation of liquid crystals, achieved by the introduction of long flexlible side chains, and the photochemical behaviour that is characterized by the fragmentation of the central ring (Scheme 3).
- Lifka, Thorsten,Meier, H.
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p. 641 - 646
(2007/10/03)
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- Reduction of Symmetric and Mixed Anhydrides of Carboxylic Acids by Sodium Borohydride with Dropwise Addition of Methanol
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Symmetric and mixed anhydrides of carboxylic acids are reduced in high yields with sodium borohydride in tetrahydrofuran with dropwise addition of methanol.
- Soai, Kenso,Yokoyama, Shuji,Mochida, Katsuko
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p. 647 - 648
(2007/10/02)
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