- New class of hantaan virus inhibitors based on conjugation of the isoindole fragment to (+)-camphor or (?)-fenchone hydrazonesv
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This work presents the design and synthesis of camphor, fenchone, and norcamphor N-acylhydrazone derivatives as a new class of inhibitors of the Hantaan virus, which causes haemorrhagic fever with renal syndrome (HFRS). A cytopathic model was developed fo
- Yarovaya, Olga I.,Kovaleva, Kseniya S.,Zaykovskaya, Anna A.,Yashina, Liudmila N.,Scherbakova, Nadezda S.,Scherbakov, Dmitry N.,Borisevich, Sophia S.,Zubkov, Fedor I.,Antonova, Alexandra S.,Peshkov, Roman Yu.,Eltsov, Ilia V.,Pyankov, Oleg V.,Maksyutov, Rinat A.,Salakhutdinov, Nariman F.
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Read Online
- 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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- Photochemical generation of acyl and carbamoyl radicals using a nucleophilic organic catalyst: Applications and mechanism thereof
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We detail a strategy that uses a commercially available nucleophilic organic catalyst to generate acyl and carbamoyl radicals upon activation of the corresponding chlorides and anhydrides via a nucleophilic acyl substitution path. The resulting nucleophilic radicals are then intercepted by a variety of electron-poor olefins in a Giese-type addition process. The chemistry requires low-energy photons (blue LEDs) to activate acyl and carbamoyl radical precursors, which, due to their high reduction potential, are not readily prone to redox-based activation mechanisms. To elucidate the key mechanistic aspects of this catalytic photochemical radical generation strategy, we used a combination of transient absorption spectroscopy investigations, electrochemical studies, quantum yield measurements, and the characterization of key intermediates. We identified a variety of off-the-cycle intermediates that engage in a light-regulated equilibrium with reactive radicals. These regulated equilibriums cooperate to control the overall concentrations of the radicals, contributing to the efficiency of the overall catalytic process and facilitating the turnover of the catalyst. This journal is
- Balletti, Matteo,De Pedro Beato, Eduardo,Mazzarella, Daniele,Melchiorre, Paolo
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p. 6312 - 6324
(2020/08/24)
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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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- METABOTROPIC GLUTAMATE RECEPTOR NEGATIVE ALLOSTERIC MODULATORS (NAMS) AND USES THEREOF
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Provided herein are small molecule active metabotropic glutamate subtype-2 and -3 receptor negative allosteric modulators (NAMs), compositions comprising the compounds, and methods of using the compounds and compositions.
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Paragraph 00348
(2016/01/01)
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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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- Double reformatsky reaction: Divergent synthesis of δ-hydroxy-β- ketoesters
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The double Reformatsky reaction, tandem addition of two molecules of zinc alkanoate to a carbonyl compound, and its synthetic application to a series of δ-hydroxy-β-ketoesters has been developed. The key to accelerate the double Reformatsky reaction is considered to be a complex-induced proximity effect of the in situ generated zinc alkoxide coordinated with the pyridyl group of the substrate or bidentate amines. A noteworthy feature of the reaction system is its high tolerance of functional groups due to the moderate nucleophilicity of organozinc reagents and the mild reaction conditions. Moreover, spectroscopic and crystallographic analyses of the zinc complex of the double Reformatsky product support the proposed mechanism of reaction site discrimination for ketones, aldehydes, nitriles, carboxylic acid anhydrides, and esters.
- Mineno, Masahiro,Sawai, Yasuhiro,Kanno, Kazuaki,Sawada, Naotaka,Mizufune, Hideya
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p. 5843 - 5850
(2013/07/26)
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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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- Point mutations (Q19P and N23K) increase the operational solubility of a 2α-o-benzoyltransferase that conveys various acyl groups from CoA to a taxane acceptor
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Two site-directed mutations within the wild-type 2-o-benzoyltransferase (tbf) cDNA, from Taxus cuspidata plants, yielded an encoded protein containing replacement amino acids at Q19P and N23K that map to a solvent-exposed loop region. The likely significant changes in the biophysical, properties invoked by these mutations caused the overexpressed, modified TBT (mTBT) to partition into the soluble enzyme fraction about 5-fold greater than the wild-type enzyme. Sufficient protein could now be acquired to examine the scope of the substrate specificity of mTBT by incubation with 7,13-O,O-diacetyl-2-Odebenzoylbaccatin III that was mixed individually with various substituted benzoyls, alkanoyls, and (E)-butenoyl CoA donors. The mTBT catalyzed the conversion of each 7,13-O,O-diacetyl-2-O-debenzoylbaccatin III to several 7,13-O,O-diacetyl-2O- acyl-2-O-debenzoylbaeeatin III analogues. The relative catalytic efficiency of mTBT with the 7,13-O,O-diacetyl-2-Odebenzoyl surrogate substrate and heterole carbonyl CoA substrates was slightly greater than with the natural aroyl substrate benzoyl CoA, while substituted benzoyl CoA thioesters were less productive. Short-chain hydrocarbon carbonyl and cyclohexanoyl CoA thioesters were also productive, where C4 substrates were transferred by mTBT with ~10- to 17-fold greater catalytic efficiency compared to the transfer of benzoyl. The described broad specificity of mTBT suggests that a plethora of 2-O-acyl variants of the antimitotic paclitaxel can be assembled through biocatalytic sequences.
- Nawarathne, Irosha N.,Walker, Kevin D.
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experimental part
p. 151 - 159
(2010/07/06)
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- An N-aroyltransferase of the bahd superfamily has broad aroyl CoA specificity in vitro with analogues of N-dearoylpaclitaxel
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The native N-debenzoyl-2'-deoxypaclitaxel:N-benzoyltransferase (NDTBT), from Taxus plants, transfers a benzoyl group from the corresponding CoA thioester to the amino group of the β -phenylalanine side chain of N-debenzoyl-2'-deoxypaclitaxel, which is purportedly on the paclitaxel (Taxol) biosynthetic pathway. To elucidate the substrate specificity of NDTBT overexpressed in Escherichia coli, the purified enzyme was incubated with semisynthetically derived N-debenzoyltaxoid substrates and aroyl CoA donors (benzoyl; ortho-, meta-, and para-substituted benzoyls; various heterole carbonyls; alkanoyls; and butenoyl), which were obtained from commercial sources or synthesized via a mixed anhydride method. Several unnatural N-aroyl-N-debenzoyl-2'-deoxypaclitaxel analogues were biocatalytically assembled with catalytic efficiencies (V max/Km) ranging between 0.15 and 1.74 nmol.min -1.mM -1. In addition, several N-acyl-N-debenzoylpaclitaxel variants werebiosynthesized when N-debenzoylpaclitaxel and N-de(tert-butoxycar-bonyl )docetaxel (i.e., 10-deacetyl-N-debenzoylpaclitaxel) were used as substrates. The relative velocity (v rel) for NDTBT with the lattertwo N-debenzoyl taxane substrates ranged between '1percent and 200pe rcent for the array of aroyl CoAs compared to benzoyl CoA. Interestingly, NDTBT transferred hexanoyl, acetyl, and butyryl more rapidly than butenoyl or benzoyl from the CoA donor to taxanes with isoserinoyl side chains, whereas N-debenzoyl-2'-deoxypaclitaxel was more rapidly converted toits N-benzoyl derivative than to its N-alkanoyl or N-butenoyl congeners . Biocatalytic N-acyl transfer of novel acyl groups to the amino functional group of N-debenzoylpaclitaxel and its 2'-deoxy precursor reveal thesurprisingly indiscriminate specificity of this transferase. This featu re of NDTBT potentially provides a tool for alternative biocatalytic N-aroylation/ alkanoylation to construct next generation taxanes or other novel bioactive diterpene compounds.
- Nevarez, Danielle M.,Mengistu, Yemane A.,Nawarathne, Irosha N.,Walker, Kevin D.
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supporting information; experimental part
p. 5994 - 6002
(2009/09/24)
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- Synthesis and biological activity of some novel N-aryl-nprime;-[5-(pyrid-4- yl)-1,3,4-thiadiazol-2-yl]ureas
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With the aim of searching for biologically active urea compounds, a series of new N-aryl-N'-[5-(pyrid-4-yl)-1,3,4-thiadiazol-2-yl]ureas have been designed and synthesized. Their structures were confirmed by IR, 1H NMR, and elemental analysis. The crystal
- Song, Xin-Jian,Tan, Xiao-Hong,Wang, Yan-Gang
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p. 1907 - 1913
(2008/02/10)
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- One-pot multistep Bohlmann-Rahtz heteroannulation reactions: Synthesis of dimethyl sulfomycinamate
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(Chemical Equation Presented) The synthesis of dimethyl sulfomycinamate, the acidic methanolysis product of the sulfomycin family of thiopeptide antibiotics, from methyl 2-oxo-4-(trimethylsilyl)but-3-ynoate is achieved in a 2,3,6-trisubstituted pyridine synthesis that proceeds with total regiocontrol in 13 steps by the Bohlmann-Rahtz heteroannulation of a 1-(oxazol-4-yl)enamine or in 12 steps and 9% yield by three-component cyclocondensation with N-[3-oxo-3-(oxazol-4-yl)propanoyl]serine and ammonia in ethanol.
- Bagley, Mark C.,Chapaneri, Krishna,Dale, James W.,Xiong, Xin,Bower, Justin
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p. 1389 - 1399
(2007/10/03)
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- Synthesis of a high-efficiency red phosphorescent emitter for organic light-emitting diodes
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Four novel red phosphorescent emitter compounds bis(1-phenylisoquinolinato- N,C2′)iridium(acetylacetonate), (piq)2Ir(acac), bis(1-(1′-naphthyl)isoquinolinato-N,C2′) iridium(acetylacetonate), (1-niq)2Ir(acac), bis(1-(2′-naphthyl) isoquinolinato-N,C2′)iridium(acetylacetonate), (2-niq) 2Ir(acac) and bis(1-phenyl-5-methylisoquinolinato-N,C 2′)iridium(acetylacetonate), (m-piq)2Ir(acac), have been synthesized and fully characterized. Electroluminescent devices with a configuration of ITO/NPB/CBP:dopant/BCP/AlQ3/Al were fabricated. All devices emitted in the red region with an emission ranging from 624 to 680 nm. (m-piq)2Ir(acac) shows a maximum brightness of 17 164 cd m -2 at a current density of J = 300 mA cm-2 and the best luminance efficiency of 8.91 cd A-1 at a current density of J = 20 mA cm-2. (1-niq)2Ir(acac) exhibits pure-red emission with 1931 CIE (Commission International de L'Eclairage) chromaticity coordinates x = 0.701, y = 0.273.
- Yang, Cheng-Hsien,Tai, Chia-Cheng,Sun, I.-Wen
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p. 947 - 950
(2007/10/03)
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- A convenient method for the preparation of hydroxamic acids
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A one-step conversion of carboxylic acid to hydroxamic acid, under neutral pH conditions is described. This simple, selective and efficient method was applied to a wide range of aliphatic/aromatic carboxylic acid derivatives that contain hydroxyl, halo, ester and other base sensitive groups as substituents. The method utilizes cheaply available reagents and hence it is a practical and cost effective strategy, compared to the other methods available in the literature. (C) 2000 Elsevier Science Ltd.
- Reddy,Kumar,Reddy
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p. 6285 - 6288
(2007/10/03)
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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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- Prodrugs of nitroxyl as potential aldehyde dehydrogenase inhibitors vis- a-vis vascular smooth muscle relaxants
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The synthesis and the chemical/biological properties of N- hydroxysaccharin (1) (2-hydroxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide), a nitroxyl prodrug, are described. When treated with 0.1 M aqueous NaOH, 1 liberated nitroxyl (HN=O), a known inhibitor o
- Nagasawa,Kawle,Elberling,DeMaster,Fukuto
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p. 1865 - 1871
(2007/10/02)
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- Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines
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The effect of 15 different amine substituents on 5-HT2A and 5-HT2C serotonin receptor binding was investigated for two series of compounds (i.e., phenylalkylamine and indolylalkylamine derivatives). In general, amine substitution decreases receptor affinity; however, N-(4-bromobenzyl) substitution results in compounds that bind at 5-HT2A receptors with high affinity (K(i) 100-fold selectivity. Although parallel structural modifications in the two series result in parallel shifts in 5- HT2C binding, these same modifications alter 5-HT2A binding in a less consistent manner.
- Glennon,Dukat,El-Bermawy,Law,De los Angeles,Teitler,King,Herrick-Davis
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p. 1929 - 1935
(2007/10/02)
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- Nickel boride reduction of symmetric and mixed anhydrides of carboxylic acids
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Symmetric and mixed anhydrides of carboxylic acids have been reduced in good yields with nickel boride generated in situ in diglyme.
- Khan, Rahat H.,Rastogi, Ramesh C.
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p. 898 - 900
(2007/10/02)
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- Studies on Quinolizine Derivatives. XXII. Syntheses and Properties of 2-Phenylazacylazine Derivatives
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By the reaction of 6-methyl-4-imino-4H-quinolizine derivatives (5, 8) with the mixed anhydrides (6a-h), 2-phenyl-1-azacylazines (7a-p, 9a-g) were obtained. 2-Phenyl-1,3,6-triazacyclazine derivatives (15a-h, 17a-h, 18a-g) were prepared by the
- Matsuda, Yoshiro,Gotou, Hiromi,Oniyama, Yukio,Katou, Keisuke,Matsumoto, Hiroshi
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p. 4307 - 4315
(2007/10/02)
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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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- PHASE MANAGED ORGANIC SYNTHESIS 2. A NEW POLYMER ASSISTED SYNTHESIS OF ACID ANHYDRIDES.
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A solid-phase copolymer of 4-vinylpyridine is shown to be a highly effective reagent/catalyst for the synthesis of acid anhydrides from mixtures containing equimolar quantities of carboxylic acid and acid chlorides.The process may be carried out in batch or column mode.
- Fife, Wilmer K.,Zhang, Zhi-dong
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p. 4933 - 4936
(2007/10/02)
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