- Fe(III)-Catalyzed Aromatic Hydroxylation with H2O2 in the Presence of a Variety of Electron-Transfer Agents
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Electron-transfer agents such as N,N,N',N'-tetramethylphenylenediamine (TMPD), ferrocenes, and phenothiazines have been found to mediate the hydroxylation of benzene with H2O2 in the presence of Fe3+.Of these, TMPD catalyst is the most effective to provide phenol in 80percent or better yield based on added H2O2 under the optimized conditions.A general mechanism, involving the rate-determining reduction of Fe3+ to Fe2+ with such mediators, is suggested.
- Tamagaki, Seizo,Sasaki, Masaaki,Tagaki, Waichiro
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Read Online
- An iGlu Receptor Antagonist and Its Simultaneous Use with an Anticancer Drug for Cancer Therapy
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Glutamate receptor antagonists have been known to play a crucial role in the treatment of many neuronal diseases. Recently, these antagonists have also shown therapeutic effects in the treatment of cancer. In this study, an ionotropic glutamate (iGlu) receptor antagonist, 4-hydroxyphenylacetyl spermine (L1), was used concurrently with a common anticancer drug, doxorubicin (Dox), for simultaneous cancer therapy. Mesoporous silica nanoparticles (MSNPs) were employed as the delivery vehicle for both L1 and Dox by conjugating the iGlu receptor antagonist on the surface and encapsulating Dox within the mesopores. Dox was then trapped within the mesopores by functionalizing a redox-cleavable capping group on the MSNP surface, and it could be released upon exposure to the reductive glutathione. In vitro studies on B16F10 and NIH3T3 cell lines revealed that the iGlu receptor antagonist L1 exhibited therapeutic as well as targeting effects. In addition, the simultaneous use of therapeutic L1 and Dox proved to be synergistic in the treatment of cancer. The present work demonstrated the feasibility of employing a delivery system to deliver both neuroprotective drug and anticancer drug for efficient anticancer treatment.
- Tan, Si Yu,Ang, Chung Yen,Luo, Zhong,Li, Peizhou,Nguyen, Kim Truc,Zhao, Yanli
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Read Online
- Synthesis and characterization of a novel Mn(III)-(γ-diketone) complex with catalytic and antifungal activity
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A novel Mn(III) complex with γ-diketone having general formula [Mn(hdo)3], where hdo = hexane-2,5-dione ligand, has been synthesized and characterized using UV–vis, FT-IR, ESI-mass and EPR spectra, elemental analysis, powder X-ray diffraction, SEM, and magnetic susceptibility measurements. The X-ray diffraction studies reveal that it has monoclinic lattice system with C2/C space group and the unit cell dimensions are a = 9.92245 ?, b = 10.50696 ?, and c = 9.80835 ?. The particle size of this complex has been found to be 32.1 nm. The complex was evaluated for its antifungal activity against Aspergillus flavus, Aspergillus niger, and Aspergillus terreus fungal species. The results indicate that the minimum inhibitory concentration of the synthesized complex was 8 ppm for A. niger while for A. flavus and A. terreus it was 6 ppm. β-Diketone Mn(III) complexes inhibit the fungal growth only partially. This communication is the first report of transformation of a keto-group to an ester group catalyzed by a metal complex.
- Dubey, Priti,Yadava, Sudha
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Read Online
- Mechanism of photosolvolytic rearrangement of p-hydroxyphenacyl esters: Evidence for excited-state intramolecular proton transfer as the primary photochemical step
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The photosolvolytic rearrangement of a variety of p-hydroxyphenacyl esters and related compounds 7-16 has been studied in solutions with up to 50% aqueous content, using product studies, triplet quenchers, and nanosecond laser flash photolysis. The p-hydroxyphenacyl moiety has recently been proposed as a new and efficient photoactivated protecting group in aqueous solution. Practical applications have been demonstrated, but much less is known about the mechanism of photoreaction. Our data support a novel mechanism in which the primary photochemical step from the singlet excited state is formal intramolecular proton transfer from the phenolic proton to the carbonyl oxygen of the distal ketone, mediated by solvent water, to generate the corresponding p-quinone methide phototautomer. This reactive intermediate (most likely in its excited state) subsequently expels the carboxylic acid with concerted rearrangement to a spiroketone intermediate, which subsequently leads to the final observed product, p- hydroxyphenylacetic acid. An alternative mechanism is deprotonation of the phenolic proton, loss of the carboxylate, and rearrangement to the spiroketone, all in one concerted primary photochemical step from S1.
- Zhang, Kai,Corrie, John E. T.,Munasinghe, V. Ranjit N.,Wan, Peter
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Read Online
- Identification and Profiling of a Novel Diazaspiro[3.4]octane Chemical Series Active against Multiple Stages of the Human Malaria Parasite Plasmodium falciparum and Optimization Efforts
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A novel diazaspiro[3.4]octane series was identified from a Plasmodium falciparum whole-cell high-throughput screening campaign. Hits displayed activity against multiple stages of the parasite lifecycle, which together with a novel sp3-rich scaffold provided an attractive starting point for a hit-to-lead medicinal chemistry optimization and biological profiling program. Structure-activity-relationship studies led to the identification of compounds that showed low nanomolar asexual blood-stage activity (50 nM) together with strong gametocyte sterilizing properties that translated to transmission-blocking activity in the standard membrane feeding assay. Mechanistic studies through resistance selection with one of the analogues followed by whole-genome sequencing implicated the P. falciparum cyclic amine resistance locus in the mode of resistance.
- Le Manach, Claire,Dam, Jean,Woodland, John G.,Kaur, Gurminder,Khonde, Lutete P.,Brunschwig, Christel,Njoroge, Mathew,Wicht, Kathryn J.,Horatscheck, André,Paquet, Tanya,Boyle, Grant A.,Gibhard, Liezl,Taylor, Dale,Lawrence, Nina,Yeo, Tomas,Mok, Sachel,Eastman, Richard T.,Dorjsuren, Dorjbal,Talley, Daniel C.,Guo, Hui,Simeonov, Anton,Reader, Janette,Van Der Watt, Mari?tte,Erlank, Erica,Venter, Nelius,Zawada, Jacek W.,Aswat, Ayesha,Nardini, Luisa,Coetzer, Theresa L.,Lauterbach, Sonja B.,Bezuidenhout, Belinda C.,Theron, Anjo,Mancama, Dalu,Koekemoer, Lizette L.,Birkholtz, Lyn-Marie,Wittlin, Sergio,Delves, Michael,Ottilie, Sabine,Winzeler, Elizabeth A.,Smith, Dennis,Fidock, David A.,Street, Leslie J.,Basarab, Gregory S.,Duffy, James,Chibale, Kelly
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supporting information
p. 2291 - 2309
(2021/03/01)
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- Discovery of novel 2,3,5-trisubstituted pyridine analogs as potent inhibitors of IL-1β via modulation of the p38 MAPK signaling pathway
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Interleukin-1β is a central mediator of innate immune responses and inflammation. It plays a key role in a wide variety of pathologies, ranging from autoinflammatory diseases to metabolic syndrome and malignant tumors. It is well established that its inhibition results in a rapid and sustained reduction in disease severity, underlining the importance of having a repertoire of drugs of this class. At present, there are only three interleukin-1β blockers approved in the clinic. All of them are biologics, requiring parenteral administration and resulting in expensive treatments. In an exercise to identify small molecule allosteric inhibitors of MAP kinases, we discovered a series of compounds that block IL-1β release produced as a consequence of a stimulus involved in triggering an inflammatory response. The present study reports the hit-to-lead optimization process that permitted the identification of the compound 13b (AIK3-305) an orally available, potent and selective inhibitor of IL-1β. Furthermore, the study also reports the results of an in vivo efficacy study of 13b in a LPS endotoxic shock model in male BALB/c mice, where IL-1β inhibition is monitored in different tissues.
- Campos, Pedro M.,Carrasco, Esther,Gomez-Gutierrez, Patricia,Messeguer, Angel,Perez, Juan J.,Vega, Miguel
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- Carboxylic Acid Reductase Can Catalyze Ester Synthesis in Aqueous Environments
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Most of the well-known enzymes catalyzing esterification require the minimization of water or activated substrates for activity. This work reports a new reaction catalyzed by carboxylic acid reductase (CAR), an enzyme known to transform a broad spectrum of carboxylic acids into aldehydes, with the use of ATP, Mg2+, and NADPH as co-substrates. When NADPH was replaced by a nucleophilic alcohol, CAR from Mycobacterium marinum can catalyze esterification under aqueous conditions at room temperature. Addition of imidazole, especially at pH 10.0, significantly enhanced ester production. In comparison to other esterification enzymes such as acyltransferase and lipase, CAR gave higher esterification yields in direct esterification under aqueous conditions. The scalability of CAR catalyzed esterification was demonstrated for the synthesis of cinoxate, an active ingredient in sunscreen. The CAR esterification offers a new method for green esterification under high water content conditions.
- Pongpamorn, Pornkanok,Kiattisewee, Cholpisit,Kittipanukul, Narongyot,Jaroensuk, Juthamas,Trisrivirat, Duangthip,Maenpuen, Somchart,Chaiyen, Pimchai
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supporting information
p. 5749 - 5753
(2021/02/01)
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- Isolation and structure–activity relationship studies of jacaranones: Anti-inflammatory quinoids from the Cuban endemic plant Jacaranda arborea (Bignoniaceae)
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The Cuban endemic plant Jacaranda arborea (Bignoniaceae) has been traditionally used in folk medicine as an acaricide and for acne treatment. Two known quinoids, methyl (1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)acetate (jacaranone) (1) and its ethyl ester 2 were isolated from this species as anti-inflammatory substances. Compound 1 prominently inhibited the production of TNF-α in both LPS-treated macrophages and mice, with low toxicity. Structure-activity relationship studies revealed that the high electrophilicity of 1 as a Michael acceptor played an important role in these effects. Unlike in previous studies, such as those on antitumor, anti-oxidant, and anti-malarial activities, ester derivatives of 1 retained their potent anti-inflammatory activity. Our results suggest that jacaranones may target specific biomacromolecule(s) at lower concentrations than hitherto expected to exhibit potent activities.
- Hirukawa, Minako,Zhang, Menghua,Echenique-Diaz, Lazaro M.,Mizota, Koji,Ohdachi, Satoshi D.,Begué-Quiala, Gerardo,Delgado-Laba?ino, Jorge L.,Gámez-Díez, Jorgelino,Alvarez-Lemus, José,Machado, Leandro Galano,Nú?ez, Miguel Suárez,Shibata, Takahiro,Kigoshi, Hideo,Kita, Masaki
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- A deprotection procedure using SO3H silica gel to remove non-silyl protecting groups
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Protecting groups are indispensable in organic synthesis and there is a great need for a variety of deprotection methods. Here, we investigated the scope of the application of a deprotection procedure using SO3H silica gel, which we have previously reported as a desilylation procedure. Under these conditions, -OMOM, -OSEM, -OTHP, and -OAc groups and dimethyl acetal were cleaved. Pivaloyloxy, benzyloxy and methoxy carbonyl groups remained intact and selective deprotection of TBS groups in the presence of other protecting groups was accomplished. We succeeded in cleaving an acetyl group on a secondary alcohol in a highly polar nortropine derivative. Our findings here provide another deprotection option and would be helpful in the synthesis of multifunctional compounds.
- Karaki, Fumika,Kuwada, Miki,Tajiri, Saki,Kanda, Misaki,Yanai, Mari,Kamimura, Mitsuhiro,Itoh, Kennosuke,Fujii, Hideaki
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p. 212 - 220
(2019/05/06)
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- Enantioselective α-Benzylation of Acyclic Esters Using π-Extended Electrophiles
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The first asymmetric cooperative Lewis base/palladium catalyzed benzylic alkylation of acyclic esters is reported. This reaction proceeds via stereodefined C1-ammonium enolate nucleophiles. Critical to its success was the identification of benzylic phosphate electrophiles, which were uniquely reactive. Alkylated products were obtained with very high levels of enantioselectivity, and this method has been applied toward the synthesis of the thrombin inhibitor DX-9065a.
- Schwarz, Kevin J.,Yang, Chao,Fyfe, James W. B.,Snaddon, Thomas N.
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supporting information
p. 12102 - 12105
(2018/09/11)
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- Synthesis method of 4-isobutoxy benzylamine
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The invention discloses a synthesis method of 4-isobutoxy benzylamine. 4-hydroxyphenylacetic acid serves as a raw material to generate 4-hydroxyphenylacetic acid methylester through an esterificationreaction; 4-hydroxyphenylacetic acid methylester is subjected to a substitution reaction to generate 4-methyl isobutoxyphenylacetic acid, and 4-isobutoxyphenylacetic acid is obtained after the obtained product is hydrolyzed; 4-isobutoxyphenylacetamide is generated through an acylation reaction; and N-(4-hydroxy benzyl)methyl carbamate is generated through a Hofmann degradation reaction, and a target product is obtained through hydrolysis. The raw materials used in the synthesis method are cheap and easy to get, the reaction condition is mild, post-treatment is simple, column chromatography isnot needed, the product can be obtained easily, and the yield is higher.
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Paragraph 0034; 0035; 0036; 0049; 0062
(2018/07/30)
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- Macrolide Synthesis through Intramolecular Oxidative Cross-Coupling of Alkenes
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A RhIII-catalyzed intramolecular oxidative cross-coupling between double bonds for the synthesis of macrolides is described. Under the optimized reaction conditions, macrocycles containing a diene moiety can be formed in reasonable yields and with excellent chemo- and stereoselectivity. This method provides an efficient approach to synthesize macrocyclic compounds containing a 1,3-conjugated diene structure.
- Jiang, Bing,Zhao, Meng,Li, Shu-Sen,Xu, Yun-He,Loh, Teck-Peng
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supporting information
p. 555 - 559
(2018/02/21)
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- Factors affecting the uncaging efficiency of 500u202fnm light-activatable BODIPY caging group
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Photoremovable protective groups, or caging groups, enable us to regulate the activities of bioactive molecules in living cells upon photoirradiation. Nevertheless, requirement of UV light for activating caging group is a significant limitation due to its cell toxicity and its poor tissue penetration. Our group previously reported a 500 nm light-activatable caging group based on BODIPY scaffold, however, its uncaging efficiency was lower than those of conventional caging groups. Here we show that the uncaging quantum yield (QY) of BODIPY caging group depends upon the driving force of photo-induced electron transfer (PeT). We also found that the uncaging QY increased in less polar solvents. We applied these findings to develop BODIPY-caged capsaicin, which is well localized to low-polarity intracellular compartments, as a tool to stimulate TRPV1 in live cells in response to blue-green light.
- Kawatani, Minoru,Kamiya, Mako,Takahashi, Hironori,Urano, Yasuteru
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supporting information
p. 1 - 5
(2017/12/06)
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- Selective HDAC inhibitors with potent oral activity against leukemia and colorectal cancer: Design, structure-activity relationship and anti-tumor activity study
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Previously, we reported the discovery of a series of N-hydroxycinnamamide-based HDAC inhibitors, among which compound 11y exhibited high HDAC1/3 selectivity. In this current study, structural derivatization of 11y led to a new series of benzamide based HDAC inhibitors. Most of the compounds exhibited high HDACs inhibitory potency. Compound 11a (with 4-methoxybenzoyl as N-substituent in the cap and 4-(aminomethyl) benzoyl as the linker group) exhibited selectivity against HDAC1 to some extent, and showed potent antiproliferative activity against several tumor cell lines. In?vivo studies revealed that compound 11a displayed potent oral antitumor activity in both hematological tumor cell U937 xenograft model and solid tumor cell HCT116 xenograft model with no obvious toxicity. Further modification of benzamide 3, 11a and 19 afforded new thienyl and phenyl compounds (50a, 50b, 63a, 63b and 63c) with dramatic HDAC1 and HDAC2 dual selectivity, and the fluorine containing compound 56, with moderate HDAC3 selectivity.
- Li, Xiaoyang,Zhang, Yingjie,Jiang, Yuqi,Wu, Jingde,Inks, Elizabeth S.,Chou, C. James,Gao, Shuai,Hou, Jinning,Ding, Qinge,Li, Jingyao,Wang, Xue,Huang, Yongxue,Xu, Wenfang
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p. 185 - 206
(2017/04/21)
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- Photoinduced Vitamin B12-Catalysis for Deprotection of (Allyloxy)arenes
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Vitamin B12 is a natural cobalt complex that, while reduced to the "supernucleophilic" Co(I) form, can easily react with electrophiles via an SN2 mechanism. It is also shown to react via an SN2′ mechanism with allylic compounds allowing for photochemical deprotection of (allyloxy)arenes. A sustainable alternative to commonly used noble metal-catalyzed deprotection reactions is presented.
- Giedyk, Maciej,Turkowska, Joanna,Lepak, Sandra,Marculewicz, Marcin,ó Proinsias, Keith,Gryko, Dorota
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supporting information
p. 2670 - 2673
(2017/05/24)
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- Cholic acid derivatives and their preparation method and medical application
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The invention relates to the field of pharmaceutical chemistry and relates to cholic acid derivatives and their preparation method and medical application and particularly relates to cholic acid derivatives having the general formula (I), their preparation method, a pharmaceutical composition containing the compounds, medical application of the cholic acid derivatives, and medical application of the cholic acid derivatives as drugs for preventing or treating hyperlipidemia, obesity or type II diabetes.
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Paragraph 0089; 0090; 0091; 0092; 0093; 0094
(2017/07/21)
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- Glutaminase inhibitors as well as compositions and applications thereof
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The invention provides a series of heterocyclic compounds expressed in a formula I. The compound comprises glutaminase inhibition activity, and can be used for treating diseases and symptoms related to dysfunction of glutaminase or raising activity of glutaminase.
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Paragraph 0603; 0699; 0700; 0701; 0702
(2018/01/09)
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- Stepwise Bay Annulation of Indigo for the Synthesis of Desymmetrized Electron Acceptors and Donor-Acceptor Constructs
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A selective stepwise annulation of indigo has been demonstrated as a means of providing both monoannulated and differentially double-annulated indigo derivatives. Disparate substitution of the electron accepting bay-annulated indigo system allows for fine control over both the electronic properties as well as donor-acceptor structural architectures. Optical and electronic properties were characterized computationally as well as through UV-vis absorption spectroscopy and cyclic voltammetry. This straightforward method provides a modular approach for the design of indigo-based materials with tailored optoelectronic properties.
- Kolaczkowski, Matthew A.,He, Bo,Liu, Yi
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supporting information
p. 5224 - 5227
(2016/11/02)
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- α-Amino Acid-Isosteric α-Amino Tetrazoles
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The synthesis of all 20 common natural proteinogenic and 4 otherα-amino acid-isosteric α-amino tetrazoles has been accomplished, whereby the carboxyl group is replaced by the isosteric 5-tetrazolyl group. The short process involves the use of the key Ugi tetrazole reaction followed by deprotection chemistries. The tetrazole group is bioisosteric to the carboxylic acid and is widely used in medicinal chemistry and drug design. Surprisingly, several of the common α-amino acid-isosteric α-amino tetrazoles are unknown up to now. Therefore a rapid synthetic access to this compound class and non-natural derivatives is of high interest to advance the field.
- Zhao, Ting,Kurpiewska, Katarzyna,Kalinowska-T?us?cik, Justyna,Herdtweck, Eberhardt,D?mling, Alexander
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supporting information
p. 3009 - 3018
(2016/03/26)
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- Production method of p-hydroxyphenylacetamide
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The invention relates to a production method of p-hydroxyphenylacetamide and belongs to the medicine field. Phenol and glyoxylic acid are taken as raw materials to be prepared into a competitive product via processes of synthesis, reduction and ammonolysis. The production method has the advantages that the optimal synthesis process is determined, yield of the obtained p-hydroxyphenylacetamide can reach over 80%, purity can reach more than 99%, and the technical process is simpler, easy to implement and environment friendly.
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Paragraph 0071; 0084-0086
(2017/10/07)
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- Ultrasound-Assisted Methyl Esterification of Carboxylic Acids ACatalyzed by Polymer-Supported Triphenylphosphine
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A convenient and efficient sonochemical method for methyl esterification of carboxylic acids catalyzed by polymer-supported triAphenylphosphine (PS-Ph3P) is reported. In the presence of 1:0.1:2 molar ratio of 2,4,6-trichloro-1,3,5-triazine/PS-Ph3P/Na2CO3, methyl esters of various carboxylic acids bearing reactive hydroxyl groups as well as acid-or base-labile functionalities could be rapidly prepared (within 10-20 min) in good to excellent yields without necessity to pre-activate the acids. Using the polymer-bound phosphine also allows easy isolation of the products which, in most of the cases, were obtained in high purities without column chromatography.
- Jaita, Subin,Phakhodee, Wong,Pattarawarapan, Mookda
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p. 2006 - 2008
(2015/09/01)
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- Branched α-d-mannopyranosides: A new class of potent FimH antagonists
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FimH is a type I fimbrial lectin located at the tip of type-1 pili of uropathogenic Escherichia coli guiding its ability to adhere and infect urothelial cells. Accordingly, blocking FimH with small-molecule antagonists is considered as a promising new therapeutic alternative to treat infections caused by uropathogenic Escherichia coli (UPEC). Herein we report that our recently disclosed α-d-mannopyranosides bearing diaryl substituted 1,3-diaminopropanol or glycerol moieties act as potent FimH antagonists in vitro, as determined by a competitive binding assay on isolated FimH lectin. Most of the assayed compounds display FimH antagonistic activity in the range of 58-1000 nM. Based on the promising results of the first series of compounds, we have designed and synthesized a new series of asymmetrically disubstituted glyceryl α-d-mannopyranosides with improved physicochemical properties. Molecular docking calculations were employed to predict compounds' binding poses leading to two possible binding modes; so-called in- and out-docking modes in the "tyrosine gate" (formed by Tyr48 and Tyr137) for one aromatic moiety, which is in accordance with previous findings, while the second aromatic moiety reaches the previously unexplored lipophilic region formed by Phe142 and Ile13. Furthermore, compounds were found to be non-cytotoxic on HepG2 cells in concentrations up to 10 μM pointing to their selective toxicity, which is one of the key features of potential therapeutics for the treatment of urinary tract infections. This journal is the Partner Organisations 2014.
- Toma?i?, Tihomir,Rabbani, Said,Gobec, Martina,Ra??an, Irena Mlinari?,Podlipnik, ?rtomir,Ernst, Beat,Anderluh, Marko
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supporting information
p. 1247 - 1253
(2014/08/05)
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- Novel 8-(p-substituted-phenyl/benzyl)xanthines with selectivity for the A2A adenosine receptor possess bronchospasmolytic activity
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A new series of 8-(p-substituted-phenyl/benzyl)xanthines has been synthesized and evaluated in vitro for adenosine receptor binding affinity and in vivo for bronchospasmolytic effects. It was observed that the nature of substituent at para-position of 8-phenyl/benzyl group on the xanthine scaffold remarkably affects the binding affinity and selectivity of xanthine derivatives for various adenosine receptor subtypes and also their bronchospasmolytic effects. Newly synthesized 8-phenylxanthines displayed potent binding affinity and significant selectivity for A2A receptors and also produced potent bronchospasmolytic effects. Replacement of phenyl ring with benzyl moiety at C8 of xanthine skeleton resulted in notable reduction in adenosine receptor affinity and broncholytic effects.
- Yadav, Rakesh,Bansal, Ranju,Kachler, Sonja,Klotz
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p. 327 - 335
(2014/03/21)
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- CYCLIC PEROXIDE OXIDATION OF AROMATIC COMPOUND PRODUCTION AND USE THEREOF
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The present invention provides a method for converting an aromatic hydrocarbon to a phenol by providing an aromatic hydrocarbon comprising one or more aromatic C-H bonds and one or more activated C-H bonds in a solvent; adding a phthaloyl peroxide to the solvent; converting the phthaloyl peroxide to a di-radical; contacting the di-radical with the one or more aromatic C-H bonds; oxidizing selectively one of the one or more aromatic C-H bonds in preference to the one or more activated C-H bonds; adding a hydroxyl group to the one of the one or more aromatic C-H bonds to form one or more phenols; and purifying the one or more phenols.
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Page/Page column 10
(2014/10/15)
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- Batchwise and continuous nanofiltration of POSS-tagged Grubbs-Hoveyda-type olefin metathesis catalysts
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New molecular-weight-enlarged metathesis catalysts, which bear polyhedral oligomeric silsesquioxane (POSS) tags, were synthesized and characterized. The catalysts can be recovered from the reaction mixture by using nanofiltration techniques and can be reused. It was found that the membranes Starmem 228 and PuraMem 280 successfully separate the catalyst from the post-reaction mixtures to below 3 ppm. The application of these POSS-tagged catalysts in a continuous metathesis reaction was also investigated. Making metathesis plus nanofiltration POSS-ible: New molecular-weight-enlarged metathesis catalysts, which bear polyhedral oligomeric silsesquioxane (POSS) tags, have been synthesized and characterized. The catalysts can be recovered from the reaction mixture by using nanofiltration techniques and can be reused. The membranes Starmem 228 and PuraMem 280 can be used to successfully separate the catalyst from the post-reaction mixtures. Copyright
- Kajetanowicz, Anna,Czaban, Justyna,Krishnan, G. Rajesh,Malinska, Maura,Wozniak, Krzysztof,Siddique, Humera,Peeva, Ludmila G.,Livingston, Andrew G.,Grela, Karol
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p. 182 - 192
(2013/03/14)
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- COMPOUNDS AND METHODS
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The present invention relates to novel retinoid-related orphan receptor gamma (RORγ) modulators and their use in the treatment of diseases mediated by RORy.
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Page/Page column 82
(2013/03/26)
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- COMPOUNDS AND METHODS
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The present invention relates to no vel retinoid-related orphan receptor gamma (RQRy) modulators and their use in the treatment of diseases mediated by RORy.
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Page/Page column 24
(2013/03/26)
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- COMPOUNDS AND METHODS
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The present invention relates to novel retinoid-reiated orphan receptor gamma (RORy) modulators and their use in the treatment of diseases mediated by RORy.
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Page/Page column 39
(2013/03/26)
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- Tyrosinase and Layer-by-Layer supported tyrosinases in the synthesis of lipophilic catechols with antiinfluenza activity
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Catechol derivatives with lipophilic properties have been selectively synthesized by tyrosinase in high yield avoiding long and tedious protection/deprotection steps usually required in traditional procedures. The synthesis was effective also with immobilized tyrosinase able to perform for more runs. The novel catechols were evaluated against influenza A virus, that continue to represent a severe threat worldwide. A significant antiviral activity was observed in derivatives characterized by antioxidant activity and long carbon alkyl side-chains, suggesting the possibility of a new inhibition mechanism based on both redox and lipophilic properties.
- Bozzini, Tiziana,Botta, Giorgia,Delfino, Michela,Onofri, Silvano,Saladino, Raffaele,Amatore, Donatella,Sgarbanti, Rossella,Nencioni, Lucia,Palamara, Anna Teresa
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p. 7699 - 7708
(2014/01/06)
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- Chemoselective deprotection of aryl tert-butyldimethylsilyl ethers promoted by phosphates
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A facile protocol to the chemoselective deprotection of aryl t-butyldimethylsilyl (TBDMS) ethers using Na3PO4 ? 12H2O as promoter is described. From aryl TBDMS ethers to the corresponding phenols, the TBDMS group could be cleaved in the presence of 0.5 equivalent of Na3PO4 ? 12H2O in dimethylformamide at room temperature with good to excellent yields in the presence of other common protecting and functional groups. K3PO 4 ? 3H2O was also found to be useful for the selective deprotection reaction. This is, to our knowledge, the first report on chemoselective deprotection of aryl TBDMS ethers using phosphates. Taylor & Francis Group, LLC.
- Yan, Lin,Zhao, Fangli,Gan, Yin,Zhao, Jin,Jiang, Zhiyong
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experimental part
p. 285 - 291
(2011/11/06)
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- NOVEL CARBOXAMIDE DERIVATIVES AS HIV INHIBITORS
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The present invention relates to carboxamide derivatives of Formula (I), where B1, B2, X, L, n, R, R1, R2, Z1, Z2, Rx and Ry are as defined in the claims, as compounds and compositions for inhibiting Human Immunodeficiency Virus (HIV) and process for making the compounds.
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Page/Page column 37
(2011/06/19)
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- Controlled anion migrations with a mixed metal Li/K-TMP amide: General application to benzylic metalations
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A general method is described for benzylic metalation of o-, m-, and p-substituted toluenes using a mixed metal amide base generated from BuLi/KOtBu/TMP at -78 °C in THF. The excellent selectivity achieved can be rationalized by the ability of the mixed metal amide base to facilitate an anion migration from the kinetic (o-aryl) to the benzylic metalation site. Remarkably, this controlled anion migration is achievable with catalytic amounts of TMP at -78 °C.
- Fleming, Patricia,Oshea, Donal F.
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p. 1698 - 1701
(2011/04/17)
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- 2-(4-METHOXYCARBONYLMETHYLPHENOXYMETHYL)BENZOIC ACID METHYL ESTER AND METHOD FOR PRODUCING THE SAME
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Dibenzoxepinacetic acid useful as an intermediate for pharmaceutical products can advantageously be produced by way of a method for producing methyl 2-(4-methoxycarbonylmethylphenoxymethyl)benzoate comprising a reaction of methyl 2-chloromethylbenzoate with methyl 4-hydroxyphenylacetate.
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Page/Page column 8
(2009/06/27)
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- TERTIARY ALKYL ESTER OF OXODIBENZOXEPIN ACETIC ACID
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A tertiary alkyl ester represented by Formula (2): wherein R1 and R2 each independently represent a C1-4 alkyl group, and a method for producing the same.
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Page/Page column 10
(2009/07/17)
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- Conversion of primary alcohols and aldehydes into methyl esters by ruthenium-catalysed hydrogen transfer reactions
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Alcohols and aldehydes are oxidised to the corresponding methyl esters by reaction with methanol in the presence of crotononitrile as a hydrogen acceptor using a catalyst combination of Ru(PPh3)3(CO)H2 with xantphos. Georg Thieme Verlag Stuttgart.
- Owston, Nathan A.,Nixon, Tracy D.,Parker, Alexandra J.,Whittlesey, Michael K.,Williams, Jonathan M. J.
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experimental part
p. 1578 - 1581
(2009/12/22)
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- Microwave-assisted esterification of diverse carboxylic acids and chiral amino acids
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A facile and efficient synthetic method of esters from their corresponding carboxylic acids and amino acids is described. The esterification reaction of carboxylic acids and amino acids could be greatly accelerated under microwave irradiation because the reactions described in this article took place in only 5 min with almost quantitative yields, and distinct acidity of catalytic acids was well tolerated. Unlike the racemation problem in microwave-assisted N-acylation reactions, the esters of chiral amino acids could be achieved with retention of configuration under this condition. Copyright Taylor & Francis Group, LLC.
- Yang, Qian,Wang, Xiao-Jian,Li, Zhi-Yu,Sun, Li,You, Qi-Dong
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experimental part
p. 4107 - 4115
(2009/04/04)
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- Oxidation of primary alcohols to methyl esters by hydrogen transfer
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The oxidation of alcohols in the presence of methanol has been achieved using a ruthenium catalyst with crotononitrile as the hydrogen acceptor. The Royal Society of Chemistry.
- Owston, Nathan A.,Parker, Alexandra J.,Williams, Jonathan M. J.
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p. 624 - 625
(2008/09/20)
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- A-[(E)-2-(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPTHALENYL)-1-PROPENYL]BENZOIC ACID ANALOGS AND METHOD OF MANUFACTURE AND AND USE THEREOF
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Analogs of 4-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-napthalenyl)-1 - propenyl]benzoic acid and methods of manufacture and use thereof, such as for use in cancer prevention and treatment.
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Page/Page column 13
(2008/06/13)
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- Solvolysis of benzyl alcohols and ethers in 1,2-diols and application to a deprotection of benzyl ether-type protecting groups
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Some kinds of benzyl alcohols and ethers react with 1,2-diols, such as ethylene glycol and propylene glycol, at 130-190°C to give 2-hydroxyethyl or 2-hydroxypropyl ethers. Application of this reaction to a deprotection of benzyl ether-type protecting groups, under neutral conditions, was also described. Copyright
- Miyake, Hideyoshi,Fujimura, Masahiro,Tsumura, Takatsugu,Sasaki, Mitsuru
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p. 778 - 779
(2007/10/03)
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- Polyglycerol-supported chromium-salen as a high-loading dendritic catalyst for stereoselective Diels-Alder reactions
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In this paper we demonstrate the application of hyperbranched polyglycerol (PG) 3 as a polymeric support for asymmetric catalysis. A new polyglycerol-supported unsymmetrical salen ligand 4 is described, which was successfully purified by gel permeation chromatography (GPC) or by ultrafiltration. After the insertion of the metal, e.g., chromium, the corresponding polymeric chromium complex was used as catalyst for asymmetric Diels-Alder reactions between Danishefsky's diene and benzaldehyde. The catalytic activities (up to 98% conversion) and enantioselectivities (up to 78% ee) were comparable to the original catalyst reported by Jacobsen. The soluble polyglycerol-supported catalysts were recovered by dialysis after the catalytic reactions and were recycled two times to afford identical reactivities as in the first run, with slightly reduced enantioselectivities. Moreover, this polymeric support catalyst showed a high retention (99.02%) in a continuously operated membrane reactor.
- Hajji, Chakib,Roller, Sebastian,Beigi, Maryam,Liese, Andreas,Haag, Rainer
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p. 1760 - 1771
(2007/10/03)
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- 3,4,5-Trisubstituted isoxazoles as novel PPARδ agonists. Part 2
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A series of PPARδ-selective agonists was investigated and optimized for a favorable in vivo pharmacokinetic profile. Isoxazole LCI765 (17d) was found to be a potent and selective PPARδ agonist with good in vivo PK properties in mouse (Cmax = 5.1 μM, t1/2 = 3.1 h). LCI765 regulated expression of genes involved in energy homeostasis in relevant tissues when dosed orally in C57BL6 mice. A co-crystal structure of compound LCI765 and the LBD of PPARδ is discussed.
- Epple, Robert,Azimioara, Mihai,Russo, Ross,Xie, Yongping,Wang, Xing,Cow, Christopher,Wityak, John,Karanewsky, Don,Bursulaya, Badry,Kreusch, Andreas,Tuntland, Tove,Gerken, Andrea,Iskandar, Maya,Saez, Enrique,Martin Seidel,Tian, Shin-Shay
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p. 5488 - 5492
(2007/10/03)
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- Synthesis of pulvinic acid and norbadione A analogues by Suzuki-Miyaura cross-coupling of benzylated intermediates
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Pulvinic acid and norbadione A analogues can be prepared by Suzuki-Miyaura cross-coupling of functionalized aryl-boronic esters with appropriate vinyl inflates, in which the hydroxy functions are protected either with methyl or benzyl groups, the latter being cleaved in a more reliable fashion at the end of the synthetic sequence. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
- Murr, Marine Desage-El,Nowaczyk, Stephanie,Le Gall, Thierry,Mioskowski, Charles
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p. 1489 - 1498
(2007/10/03)
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- An efficient asymmetric synthesis of (S)-atenolol: Using hydrolytic kinetic resolution
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Enantiomerically pure (S)-atenolol was prepared by using (R,R) salen Co(III) complex for the resolution of terminal epoxide. This process was carried out at room temperature in excellent enantio selectivity. The method can be applied for large-scale preparation of (S)-atenolol without any problem.
- Subhas Bose,Venkat Narsaiah
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p. 627 - 630
(2007/10/03)
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- Mesogens based on palladium orthometallated complexes with carboxylato bridges: Tuning and shaping a non-planar molecule
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The binuclear cyclopalladated compounds [Pd2(μ-OH) 2(Ln)2] (1) derived from imines HLn = p-CnH2n + 1O-C6H4-CHN-C 6H4-OCnH2n + 1-p (n = 6,10) react with carboxylic acids to give the derivatives [Pd2(μ-ox) 2(Ln)2] (2) with a planar core for oxalic acid, and [Pd2(μ-OOCR)2(Ln)2] (3-7) compounds with a non-planar ridge tent structure for other RCOOH acids: (3) R = CmH2m + 1 (m = 1, 3, 5, 7, 9, 11, 13, 15, 17); (4) R = CH2(OCH2CH2)pOCH3 (p = 1, 2); (5) R = CH2-C6H4-OCqH 2q + 1-p (q = 2, 4, 6, 8, 10, 12); (6) R = C6H 4-OCrH2r + 1-p (r = 4, 10); (7) R = C*H(OH)CH3. The acids used were designed to explore the effect on the thermal properties of the compounds prepared of systematic variations in the type of carboxylato ligand, which induce structure, packing, and polarity changes, and in the length of the carboxylato chain. Most of the complexes prepared, even when far from planar, show liquid crystal behavior and display nematic, smectic A and smectic C phases.
- Díez, Laura,Espinet, Pablo,Miguel, Jesús A.,Rodríguez-Medina, M. Paz
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p. 261 - 268
(2007/10/03)
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- (Hetero)aryl-bicyclic heteroaryl derivatives, their preparation and their use as protease inhibitors
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The present invention provides novel compounds of the Formula (I): A-B, its prodrug forms, or pharmaceutically acceptable salts thereof, wherein A represents a saturated, unsaturated, or a partially unsaturated bicyclic heterocyclic ring structure, and B represents an aryl or a heteroaryl group. Preferred compounds of the present invention comprise a benzimidazole or indole nucleus. The compounds of this invention are inhibitors of serine proteases, Urokinase (uPA), Factor Xa (FXa), and/or Factor VIIa (FVIIa), and have utility as anti cancer agents and/or as anticoagulants for the treatment or prevention of thromboembolic disorders in mammals.
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Page/Page column 80
(2010/02/11)
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- Simple deprotection of acetal type protecting groups under neutral conditions
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Heating acetals with ethylene glycol causes the deprotection of acetal type protecting groups. When acetals such as MOM ethers, MEM ethers, and THP ethers were heated in ethylene glycol or propylene glycol, solvolysis proceeded smoothly to produce alcohols in excellent yield. This reaction is a very promising method for chemoselective deprotection of acetal type protecting groups.
- Miyake, Hideyoshi,Tsumura, Takatsugu,Sasaki, Mitsuru
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p. 7213 - 7215
(2007/10/03)
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- A highly convenient, efficient, and selective process for preparation of esters and amides from carboxylic acids using Fe3+-K-10 montmorillonite clay
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In the presence of Fe3+-K-10 montmorillonite clay as a catalyst, aliphatic carboxylic acids selectively produced the corresponding esters in the presence of aromatic carboxylic acids by treatment with alcohols. Both the aliphatic and aromatic carboxylic acids formed the amides by reacting with the aliphatic amines, but only the aliphatic carboxylic acids yielded the anilides by treatment with aromatic amines. The catalyst is recoverable and recyclable.
- Srinivas,Das, Biswanath
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p. 1165 - 1167
(2007/10/03)
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- Novel thieno oxazine analogues as antihyperglycemic and lipid modulating agents
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A series of phenyl acetic acid and α-hydroxy propionic acid derivatives were synthesized. In vivo studies of the compounds indicated compound 2c as the most potent in one of the series, which has both glucose and lipid lowering properties. The syntheses and biological studies have been discussed.
- Das, Saibal Kumar,Reddy, K. Anantha,Abbineni, Chandrasekhar,Iqbal, Javed,Suresh,Premkumar,Chakrabarti, Ranjan
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p. 399 - 403
(2007/10/03)
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- Probing crucial metabolic pathways in fungal pathogens of crucifers: Biotransformation of indole-3-acetaldoxime, 4-hydroxyphenylacetaldoxime, and their metabolites
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Indole-3-acetaldoxime is an intermediate of crucial importance in the biosynthesis of diverse plant secondary metabolites of Cruciferae. The metabolism of indole-3-acetaldoxime to indole-3-acetic acid via indole-3-acetonitrile by fungi that cause important plant diseases in crucifers, Leptosphaeria maculans (asexual stage Phoma lingam) causative agent of blackleg disease, Rhizoctonia solani causative agent of root rot disease, and Sclerotinia sclerotiorum causative agent of stem rot disease, is described. As well, the antifungal activity of indole-3-acetaldoxime and metabolites and the synthesis and biotransformation of 4-hydroxyphenylacetaldoxime by the same plant pathogens and by an insect fungal pathogen, Beauveria bassiana, are reported.
- Pedras, M. Soledade C.,Montaut, Sabine
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p. 3115 - 3120
(2007/10/03)
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- Isothiazole derivatives and their use as pesticides
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A compound of formula (I), where A is optionally substituted alkylene, alkenylene, alkynylene, cycloalkylene, alkylenoxy, oxy(C1-6)alkylene, alkylenethio, thio(C1-6)alkylene, C1-6alkylenamino, amino(C1-6)alkylene, [C1-6alkyleneoxy(C1-6)alkylene], [C1-6alkylenethio(c1-6)alkylene], [1-6alkylenesulfinyl(c1-6)alkylene], [c1-6alkylenesulfonyl(C1-6)alkylenc] or [C1-6alkyleneamino(C1-6)alkylene]; provided that A is not CH2 or CH2O; B is N, N-oxide or CR8; Y is O, S or NR9; Z is O, S or NR10; and R1, R2, R3, R4, R5, R6, R7, R8, R9, R10 are specified radicals; compositions containing them; processes for making them; and their use as insecticides or fungicides.
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Page/Page column 36
(2010/11/29)
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- A mild, efficient and selective deprotection of t-butyldimethylsilyl-protected phenols using cesium carbonate
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A mild and efficient method for the deprotection of aryl t-butyldimethysilyl (TBS) ethers is described. The protecting group TBS could be cleaved from aryl silyl ethers using cesium carbonate in DMF-H2O at room temperature to give the corresponding phenols in excellent yields. The reaction conditions allowed selective deprotection of aryl TBS-protected phenols in the presence of TBS, phenyloxycarbonyl or tetrahydropyranyl-protected alcohols.
- Jiang, Zhi-Yong,Wang, Yan-Guang
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p. 3859 - 3861
(2007/10/03)
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