- Quinazolinone compounds as well as preparation method and application thereof
-
The invention relates to quinazolinone compounds as well as a preparation method and application thereof, three kinases of EGFR (epidermal growth factor receptor), VEGFR-2 (vascular endothelial growthfactor receptor 2) and FGFR1 (fibroblast growth factor
- -
-
Paragraph 0034
(2020/04/02)
-
- Synthesis, biological evaluation and molecular modeling studies of substitutedN-benzyl-2-phenylethanamines as cholinesterase inhibitors
-
In this work, we report the synthesis of a series of derivatives ofN-benzyl-2-phenylethanamine which is the framework of norbelladine, the natural common precursor of the Amaryllidaceae alkaloids. These compounds were assessed in the inhibition of both AChE and BChE which are the enzymes responsible for the breakdown of acetylcholine and hence they constitute targets in the palliative treatment of Alzheimer's disease. In particular, brominated derivatives exhibited the lowest IC50values against AChE. Interestingly, the presence of iodine in one of the aromatic rings highly increased the inhibition of BChE compared to its analogues, with an IC50value similar to that of galantamine, which is the reference compound currently used in the treatment of AD. A possible mechanism of action for these compounds was determined by molecular modeling studies using combined techniques of docking and molecular dynamics simulations.
- Carmona-Viglianco, Florencia,Enriz, Ricardo D.,Feresin, Gabriela E.,Garro, Adriana,Kurina-Sanz, Marcela,Orden, Alejandro A.,Parravicini, Oscar,Zaragoza-Puchol, Daniel
-
p. 9466 - 9476
(2020/06/17)
-
- SUBSTITUTED PROPANAMIDES AS INHIBITORS OF NUCLEASES
-
The invention provides compounds represented by the structural formula (1): wherein R1, R2, R3, R4, R5, R6 are as defined in the claims. The compounds are inhibitors of nucleases, and are useful in particular in a method of treatment and/or prevention of proliferative diseases, neurodegenerative diseases, and other genomic instability associated diseases.
- -
-
Page/Page column 11; 19
(2019/11/12)
-
- Imidazo ring PAR4 antagonist and medical applications thereof
-
The invention relates to an imidazo ring compound represented by formula (I) or formula (II), or a pharmaceutically acceptable salt or ester or solvate thereof. The compound disclosed by the inventioncan be used for preparing medicines for preventing or treating thromboembolic diseases.
- -
-
Paragraph 0274-0277
(2020/01/12)
-
- Discovery of Novel Bromophenol-Thiosemicarbazone Hybrids as Potent Selective Inhibitors of Poly(ADP-ribose) Polymerase-1 (PARP-1) for Use in Cancer
-
Poly(ADP-ribose) polymerase-1 (PARP-1) is a new potential target for anticancer drug discovery. A series of bromophenol-thiosemicarbazone hybrids as PARP-1 inhibitors were designed, synthesized, and evaluated for their antitumor activities. Among them, the most promising compound, 11, showed excellent selective PARP-1 inhibitory activity (IC50 = 29.5 nM) over PARP-2 (IC50 > 1000 nM) and potent anticancer activities toward the SK-OV-3, Bel-7402 and HepG2 cancer cell lines (IC50 = 2.39, 5.45, and 4.60 μM), along with inhibition of tumor growth in an in vivo SK-OV-3 cell xenograft model. Further study demonstrated that compound 11 played an antitumor role through multiple anticancer mechanisms, including the induction of apoptosis and cell cycle arrest, cellular accumulation of DNA double-strand breaks, DNA repair alterations, inhibition of H2O2-triggered PARylation, antiproliferative effects via the production of cytotoxic reactive oxygen species, and autophagy. In addition, compound 11 displayed good pharmacokinetic characteristics and favorable safety. These observations demonstrate that compound 11 may serve as a lead compound for the discovery of new anticancer drugs.
- Guo, Chuanlong,Wang, Lijun,Li, Xiuxue,Wang, Shuaiyu,Yu, Xuemin,Xu, Kuo,Zhao, Yue,Luo, Jiao,Li, Xiangqian,Jiang, Bo,Shi, Dayong
-
p. 3051 - 3067
(2019/03/29)
-
- Cobalt-Mediated [2+2+2] Cycloadditions of Alkynes to Benzo-[ b ]furans and Benzo[ b ]thiophenes: A Potential Route toward Morphanoids
-
Exploratory studies of the CpCo-mediated [2+2+2] cycloaddition of alkynes to the 2,3-double bond of benzo[ b ]furans (and some benzo[ b ]thiophenes) are presented, with the general aim to access morphinan substructures. The basic feasibility of constructing Co-complexed tetrahydrophenanthro[4,5- bcd ]furans (and -thiophenes) in moderate to good yields is demonstrated, with complete to extensive diastereoselectivity. Limitations are the apparent necessity for bulky (silylated) monoalkynes, the lack of regioselectivity in the cocyclization with unsymmetrical alkynes, and the sensitivity of the ligands, both complexed and uncomplexed, with respect to ring opening and rearrangement.
- Aechtner, Tobias,Barry, David A.,David, Ellen,Ghellamallah, Cédric,Harvey, Daniel F.,De La Houpliere, Alix,Knopp, Monika,Malaska, Michael J.,Pérez, Dolores,Sch?rer, Kaspar A.,Siesel, Brian A.,Vollhardt, K. Peter C.,Zitterbart, Robert
-
p. 1053 - 1089
(2017/12/28)
-
- Step-economical synthesis of 3-amido-2-quinolones by dendritic copper powder-mediated one-pot reaction
-
The one-pot protocol by the dendritic copper powder-mediated Knoevenagel condensation/annelation is delineated here for the synthesis of 3-amido-2-quinolones. It is practical with moisture tolerance and easy setup, and is compatible with many functional g
- Ahn, Byung Hoon,Lee, Ill Young,Lim, Hee Nam
-
p. 7851 - 7860
(2018/11/21)
-
- Synthesis of Polysubstituted 3-Methylisoquinolines through the 6π-Electron Cyclization/Elimination of 1-Azatrienes derived from 1,1-Dimethylhydrazine
-
A convenient one pot microwave-assisted 6π-electron cyclization/aromatization approach toward 3-methylisoquinolines is reported. The starting 1-azatriene derivatives were prepared in situ by reaction of 2-propenylbenzaldehydes with 1,1-dimethylhydrazine, which exhibited superior performance when compared with other hydrazine derivatives. Minor amounts of the related 3,4-dihydro isoquinolines were formed concomitantly with the isoquinolines, and a mechanism for their generation was proposed. The reaction conditions were optimized, and its scope and limitations were explored. In general, the transformation proceeded in moderate to good yields.
- Vargas, Didier F.,Larghi, Enrique L.,Kaufman, Teodoro S.
-
p. 5605 - 5614
(2018/10/09)
-
- Novel method for preparing decumbenine B
-
The invention provides a novel method for preparing a natural compound decumbenine B. The method comprises the following steps: (i) enabling a compound shown as a formula 4 and a compound shown as a formula 5 to be in contact under a condition suitable for carbon-carbon coupling, so as to generate a compound shown as a formula 3; (ii) carrying out cyclization on the compound shown as the formula 3and ammonium acetate under a suitable condition, so as to generate a compound 2; (iii) enabling the compound shown as the formula 2 and paraformaldehyde to react under the suitable condition, so as to generate the compound decumbenine B shown as a formula 1. (The formula 5, the formula 4, the formula 3, the formula 2 and the formula 1 are shown in the description.).
- -
-
Paragraph 0025; 0026
(2018/07/30)
-
- Intermediate of salvianolic acid A and preparation method of intermediate as well as preparation method of salvianolic acid A
-
The invention relates to an intermediate for preparing salvianolic acid A and a preparation method of the intermediate as well as a method for preparing the salvianolic acid A (shown as a formula I) by the intermediate. Specifically, the invention relates
- -
-
Paragraph 0016; 0118-0119
(2018/11/22)
-
- Improved synthesis of nigricanin
-
An ellagic acid-related natural product, nigricanin (1), was synthesized via the Ullmann coupling reaction of 2-bromo-3,4-dialkoxybenzaldehyde (4) followed by the Cannizzaro reaction for desymmetrization of the symmetric biaryl compound (5). Compared to o
- Abe, Hitoshi,Nagai, Takanori,Imai, Haruka,Horino, Yoshikazu
-
p. 1078 - 1080
(2017/11/17)
-
- Controlling the Substitution Pattern of Hexasubstituted Naphthalenes by Aryne/Siloxyfuran Diels–Alder Additions: Regio- and Stereocontrolled Synthesis of Arizonin C1 Analogs
-
3,4-Dimethoxybenz-1-yne and 2-siloxylated furans without or with a bromine atom at C-3 undergo Diels–Alder reactions with orientational selectivity. Hydrolysis furnished a bromine-free or a bromine-containing naphthalene, respectively. Bromination of the former provided a regioisomer of the latter. Either of the two compounds was processed to give a variety of unnatural naphthoquinonopyrano-γ-lactones. This occurred by a succession of (1) Heck coupling, (2) asymmetric dihydroxylation, (3) oxa-Pictet–Spengler cyclization, and (4) oxidation. The fifteen monomeric naphthoquinonopyrano-γ-lactone structures that we prepared resemble the natural product (–)-arizonin C1 or its C-5 epimer. Accordingly, they represent hexasubstituted naphthalenes likewise. The sixteenth naphthoquinonopyrano-γ-lactone that we synthesized is a kind of dimer. Its moieties are bridged differently than those in naturally occurring naphthoquinonopyrano-γ-lactone dimers.
- Neumeyer, Markus,Kopp, Julia,Brückner, Reinhard
-
p. 2883 - 2915
(2017/06/06)
-
- Establishing Consensus Stereostructures for the Naphthoquinonopyrano-γ-lactone Natural Products (–)-Arizonin B1 and (–)-Arizonin C1 by Total Syntheses. Diastereocontrol of Oxa-Pictet–Spengler Cyclizations by Protective-Group Optimization
-
Previous total syntheses of arizonin C1 (4) led to opposite assignments of its absolute configuration. Here, we report the fourth total synthesis thereof. In addition, we disclose the first total synthesis of arizonin B1 (3) proceeding differently than via arizonin C1. The stereocenters of the two targets stemmed from an asymmetric dihydroxylation and an ensuing oxa-Pictet–Spengler cyclization. Their configurations were in line with Fernandes' assignments. Protective-group variation in the substrate modulated the diastereoselectivity of the Pictet–Spengler cyclization between 77:23 in favor of a trans disubstitution at C-3a vs. C-5 – used for preparing the natural (–)-arizonins C1 and B1 – and 100:0 in favor of a cis disubstitution – exploited for synthesizing the unnatural (+)-5-epi-arizonins C1 and B1. All naphthalenes of the present study were derived from the (benzyloxy)methoxynaphthalenediol 19. It resulted from a Diels–Alder reaction of the aryne 17a with the siloxyfuran 18a.
- Neumeyer, Markus,Brückner, Reinhard
-
p. 2512 - 2539
(2017/05/15)
-
- A synthesizing methyl emulsion method of alkali
-
The invention provides a synthetic method for methyl caulophine. The method comprises the following steps: with isovanillin and p-hydroxyanisole as raw materials, successively subjecting isovanillin to bromination and methylation so as to obtain 2-bromo-3
- -
-
Paragraph 0039; 0040
(2016/10/10)
-
- With anti-tumor activity of a biphenyl amide compound and its preparation method and application
-
The invention discloses a biphenyl amide compound with antitumor activity as well as a preparation method and application thereof. The structural formula of the compound is shown in the specification, wherein in the structural formula, R1 is hydrogen or halogen; R2 is alkoxy with carbon number of 1-4; the terminal of R2 is replaced by tert-amido; R2 is linked to the para-position of amide via an oxygen atom. The compound has good tumor cell inhibiting activity in vitro and can be used for preparing antitumor drugs, especially anti-hepatoma drugs and anti-breast cancer drugs. The preparation method of the biphenyl amide compound, provided by the invention, has the advantages that the raw materials are accessible, the reaction conditions are mild, the reaction process is simple to operate, and the used reagent is cheap.
- -
-
Paragraph 0048; 0054; 0055
(2016/11/24)
-
- Design, Synthesis, and Biological Evaluation of Chalcone Derivatives as Novel Anticandidal Agents
-
Twenty chalcone derivatives were designed and synthesized with a view to developing novel anticandidal agents. All the compounds were evaluated for their antifungal activity against Candida albicans (ATCC 10231 and ten clinical isolates). Most of them exhibited moderate anticandidal potency with MIC values ranging from 2.0 to 32.0 μg/mL. Four compounds (T4, T6, T19, T20) displayed potent anticandidal activity with MIC values of 2.0 μg/mL. Compound T6 showed the most potent activity against Candida albicans (ATCC 10231 and four clinical isolates). In addition, attempts have also been made to correlate anticandidal activity to physicochemical properties. The results indicated that incorporation of halogen on the benzene ring is beneficial for anticandidal activity.
- Shan, Yuanyuan,Lei, Jine,Zhang, Li,Fan, Te,Wang, Maoyi,Ma, Ying
-
p. 620 - 625
(2015/08/24)
-
- Asymmetric total synthesis of (S)-isocorydine
-
The asymmetric total synthesis of (S)-isocorydine, a potential drug for the cure of hepatocellular carcinoma, is described. Asymmetric transfer hydrogenation of 3,4-dihydroisoquinoline using a chiral Ru(II) catalyst was applied to the synthesis of isocory
- Zhong, Mei,Jiang, Yunbin,Chen, Yali,Yan, Qian,Liu, Junxi,Di, Duolong
-
p. 1145 - 1149
(2015/10/28)
-
- Discovery of biphenyl-based VEGFR-2 inhibitors. Part 3: Design, synthesis and 3D-QSAR studies
-
VEGFR-2 plays an essential role in angiogenesis and is a central target for anticancer drug discovery. In order to develop novel VEGFR-2 inhibitors, we designed and synthesized 33 biphenyl amides based on our previously reported lead compound. The biological results indicated that four compounds (18b, 20e, 20h and 20j) are potent VEGFR-2 inhibitors which are comparable to positive control. Compound 18b displayed the most potent VEGFR-2 inhibition with IC50 value of 2.02 nM. Moreover, it exhibited promising antiproliferative activity against MCF-7 and SMMC-7721 cells with IC50 values of 1.47 μM and 5.98 μM, respectively. Molecular docking and 3D-QSAR studies were also carried out. The results indicated that these biphenyl amides could serve as promising leads for further optimization as novel VEGFR-2 inhibitors.
- Lu, Wen,Li, Pengfei,Shan, Yuanyuan,Su, Ping,Wang, Jinfeng,Shi, Yaling,Zhang, Jie
-
p. 1044 - 1054
(2015/03/04)
-
- 1 -HYDROXY-BENZOOXABOROLES AS ANTIPARASITIC AGENTS
-
Provided are compounds useful for controlling endoparasites both in animals and agriculture. Further provided are methods for controlling endoparasite infestations of an animal by administering an effective amount of a compound as described above, or a pharmaceutically acceptable salt thereof, to an animal, as well as formulations for controlling endoparasite infestations using the compounds described above or an acceptable salt thereof, and an acceptable carrier. The claimed compounds are described by the following Markush formula:A typical example for a compound according to above formula is: A typical example for a compound according to above formula is:
- -
-
Page/Page column 102; 132-133
(2014/10/03)
-
- Chemoenzymatic formal total synthesis of ent-codeine and other morphinans via nitrone cycloadditions and/or radical cyclizations. comparison of strategies for control of C-9/C-14 stereogenic centers
-
Formal total syntheses of ent-codeine and other morphinans were accomplished from 1- phenyl-2-acetoxyethane, which was subjected to enzymatic dihydroxylation by toluene dioxygenase overexpressed in Eschericia coli JM109 (pDTG601A). The resulting cis-dihyd
- Endoma-Arias, Mary Ann A.,Hudlicky, Jason Reed,Simionescu, Razvan,Hudlicky, Tomas
-
supporting information
p. 333 - 339
(2014/05/20)
-
- Chemoselective zinc/HCl reduction of halogenated β-nitrostyrenes: Synthesis of halogenated dopamine analogues
-
A detailed account regarding the synthesis of 2- and 5-halogenated dopamine is given. The key step is a chemoselective reduction of a nitrostyrene by Zn/HCl at 0 °C. These conditions represent a simple, low-cost alternative to reduction by water-sensitive hydride donors and two-step procedures. Under these conditions, aryl fluoride, chloride, and bromide groups are stable. However, iodine undergoes significant reductive dehalogenation.
- Maresh, Justin J.,Ralko, Arthur A.,Speltz, Tom E.,Burke, James L.,Murphy, Casey M.,Gaskell, Zachary,Girel, Joann K.,Terranova, Erin,Richtscheidt, Conrad,Krzeszowiec, Mark
-
supporting information
p. 2891 - 2894
(2015/02/02)
-
- Collective asymmetric synthesis of (-)-Antofine, (-)-cryptopleurine, (-)-tylophorine, and (-)-tylocrebrine with tert- butanesulfinamide as a chiral auxiliary
-
A collective asymmetric synthesis of phenanthroindolizidine and phenanthroquinolizidine alkaloids (-)-antofine, (-)-cryptopleurine, (-)-tylophorine, and (-)-tylocrebrine was achieved by means of a reaction sequence involving efficient generation of chiral homoallylic amine intermediates by asymmetric allylation of the corresponding tert-butanesulfinyl imine. From these intermediates, the pyrrolidine and piperidine rings were constructed by means of an intramolecular SN2 substitution reaction and a ring-closing metathesis reaction, respectively. The unusual C5-methoxy-substituted phenanthrene moiety of (-)-tylocrebrine was generated by means of an InCl3-catalyzed cycloisomerization reaction of an o-propargylbiaryl compound.
- Zheng, Yanlong,Liu, Yuxiu,Wang, Qingmin
-
supporting information
p. 3348 - 3357
(2014/05/06)
-
- Total synthesis of (+)-pentamethylsalvianolic acid C
-
The total synthesis of a methylated analogue of (+)-Salvianolic acid C has been achieved. Key aspects of the synthetic route include an economical Cu(i) acetylide coupling, unique carboxyl activation conditions via microwave irradiation and a novel lipase catalysed kinetic resolution of a racemic mixture of secondary alcohol Danshensu. The preparation of this methylated analogue will not only improve the bioavailability, but also enable access to new and wider bioactivity applications for (+)-Salvianolic acid C.
- Alford, Benjamin L.,Huegel, Helmut M.
-
supporting information
p. 2724 - 2727
(2013/06/04)
-
- Synthesis of novel taspine diphenyl derivatives as fluorescence probes and inhibitors of breast cancer cell proliferation
-
Two novel taspine diphenyl derivatives (Ta-dD) were designed and synthesized by introducing different coumarin fluorescent groups into the basic structure of Ta-dD. The main advantage of these two compounds is that they can be used as fluorescence probes and inhibitors simultaneously. In the present study, the fluorescent properties of the probes were measured and their inhibition of four breast cancer cell lines was tested. Different concentrations of the fluorescence probe were added to MCF-7 breast cancer cells for fluorescence imaging analysis under normal conditions. The results suggested that both of the new compounds have not only fluorescence but also the ability to inhibit effects on different breast cancer cell lines, which indicates their possible further use as dual functional fluorescence probes in tracer analysis. Copyright
- He, Huaizhen,Zhan, Yingzhuan,Zhang, Yanmin,Zhang, Jie,He, Langchong
-
scheme or table
p. 310 - 314
(2012/10/18)
-
- Chemoenzymatic total synthesis of ent-neopinone and formal total synthesis of ent -codeinone from β-bromoethylbenzene
-
Formal total synthesis of ent-codeinone and ent-codeine was accomplished via the total synthesis of ent-neopinone attained in 14 steps from β-bromoethylbenzene. The key steps included (i) enzymatic dihydroxylation of β-bromoethylbenzene with E. coli JM109
- Duchek, Jan,Piercy, T. Graeme,Gilmet, Jacqueline,Hudlicky, Tomas
-
p. 709 - 728
(2011/11/13)
-
- A total synthesis of (±)-codeine by 1,3-dipolar cycloaddition
-
Nitrone cycloaddition on a dearomatized bicyclic phenol enabled the facile construction of the correctly configured phenanthrene skeleton of codeine. Further steps yielded allopseudocodeine in a completely diastereoselective manner and finally (±)-codeine by allylic transposition through the hydrolysis of chlorocodides.
- Erhard, Thomas,Ehrlich, Gunnar,Metz, Peter
-
scheme or table
p. 3892 - 3894
(2011/06/24)
-
- Synthesis and cytotoxic evaluation of novel symmetrical taspine derivatives as anticancer agents
-
It has been demonstrated that taspine derivatives act as anticancer agents, thus we designed and synthesized a novel class of symmetrical biphenyl derivatives. We evaluated the cytotoxicity and antitumor activity of biphenyls against five human tumor and normal cell lines. The results indicated that the majority of the compounds exhibited anticancer activity equivalent to or greater than the positive control. Compounds (11) and (12) demonstrated the most potent cytotoxic activity with IC50 values between 19.41 μM and 29.27 μM. The potent antiproliferative capabilities of these compounds against ECV304 human transformed endothelial cells indicated that these biphenyls could potentially serve as antiangiogenic agents. We also reviewed the relationship between structure and activity based on the experimental results. Our findings provide a good starting point for further development of symmetrical biphenyl derivatives as potential novel anticancer agents.
- Zhang, Jie,Zhang, Yanmin,Pan, Xiaoyan,Wang, Sicen,He, Langchong
-
experimental part
p. 286 - 294
(2012/05/05)
-
- Synthesis and preliminary biological evaluation of novel taspine derivatives as anticancer agents
-
Antiangiogenic therapy might represent a new promising anticancer therapeutic strategy. Taspine can significantly inhibit cell proliferation of human umbilical vein endothelial cells (HUVECs) induced by vascular endothelial growth factor-165, which is crucial for angiogenesis. In this study, a series of novel taspine derivatives were synthesized and screened for in vitro anticancer and antiangiogenesis activities. The majority of the derivatives demonstrated a moderate degree of cytotoxicity against human cancer cell lines. One of them (14) exhibited much better antiproliferative activity against CACO-2 (IC 50 = 52.5 μM) and ECV304 (IC50 = 2.67 μM) cells than taspine did. Some of them were also effective in antiproliferative assays against HUVECs. The in silico estimate of solubility of title compounds were higher than that of taspine.
- Zhang, Jie,Zhang, Yanmin,Shan, Yuanyuan,Li, Na,Ma, Wei,He, Langchong
-
experimental part
p. 2798 - 2805
(2010/08/20)
-
- SYNTHESIS OF MORPHINE AND RELATED DERIVATIVES
-
The present invention relates to methods for the synthesis of galanthamine, morphine, intermediates, salts and derivatives thereof, wherein the starting compound is biphenyl.
- -
-
Page/Page column 67-68
(2010/12/17)
-
- Chiral diene as the ligand for the synthesis of axially chiral compounds via palladium-catalyzed suzuki-miyaura coupling reaction
-
The first palladium-diene-catalyzed asymmetric Suzuki-Miyaura coupling reaction has been achieved. A number of functionalized biaryls were obtained in high yields and in moderate to high enantioselectivities. The existence of an ortho-formyl group greatly
- Zhang, Shu-Sheng,Wang, Zhi-Qian,Xu, Ming-Hua,Lin, Guo-Qiang
-
supporting information; experimental part
p. 5546 - 5549
(2011/03/18)
-
- Short synthesis of noscapine, bicuculline, egenine, capnoidine, and corytensine alkaloids through the addition of 1-siloxy-isobenzofurans to imines
-
A concise diastereotioselective strategy for the synthesis of noscapine, bicuculline, and egenine (1a-c), as well as capnoidine and corytensine (2a,b), was developed using diastereoselective addition of 1-siloxy-isobenzofurans 4a and 4b to iminium ion 5 in a one-pot approach. The synthesis features the use of imine 13 obtained through Bischler-Napieralsky reaction from amine 11. The addition of ionic liquids as addictives in the reactions afforded erythro configuration in major adduct compounds. The synthetic route can also be applied in the total synthesis of promising tubulin binding agent EM105 (3).
- Soriano, Maria Del Pilar C.,Shankaraiah, Nagula,Santos, Leonardo Silva
-
scheme or table
p. 1770 - 1773
(2010/05/18)
-
- Facile and efficient total synthesis of taspine
-
The facile and efficient total synthesis of taspine was achieved in 10 steps in high yield (16.5% overall) from commercially available isovanillin. Key steps in the synthesis are preparation of a symmetrical homodimer employing a classical Ullmann coupling reaction, and introduction of an allyl substituent by the Claisen rearrangement reaction. Significantly, the facile synthetic scheme proposed in this work has the characteristics of mild reaction conditions, inexpensive reagents, higher yield, and simple operation. Georg Thieme Verlag Stuttgart.
- Cheng, Bin,Zhang, Sanqi,Zhu, Liyong,Zhang, Jie,Li, Qiang,Shan, Ailin,He, Langchong
-
experimental part
p. 2501 - 2504
(2009/12/08)
-
- Concise syntheses of (-)-galanthamine and (±)-codeine via intramolecular alkylation of a phenol derivative
-
(Figure Presented). A new solution-processable fabrication protocol using a soluble tetrabenzoporphyrin (BP) precursor and bis(dimethylphenylsilylmethyl) [60]fullerene (SIMEF) created three-layered p-i-n photovoltaic devices, in which the i-layer possesses a well-defined bulk heterojunction structure in which columnar BP crystals grow vertically from the bottom p-layer. The device showed a power conversion efficiency of 5.2% (VOC = 0.75 V; JSC = 10.5 mA/cm2; FF = 0.65).
- Magnus, Philip,Sane, Neeraj,Fauber, Benjamin P.,Lynch, Vince
-
supporting information; experimental part
p. 16045 - 16047
(2010/02/16)
-
- A novel simple and efficient bromination protocol for activated arenes
-
An efficient, high yielding, and environmentally benign bromination using an alkali metal bromide as the bromine source is disclosed. Investigation of the protocol revealed that the method operates for activated arenes producing the corresponding monobrominated products in good to excellent yields.
- Tsoukala, Anna,Liguori, Lucia,Occhipinti, Giovanni,Bj?rsvik, Hans-Rene?
-
supporting information; experimental part
p. 831 - 833
(2009/05/07)
-
- Ester derivatives as phosphodiesterase inhibitors
-
The invention relates to inhibitors of the phosphodiesterase 4 (PDE4) enzyme. More particularly, the invention relates to compounds that are new ester derivatives, methods of preparing such compounds, compositions containing them and therapeutic use thereof
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-
Page/Page column 16
(2009/07/10)
-
- Expedient routes to valuable bromo-5,6-dimethoxyindole building blocks
-
The synthesis of 3-, 4-, 7-bromo and 4,7-dibrominated 5,6-dihydroxyindole (DHI) and 5,6-dihydroxyindole-2-carboxylic acid (DHICA) derivatives is reported. Hemetsberger and Bartoli indole syntheses were investigated and expedient routes to the desired compounds were developed. These indoles are valuable substrates for elaboration using transition metal-mediated cross-coupling chemistry.
- Huleatt, Paul B.,Choo, Sze Shiong,Chua, Sheena,Chai, Christina L.L.
-
p. 5309 - 5311
(2008/12/22)
-
- Synthesis of multi-substituted dibenzo[b,d]furan
-
(Chemical Equation Presented) The synthesis of multi-substituted dibenzo[b,d]furan derivatives 7a-b and 11a-b from readily available starting materials is described. These compounds are important intermediates for synthesis of molecules having wide therap
- Gajera, Jitendra M.,Gopalan, Balasubramanian,Yadav, Pravin S.,Patil, Sandip D.,Gharat, Laxmikant A.
-
p. 797 - 801
(2008/09/20)
-
- A concise first total synthesis of narceine imide
-
A concise and efficient total synthesis of alkaloid narceine imide is disclosed. The key steps are based upon the sequential construction of the isoindolinone template followed by metalation and coupling with an isoquinolinium salt. Subsequent E1cb elimin
- Lamblin, Marc,Couture, Axel,Deniau, Eric,Grandclaudon, Pierre
-
p. 1466 - 1471
(2008/01/06)
-
- The synthesis of a combretastatin A-4 based library and discovery of new cooperative ortho-effects in Wittig reactions leading to (Z)-stilbenes
-
A synthesis of combretastatin A-4 and a small library of analogues led to the discovery of some new cooperative orthoeffects allowing (Z)-stilbenes to be prepared in high yield and diastereomeric ratio. Georg Thieme Verlag Stuttgart.
- Harrowven, David C.,Guy, Ian L.,Howell, Melanie,Packham, Graham
-
p. 2977 - 2980
(2008/03/13)
-
- Divergent enantioselective synthesis of (-)-galanthamine and (-)-morphine
-
An efficient divergent synthetic strategy for the synthesis of the opiate and amaryllidaceae alkaloids emerges by employing a Pd-catalyzed asymmetric allylic alkylation (AAA) to set the stereochemistry. Three generations of syntheses of galanthamine are discussed in detail with particular focus on the scope of the palladium-catalyzed AAA reactions and intramolecular Heck reactions. The pivotal tricyclic intermediate is available in six steps from 2-bromovanillin and the monoester of methyl 6-hydroxycyclohexene-1-carboxylate. This intermediate requires only two steps to convert to (-)-galanthamine. Using a Heck vinylation, we found that the fourth ring of codeine/morphine could be formed. The final ring formation involves a novel visible light-promoted hydroamination. Thus, six steps are required to convert the pivotal tricyclic intermediate into codeine, which has been demethylated in high yield to morphine.
- Trost, Barry M.,Tang, Weiping,Toste, F. Dean
-
p. 14785 - 14803
(2007/10/03)
-
- NOVEL TRICYCLIC COMPOUNDS USEFUL FOR THE TREATMENT OF INFLAMMATORY AND ALLERGIC DISORDERS: PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
-
The present invention relates to novel tricyclic compounds useful for the treatment of inflammatory conditions, diseases of the central nervous and insulin resistant diabetes.
- -
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- A new stereoselective approach towards the galanthamine ring system via an intramolecular Heck reaction
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We have developed a new synthetic access to the galanthamine ring structure employing a stereoselective intramolecular Heck reaction as the key step. Our route also allows for variation of the c- and d-ring sizes of galanthamine which has not been reporte
- Pilger,Westermann,Florke,Fels
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p. 1163 - 1165
(2007/10/03)
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- Compounds and pharmaceutical use thereof
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PCT No. PCT/JP97/00291 Sec. 371 Date Aug. 6, 1998 Sec. 102(e) Date Aug. 6, 1998 PCT Filed Feb. 6, 1997 PCT Pub. No. WO97/29079 PCT Pub. Date Aug. 14, 1997The compounds of the formula (I) wherein each symbol is as defined in the specification, pharmaceutically acceptable salts thereof and pharmaceutical use thereof. The Compound (I) and pharmaceutically acceptable salts thereof of the present invention selectively act on cannabinoid receptors, particularly peripheral receptors, cause less side effects on the central system, and have superior immunoregulating action, antiinflammatory action, antiallergic action and therapeutic effect on nephritis. Therefore, they are useful as cannabinoid receptor, particularly peripheral cannabinoid receptor activators and antagonists, immunoregulators, therapeutic agents for autoimmune diseases, antiinflammatory agents, antiallergic agents and therapeutic agents for nephritis.
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- A novel method for the synthesis of phenanthrenes and benzo[a]carbazoles
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The synthesis of several phenanthrenes and carbazoles utilising a novel reaction mediated by potassium t-butoxide and light through a quartz filter is described.
- De Koning, Charles B.,Michael, Joseph P.,Rousseau, Amanda L.
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p. 8725 - 8728
(2007/10/03)
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- Synthesis of the salutaridine and aporphine skeleton via palladium(0) catalyzed cyclization and S(RN)1 reaction of 2'-bromoreticulines
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The intramolecular aryl-aryl-coupling reactions of 2'-bromoreticulines are described. Their regioselectivity depends on the cyclization method. The palladium(0) catalyzed reaction of 22 leads preferentially to the salutaridine derivative 27, whilst via the photochemically induced S(RN)1 reaction of 22 the aporphine skeleton 24 is obtained.
- Wiegand,Schafer
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p. 5341 - 5350
(2007/10/02)
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- SELECTIVE MONOBROMINATION OF PHENOLS
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A method is proposed for the selective monobromination of the hydroxy derivatives of benzene with bis(dimethylacetamide)hydrogen tribromide in aprotic media as brominating agent.
- Mikhailov, V. A.,Savelova, V. A.,Rodygin, M. Yu.
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p. 1868 - 1870
(2007/10/02)
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- Studies Culminating in the Total Synthesis of (dl)-Morphine
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The development of a vinyl sulfone based strategy that resulted in the synthesis of (dl)-morphine from 2-allylcyclohexane-1,3-dione and isovanillin is detailed.
- Toth, J. E.,Hamann, P. R.,Fuchs, P. L.
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p. 4694 - 4708
(2007/10/02)
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- General Method for the Synthesis of Phthalaldehydic Acids and Phthalides from o-Bromobenzaldehydes via Ortho-Lithiated Aminoalkoxides
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A general method for the synthesis of phthalaldehydic acids and phthalides, many of which are key intermediates in natural product synthesis, has been developed. o-Bromobenzaldehydes 1a-f were first protected in situ as α-morpholinoalkoxides by reaction with lithium morpholide.Treatment of the α-morpholinoalkoxides 3a-f with n-butyllithium (to exchange bromine with lithium) followed by sequential treatment with solid CO2 and dilute acid afforded the phthalaldehydic acids 6a-f, respectively.Reduction of 6a-f with NaBH4 in EtOH furnished the phthalides 7a-f, respectively, in nearly quantitative yields.Efficient methods for the synthesis of the o-bromobenzaldehydes 1a-d, which were not readily available, are also described.
- Sinhababu, Achintya K.,Borchardt, Ronald T.
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p. 2356 - 2360
(2007/10/02)
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