- The Role of Ligand Topology in the Decomplexation of Luminescent Lanthanide Complexes by Dipicolinic Acid
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In this study, we present the aqueous solution behavior of two luminescent lanthanide antenna complexes (Eu3+?1, Dy3+?9) with different ligand topologies in the presence of dipicolinic acid (DPA, pyridine-2,6-dicarboxylic acid). Macrocyclic (1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acid, DO3A, 9) and acyclic (1,4,7-triazaheptane-1,1,7,7-tetraacetic acid, DTTA, 1) ligands have been selected to form a ratiometric pair in which Dy3+?9 acts as a reference and Eu3+?1 acts as a probe for the recognition of DPA. The pair of luminescent complexes in water reveals the capability to work as a DPA luminescent sensor. The change of emission intensity of Eu3+ indicates the occurrence of a new sensitization path for the lanthanide cation through excitation of DPA. NMR evidence implies the presence of free 1 and mass spectrometry shows the formation of emitting [EuDPA2]? as a result of a ligand exchange reaction.
- Mian, Federica,Bottaro, Gregorio,Seraglia, Roberta,Cavazzini, Marco,Quici, Silvio,Armelao, Lidia
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Read Online
- Synthesis of the Core Structure of Palhinine A
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We present a strategy to the core structure of the alkaloid palhinine A passing through a 2,5-difunctionalized cyclohexenone. This enone was prepared by a domino Michael/aldol condensation sequence. An allylation reaction on the cyclohexenone followed by
- Gaugele, Dominik,Maier, Martin E.
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Read Online
- A Chiral Copper Catalyzed Site-Selective O-Alkylation of Carbohydrates
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Highly regioselective alkylation of sugar hydroxyl groups has always been an important challenge in carbohydrate chemistry, especially for the selective alkylation of trans diols, there is no direct and efficient catalytic method so far. A chiral copper c
- Ren, Bo,Wang, Jiaxi,Zhang, Mengyao,Chen, Yue,Zhao, Wei
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supporting information
p. 665 - 670
(2021/12/02)
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- Total stereocontrolled synthesis of a novel pyrrolizidine iminosugar
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Herein we describe a versatile approach to the pyrrolizidine alkaloids skeleton by tailoring our original strategy already used for the pyrrolidine iminosugars synthesis. The key steps are the regio- and stereoselective azidolysis of the suitable chiral v
- De Angelis, Martina,Primitivo, Ludovica,Lizzio, Federica,Agostinelli, Sonia,Sappino, Carla,Ben Romdan, Ilaria,Bonanni, Luciano,D'Annibale, Andrea,Antonioletti, Roberto,Ricelli, Alessandra,Righi, Giuliana
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- Composition for controlling pine wood nematode containing benzyloxyalcohol
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The present invention relates to a composition for controlling pine nematode comprising a benzyloxyalcohol compound and a method for controlling pine nematode using the same.
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Paragraph 0055-0056
(2021/06/15)
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- Employing in vitro metabolism to guide design of F-labelled PET probes of novel α-synuclein binding bifunctional compounds
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A challenge in the development of novel 18F-labelled positron emission tomography (PET) imaging probes is identification of metabolically stable sites to incorporate the 18F radioisotope. Metabolic loss of 18F from PET probes in vivo can lead to misleading biodistribution data as displaced 18F can accumulate in various tissues. In this study we report on in vitro hepatic microsomal metabolism of novel caffeine containing bifunctional compounds (C8-6-I, C8-6-N, C8-6-C8) that can prevent in vitro aggregation of α-synuclein, which is associated with the pathophysiology of Parkinson’s disease. The metabolic profile obtained guided us to synthesize stable isotope 19F-labelled analogues in which the fluorine was introduced at the metabolically stable N7 of the caffeine moiety. An in vitro hepatic microsomal metabolism study of the 19F-labelled analogues resulted in similar metabolites to the unlabelled compounds and demonstrated that the fluorine was metabolically stable, suggesting that these analogues are appropriate PET imaging probes. This straightforward in vitro strategy is valuable for avoiding costly stability failures when designing radiolabelled compounds for PET imaging.
- Aigbogun, Omozojie P.,Allen, Kevin J. H,Krol, Ed S.,Lee, Jeremy S.,Nwabufo, Chukwunonso K.,Owens, Madeline N.,Phenix, Christopher P.
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supporting information
p. 885 - 900
(2021/07/09)
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- Nematicidal activity of benzyloxyalkanols against pine wood nematode
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Pine wilt disease (PWD) is caused by the pine wood nematode (PWN; Bursaphelenchus xylophilus) and causes severe environmental damage to global pine forest ecosystems. The current strategies used to control PWN are mainly chemical treatments. However, the continuous use of these reagents could result in the development of pesticide-resistant nematodes. Therefore, the present study was undertaken to find potential alternatives to the currently used PWN control agents abamectin and emamectin. Benzyloxyalkanols (BzOROH; R = C2–C9 ) were synthesized and the nematicidal activity of the synthetic compounds was investigated. Enzymatic inhibitory assays (acetylcholinesterase (AChE) and glutathione S-transferase (GST)) were performed with BzOC8OH and BzOC9OH to understand their mode of action. The benzyloxyalkanols showed higher nematicidal activity than did benzyl alcohol. Among the tested BzOROHs, BzC8OH and BzC9OH showed the strongest nematicidal activity. The LD50 values of BzC8OH and BzC9OH were 246.1 and 158.0 ppm, respectively. No enzyme inhibitory activity was observed for BzC8OH and BzC9OH. The results suggested that benzyloxyalcohols could be an alternative nematicidal agent.
- Kim, Junheon,Lee, Su Jin,Park, Joon Oh,Yoon, Kyungjae Andrew
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- Total Synthesis of the Diterpene Waihoensene
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A racemic and scalable enantioselective total synthesis of (+)-waihoensene was accomplished. (+)-Waihoensene belongs to the diterpene natural product family, and it features an angular triquinane substructure motif. Its tetracyclic [6.5.5.5]backbone is al
- Rosenbaum, Lisa-Catherine,H?fner, Maximilian,Gaich, Tanja
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supporting information
p. 2939 - 2942
(2020/12/15)
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- Gold-Catalyzed Formal Hexadehydro-Diels-Alder/Carboalkoxylation Reaction Cascades
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A dual gold-catalyzed hexadehydro-Diels-Alder/carboalkoxylation cascade reaction is reported. In this transformation, the gold catalyst participated in the hexadehydro-Diels-Alder step, switching the mechanism from a radical type to a cationic one, and then the catalyst activated the resulting aryne to form an ortho-Au phenyl cation species, which underwent a carboalkoxylation rearrangement rather than the expected aryne-ene reaction.
- Wang, Hong-Fa,Guo, Lin-Na,Fan, Zhi-Bo,Tang, Tian-Hua,Zi, Weiwei
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supporting information
p. 2676 - 2681
(2021/04/12)
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- Design, Synthesis, and Evaluation of VHL-Based EZH2 Degraders to Enhance Therapeutic Activity against Lymphoma
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Traditional EZH2 inhibitors are developed to suppress the enzymatic methylation activity, and they may have therapeutic limitations due to the nonenzymatic functions of EZH2 in cancer development. Here, we report proteolysis-target chimera (PROTAC)-based EZH2 degraders to target the whole EZH2 in lymphoma. Two series of EZH2 degraders were designed and synthesized to hijack E3 ligase systems containing either von Hippel-Lindau (VHL) or cereblon (CRBN), and some VHL-based compounds were able to mediate EZH2 degradation. Two best degraders, YM181 and YM281, induced robust cell viability inhibition in diffuse large B-cell lymphoma (DLBCL) and other subtypes of lymphomas, outperforming a clinically used EZH2 inhibitor EPZ6438 (tazemetostat) that was only effective against DLBCL. The EZH2 degraders displayed promising antitumor activities in lymphoma xenografts and patient-derived primary lymphoma cells. Our study demonstrates that EZH2 degraders have better therapeutic activity than EZH2 inhibitors, which may provide a potential anticancer strategy to treat lymphoma.
- Tu, Yalin,Sun, Yameng,Qiao, Shuang,Luo, Yao,Liu, Panpan,Jiang, Zhong-Xing,Hu, Yumin,Wang, Zifeng,Huang, Peng,Wen, Shijun
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p. 10167 - 10184
(2021/07/26)
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- Small molecule compound based on EZH2 protein degradation, and application thereof
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The invention discloses a series of small molecule compounds capable of selectively degrading EZH2 protein, and application thereof. The compounds can be prepared into proper pharmaceutical dosage forms for EZH2-mediated related tumor treatment.
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Paragraph 0031; 0049-0052
(2021/08/07)
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- Regio/site-selective alkylation of substrates containing a: Cis -, 1,2- or 1,3-diol with ferric chloride and dipivaloylmethane as the catalytic system
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In this study, we reported the regio/site-selective alkylation of substrates containing a cis-, 1,2- or 1,3-diol with FeCl3 as a key catalyst. A catalytic system consisting of FeCl3 (0.01-0.1 equiv.) and dipivaloylmethane (FeCl3/dipivaloylmethane = 1/2) was used to catalyze the alkylation in the presence of a base. The produced selectivities and isolated yields were similar to those obtained by methods using the same amount of FeL3 (L = acylacetone ligand) as the catalyst in most cases. The previously reported FeL3 catalysts for alkylation are not commercially available and have to be synthesized prior to use. In contrast, FeCl3 and dipivaloylmethane (Hdipm) are very common and inexpensive nontoxic reagents in the lab, thereby making the method much greener and easier to handle. Mechanism studies confirmed for the first time that FeCl3 initially reacts with two equivalents of Hdipm to form [Fe(dipm)3] in the presence of a base in acetonitrile, followed by the formation of a five or six-membered ring intermediate between [Fe(dipm)3] and two hydroxyl groups of the substrate. A subsequent reaction between the cyclic intermediate and the alkylating agent results in selective alkylation of the substrate.
- Lv, Jian,Liu, Yu,Zhu, Jia-Jia,Zou, Dapeng,Dong, Hai
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supporting information
p. 1139 - 1144
(2020/03/11)
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- ANANDAMIDE COMPOUNDS
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The present application provides anandamide and 2-arachidonyl glycerol compounds useful for treating a disease or disorder in a subject in need thereof. Pharmaceutical compositions comprising the compounds and methods of treating diseases or disorders are also provided.
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Page/Page column 39-40
(2020/07/25)
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- Antibody drug conjugate, intermediate, preparation method, pharmaceutical composition and uses thereof
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Disclosed are an antibody drug conjugate IB, which uses ether linkages for connection, and improves the water solubility, stability and cytotoxicity in vivo and in intro, and an intermediate, a pharmaceutical composition, and uses of the antibody drug conjugate. The antibody drug conjugate has simple synthetic steps and a high yield.
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Page/Page column 170; 172
(2019/11/11)
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- Trogoderma granarium sex pheromone and preparation method thereof
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The invention discloses trogoderma granarium sex pheromone and a preparation method thereof. The preparation method comprises the following steps: enabling (R)-2-methylbutanol to react with 5-sulfydryl-1-phenyltetrazole Mitsnobu to obtain A; enabling A to react with peroxy acid to obtain B; enabling 1,3-propanediol to react with benzyl chloride under an alkaline condition to obtain C; oxidizing Cto obtain a compound D; enabling B to react with D and hexamethyldisilamine lithium salt to obtain E; catalytically hydrogenating E by virtue of palladium to obtain F; enabling F, iodine, tertiary phosphine and imidazole to obtain G; obtaining H by using 1,8-octylene glycol and benzyl chloride and alkali; oxidizing H to obtain I; obtaining J by using I, carbon tetrabromide and triphenylphosphine Corey-Fush; obtaining K by using J and strong alkali; obtaining L by using K and G and alkali; obtaining M by using L, ethyl mercaptan and boron trifluoride diethyl etherate solution; catalytically hydrogenating M by virtue of metal to obtain N; and oxidizing N to obtain a target product, wherein a chemical name of the target product is (R,Z)-14-methylhexadeca-8-ene-1-aldehyde, thus obtaining the trogoderma granarium sex pheromone. The preparation method disclosed by the invention is low in cost and high in yield.
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Paragraph 0041; 0056; 0059; 0060; 0061
(2019/02/17)
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- P-Methylbenzyl Group: Oxidative Removal and Orthogonal Alcohol Deprotection
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We describe the practical removal of p-methylbenzyl (MBn) protections of alcohols by treatment with 2,3-dichloro-5,6-dicyano-p-benzoquinone. When a molecule bears benzyl and MBn groups, the oxidant selectively removes the latter groups. Further, the MBn groups tolerate ceric ammonium nitrate, resulting in chemoselective removal of the p-methoxybenzyl group in the presence of the MBn groups. These orthogonal alcohol deprotections would provide novel synthetic strategies of organic compounds.
- Ikeuchi, Kazutada,Murasawa, Kentaro,Ohara, Kenya,Yamada, Hidetoshi
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supporting information
p. 6638 - 6642
(2019/09/30)
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- Practical preparation of diphenylmethyl ethers from 2-diphenylmethoxypyridine using catalytic iron(III) chloride
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A novel facile synthetic method for producing diphenylmethyl (DPM) ethers from 2-diphenylmethoxypyridine was developed. A variety of DPM ethers was successfully achieved with high yield via treatment of alcohols with 2-diphenylmethoxypyridine in the presence of catalytic FeCl3. The procedure is a practical and efficient synthetic procedure to protect various alcohols, and it can be applied to prepare bioactive compounds.
- Tran, Van Hieu,La, Minh Thanh,Kim, Hee-Kwon
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p. 6221 - 6228
(2019/07/04)
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- Chemoselective oxidation and deprotection of para-methoxybenzylic position with (diacetoxyiodo)benzene in acetic-trifluoroacetic acid
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(Diacetoxyiodo)benzene in the presence of acetic–trifluoroacetic acid in THF has been developed for the chemoselective para-methoxybenzylic C–H bond oxidation to provide aryl carbonyl compounds at room temperature. The reaction condition is also applicable for the chemoselective deprotection of para-methoxybenzyl (PMB) ether in the presence of benzyl ether.
- Lin, Chun-Yu,Yang, Ping-Shin,Chou, Pang-Yu,Ong, Chi Wi
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p. 365 - 367
(2018/01/01)
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- Enantioselective Radical Cyclization for Construction of 5-Membered Ring Structures by Metalloradical C-H Alkylation
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Radical cyclization represents a powerful strategy for construction of ring structures. Traditional radical cyclization, which is based on radical addition as the key step, necessitates the use of unsaturated substrates. Guided by the concept of metalloradical catalysis, a different mode of radical cyclization that can employ saturated C-H substrates is demonstrated through the development of a Co(II)-based system for catalytic activation of aliphatic diazo compounds for enantioselective radical alkylation of various C(sp3)-H bonds. It allows for efficient construction of chiral pyrrolidines and other valuable 5-membered cyclic compounds. This alternative strategy of radical cyclization provides a new retrosynthetic paradigm to prepare five-membered cyclic molecules from readily available open-chain aldehydes through the union of C-H and C=O elements for C-C bond formation.
- Wang, Yong,Wen, Xin,Cui, Xin,Zhang, X. Peter
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supporting information
p. 4792 - 4796
(2018/04/17)
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- Asymmetric Syntheses of (2 R,3 S)-3-Hydroxyproline and (2 S,3 S)-3-Hydroxyproline
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Two synthetic routes have been developed for the asymmetric syntheses of (2R,3S)- and (2S,3S)-3-hydroxyproline. The key synthetic step in each of these strategies is the conversion of protected α,δ-dihydroxy-β-amino esters (either 2,3-anti- or 2,3-syn-configured) into β,δ-dihydroxy-α-amino esters (protected forms thereof), via the intermediacy of the corresponding aziridinium ions. The products of these stereospecific rearrangements were then cyclized and deprotected to afford (2R,3S)-3-hydroxyproline and (2S,3S)-3-hydroxyproline as single diastereoisomers (>99:1 dr) in >26% overall yield.
- Davies, Stephen G.,Fletcher, Ai M.,Linsdall, Sean M.,Roberts, Paul M.,Thomson, James E.
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supporting information
p. 4135 - 4139
(2018/07/15)
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- Piers' borane-mediated hydrosilylation of epoxides and cyclic ethers
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We report the first diarylborane-catalysed hydrosilylation of epoxides and cyclic ethers. Mechanistic studies on the in situ generated Piers' borane (C6F5)2BH with hydrosilanes in the presence of an epoxide revealed that an alkyloxy(diaryl)borane (C6F5)2BOR is readily formed as a catalytically competent species for the outer-sphere hydrosilylation of epoxides and cyclic ethers.
- Zhang, Jianbo,Park, Sehoon,Chang, Sukbok
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supporting information
p. 7243 - 7246
(2018/07/05)
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- A formal anti-Markovnikov hydroalkoxylation of allylic alcohols with a ruthenium catalyst
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Hydroalkoxylation of C-C double bonds was achieved through the use of a ruthenium catalyst. The reaction of allylic alcohols with nucleophilic alcohols was carried out in the presence of a ruthenium catalyst prepared by RuClH(CO)(PPh3)3 and 2,6-bis(n-butyliminomethyl)-4-(piperidin-1-yl)pyridine under mild reaction conditions to afford the corresponding γ-alkoxypropanols in good yield.
- Nakamura, Yushi,Ohta, Tetsuo,Oe, Yohei
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supporting information
p. 288 - 291
(2018/02/14)
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- Regioselective alkylation of carbohydrates and diols: A cheaper iron catalyst, new applications and mechanism
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As an extension of our previous research on the regioselective protection of carbohydrates and diols, we developed an iron catalyst, Fe(dibm)3 (dibm = diisobutyrylmethane), which has an unusually broad catalytic scope in the selective monoalkyl
- Ren, Bo,Yan, Ningning,Gan, Lu
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p. 46257 - 46262
(2017/10/11)
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- Visible-light-mediated achmatowicz rearrangement
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Visible-light-mediated photoredox catalysis is a viable method to access highly reactive intermediates from cheap, readily available, and shelfstable reagents to perform clean chemical transformations. Here, we report the first photoredox-catalyzed Achmatowicz reaction of furfuryl alcohol derivatives to produce functionalized dihydropyranones while only forming easily separable NaHSO4 as a byproduct. The water solubility of the byproduct facilitates direct Boc-protection of the resulting hemiacetal without the need for column purification. The reaction is very robust and permits the use of various aqueous solutions and light sources including sunlight.
- Plutschack, Matthew B.,Seeberger, Peter H.,Gilmore, Kerry
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supporting information
p. 30 - 33
(2017/11/28)
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- 2-AMINO-1,3,4-THIADIAZINE AND 2-AMINO-1,3,4-OXADIAZINE BASED ANTIFUNGAL AGENTS
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The invention provides a compound which is a diazine of formula (I) or a tautomer thereof, or a pharmaceutically acceptable salt thereof, for use as an antifungal agent: (I) wherein X, N', C', A and E are as defined herein. The invention also provides a compound of Formula (I) as defined herein.
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Page/Page column 111; 112
(2017/02/09)
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- An Iron(III) Catalyst with Unusually Broad Substrate Scope in Regioselective Alkylation of Diols and Polyols
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In this study, [Fe(dibm)3] (dibm=diisobutyrylmethane) is shown to have unusually broad scope as a catalyst for the selective monoalkylation of a diverse set of 1,2- and 1,3-diol-containing structures. The mechanism is proposed to proceed via a cyclic dioxolane-type intermediate, formed between the iron(III) species and two adjacent hydroxyl groups. This approach represents the first transition-metal catalysts that are able to replace stoichiometric amounts of organotin reagents in regioselective alkylation. The reactions generally lead to very high regioselectivities and high yields, on par with, or better than, previous methods used for regioselective alkylation.
- Ren, Bo,Ramstr?m, Olof,Zhang, Qiang,Ge, Jiantao,Dong, Hai
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p. 2481 - 2486
(2016/02/12)
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- A concise stereoselective synthesis of (+)-1-deoxy-6-epi-castanospermine
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A concise stereoselective synthesis of (+)-1-deoxy-6-epi-castanospermine has been developed through stereoselective approach from the chiral precursor R-Glycidol. The key steps in the synthesis involve Grignard reaction through Weinreb amide, followed by Sharpless dihydroxylation and stereoselective reduction of imine assigned the required stereochemical feature of indolizidine azasugar (+)-1-deoxy-6-epi-castanospermine.
- Gajare, Vikas S.,Khobare, Sandip R.,Datrika, Rajender,Reddy, K. Srinivasa,Rajana, Nagaraju,Babu, B. Kishore,Rao, B. Venkateswara,Syam Kumar
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supporting information
p. 1486 - 1488
(2016/03/12)
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- Effect of Partially Fluorinated N-Alkyl-Substituted Piperidine-2-carboxamides on Pharmacologically Relevant Properties
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The modulation of pharmacologically relevant properties of N-alkyl-piperidine-2-carboxamides was studied by selective introduction of 1–3 fluorine atoms into the n-propyl and n-butyl side chains of the local anesthetics ropivacaine and levobupivacaine. The basicity modulation by nearby fluorine substituents is essentially additive and exhibits an exponential attenuation as a function of topological distance between fluorine and the basic center. The intrinsic lipophilicity of the neutral piperidine derivatives displays the characteristic response noted for partially fluorinated alkyl groups attached to neutral heteroaryl systems. However, basicity decrease by nearby fluorine substituents affects lipophilicities at neutral pH, so that all partially fluorinated derivatives are of similar or higher lipophilicity than their non-fluorinated parents. Aqueous solubilities were found to correlate inversely with lipophilicity with a significant contribution from crystal packing energies, as indicated by variations in melting point temperatures. All fluorinated derivatives were found to be somewhat more readily oxidized in human liver microsomes, the rates of degradation correlating with increasing lipophilicity. Because the piperidine-2-carboxamide core is chiral, pairs with enantiomeric N-alkyl groups are diastereomeric. While little response to such stereoisomerism was observed for basicity or lipophilicity, more pronounced variations were observed for melting point temperatures and oxidative degradation.
- Vorberg, Raffael,Trapp, Nils,Zimmerli, Daniel,Wagner, Bj?rn,Fischer, Holger,Kratochwil, Nicole A.,Kansy, Manfred,Carreira, Erick M.,Müller, Klaus
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p. 2216 - 2239
(2016/10/19)
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- Synthesis of the Acyclic Carbon Skeleton of Filipin III
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The synthesis of the carbon skeleton of filipin III, a polyenic macrolactone possessing 11 stereogenic centers, was achieved using a convergent strategy with the longest linear sequence of 19 steps starting from hexanal. Construction of the polyene was re
- Brun, Elodie,Bellosta, Véronique,Cossy, Janine
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p. 8206 - 8221
(2016/09/28)
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- Pharmacophore elucidation of phosphoiodyn A - Potent and selective peroxisome proliferator-activated receptor β/δ agonists with neuroprotective activity
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We report the pharmacophore of the peroxisome proliferator-activated receptor δ (PPARδ) agonist natural product phosphoiodyn A is the phosphonate core. Synthesis of simplified phosphonate esters 13 and 15 provide structurally novel, highly selective and potent PPARδ agonists (EC50 = 78 and 112 nM, respectively). Further, both compounds demonstrate significant neuroprotective activity in an in vitro cellular model indicating that phosphonates may be an effective novel scaffold for the design of therapeutics for the treatment of neurodegenerative disorders.
- Kinarivala, Nihar,Suh, Ji Ho,Botros, Mina,Webb, Paul,Trippier, Paul C.
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supporting information
p. 1889 - 1893
(2016/04/05)
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- C-20 STEROID COMPOUNDS, COMPOSITIONS AND USES THEREOF TO TREAT TRAUMATIC BRAIN INJURY (TBI), INCLUDING CONCUSSIONS
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The present invention relates to C-20 steroid compounds, compositions and methods of use thereof to treat, minimize and/or prevent traumatic brain injury (TBI), including severe TBI, moderate TBI and mild TBI, including concussions.
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Page/Page column 38; 53; 54
(2016/04/09)
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- C-20 STEROID COMPOUNDS, COMPOSITIONS, AND USES THEREOF TO TREAT TRAUMATIC BRAIN INJURY (TBI), INCLUDING CONCUSSIONS
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The present invention relates to C-20 steroid compounds, compositions and methods of use thereof to treat, minimize and/or prevent traumatic brain injury (TBI), including severe TBI, moderate TBI and mild TBI, including concussions.
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Page/Page column 64; 65
(2017/01/09)
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- COMPOUND WITH BRANCHING ALKYL CHAINS, METHOD FOR PREPARING THE SAME, AND USE THEREOF IN PHOTOELECTRIC DEVICE
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The invention discloses a compound having branching alkyl chains, the method for preparing the same and use thereof in photoelectric devices. By applying the branching alkyl chains as the solubilizing group to the preparation of organic conjugated molecules (for example, organic conjugated polymers), the number of methylenes between the resultant alky side chains and the backbone, i.e., m>1, which can effectively reduce the effect of the alkyl chains on the backbone π-π stacking, thereby ensuring the solubility of the organic conjugated molecule while greatly increasing the mobility of their carriers. It is suitable for an organic semiconductor material in photoelectric devices such as organic solar cells, organic light emitting diodes and organic field effect transistors, etc.
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Paragraph 0109; 0110
(2016/03/05)
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- Total Synthesis of (+)-Cryptocaryol A Using a Prins Cyclization/Reductive Cleavage Sequence
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The total synthesis of (+)-cryptocaryol A was achieved in 20 steps from (R)-glycidol. The key steps were a Prins cyclization/reductive cleavage sequence to construct the C5-C11 polyol fragment, a diastereoselective aldol reaction to control the stereogeni
- Brun, Elodie,Bellosta, Véronique,Cossy, Janine
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p. 8668 - 8676
(2015/09/15)
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- Stereoselective synthesis of two highly potent 5-oxo-ETE receptor antagonists
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Enantioselective synthesis of highly potent 5-oxo-ETE receptor antagonists 5a and 6a with a high level of enantiomeric purity is described. The main feature of this work is the simple and efficient synthesis of the bi-functionalized 3-(S)-methyl-pentanedi
- Nagendra Reddy, Chintam,Ye, Qiuji,Chourey, Shishir,Gravel, Sylvie,Powell, William S.,Rokach, Joshua
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p. 6896 - 6899
(2015/11/27)
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- Oxidative asymmetric umpolung alkylation of Evans' β-ketoimides using dialkylzinc nucleophiles
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Umpolung alkylation of Evans' auxiliary substituted β-ketoimides affords the diastereomerically pure products in yields ranging from 40 to 80%. The reaction itself proceeds with diastereoselectivities between 3:1 and 18:1. Dialkylzinc serves as the nucleo
- Targel, Tom A.,Kumar, Jayprakash N.,Shneider, O. Svetlana,Bar, Sukanta,Fridman, Natalia,Maximenko, Shimon,Szpilman, Alex M.
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supporting information
p. 2546 - 2549
(2015/04/14)
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- SYNTHESIS OF ENT-PROGESTERONE AND INTERMEDIATES THEREOF
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The present invention relates to the synthesis of ent-progesterone and intermediates thereof.
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Paragraph 0083; 0176
(2015/07/02)
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- Synthesis of Silodosin by Copper-Catalysed C-C Arylation
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The synthesis of silodosin, an antidysuria drug, has been accomplished starting from commercially available indoline. The synthetic strategy is based on CuI-catalysed C-C arylation, regioselective cyanation, and diastereoselective reductive amination. The enantiopure compound was obtained by selective crystallisation of a diasteroisomeric mixture.
- Calogero, Francesco,Allegrini, Pietro,Attolino, Emanuele,Passarella, Daniele
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p. 6011 - 6016
(2015/09/22)
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- METHOD OF PREPARING ADRENERGIC ANTAGONIST
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PROBLEM TO BE SOLVED: To provide a method of preparing a selective adrenergic antagonist for an α-1A-adrenergic receptor and a useful intermediate thereof. SOLUTION: This invention provides an advantageous production method of a novel intermediate particularly fitted for production on an industrial scale, regarding the production of a pharmaceutical compound represented by formula (I), silodosin: 1-(3-hydroxypropyl)-5-[(2R)-({2-[2-[2-(2,2,2-trifluoroethoxy) phenoxy]ethyl}amino) propyl]indoline-7-carboxamide, or salt thereof. COPYRIGHT: (C)2015,JPOandINPIT
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Paragraph 0115
(2016/10/10)
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- Sustainable, mild and efficient p-methoxybenzyl ether deprotections utilizing catalytic DDQ
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A procedure for the selective deprotection of p-methoxybenzyl ethers using catalytic amounts of DDQ and of sodium nitrite, with oxygen as the terminal oxidant, is reported.
- Walsh, Katie,Sneddon, Helen F.,Moody, Christopher J.
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p. 7380 - 7387
(2017/09/13)
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- A general and enantioselective approach to pentoses: A rapid synthesis of PSI-6130, the nucleoside core of sofosbuvir
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An efficient route towards biologically relevant pentose derivatives is described. The de novo synthetic strategy features an enantioselective α-oxidation reaction enabled by a chiral amine in conjunction with copper(II) catalysis. A subsequent Mukaiyama aldol coupling allows for the incorporation of a wide array of modular two-carbon fragments. Lactone intermediates accessed via this route provide a useful platform for elaboration, as demonstrated by the preparation of a variety of C-nucleosides and fluorinated pentoses. Finally, this work has facilitated expedient syntheses of pharmaceutically active compounds currently in clinical use.
- Peifer, Manuel,Berger, Rapha?lle,Shurtleff, Valerie W.,Conrad, Jay C.,Macmillan, David W. C.
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supporting information
p. 5900 - 5903
(2014/05/20)
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- Synthetic studies on lycopodine: Construction of hexahydrojulolidine core by intramolecular Mannich reaction
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The tricyclic core skeleton of lycopodine was constructed by the intramolecular Mannich reaction of a 12-membered cyclic amine. The concise assembly of the macrocyclic intermediate was executed by the sequential inter- and intramolecular N-alkylation of a
- Sato, Takanao,Ueda, Hirofumi,Tokuyama, Hidetoshi
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supporting information
p. 7177 - 7180
(2015/01/09)
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- Synthesis of four diastereomers and structural revision of tetradenolide
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Four diastereomers of tetradenolide, a cytotoxic α-pyrone isolated from Tetradenia riparia, were synthesized stereoselectively using the Z-selective Horner-Emmons reaction followed by acid catalyzed lactonization. Making comparison of the 1H an
- Tokuda, Maki,Kurogome, Yuji,Katoh, Rieko,Nohara, Yukie,Hattori, Yasunao,Makabe, Hidefumi
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p. 4189 - 4192
(2014/07/22)
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- Simple stereoselective synthesis of unsaturated lactone intermediates and their conversion into natural dihydropyranones and their enantiomers#
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The stereoselective synthesis of the unsaturated lactone intermediates, (S) - and (R)-2-(6-oxo-3, 6-dihydro-2Hpyran-2-yl) acetaldehydes has been accomplished from propane 1,3 diol employing Maruoka asymmetric allylation and ring closing metathesis reaction. The intermediates were converted into two natural dihydropyranones, 6 (R)-4-oxopent-2-enyl 5,6-dihydro-2H-pyran-2-one and (R)- rugulactone and their enantiomers through Wittig olefination.
- Shinde, Digambar Balaji,Kanth, Boddu Shashi,Satyakumar, Avula,Kamble,Das, Biswanath
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p. 317 - 323
(2013/07/26)
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- Enantioselective synthesis of the natural product (S)-rugulactone
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A simple and efficient enantioselective synthesis of (6S)-5,6-dihydro-6- [(2E)-4-oxo-6-phenylhex-2-en-1-yl]-2H-pyran-2-one (=(S)-rugulactone) has been accomplished. The synthesis started from commercially available propane-1,3-diol and ethyl 3-phenylpropa
- Nagaiah, Burea,Narsaiah, Akkirala Venkat
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p. 1948 - 1954
(2013/11/06)
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- NiCl2·6H2O/NaBH4 in methanol: A mild and efficient strategy for chemoselective deallylation/debenzylation of aryl ethers
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Deprotection of allyl/benzyl aryl ethers was achieved chemoselectively. The mild and inexpensive reagent combination of NiCl2·6H 2O/NaBH4 in methanol afforded the products in high yields, within a reaction time of 5-10 min.
- Chouhan, Mangilal,Kumar, Kapil,Sharma, Ratnesh,Grover, Vikas,Nair, Vipin A.
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supporting information
p. 4540 - 4543
(2013/08/23)
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- The first stereoselective total synthesis of (Z)-cryptomoscatone D2, a natural G2 checkpoint inhibitor
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The first stereoselective synthesis of (Z)-cryptomoscatone D2, a naturally occurring G2 checkpoint inhibitor, was accomplished using propane-1,3-diol as the starting material. The Maruoka asymmetric allylation, ring closing metathesis and the h
- Reddy, Gandolla Chinna,Balasubramanyam, Penagaluri,Salvanna,Reddy, Thummala Sreenivasulu,Das, Biswanath
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scheme or table
p. 2415 - 2417
(2012/05/05)
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- Concise total synthesis of dihydrocorynanthenol, protoemetinol, protoemetine, 3-epi-protoemetinol and emetine
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A concise asymmetric assembly of secologanine tryptamine and dopamine alkaloids by means of a one-pot three-component cascade reaction methodology is disclosed. This is demonstrated by the expeditious total syntheses of (-)-dihydrocorynanthenol, (-)-protoemetinol, (-)-protoemetine, (-)-3-epi-protoemetinol, and emetine (3-6 steps). The biomimetic synthetic strategy involved the following key steps: (i) One-pot three-component highly enantioselective catalytic Michael/Pictet-Spengler/lactamization cascade reactions; (ii) One-pot tandem Swern oxidation/Wittig sequences; (iii) One-pot tandem hydrogenation sequences. Copyright
- Lin, Shuangzheng,Deiana, Luca,Tseggai, Abrehet,Cordova, Armando
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supporting information; experimental part
p. 398 - 408
(2012/02/16)
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- Synthetic studies toward potent cytostatic macrolide bryostatin: An expedient synthesis of C1-C10 fragment
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The stereoselective synthesis of C1-C10 fragment of cytostatic macrolide bryostatin is described. Two of the three chiral centers have been established via the Sharpless kinetic resolution of racemic allylic alcohol 15 followed by regioselective reduction
- Yadav, J. S.,Aravind, S.,Kumar, G. Mahesh,Reddy, B. V. Subba
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p. 6163 - 6166,4
(2012/12/11)
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- Synthetic studies toward potent cytostatic macrolide bryostatin: An expedient synthesis of C1-C10 fragment
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The stereoselective synthesis of C1-C10 fragment of cytostatic macrolide bryostatin is described. Two of the three chiral centers have been established via the Sharpless kinetic resolution of racemic allylic alcohol 15 followed by regioselective reduction
- Yadav,Aravind,Kumar, G. Mahesh,Reddy, B.V.Subba
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p. 6163 - 6166
(2013/01/14)
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