- Solid-liquid phase transfer catalytic method for the preparation of acyclic and cyclic ketene acetals
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Solid-liquid phase transfer catalytic elimination reaction for the preparation of acyclic and cyclic ketene acetals has been developed.
- Zheng, Qi-Huang,Su, Jing
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Read Online
- A short and simple synthesis of ketene acetals
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A novel and convenient synthesis of ketene acetals 1a-g in moderate to good yield has been achieved starting from acetonitrile by using Pinner reaction approach.
- Argade,Joglekar
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Read Online
- Photoinduced Cross-Coupling of Aryl Iodides with Alkenes
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A protocol for photoinduced cross-coupling of aryl iodides having polar π-functional groups or elongated π-conjugation with alkenes has been developed. The radical cascade mechanism involving generation of aryl radicals via C-I bond homolysis of photoexcited aryl iodides and their subsequent addition to alkenes is proposed. The method enables iodide-selective cross-coupling over other halogen leaving groups with functional group compatibility on both arene and alkene motifs.
- Liu, Yuliang,Li, Haoyu,Chiba, Shunsuke
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supporting information
p. 427 - 432
(2021/01/26)
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- CYCLOBUTYL NUCLEOSIDE ANALOGS AS ANTI-VIRALS
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Described herein are cyclobutyl nucleoside analogs of Formula (I), pharmaceutical compositions that include one or more cyclobutyl nucleoside analogs and methods of using the same to treat HBV, HDV and/or HIV.
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Paragraph 0250; 0257
(2020/07/07)
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- Design, Synthesis, and Evaluation of a Series of Novel Benzocyclobutene Derivatives as General Anesthetics
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In the present work, a series of structurally novel benzocyclobutene derivatives were identified as general anesthetics through the loss of righting reflex (LORR) experiment on mice. Our initial efforts found compound 1a with a fused four-membered ring on the 2,3-position of the phenol ring could significantly improve the safety profile. Further SAR study revealed that small hydrogen bond acceptor (HBA) groups are optimal for good ED50 along with much broader therapeutic windows, such as compounds 16b and 17. Present work demonstrates the superiority of this novel benzocyclobutene scaffold.
- Zhang, Chen,Li, Fangqiong,Yu, Yan,Huang, Anbang,He, Ping,Lei, Ming,Wang, Jianmin,Huang, Longbin,Liu, Zhenhong,Liu, Jianyu,Wei, Yonggang
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supporting information
p. 3618 - 3625
(2017/05/19)
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- As neuraminidase inhibitor compound and its use in medicine
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The invention discloses a compound serving as a neuraminidase inhibitor and application of the compound in a medicament and relates to a four-membered ring compound, application of the four-membered ring compound in a medicament and especially application of the four-membered ring compound in the medicament for preventing, treating, curing or alleviating an influenza virus disease. The compound has good action of inhibiting neuraminidase of influenza viruses. Particularly, the invention relates to a compound shown in a general formula (I) or a stereoisomer, a geometric isomer, a tautomer, nitrogen oxide, a hydrate, a solvate, a metabolite and a pharmaceuticallyacceptable salt or prodrug of the compound shown in the general formula (I), wherein all the variables are defined as a specification. The invention also relates to a medicament composition containing the compound shown in the general formula (I) and a method of treating an influenza disease by using the compound shown in the general formula (I) or the medicament composition of the compound. The formula is shown in the specification.
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Paragraph 0179; 0182-0184
(2018/02/04)
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- Process for the synthesis of 3,4-dimethoxybicyclo[4.2.0]OCTA-1,3,5-triene-7-carbonitrile, and application in the synthesis of ivabradine and addition salts thereof with a pharmaceutically acceptable acid
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Process for the synthesis of the compound of formula (I): Application in the synthesis of ivabradine, addition salts thereof with a pharmaceutically acceptable acid and hydrates thereof.
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Page/Page column 5; 6
(2014/10/29)
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- Reaction of dimethoxycarbene with strained cyclic carbonyl compounds
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A cyclopropanone, a cyclopropenone, cyclobutanones, a cyclobutane-1,3-dione, and a cyclobutene-1,2-dione reacted with dimethoxycarbene to afford acetals of the next larger ring by formal insertion of the carbene into a C-C bond α to the carbonyl group. When either of two saturated α-ring carbons could be involved in the process, the ring expansion was selective, affording primarily the product of apparent insertion into the more substituted ring bond. With 2,3-dimethoxycyclobutene-1,2-dione, insertion occurred between the carbonyl groups and with β-propiolactone it occurred at the lactone bond. β-Propiolactam, however, reacted by insertion of the carbene into the N-H bond.
- Venneri,Warkentin
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p. 1194 - 1203
(2007/10/03)
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- Synthesis, biological activity, and molecular modeling of ribose- modified deoxyadenosine bisphosphate analogues as P2Y1 receptor ligands
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The structure-activity relationships of adenosine-3',5'-bisphosphates as P2Y1 receptor antagonists have been explored, revealing the potency- enhancing effects of the N6-methyl group and the ability to substitute the ribose moiety (Nandanan et al. J. Med. Chem. 1999, 42, 1625-1638). We have introduced constrained carbocyclic rings (to explore the role of sugar puckering), non-glycosyl bonds to the adenine moiety, and a phosphate group shift. The biological activity of each analogue at P2Y1 receptors was characterized by measuring its capacity to stimulate phospholipase C in turkey erythrocyte membranes (agonist effect) and to inhibit its stimulation elicited by 30 nM 2-methylthioadenosine-5'-diphosphate (antagonist effect). Addition of the N6-methyl group in several cases converted pure agonists to antagonists. A carbocyclic N6-methyl-2'-deoxyadenosine bisphosphate analogue was a pure P2Y1 receptor antagonist and equipotent to the ribose analogue (MRS 2179). In the series of ring-constrained methanocarba derivatives where a fused cyclopropane moiety constrained the pseudosugar ring of the nucleoside to either a Northern (N) or Southern (S) conformation, as defined in the pseudorotational cycle, the 6-NH2 (N)-analogue was a pure agonist of EC50 155 nM and 86-fold more potent than the corresponding (S)-isomer. The 2-chloro-N6-methyl-(N)-methanocarba analogue was an antagonist of IC50 51.6 nM. Thus, the ribose ring (N)-conformation appeared to be favored in recognition at P2Y1 receptors. A cyclobutyl analogue was an antagonist with IC50 of 805 nM, while morpholine ring-containing analogues were nearly inactive. Anhydrohexitol ring-modified bisphosphate derivatives displayed micromolar potency as agonists (6-NH2) or antagonists (N6-methyl). A molecular model of the energy-minimized structures of the potent antagonists suggested that the two phosphate groups may occupy common regions. The (N)- and (S)-methanocarba agonist analogues were docked into the putative binding site of the previously reported P2Y1 receptor model.
- Nandanan, Erathodiyil,Jang, Soo-Yeon,Moro, Stefano,Kim, Hea Ok,Siddiqui, Maqbool A.,Russ, Pamela,Marquez, Victor E.,Busson, Roger,Herdewijn, Piet,Harden, T. Kendall,Boyer, José L.,Jacobson, Kenneth A.
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p. 829 - 842
(2007/10/03)
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- 12-hetero substituted 6,11-ethano-6,11-dihydrobenzo (b) quinolizinium salts and compositions and method of use thereof
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1-Hetero substituted 6,11-ethano-6,11-dihydrobenzo[b]quinolizinium salts, pharmaceutical compositions containing them, and methods for the treatment or prevention of neurodegenerative disorders or neurotoxic injuries utilizing them.
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- Process for preparing ketene acetals
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The invention relates to a process for preparing ketene acetals by dehydrohalogenation of 2-haloaldehyde acetals. If the 2-haloaldehyde acetal is open chain, the dehydrohalogenation is carried out in the presence of an alkali metal hydroxide or alkaline earth metal hydroxide and a phase transfer catalyst and/or a secondary or tertiary alcohol or a secondary or tertiary diol. If the 2-haloaldehyde acetals is cyclic, the dehydrohalogenation is carried out in the presence of an alkali metal hydroxide or alkaline earth metal hydroxide and a phase transfer catalyst and with or without a secondary or tertiary alcohol or a secondary or tertiary diol, or carried out in the presence of an alkali metal hydroxide or alkaline earth metal hydroxide and a secondary or tertiary diol. The ketene acetals which can be prepared by the process of the invention serve as intermediates in organic synthesis and are suitable as monomers or comonomers in free radical polymerization for the production of biodegradable plastics.
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- 13C NMR study of the structures of some acyclic and cyclic ketene acetals
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A 13C NMR study of the spatial structures of some acyclic and cyclic ketene acetals (for example, ketene dimethyl acetal and 2-methylene-1,3-dioxolane) has been carried out. The conclusions obtained are based on observation of the effect of structural changes on the 13C NMR chemical shift of the β carbon on the ketene moity. Since the extent of p-π conjugation and hence the 13C chemical shift of this carbon depend on the spatial orientation of the alkoxy groups about the O-C(sp2) bonds, the shift concerned may be used as a measure of the planarity of the system. The most stable retamers of ketene dimethyl acetal are s-cis,s-cis (planar) and s-cis,gauche (slightly nonplanar), in the order of decreasing stability. For ketene dialkyl acetals, the relative stability of the planar s-cis,s-cis form decreases with increasing bulkiness of the alkyl groups, but at least for primary and secondary alkyl groups, the s-cis,s-cis rotamer appears to be the most favored species. The conformations of 5- to 8-membered cyclic ketene acetals are discussed and compared with those of the corresponding cyclic vinyl ethers and hydrocarbons.
- Taskinen,Pentikaeinen
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p. 2365 - 2370
(2007/10/04)
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