- Formal Asymmetric Catalytic Thiolation with a Bifunctional Catalyst at a Water-Oil Interface: Synthesis of Benzyl Thiols
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The enantioselective conjugated addition of tritylthiol to in situ generated ortho-quinone methides (o-QMs) is catalyzed by an acid-base bifunctional squaramide organocatalyst. The transformation proceeds with high yield (up to 99%) and stereoselectivity (up to 97:3 e.r.) using water as solvent under mild conditions. The catalyst system provides a new strategy for the synthesis of optically active benzyl mercaptans. Control experiments suggested that o-QMs are generated by the tertiary amine moiety of the squaramide organocatalyst and that the water-oil biphase is crucial for achieving high reactivity and stereoselectivity.
- Guo, Wengang,Wu, Bo,Zhou, Xin,Chen, Ping,Wang, Xu,Zhou, Yong-Gui,Liu, Yan,Li, Can
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Read Online
- Synthesis and Antioxidant Capacity of Some Derivatives of Sesamol at the C-6 Position
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Several synthetic approaches (aminomethylation, alkylation, condensation, etc.) have been used to synthesize derivatives based on the sesamol (1), natural phenol. The set of methods, including the study of antioxidant activity (AOA) by the ability to inhibit the initiated oxidation of animal lipids, radical scavenging activity, Fe2+-chelation ability, as well as a comparative assessment of membrane-protective activity under the conditions of H2O2-induced hemolysis of mice red blood cells (RBCs), was used to analyze the antioxidant potential of the synthesized compounds. The synthesized derivatives have demonstrated different activity in the listed test systems, and we have identified compounds which appear to be most promising for a detailed study of their pharmacological properties.
- Buravlev, Evgeny V.,Shevchenko, Oksana G.,Suponitsky, Kyrill Yu.
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Read Online
- Stable Axially Chiral Isomers of Arylnaphthalene Lignan Glycosides with Antiviral Potential Discovered from Justicia procumbens
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Arylnaphthalene lignans (ANLs) were known to have axial chirality due to the biphenyl skeleton with hindered rotation at the single bond. However, the stable ANL atropisomers have not been isolated from nature until the present study. Phytochemical separation of the methanol extract of the stems and barks of Justicia procumbens led to the isolation of 11 ANL glycosides including four pairs of new atropisomers with stable confirmations at room temperature. Their structures were deduced from elucidation of the extensive spectral data, and their absolute configurations were determined by the circular dichroism, electronic circular dichroism, and X-ray methods as well as the total synthesis of one pair of the atropisomers. The ANL compounds were evaluated for their antiviral potential, and it was found that they displayed great antiviral activity discrepancy between a pair of atropisomers due to the geometric orientation. The 1′P-oriented atropisomers showed much more significant antiviral potency than their corresponding 1′M-oriented counterparts. The biological activity discrepancy caused by the axial chirality will not only inspire synthetic design of novel ANL atropisomers to enrich the structural diversity, but also provide important hints to direct the synthetic approaches toward the antiviral drug development of ANL compounds.
- Zhao, Yang,Ku, Chuen-Fai,Xu, Xin-Ya,Tsang, Nga-Yi,Zhu, Yu,Zhao, Chen-Liang,Liu, Kang-Lun,Li, Chuang-Chuang,Rong, Lijun,Zhang, Hong-Jie
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p. 5568 - 5583
(2021/05/07)
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- Phosphine-catalyzed sequential (2+3)/(2+4) annulation of γ-vinyl allenoates: Access to the synthesis of chromeno[4,3-: B] pyrroles
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A phosphine-catalyzed cascade (2+3)/(2+4) cyclization reaction of γ-vinyl allenoates with aldimine esters has been developed to provide a series of chromeno[4,3-b]pyrrole derivatives that contain three contiguous stereogenic centers. The method gives a good yield, excellent chemoselectivity and diastereoselectivity under mild conditions.
- Huang, You,Li, Xiaohu
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supporting information
p. 9934 - 9937
(2021/10/12)
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- Diastereoselective Synthesis of Benzoxanthenones
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An oxidative catalytic vanadium(V) system was developed to access the naturally nonabundant diastereomers of carpanone from the corresponding alkenyl phenol monomer in one pot by tandem oxidation, oxidative coupling, and 4+2 cyclization. This system was applied to the synthesis of two other analogues of carpanone. Mild oxidizing silver salts were used as the terminal oxidant to minimize background oxidation which produces the natural diastereomer of carpanone. Further, the first examples of enantioselective oxidative benzoxanthenone formation are reported. Solvent polarity has a strong effect on enantioselectivity, consistent with a mechanism involving binding of vanadium Schiff base catalysts to the alcoholic moiety of the alkenyl phenols during the cyclization step.
- Neuhaus, William C.,Kozlowski, Marisa C
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supporting information
p. 1039 - 1043
(2020/03/13)
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- An unexpected Pummerer rearrangement in the synthetic route to ethyl (2′-hydroxy-4′,5′-methylenedioxyphenyl)acetate: An alternative approach to 2,3-dimethylthio benzofurans
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The synthesis of ethyl (2′-hydroxy-4′,5′-methylendioxophenyl)acetate, a fragment of the antihyperglycemic natural coumarin subcoriacin, is reported. We found an expeditious route to the title compound in five steps. Final metal catalyzed acid ethanolysis of the vinylic 1,1-methylthio methylsulfoxide derivative afforded the required aryl acetic ester, but in the absence of metal catalyst, an unexpected Pummerer rearrangement produced the 2,3-dimethylthiofuran derivative as the major product. This last result provides an alternative entry to 2,3-dimethlythiobenzofurans.
- Carre?o-Montero, Ariel,Maldonado, Luis A.,Chávez, María Isabel,Hernández-Ortega, Simón,Delgado, Guillermo
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- Phenyl benzofuran compound as well as preparation method, composition, and medical applications thereof
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The invention discloses a phenyl benzofuran compound as well as a preparation method, a composition, and medical applications thereof. The structure of the phenyl benzofuran compound is: characterizedin that the formulas are shown in the specificationdescription. The invention discloses a traditional Chinese medicine extracting method of the phenyl benzofuran compound using a moonseed rhizomerhizoma menispermirough powder as a raw material.The invention discloses a chemical synthetic method of phenyl benzofuran compound using 2,4-dihydroxybenzoic acid as starting materials.The invention discloses a composition containing the phenyl benzofuran compound, and an active ingredient of the composition is the phenyl benzofuran compound.The invention also discloses the application of the phenyl benzofuran compound in the preparation of a drug or food or health product preventing or treating a tumor, and the tumor is nasopharyngeal carcinoma.According to the invention, the phenyl benzofuran compound can be prepared by the traditional Chinese medicine extracting method and the chemical synthetic method, and meanwhile, an in vitro tumor cell experiment proves that phenyl benzofuran has an inhibiting effect on both nasopharyngeal carcinoma cells CNE-1 and CNE-2.
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Paragraph 0075-0077; 0081; 0084; 0088; 0091; 0095
(2019/01/08)
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- Chiral multi-substituted 4 - hydroxy chroman compound and its preparation method and application
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The invention discloses a chiral polysubstituted 4-hydroxychroman compound, and a preparation method and application thereof. The compound has a general structural formula as shown in a formula I which is described in the specification. The preparation method comprises a step of subjecting a salicylaldehyde compound as shown in a general structural formula II and a tertiary alkenyl amide as shown in a general structural formula III to an intermolecular nucleophilic tandem reaction in the presence of a chiral Lewis acid catalyst so as to realize high-efficiency high-selectivity preparation of the chiral polysubstituted 4-hydroxychroman compound. According to the method, the raw material alkenyl amide which can be easily prepared on large scale and the cheap and easily available chiral catalyst are used, and the novel chiral polysubstituted 4-hydroxychroman bicyclo derivative product which cannot be synthesized by using other methods is prepared under mild reaction conditions; and the produce has a stable structure, high yield and enantioselectivity and good application prospects and can be easily separated and purified.
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Paragraph 0211; 0212; 0213
(2017/07/01)
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- Phosphine-Catalyzed [4 + 2] Annulation of Allenoate with Sulfamate-Derived Cyclic Imines: A Reaction Mode Involving γ′-Carbon of α-Substituted Allenoate
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A phosphine-catalyzed [4 + 2] cycloaddition of cyclic α-substituted allenoates with sulfamate-derived cyclic imines has been reported. Using dibenzylphenylphosphine as the nucleophilic catalyst, the reaction worked efficiently to yield various fused multicyclic heterocyclic compounds in high yields with excellent diastereoselectivities. It undergoes a new reaction mode involving γ′-carbon of α-substituted allenoate.
- Mao, Biming,Shi, Wangyu,Liao, Jianning,Liu, Honglei,Zhang, Cheng,Guo, Hongchao
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supporting information
p. 6340 - 6343
(2017/12/08)
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- Controllable Rh(III)-Catalyzed Annulation between Salicylaldehydes and Diazo Compounds: Divergent Synthesis of Chromones and Benzofurans
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A Rh(III)-catalyzed annulation between salicylaldehydes and diazo compounds with controllable chemoselectivity is described. AgNTf2 favored benzofurans via a tandem C-H activation/decarbonylation/annulation process, while AcOH led to chromones through a C-H activation/annulation pathway. The reaction exhibited good functional group tolerance and scalability. Moreover, only a single regioisomer of benzofuran was obtained due to the in situ decarbonylation orientation effect.
- Sun, Peng,Gao, Shang,Yang, Chi,Guo, Songjin,Lin, Aijun,Yao, Hequan
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supporting information
p. 6464 - 6467
(2016/12/23)
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- BORONIC ACID BEARING LIPHAGANE COMPOUNDS AS INHIBITORS OF P13K- a AND/OR B
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Compounds with unique liphagane meroterpenoid scaffold having boronic acid functionality in the skeleton are described (formula 1) together with pharmacological potential of these compounds as anticancer agents. A method of preparation and inhibiting the activity of phosphoinositide-3-kinase (PI3K-alpha and beta) has been presented. In particular, the invention describes a method of inhibiting PI3K isoforms, wherein the compounds are novel structures based on liphagane scaffold with unique boronic acid functionality. The methods and uses thereof are described herein this invention.
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Paragraph 0114; 0123
(2015/02/25)
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- Novel 3,4-methylenedioxyde-6-X-benzaldehyde-thiosemicarbazones: Synthesis and antileishmanial effects against Leishmania amazonensis
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A series of eleven 3,4-methylenedioxyde-6-X-benzaldehyde-thiosemicarbazones (16-27) was synthesised as part of a study to search for potential new drugs with a leishmanicidal effect. The thiosemicarbazones, ten of which are new compounds, were prepared in good yields (85-98%) by the reaction of 3,4-methylenedioxyde-6-benzaldehydes (6-X-piperonal), previously synthesised for this work by several methodologies, and thiosemicarbazide in ethanol with a few drops of H2SO4. These compounds were evaluated against Leishmania amazonensis promastigotes, and derivatives where X = I (22) and X = CN (23) moieties showed impressive results, having IC50 = 20.74 μM and 16.40 μM, respectively. The intracellular amastigotes assays showed IC50 = 22.00 μM (22) and 17.00 μM (23), and selectivity index >5.7 and >7.4, respectively, with a lower toxicity compared to pentamidine (positive control, SI = 4.5). The results obtained from the preliminary QSAR study indicated the hydrophobicity (log P) as a fundamental parameter for the 2D-QSAR linear model. A molecular docking study demonstrated that both compounds interact with flavin mononucleotide (FMN), important binding site of NO synthase.
- De Melos, Jorge Luiz R.,Torres-Santos, Eduardo Caio,Fai?es, Viviane Dos S.,De Nigris Del Cistia, Catarina,Sant'Anna, Carlos Maurício R.,Rodrigues-Santos, Cláudio Eduardo,Echevarria, Aurea
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p. 409 - 417
(2015/09/28)
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- Ethyl cinnamate derivatives as promising high-efficient acaricides against Psoroptes cuniculi: Synthesis, bioactivity and structure-activity relationship
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This paper reported the synthesis, structure-activity relationship (SAR) and acaricidal activity in vitro against Psoroptes cuniculi, a mange mite, of 25 ethyl cinnamate derivatives. All target compounds were synthesized and elucidated by means of MS, 1H- and 13C-NMR analysis. The results showed that 24 out of 25 tested compounds at 1.0 mg/mL demonstrated acaricidal activity in varying degrees. Among them, 6, 15, 26, 27 and 30 showed significant activity with median lethal concentration values (LC50) of 89.3, 119.0, 39.2, 29.8 and 41.2 μg/mL, respectively, which were 2.1- to 8.3-fold the activity of ivermectin (LC50=247.4 μg/mL), a standard drug in the treatment of Psoroptes cuniculi. Compared with ivermectin, with a median lethal time value (LT50) of 8.9 h, 27 and 30 showed smaller LTM50 values of 7.9 and 1.3 h, respectively, whereas 6, 15 and 26 showed slightly larger LT50 values of 10.6, 11.0 and 10.4 h at 4.5 μmol/mL. SARs showed that the presence of o-NO2 or m-NO2 on the benzene ring significantly improved the activity, whereas the introduction of a hydroxy, methoxy, acetoxy, methylenedioxy, bromo or chloro group reduced the activity. (E)-Cinnamates were more effective than their (Z)-isomer. Nevertheless, the carbon-carbon double bond in the acrylic ester moiety was proven not to be essential to improve the activity of cinnamic acid esters. Thus, the results strongly indicate that cinnamate derivatives, especially their dihydro derivatives, should be promising candidates or lead compounds for the development of novel acaricides for the effective control of animal or human acariasis.
- Zhang, Bingyu,Lv, Chao,Li, Weibo,Cui, Zhiming,Chen, Dongdong,Cao, Fangjun,Miao, Fang,Zhou, Le
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p. 255 - 262
(2015/04/22)
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- Synthesis of novel 5-oxaprotoberberines as bioisosteres of protoberberines
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5-Oxaprotoberberinones and 5-oxaprotoberberinium were synthesized as bioisosteres of protoberberines. 5-Oxaprotoberberinones were prepared by linking phenol with the isoquinolone ring of 3-phenolisoquinolones by methyleneoxy bridge, while the quaternary 5-oxaprotoberberinium salt was synthesized by reduction and oxidation of the lactam moiety of 5-oxaprotoberberinone.
- Jin, Yifeng,Khadka, Daulat Bikram,Yang, Su Hui,Zhao, Chao,Cho, Won-Jea
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supporting information
p. 1366 - 1369
(2014/03/21)
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- Syntheses of the fungal metabolites Boletopsins 7, 11, and 12 from the Papua New Guinea medicinal mushroom Boletopsis sp.
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Boletopsins 7 (1), 11 (2), and 12 (3) are p-terphenyl dibenzofuran compounds, isolated from the Papua New Guinean medicinal mushroom Boletopsis sp. The first syntheses of these fungal metabolites are reported, allowing for an investigation of their antibiotic activity. The key steps include sequential Suzuki-Miyaura couplings to rapidly form the p-terphenyl backbone and an Ullmann ether synthesis on a formate ester to create the dibenzofuran moiety. Biological evaluation of the synthetic compounds and intermediates against a panel of bacterial nosocomial pathogens was performed.
- Beekman, Andrew M.,Barrow, Russell A.
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p. 1017 - 1024
(2014/03/21)
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- BORONIC ACID BEARING LIPHAGANE COMPOUNDS AS INHIBITORS OF PI3K-alpha AND/OR beta
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Compounds with unique liphagane meroterpenoid scaffold having boronic acid functionality in the skeleton are described [formula 1] together with pharmacological potential of these compounds as anticancer agents. A method of preparation and inhibiting the activity of phosphoinositide-3-kinase (PI3K-alpha and beta) has been presented. In particular, the invention describes a method of inhibiting PI3K isoforms, wherein the compounds are novel structures based on liphagane scaffold with unique boronic acid functionality. The methods and uses thereof are described herein this invention. The claimed Markush formula is: [Formular 1], Y can be O, NH, NR, S; Representative compounds are: [Compounds A, B, C, D]
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Page/Page column 19; 23
(2013/10/08)
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- 6-endo heck cyclization of 3-(2-iodophenoxy)methylbenzofurans: A useful approach to pterocarpenes
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Mitsunobu coupling of 3-hydroxymethylbenzofurans with o-iodophenols affords 3-(2-iodophenoxy)methylbenzofurans which under go a useful 6-endo Heck cyclization under Jeffery conditions to afford pterocarpene-type heterocycles. The unsubstituted parent pterocarpene thus prepared was readily converted to coumestan via subsequent PCC oxidation. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications1 to view the free supplemental file. Copyright Taylor & Francis Group, LLC.
- Fowler, Katherine J.,Ellis, Jillian L.,Morrow, Gary W.
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supporting information
p. 1676 - 1682
(2013/05/21)
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- Analogues of doxanthrine reveal differences between the dopamine D 1 receptor binding properties of chromanoisoquinolines and hexahydrobenzo[a]phenanthridines
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Efforts to develop selective agonists for dopamine D1-like receptors led to the discovery of dihydrexidine and doxanthrine, two bioisosteric β-phenyldopamine-type full agonist ligands that display selectivity and potency at D1-like receptors. We report herein an improved methodology for the synthesis of substituted chromanoisoquinolines (doxanthrine derivatives) and the evaluation of several new compounds for their ability to bind to D1- and D2-like receptors. Identical pendant phenyl ring substitutions on the dihydrexidine and doxanthrine templates surprisingly led to different effects on D1-like receptor binding, suggesting important differences between the interactions of these ligands with the D1 receptor. We propose, based on the biological results and molecular modeling studies, that slight conformational differences between the tetralin and chroman-based compounds lead to a shift in the location of the pendant ring substituents within the receptor.
- Cueva, Juan Pablo,Chemel, Benjamin R.,Juncosa Jr., Jose I.,Lill, Markus A.,Watts, Val J.,Nichols, David E.
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experimental part
p. 97 - 107
(2012/03/22)
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- Oxidative dimerization of (E)- and (Z)-2-propenylsesamol with O2 in the presence and absence of laccases and other catalysts: Selective formation of carpanones and benzopyrans under different reaction conditions
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The oxidative dimerization of 2-propenylsesamol to carpanone with O 2 as the oxidant, which probably proceeds as a domino phenol oxidation/anti-β,β-radical coupling/intramolecular hetero Diels-Alder reaction, can be efficiently catalyzed by laccases. Experiments with laccases and other catalysts like a Co(salen) type catalyst and PdCl2 clearly demonstrate that the diastereoselectivity of the carpanone formation does not depend on the catalyst but on the double-bond geometry of the substrate. With (E)-2-propenylsesamol as the substrate, carpanone and a so far unknown carpanone diastereoisomer are formed in a 9:1 ratio. When (Z)-2-propenylsesamol is used as starting material, carpanone is accompanied by two carpanone diastereoisomers unknown so far in a 5:1:4 ratio. All three carpanone diastereoisomers have been separated by HPLC, and their structures have been elucidated unambiguously by NMR spectroscopy, DFT calculations, and spin work analysis. When the oxidation of 2-propenylsesamol with O2 is performed in the absence of any catalyst two diastereoisomeric benzopyrans are formed, probably as the result of a domino oxidation/intermolecular hetero Diels-Alder reaction. Under these conditions, carpanone is formed in trace amounts only.
- Constantin, Mihaela-Anca,Conrad, Juergen,Merisor, Elena,Koschorreck, Katja,Urlacher, Vlada B.,Beifuss, Uwe
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p. 4528 - 4543
(2012/07/03)
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- Toward establishing structure-activity relationships for oxygenated coumarins as differentiation inducers of promonocytic leukemic cells
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The presumption that some coumarins might be lead compounds in the search for new differentiation agents against leukemia is based on the fact that natural coumarins, 5-(3-methyl-2-butenyloxy)-6,7-methylenedioxycoumarin (C-2) and 5-methoxy-6,7-methylenedioxycoumarin (C-1) inhibit proliferation and induce differentiation in U-937 cells [Riveiro, M. E.; Shayo, C.; Monczor, F.; Fernandez, N.; Baldi, A.; De Kimpe, N.; Rossi, J.; Debenedetti, S.; Davio, C. Cancer Lett. 2004, 210, 179-188]. These promising findings prompted us to investigate the anti-leukemia activity of a broader range of related polyoxygenated coumarins. Twenty related natural or synthetically prepared coumarins, including a range of 5-substituted ayapin derivatives which have become easy accessible via newly developed synthesis methods, were evaluated, where treatments with 5-(2,3-dihydroxy-3-methylbutoxy)-6,7-methylenedioxycoumarin (D-3) and 5-(2-hydroxy-3-methoxy-3-methylbutoxy)-6,7-methylenedioxycoumarin (D-2) were able to inhibit the cell growth and induce the differentiation of U-937 cells after 48 h treatment. These results provide insight into the correlation between some structural properties of polyoxygenated coumarins and their in vitro leukemic differentiation activity.
- Riveiro, Maria E.,Maes, Dominick,Vazquez, Ramiro,Vermeulen, Monica,Mangelinckx, Sven,Jacobs, Jan,Debenedetti, Silvia,Shayo, Carina,De Kimpe, Norbert,Davio, Carlos
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scheme or table
p. 6547 - 6559
(2009/12/09)
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- ortho-Formylation of oxygenated phenols
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Oxygenated phenols are mono-formylated using a mixture of paraformaldehyde, MgCl2, and Et3N in THF. In all cases but one, only one regioisomer of the salicylaldehyde is obtained in good to high yield.
- Akselsen, ?yvind W.,Skatteb?l, Lars,Hansen, Trond Vidar
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experimental part
p. 6339 - 6341
(2010/02/27)
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- Total synthesis of polemannones B and C
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The first total synthesis of polemannones B and C, higly oxygenated benzoxanthenones derivatives from Polemannia montana, is reported employing our new catalytic Cu(II)/sparteine system for β,β-phenolic couplings and tandem inverse-electron demand Diels-Alder reaction cascade in 75-90% yield.
- Fadeyi, Olugbeminiyi O.,Nathan Daniels,DeGuire, Sean M.,Lindsley, Craig W.
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body text
p. 3084 - 3087
(2009/10/04)
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- TRANS-FUSED CHROMENOISOQUINOLINES SYNTHESIS AND METHODS FOR USE
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Optionally substituted chromenoisoquinolines and analogs and derivatives thereof are described herein. In addition, syntheses of these compounds are described herein. In addition, uses of these compounds as dopamine receptor binding compounds are described herein.
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Page/Page column 12
(2009/02/11)
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- Alcohol uncaging with fluorescence reporting: Evaluation of o-acetoxyphenyl methyloxazolone precursors
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(Chemical Equation Presented) This paper evaluates a series of photolabile protecting groups with built-in fluorescence reporting. They rely on readily available o-acetoxyphenyl methyloxazolones as activated precursors. Alcohol substrates are easily caged. The resulting photoactivable esters exhibit large one- and two-photon uncaging cross sections. The alcohol substrates are quantitatively released in a 1:1 molar ratio with a strongly fluorescent coumarin coproduct that serves as a reporter to quantify substrate delivery.
- Gagey, Nathalie,Emond, Matthieu,Neveu, Pierre,Benbrahim, Chouaha,Goetz, Bernard,Aujard, Isabelle,Baudin, Jean-Bernard,Jullien, Ludovic
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supporting information; experimental part
p. 2341 - 2344
(2009/06/06)
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- Two-photon uncaging with fluorescence reporting: Evaluation of the o-hydroxycinnamic platform
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This paper evaluates the ohydroxycinnamic platform for designing efficient caging groups with fluorescence reporting upon one- and two-photon excitation. The model cinnamates are easily prepared in one step by coupling commercial or readily available synthons. They exhibit a large one-photon absorption that can be tuned in the near-UV range. Uncaging after one-photon excitation was investigated by 1H NMR, UV-vis absorption, and steady-state fluorescence emission. In the whole investigated series, the caged substrate is quantitatively released upon photolysis. At the same time, uncaging releases a strongly fluorescent coproduct that can be used as a reporter for quantitative substrate delivery. The quantum yield of double bond photoisomerization leading to uncaging after one-photon absorption mostly lies in the 10% range. Taking advantage of the favorable photophysical properties of the uncaging coproduct, we use a series of techniques based on fluorescence emission to measure the action uncaging cross sections with two-photon excitation of the present cinnamates. Exhibiting values in the 1-10 GM range at 750 nm, they satisfactorily compare with the most efficient caging groups reported to date. Noticeably, the uncaging behavior with two-photon excitation is retained in vivo as suggested by the results observed in living zebrafish embryos. Reliable structure property relationships were extracted from analysis of the present collected data. In particular, the careful kinetic analysis allows us to discuss the relevance of the ohydroxycinnamic platform for diverse caging applications with one- and two-photon excitation.
- Gagey, Nathalie,Neveu, Pierre,Benbrahim, Chouaha,Goetz, Bernard,Aujard, Isabelle,Baudin, Jean-Bernard,Jullien, Ludovic
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p. 9986 - 9998
(2008/02/12)
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- Synthesis and glycogen phosphorylase inhibitor activity of 2,3-dihydrobenzo[1,4]dioxin derivatives
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Novel 5-benzyl and 5-benzylidene-thiazolidine-2,4-diones carrying 2,3-dihydrobenzo[1,4]dioxin pharmacophore were synthesized and their glycogen phosphorylase inhibitor activity was also studied.
- Juhasz, Laszlo,Docsa, Tibor,Brunyaszki, Attila,Gergely, Pal,Antus, Sandor
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p. 4048 - 4056
(2008/03/12)
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- trans-2,3-dihydroxy-6a,7,8,12b-tetrahydro-6H-chromeno[3,4-c]isoquinoline: Synthesis, resolution, and preliminary pharmacological characterization of a new dopamine D1 receptor full agonist
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We report the synthesis of trans-2,3-dihydroxy-6a,7,8,12b-tetrahydro-6H- chromeno[3,4-c]isoquinoline hydrochloride 6 and the resolution of its enantiomers. This new compound is an oxygen bioisostere of the potent dopamine D1-selective full agonist dihydrexidine. The initial synthetic approach involved, as a key step, a Suzuki coupling between a chromene triflate and a boronate ester, followed by isoquinoline formation and reduction of the resulting isoquinoline. Subsequently, a more efficient route was developed that involved conjugate addition of an aryl Grignard reagent to a 2-nitrochromene. The title compound possessed high affinity (Ki = 20-30 nM) for porcine D1-like receptors in native striatal tissue and full intrinsic activity at cloned human dopamine D1 receptors but had much lower affinity at dopamine D2-like receptors (Ki = 3000 nM). The binding and functional properties of this compound illustrate again the utility of constructing dopamine D1 agonist ligands around the β-phenyldopamine pharmacophore template.
- Cueva, Juan Pablo,Giorgioni, Gianfabio,Grubbs, Russell A.,Chemel, Benjamin R.,Watts, Val J.,Nichols, David E.
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p. 6848 - 6857
(2007/10/03)
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- Synthesis and structural revision of naturally occurring ayapin derivatives
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The synthesis of three highly oxygenated naturally occurring coumarins, 8-methoxy-6,7-methylenedioxycoumarin, 5-methoxy-6,7-methylenedioxycoumarin and 5,8-dimethoxy-6,7-methylenedioxycoumarin is described for the first time, together with a new method for the preparation of ayapin (6,7- methylenedioxycoumarin). Comparison of the spectroscopic data of the synthetic tetraoxygenated coumarin 5,8-dimethoxy-6,7-methylenedioxycoumarin with literature reports resulted in the structural revision of several natural coumarins. Two coumarins, both identified as 5,8-dimethoxy-6,7- methylenedioxycoumarin must have other structures, while the structure of another coumarin, described as the isomeric 7,8-dimethoxy-5,6- methylenedioxycoumarin has to be revised to 5,8-dimethoxy-6,7- methylenedioxycoumarin.
- Maes, Dominick,Vervisch, Stijn,Debenedetti, Silvia,Davio, Carlos,Mangelinckx, Sven,Giubellina, Nicola,De Kimpe, Norbert
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p. 2505 - 2511
(2007/10/03)
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- Synthesis and HIV-1 integrase inhibitory activities of caffeic acid dimers derived from Salvia officinalis
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The synthesis of two caffeoyl-coumarin conjugates, derived from sagecoumarin, has been accomplished, starting from ferulic acid, isoferulic acid and sesamol. Both compounds exhibited potent inhibitory activities at micromolar concentrations against HIV-1 integrase in 3′-end processing reaction but were less effective against HIV-1 replication in a single-round infection assay of HeLa-β-gal-CD4+ cells.
- Bailly, Fabrice,Queffelec, Clemence,Mbemba, Gladys,Mouscadet, Jean-Francois,Cotelle, Philippe
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p. 5053 - 5056
(2007/10/03)
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- BENZOPYRAN COMPOUNDS USEFUL FOR TREATING INFLAMMATORY CONDITIONS
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The subject invention concerns methods and compounds that have utility in the treatment of a condition associated with cyclooxygenase-2 mediated disorders. Compounds of particular interest are benzopyrans and their analogs defined by formula (1). Wherein Z, X, R1, R2, R3, and R4 are as described in specification.
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Page 272-273
(2010/02/08)
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- CHROMENE DERIVATIVES AS ANTI-INFLAMMATORY AGENTS
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The subject invention concerns methods and compounds that have utility in the treatment of a condition associated with cyclooxygenase-2 mediated disorders. Compounds of particular interest are benzopyrans and their analogs defined by formula (I). Wherein Z, X, R1, R2, R3, and R4 are as described in the specification.
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Page 272-273
(2010/02/08)
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- PROCESS FOR PREPARATION OF ESCULETIN COMPOUNDS, ESCULETIN COMPOUNDS AND INTERMEDIATES THEREOF, AND USE OF BOTH
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An esculetin compound, an intermediate thereof, a process for manufacturing an esculetin compound, and an antifungal composition for agriculture and horticulture and an herbicide comprising an esculetin compound or an intermediate thereof are provided. The process for manufacturing an esculetin compound is a low-cost, high-yield, and industrially practicable process, and comprises the following step.A process for manufacturing an esculetin compound of the formula (2): characterized by cyclizing a trihydroxybenzaldehyde compound of the formula (1): in an aprotic polar solvent in the presence of a weak base, with acetic anhydride or the like.
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Page/Page column 18
(2010/01/31)
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- Phosphonic acid compounds, their production and use
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The present invention relates to a compound of the general formula (I): STR1 wherein ring A is a benzene ring that may be substituted; Y is a divalent group as a constituent member of ring B forming a 5- to 8-membered ring; Q1 is a group of the formula --X--P(O)(OR1)(OR2) wherein X is a bond or a divalent group; R1 and R2, identical or different, are hydrogen or a lower alkyl, or may be combined together to form a ring; Q2 is hydrogen, a hydrocarbon group that may be substituted or a heterocyclic group that may be substituted; and the group of the formula --CON(Q1)(Q2) is connected to the a- or b-position carbon atom, or a salt thereof, which is useful as prophylactic and therapeutic agents of various metabolic bone diseases such as osteoporosis.
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- Synthetic approaches toward ecteinascidins. Part 1. Preparation of an (E)-2-arylidene-3-benzyl-1,5-imino-3-benzazocin-4-one having a protected phenol in the E-ring
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A synthetic strategy for the preparation of ecteinascidins isolated from the Caribbean tunicate Ecteinascidia turbinata and an efficient synthesis of a key tricyclic lactam intermediate 32 are described.The key step is the intramolecular cyclization of the allylic alcohol 15 to the (E)-1,5-imino-3-benzazocine 16.Cyclization of 15 (R = Me, Bn) afforded the desired product 16 in good yield.However, treatment of 15 (R = MOM) under acidic conditions gave compound 18 in high yield, the structure of which was determined by X-ray crystallography.Finally, 16 was converted into (E)-N-methyltricyclic lactam 32 that can serve as a synthetic precursor of ecteinascidins.
- Saito, Naoki,Tashiro, Kyoichi,Maru, Yukie,Yamaguchi, Kentaro,Kubo, Akinori
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- A Convenient & Short Route for the Synthesis of Ayapin & Scoparone
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A short, convenient and general route to synthesise two important intermediates in coumarin synthesis, viz. 2-hydroxy-4,5-methylenedioxybenzaldehyde (4a) and 2-hydroxy-4,5-dimethoxybenzaldehyde (4b), is described.These have been converted by Wittig reaction into the naturally occurring coumarins, ayapin (1a) and scoparone (1b), respectively.
- Kelkar, Shriniwas L.,Phadke, Chetan P.,Marina, Sister
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p. 458 - 459
(2007/10/02)
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- ANODIC OXIDATION OF 2-PROPENYLPHENOLS
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Anodic oxidation of 2-propenylphenols in MeOH was carried out under various conditions, using an undivided cell, to afford several oxidation products including the corresponding asatone-, carpanone-, arylpropanoid-, and austrobailignan-type compounds.Among them, the carpanone-type neolignans can be produced via the corresponding bis-o-quinonemethides.
- Iguchi, Masanobu,Nishiyama, Atsuko,Eto, Hideo,Yamamura,Shosuke
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p. 939 - 942
(2007/10/02)
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