- Synthesis method of isolicoflavonol
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The invention provides a synthesis method of isolicoflavonol, which comprises the following steps: carrying out condensation reaction on 2,4-O-R1(protective group, the same below)-6-hydroxyacetophenone and 4-O-R2(protective group, the same below)-benzaldehyde to generate 2',4'-O-R1-6'-hydroxy-4-O-R2-chalcone; oxidizing the chalcone to generate flavonol; carrying out selective protection on 3-OH ofthe flavonol to obtain 3,5,7-O-R1-4'-O-R2-flavonol; removing the protecting group R2 from the 3,5,7-O-R1-4'-O-R2-flavonol to obtain 3,5,7-O-R1-4'-hydroxyflavonol; carrying out 1,1-dimethylpropargyl reaction on the 4,4'-OH site to obtain 3,5,7-O-R1-4'-O-(1',1''-dimethyl propargyl)flavonol; carrying out partial hydrogenation on the alkynyl of the 3,5,7-O-R1-4'-O-(1',1''-dimethyl propargyl)flavonolunder the action of a catalyst to obtain 3,5,7-O-R1-4'-O-(1',1''-dimethylpropenyl)flavonol and carrying out Claisen rearrangement on the 3,5,7-O-R1-4'-O-(1',1''-dimethylpropenyl)flavonol to obtain 3,5,7-O-R1-isolicoflavonol, and removing the protecting group R1 from the 3,5,7-O-R1-isolicoflavonol to obtain the isolicoflavonol.
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Paragraph 0111; 0183-0187
(2020/12/29)
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- Butenolide derivative as well as preparation method and application thereof
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The invention discloses a butenolide compound as well as a preparation method and an application thereof. The butenolide derivative has the inhibitory activity of protein tyrosine phosphatase 1B (PTP1B), improves insulin resistance of HepG2 cells, generates a remarkable hypoglycemic effect and can be used for preparing a medicine for treating diabetes mellitus.
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Paragraph 0034-0037
(2020/07/21)
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- Ancillary ligands switch the activity of Ru–NHC-based oxidation precatalysts
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Herein we demonstrate how the inner-sphere coordinating ligands switch the activity of Ru–NHC-based oxidation precatalysts in the oxidative conversion of olefins to carbonyl compounds, with the help of a series of systematically varied imidazolydene-NHC (Im-NHC) and triazolydene-NHC (Tz-NHC)-based ruthenium(II)-complexes. It is shown that the catalytic activity of the para-cymene-containing precatalysts varies in the order of [(Tz-NHC)Ru(para-cymene)Cl]+ > [(Im-NHC)Ru(para-cymene)Cl]+, while the order of activity of the MeCN-containing precatalysts is found to be reversed, i.e., [(Im-NHC)Ru(MeCN)4]2+ > [(Tz-NHC)Ru(MeCN)4]2+. Along with the electronic influence of the NHC ligands, the effect of the lability of the para-cymene and MeCN ligands, and the overall charge of the complexes might be attributed toward such a switching of catalytic activity. This finding led to develop a new precatalyst with improved activity which was further utilized in selective oxidation of a series of styrene substrates containing other oxidation-sensitive functionalities.
- Gupta, Suraj K.,Mandal, Tanmoy,Gangber, Tejaswinee,Singh, Vivek,Choudhury, Joyanta
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supporting information
(2019/10/28)
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- Prenylated Curcumin Analogues as Multipotent Tools to Tackle Alzheimer's Disease
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Alzheimer's disease is likely to be caused by copathogenic factors including aggregation of Aβ peptides into oligomers and fibrils, neuroinflammation, and oxidative stress. To date, no effective treatments are available, and because of the multifactorial nature of the disease, it emerges the need to act on different and simultaneous fronts. Despite the multiple biological activities ascribed to curcumin as neuroprotector, its poor bioavailability and toxicity limit the success in clinical outcomes. To tackle Alzheimer's disease on these aspects, the curcumin template was suitably modified and a small set of analogues was attained. In particular, derivative 1 turned out to be less toxic than curcumin. As evidenced by capillary electrophoresis and transmission electron microscopy studies, 1 proved to inhibit the formation of large toxic Aβ oligomers, by shifting the equilibrium toward smaller nontoxic assemblies and to limit the formation of insoluble fibrils. These findings were supported by molecular docking and steered molecular dynamics simulations which confirmed the superior capacity of 1 to bind Aβ structures of different complexity. Remarkably, 1 also showed in vitro anti-inflammatory and antioxidant properties. In summary, the curcumin-based analogue 1 emerged as multipotent compound worthy to be further investigated and exploited in the Alzheimer's disease multitarget context.
- Bisceglia, Federica,Seghetti, Francesca,Serra, Massimo,Zusso, Morena,Gervasoni, Silvia,Verga, Laura,Vistoli, Giulio,Lanni, Cristina,Catanzaro, Michele,De Lorenzi, Ersilia,Belluti, Federica
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p. 1420 - 1433
(2019/01/11)
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- Natural and semisynthetic oxyprenylated aromatic compounds as stimulators or inhibitors of melanogenesis
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It has been very recently shown how naturally occurring oxyprenylated coumarins are effective modulators of melanogenesis. In this short communication we wish to generalize the potentialities as skin tanning or whitening agents of a wider panel of natural and semisynthetic aromatic compounds, including coumarins, cinnamic and benzoic acids, cinnamaldehydes, benzaldehyde, and anthraquinone derivatives. A total number of 43 compounds have been tested assaying their capacity to inhibit or stimulate melanin biosynthesis in cultured murine Melan A cells. The wider number of chemicals herein under investigation allowed to depict a detailed structure-activity relationship, as the following: (a) benzoic acid derivatives are slightly pigmenting agent, for which the effect is more pronounced in compounds with longer O-side chains; (b) independently from the type of substitution, cinnamic acids are able to increase melanin biosynthesis, while benzaldehydes are able to decrease it; (c) coumarins with a 3,3-dimethylallyl or shorter skeletons as substituents in position 7 are tanning agents, while coumarins with farnesyloxy groups are whitening ones; (d) double oxyprenylation in position 6 and 7 and 3,3-dimethylallyl or geranyl skeletons have slight depigmenting capacities, while farnesyl skeletons tend to marginally increase the tanning effect; (e) the presence of electron withdrawing groups (acetyl, COOH, and -Cl) and geranyl or farnesyl oxyprenylated chains respectively in positions 3 and 7 of the coumarin nucleus lead to a whitening effect, and finally (f) oxyprenylated anthraquinones have only a weak depigmenting capacity.
- Genovese, Salvatore,Epifano, Francesco,Medina, Philippe de,Caron, Nicolas,Rives, Arnaud,Poirot, Marc,Poirot, Sandrine Silvent,Fiorito, Serena
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p. 181 - 190
(2019/03/23)
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- Excavating precursors from the traditional Chinese herb Polygala tenuifolia and Gastrodia elata: Synthesis, anticonvulsant activity evaluation of 3,4,5-trimethoxycinnamic acid (TMCA)ester derivatives
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Epilepsy is a group of neurological disorders characterized by recurrent seizures that disturbs about 60 million people worldwide. In this article, a novel series of 3,4,5-trimethoxycinnamic acid (TMCA)ester derivatives 1–35 were designed inspired from the traditional Chinese herb pair drugs Polygala tenuifolia and Gastrodia elata and synthesized followed by in vivo and in silico evaluation of their anticonvulsant potential. All the synthesized derivatives were biologically evaluated for their anticonvulsant potential using two acute model of seizures induced in mice, the maximal electroshock (MES)and sc-pentylenetetrazole (PTZ)models. Simultaneously, the motor impairment as a surrogate of acute neurotoxicity and in vitro screening of cytotoxicity against HepG-2 cells line were assessed through the rotarod performance test and CCK-8 assay, respectively. In addition, the physicochemical and pharmacokinetic parameters of the active compounds were determined. Our results showed that compounds 5, 7, 8, 13, 20, 25, 28, 30 and 32 exhibited preferable anticonvulsant activity in primary evaluation, with compounds 28 and 32 being the most promising anticonvulsant agents in according to results of subsequent pharmacology and toxicity evaluation. Additionally, the molecular modeling experiments predicted good binding interactions of part of the obtained active molecules with the gamma-aminobutyric acid (GABA)transferas. Therefore, it could be concluded that the synthesized derivatives 28 and 32 would represent useful lead compounds for further investigation in the development of anticonvulsant agents.
- Zhao, Zefeng,Bai, Yajun,Xie, Jing,Chen, Xufei,He, Xirui,Sun, Ying,Bai, Yujun,Zhang, Yangyang,Wu, Shaoping,Zheng, Xiaohui
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- Coordination Booster-Catalyst Assembly: Remote Osmium Outperforming Ruthenium in Boosting Catalytic Activity
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Presented herein is a set of bimetallic and trimetallic “coordination booster-catalyst” assemblies in which the coordination complexes [RuII(terpy)2] and [OsII(terpy)2] acted as boosters for enhancement of the catalytic activity of [RuII(NHC)(para-cymene)]-based catalytic site. The boosters accelerated the oxidative loss of para-cymene from the catalytic site to generate the active catalyst during the oxidation of alkenes and alkynes into corresponding aldehydes, ketones and diketones. It was found that the boosting efficiency of the [OsII(terpy)2] units was considerably higher than its congener [RuII(terpy)2] unit in these assemblies. Mechanistic studies were conducted to understand this unique improvement.
- Mandal, Tanmoy,Singh, Vivek,Choudhury, Joyanta
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supporting information
p. 4774 - 4779
(2019/11/11)
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- Design and synthesis of a novel mPGES-1 lead inhibitor guided by 3D-QSAR CoMFA
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The search of novel mPGES-1 inhibitors has recently intensified probably due to the superior safety in comparison to existing anti-inflammatory drugs. Although two mPGES-1 inhibitors have entered clinical trials, none has yet reached the market. In this study, we performed modifications guided by 3D-QSAR CoMFA on 2, which is an unsymmetrical curcumin derivative with low binding affinity towards mPGES-1. To counter the PAINS properties predicted for 2, the diketone linker was replaced with a pyrazole ring. On the other hand, both prenyl and carboxylate ester groups were introduced to improve the activity. When tested in vitro, 11 suppressed PGE2 biosynthesis in activated macrophages and showed promising human mPGES-1 inhibition in microsomes of interleukin-1β-stimulated A549 cells. Altogether, 11 has been identified as a potential mPGES-1 inhibitor and could be a promising lead for a novel class of mPGES-1 inhibitors.
- Fasihi Mohd Aluwi, Mohd Fadhlizil,Rullah, Kamal,Koeberle, Andreas,Werz, Oliver,Abdul Razak, Nur Sakinah,Wei, Leong Sze,Salim, Fatimah,Ismail, Nor Hadiani,Jantan, Ibrahim,Wai, Lam Kok
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p. 844 - 850
(2019/07/12)
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- 2,3-dimethyl allyl chalcone type compound as well as preparation and application thereof
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The invention discloses a 2,3-dimethyl allyl chalcone type compound as well as a preparation method and application thereof. The structure of the compound is shown as a formula (I), wherein R1 is selected from H, C1 to C5 alkoxy, C2 to C5 allyloxy, hydroxy, RRN-, substituted or unsubstituted quintuple or hexahydric nitrogen heterocyclic ring; R2 and R3 are independently selected from C1 to C5 alkyl or C2 to C5 vinyl; substituent groups on the quintuple or hexahydric nitrogen heterocyclic ring are one or a plurality of groups in C1 to C5 alkyl. The pharmacological results show that the 2,3-dimethyl allyl chalcone type compound can effectively inhibit the PTP1B activity and has potential antidiabetic medicine effect. The formula (I) is shown in description.
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Paragraph 0028; 0029
(2018/10/11)
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- Structure-Activity Relationships of New Natural Product-Based Diaryloxazoles with Selective Activity against Androgen Receptor-Positive Breast Cancer Cells
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Targeted therapies for ER+/PR+ and HER2-amplified breast cancers have improved patient survival, but there are no therapies for triple negative breast cancers (TNBC) that lack expression of estrogen and progesterone receptors (ER/PR), or amplification or
- Robles, Andrew J.,McCowen, Shelby,Cai, Shengxin,Glassman, Michaels,Ruiz, Francisco,Cichewicz, Robert H.,McHardy, Stanton F.,Mooberry, Susan L.
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p. 9275 - 9289
(2017/11/30)
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- Isoglycyrrhiza derivatives and its use (by machine translation)
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The invention discloses a different of glycyrrhizin derivatives and their use, the structure of the isoliquiritigenin main body: wherein R 1 is H, methyl, cyclopropane methyl, 3-methyl-2-butenyl, is d acyl, alkyl in the isobutene, R 2 is H, methyl, cyclopropane methyl, 3-methyl-2-butenyl, is d acyl, alkyl of isobutene. Said compound can be used for the treatment of atrial fibrillation, and is capable of effectively inhibiting potassium channel function of the patient and small side effect. (by machine translation)
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Paragraph 0051; 0052; 0053
(2017/05/20)
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- Synthesis and biological evaluation of allylated and prenylated mono-carbonyl analogs of curcumin as anti-inflammatory agents
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Curcumin has been shown to possess anti-inflammatory activities but has been limited for its low stability and poor bioavailability. We have previously reported four series of 5-carbon linker-containing mono-carbonyl analogs of curcumin (MACs). In continuation of our ongoing research, we designed and synthesized 33 novel allylated or prenylated MACs here, and evaluated their anti-inflammatory effects in RAW 264.7 macrophages. A majority of them effectively inhibited the LPS-induced expression of TNF-α and IL-6, especially IL-6. The preliminary SAR and quantitative SAR analysis were conducted. Compound 14q is the most potent analog among them, and exhibits significant protection against LPS-induced death in septic mice. Together, these data present a series of new analogs of curcumin as promising anti-inflammatory agents.
- Liu, Zhiguo,Tang, Longguang,Zou, Peng,Zhang, Yali,Wang, Zhe,Fang, Qilu,Jiang, Lili,Chen, Gaozhi,Xu, Zheng,Zhang, Huajie,Liang, Guang
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p. 671 - 682
(2014/03/21)
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- Highly efficient and selective deprotection method for prenyl, geranyl, and phytyl ethers and esters using borontrifluoride-etherate
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An efficient, simple, and practical method has been developed for the deprotection of prenyl, geranyl, and phytyl ethers and esters of aromatic and aliphatic compounds using borontrifluoride-etherate (BF3· OEt2) at room temperature in good to excellent yields for the first time. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file. Copyright Taylor & Francis Group, LLC.
- Narender,Venkateswarlu,Madhur,Reddy, K. Papi
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- Nelumal A, the active principle from Ligularia nelumbifolia, is a novel farnesoid X receptor agonist
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A series of 29 oxyprenylated and azoprenylated phenylpropanoids were chemically synthesized and tested in transfected cultured HepG2 cells by means of the dual-luciferase assay as farnesoid X receptor (FXR) agonists, using the endogenous ligand chenodeoxy
- Epifano, Francesco,Genovese, Salvatore,James Squires,Gray, Matthew A.
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scheme or table
p. 3130 - 3135
(2012/06/04)
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- First asymmetric total synthesis of (R,E)-1-[4-(3-hydroxyprop-1-enyl) phenoxyl]-3-methylbutane-2,3-diol
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(Chemical Equation Presented) A new anti-inflammatory active phenylpropenoid, (R,E)-1-[4-(3-hydroxyprop-1-enyl) phenoxyl]-3-methylbutane-2,3- diol (1), isolated from the stem wood of Zanthoxylum integrifoliolum, has been synthesized for the first time usi
- Suresh,Rajesh,Selvam,Venkateswarlu
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experimental part
p. 993 - 998
(2011/04/25)
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- Synthesis of (±)Abyssinone I and related compounds: Their anti-oxidant and cytotoxic activities
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An efficient and facile synthesis of naturally occurring prenylated flavonoids and their analogs have been described. Abyssinone I (9a) was prepared by condensing 2,2-dimethyl chrom-3-en-6-carboxaldehyde (5a) with protected resacetophenone under phase transfer conditions followed by deprotection and cyclization. The influence of prenyl group on anti-oxidant and cytotoxic activities was studied. The presence of 3′-prenyl group as in 8c enhanced radical scavenging activity but decreased reducing power activity when compared to non-prenylated analog 8f. In vitro testing in MCF-7 cell line revealed that prenylated chalcones and flavanones showed better inhibitory activity than their non-prenylated counterparts. Abyssinone I and its chalcone though exhibited negligible anti-oxidant activity their cytotoxic activities were comparable with other prenylated analogs.
- Rao, Gudapati Venkateswara,Swamy, Badrappa Narayana,Chandregowda, Venkateshappa,Reddy, G. Chandrasekara
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experimental part
p. 2239 - 2245
(2009/09/08)
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- Synthesis of O-prenylated and O-geranylated derivatives of 5-benzylidene2,4-thiazolidinediones and evaluation of their free radical scavenging activity as well as effect on some phase II antioxidant/detoxifying enzymes
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A series of 5-arylidene-2,4-thiazolidinediones and its geranyloxy or prenyloxy derivative were synthesized and studied for their radical scavenging activity using 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. Their comparable scavenging activities were expr
- Hossain, Sk. Ugir,Bhattacharya, Sudin
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p. 1149 - 1154
(2007/10/03)
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- Synthesis and biological evaluation of (±)-abyssinone II and its analogues as aromatase inhibitors for chemoprevention of breast cancer
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An efficient and economical synthesis of the naturally occurring aromatase inhibitor abyssinone II was performed. The synthesis features an optimized aromatic prenylation reaction in which an arylcopper intermediate is reacted with prenyl bromide to afford a key intermediate that was converted to a prenylated aromatic aldehyde. Condensation of the aldehyde with an o-hydroxyacetophenone under Claisen-Schmidt conditions afforded a chalcone that was deprotected and cyclized in the presence of sodium acetate in refluxing ethanol to afford (±)-abyssinone II. The synthesis proved to be versatile enough to provide an array of abyssinone II derivatives that were evaluated as aromatase inhibitors. Methylation of the 4′-hydroxyl group of (±)-abyssinone II resulted in a significant increase in aromatase inhibitory activity, and further smaller increases in activity resulted from the methylation of the 7-hydroxyl group and removal of the prenyl side chain. As a result of these structural changes, the most active flavanone of the series was 20 times more potent than (±)-abyssinone II (IC50 40.95 μM).
- Maiti, Arup,Cuendet, Muriel,Croy, Vicki L.,Endringer, Denise C.,Pezzuto, John M.,Cushman, Mark
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p. 2799 - 2806
(2008/02/06)
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- One-pot synthesis of phenols from aromatic aldehydes by Baeyer-Villiger oxidation with H2O2 using water-tolerant Lewis acids in molecular sieves
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The heterogeneous oxidation systems Sn-Beta/H2O2 and Al-Beta/H2O2 were both active for the Baeyer-Villiger oxidation of aromatic aldehydes. With alkoxy substituents in ortho and especially in para position, the corresponding formate ester was the primary reaction product with excellent selectivity. The highest selectivity toward the ester was obtained with the Sn-Beta catalyst in dioxane as solvent. High selectivities of the corresponding phenol could be obtained by employing ethanol or aqueous acetonitrile as solvent with Sn-Beta. Al-Beta was more efficient as catalyst for both Baeyer-Villiger oxidation and ester hydrolysis and, thus achieved high yields for the corresponding alcohol. However, this was a less selective catalyst than Sn-Beta zeolite. Sn-Beta was a chemoselective catalyst when the aldehyde reactant contained olefinic groups in an alkyl chain. With these reactants, the Al-zeolite gave no activity. Other classical BV oxidants, e.g., peracids, also yielded the epoxidation products. Thus, Sn-Beta catalysts open a new entry to aromatic phenols with unsaturated alkyl substituents that are interesting intermediates in the chemical industry.
- Corma, Avelino,Fornes, Vicente,Iborra, Sara,Mifsud, Maria,Renz, Michael
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- Synthesis of 5,7-dihydroxy-6,8-di-C-prenyl-4′-O-prenyl-flavanone
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The prenylated flavanone (9) has been synthesized from phloroacetophenone (1). All the new products have been characterized by the spectral data and microanalysis.
- Hossain, M. Amzad,Saravanand,Ismail, Zhari
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p. 332 - 335
(2007/10/03)
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- CeCl3·7H2O-promoted highly chemoselective hydrolysis of 1,3-oxathio- and dithioacetals
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A highly selective hydrolysis of the 1,3-oxathio- and 1,3-dithioacetals has been achieved in high yields using CeCl3·7H2O-NaI in acetonitrile at reflux temperature under neutral conditions. This method is mild and compatible with a wide range of functional groups such as TBDPS, THP, PMB, MOM, allyl, propargyl, prenyl, benzyl ethers, carbamates and acetate, etc., present in the substrate.
- Yadav,Reddy,Raghavendra,Satyanarayana
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p. 4679 - 4681
(2007/10/03)
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- N-methoxy-N-acylnitrenium ions: application to the formal synthesis of (-)-TAN1251A.
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[structure: see text]. A formal synthesis of the muscarinic M(1) receptor antagonist (-)-TAN1251A (7) from L-tyrosine is described. Central to this venture has been the construction of the 1-azaspiro[4.5]decane skeleton present in the natural product by a
- Wardrop,Basak
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p. 1053 - 1056
(2007/10/03)
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- Facile cleavage reactions of styrylic olefins using electrochemical methods
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Negative constant current electrolysis of styrylic olefins in an aqueous solvent resulted in the oxidative cleavage of the double bonds, giving carbonyl compounds in good yields. The double bond conjugated with more than one aromatic ring was selectively cleaved.
- Maki, Shojiro,Niwa, Haruki,Hirano, Takashi
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p. 1385 - 1386
(2007/10/03)
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