- Compound with plant growth regulating activity and preparation method thereof
-
The invention provides a compound with regulation and control of plant growth activity and and a preparation method of the compound. In addition, the invention relates to an application of the compound in preparation of a regulation and control plant growth medicament, and for regulating and controlling plant growth.
- -
-
Paragraph 0043; 0048-0051
(2021/11/14)
-
- Chromium-Salen Complex/Nitroxyl Radical Cooperative Catalysis: A Combination for Aerobic Intramolecular Dearomative Coupling of Phenols
-
We describe an aerobic intramolecular dearomative coupling reaction of tethered phenols using a catalytic system consisting of a chromium-salen (Cr-salen) complex combined with a nitroxyl radical. This novel catalytic system enables formation of various spirocyclic dienone products including those unable to be accessed by previously reported methods efficiently under mild reaction conditions.
- Nagasawa, Shota,Fujiki, Shogo,Sasano, Yusuke,Iwabuchi, Yoshiharu
-
p. 6952 - 6968
(2021/05/29)
-
- Sequential Cleavage of Lignin Systems by Nitrogen Monoxide and Hydrazine
-
The cleavage of representative lignin systems has been achieved in a metal-free two-step sequence first employing nitrogen monoxide for oxidation followed by hydrazine for reductive C?O bond scission. In combining nitrogen monoxide and lignin, the newly developed valorization strategy shows the particular feature of starting from two waste materials, and it further exploits the attractive conditions of a Wolff-Kishner reduction for C?O bond cleavage for the first time. (Figure presented.).
- Altmann, Lisa-Marie,Heinrich, Markus R.,Hofmann, Dagmar,Hofmann, Laura Elena,Prusko, Lea
-
supporting information
(2020/03/27)
-
- Vanadium-Catalyzed Oxidative Intramolecular Coupling of Tethered Phenols: Formation of Phenol-Dienone Products
-
A mild and efficient method for the vanadium-catalyzed intramolecular coupling of tethered free phenols is described. The corresponding phenol-dienone products are prepared directly in good yields with low catalyst loadings. Electronically diverse tethered phenol precursors are well tolerated, and the catalytic method was effectively applied as the key step in syntheses of three natural products and a synthetically useful morphinan alkaloid precursor.
- Gilmartin, Philip H.,Kozlowski, Marisa C.
-
supporting information
p. 2914 - 2919
(2020/04/10)
-
- Iron(III)/O2-Mediated Regioselective Oxidative Cleavage of 1-Arylbutadienes to Cinnamaldehydes
-
A simple, efficient, and environmentally benevolent regioselective oxidative cleavage of 1-arylbutadienes to cinnamaldehydes mediated by iron(III) sulfate/O2 has been developed. The reaction offered good yields and excellent regioselectivity and showed good functional group tolerance (31 examples). The method is important, as few reports with limited substrate scope are available for such excellent oxidative cleavage of conjugated dienes.
- Bhowmik, Amit,Fernandes, Rodney A.
-
supporting information
p. 9203 - 9207
(2019/11/14)
-
- Synthetic method for dihydrostilbenes and anti-inflammatory compounds containing thereof
-
The present invention aims to provide an effective anti-inflammatory agent without side effects. The present inventors have invented a method for efficiently synthesizing dihydrostilbene and derivatives (compounds 1 to 5) from starting materials at a high yield. In addition, the anti-inflammatory effects were evaluated in LPS-induced RAW-264.7 macrophages. The compounds of dihydrostilbene do not exhibit cytotoxicity and are shown to weakly or well inhibit nitric oxide production induced by LPS at the concentration of 10 andmu;M.COPYRIGHT KIPO 2018
- -
-
Paragraph 0104; 0111-0113; 0116; 0118; 0119
(2018/05/03)
-
- Asymmetric total synthesis of (+)-ovafolinins A and B
-
(+)-Ovafolinins A and B are two homologous lignans containing unique polycyclic skeletons. Benefiting from a highly diastereoselective alkylation of (S)-Taniguchi lactone, a double Friedel-Crafts reaction, a global debenzylation and a Cu(OAc)2-
- Fang, Xianhe,Shen, Lei,Hu, Xiangdong
-
supporting information
p. 7539 - 7541
(2018/07/13)
-
- A process for preparing a broad pH fluorescent probe of the organic compound and use thereof (by machine translation)
-
The present invention discloses a process for the preparation of a wide range of fluorescent probe in the pH of the organic compound, the organic compound can be produced according to the actual need to carry out any proportion of combination, and can be fixed in the hydrophilic high polymer further preparing and detecting water environment acidity and alkalinity of the product. The product can be realized to the pH value of the continuous measuring, thereby greatly improving the efficiency, sensitivity and repeatability. (by machine translation)
- -
-
Paragraph 0117; 0118
(2018/04/03)
-
- Naamines and naamidines as novel agents against a plant virus and phytopathogenic fungi
-
Naamines, naamidines and various derivatives of these marine natural products were synthesized and characterized by means of nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry. The activities of these alkaloids against a plant virus and phytopathogenic fungi were evaluated for the first time. A benzyloxy naamine derivative 15d displayed excellent in vivo activity against tobacco mosaic virus at 500 μg/mL (inactivation activity, 46%; curative activity, 49%; and protective activity, 41%); its activities were higher than the corresponding activities of the commercial plant virucide ribavirin (32%, 35%, and 34%, respectively), making it a promising new lead compound for antiviral research. In vitro assays revealed that the test compounds exhibited very good antifungal activity against 14 kinds of phytopathogenic fungi. Again, the benzyloxy naamine derivative 15d exhibited broad-spectrum fungicidal activity, emerging as a new lead compound for fungicidal research. Additional in vivo assays indicated that many of the compounds displayed inhibitory effects >30%.
- Guo, Pengbin,Li, Gang,Liu, Yuxiu,Lu, Aidang,Wang, Ziwen,Wang, Qingmin
-
-
- Novel HIV-1 Non-nucleoside Reverse Transcriptase Inhibitor Agents: Optimization of Diarylanilines with High Potency against Wild-Type and Rilpivirine-Resistant E138K Mutant Virus
-
Three series (6, 13, and 14) of new diarylaniline (DAAN) analogues were designed, synthesized, and evaluated for anti-HIV potency, especially against the E138K viral strain with a major mutation conferring resistance to the new-generation non-nucleoside reverse transcriptase inhibitor drug rilpivirine (1b). Promising new compounds were then assessed for physicochemical and associated pharmaceutical properties, including aqueous solubility, log P value, and metabolic stability, as well as predicted lipophilic parameters of ligand efficiency, ligand lipophilic efficiency, and ligand efficiency-dependent lipophilicity indices, which are associated with ADME property profiles. Compounds 6a, 14c, and 14d showed high potency against the 1b-resistant E138K mutated viral strain as well as good balance between anti-HIV-1 activity and desirable druglike properties. From the perspective of optimizing future NNRTI compounds as clinical trial candidates, computational modeling results provided valuable information about how the R1 group might provide greater efficacy against the E138K mutant.
- Liu, Na,Wei, Lei,Huang, Li,Yu, Fei,Zheng, Weifan,Qin, Bingjie,Zhu, Dong-Qin,Morris-Natschke, Susan L.,Jiang, Shibo,Chen, Chin-Ho,Lee, Kuo-Hsiung,Xie, Lan
-
p. 3689 - 3704
(2016/05/24)
-
- Dihydrostilbenes and diarylpropanes: Synthesis and in vitro pharmacological evaluation as potent nitric oxide production inhibition agents
-
An efficient synthesis of dihydrostilbenes (1–5) and diarylpropanes (6–10) is achieved from the commercially available starting materials and Wittig-Horner reaction, Claisen–Schmidt condensation and hydrogenation as key steps. Later, their nitric oxide (NO) production inhibition effects were evaluated in lipopolysaccharide (LPS)-induced RAW-264.7 macrophages as an indicator of anti-inflammatory activity. All the tested compounds significantly decreased NO production in a concentration-dependent manner except compounds 2, 6 and 8 and did not show notable cytotoxicity except compound 1. Two compounds i.e., compound 9 (hindsiipropane B) (100%; IC50?=?1.84?μM) possessed the most potent NO inhibitory activity which was even stronger than the positive control, L-NMMA (90.1%; IC50?=?2.73?μM) followed by compound 4 (75.5%; IC50?=?2.98?μM) at 10?μM concentration and this finding was also further correlated by suppressed expression of LPS stimulated inducible NO synthase. Our study revealed that compound 9, a 1,3-diarylpropane scaffold with 3″,4″-dimethoxyphenyl and 3′,4′-dihydroxy-2′-methoxyphenyl motifs could be considered as potential compound or lead compound for further development of NO production-targeted anti-inflammatory agents.
- Jang, Ha Young,Park, Hyeong Jin,Damodar, Kongara,Kim, Jin-Kyung,Jun, Jong-Gab
-
supporting information
p. 5438 - 5443
(2016/11/09)
-
- Photocatalytic Oxidation of Lignin Model Systems by Merging Visible-Light Photoredox and Palladium Catalysis
-
Lignin valorization has long been recognized as a sustainable solution for the renewable production of aromatic compounds. Two-step oxidation/reduction strategies, whereby the first oxidation step is required to "activate" lignin systems for controlled fragmentation reactions, have recently emerged as viable routes toward this goal. Herein we describe a catalytic protocol for oxidation of lignin model systems by combining photoredox and Pd catalysis. The developed dual catalytic protocol allowed the efficient oxidation of lignin model substrates at room temperature to afford the oxidized products in good to excellent yields.
- K?rk?s, Markus D.,Bosque, Irene,Matsuura, Bryan S.,Stephenson, Corey R. J.
-
supporting information
p. 5166 - 5169
(2016/10/14)
-
- Chemoselective oxidant-free dehydrogenation of alcohols in lignin using Cp?Ir catalysts
-
A remarkably effective method of chemoselective dehydrogenation of alcohols in lignin has been developed with an iridium catalyst. An additional operation of Zn/NH4Cl via a two-step one pot process could further promote the cleavage of the C-O bond in β-O-4 units in lignin. And this reaction system was also applicable to native lignin as the molecular weight of native lignin decreased obviously as detected by gel permeation chromatography (GPC). Additionally, this is the first to date generation of the by-product H2 from native lignin and the by-product was straightforwardly captured by 1-decene. A probable mechanistic pathway was also proposed with the help of density functional theory (DFT) calculations.
- Zhu, Rui,Wang, Bing,Cui, Minshu,Deng, Jin,Li, Xinglong,Ma, Yingbo,Fu, Yao
-
supporting information
p. 2029 - 2036
(2016/04/19)
-
- Synthesis of enantiomerically pure lignin dimer models for catalytic selectivity studies
-
A series of highly enantioselective transformations, such as the Sharpless asymmetric epoxidation and Jacobsen hydrolytic kinetic resolution, were utilized to achieve the complete stereoselective synthesis of β-O-4 lignin dimer models containing the S, G, and H subunits with excellent ee (>99%) and moderate to high yields. This unprecedented synthetic method can be exploited for enzymatic, microbial, and chemical investigations into lignins degradation and depolymerization as related to its stereochemical constitution. Preliminary degradation studies using enantiopure Co(salen) catalysts are also reported.
- Njiojob, Costyl N.,Rhinehart, Jennifer L.,Bozell, Joseph J.,Long, Brian K.
-
p. 1771 - 1780
(2015/02/19)
-
- Isolation of functionalized phenolic monomers through selective oxidation and CO bond cleavage of the β-O-4 linkages in Lignin
-
Functionalized phenolic monomers have been generated and isolated from an organosolv lignin through a two-step depolymerization process. Chemoselective catalytic oxidation of β-O-4 linkages promoted by the DDQ/tBuONO/ O2 system was achieved in model compounds, including polymeric models and in real lignin. The oxidized β-O-4 linkages were then cleaved on reaction with zinc. Compared to many existing methods, this protocol, which can be achieved in one pot, is highly selective, giving rise to a simple mixture of products that can be readily purified to give pure compounds. The functionality present in these products makes them potentially valuable building blocks.
- Lancefield, Christopher S.,Ojo, O. Stephen,Tran, Fanny,Westwood, Nicholas J.
-
supporting information
p. 258 - 262
(2015/02/19)
-
- METHOD FOR PREPARING FUROFURAN LIGNAN COMPOUND
-
The present invention relates to a method for preparing a furofuran lignan compound, comprising a step of selecting and alkylating an epoxy alcohol compound and an optical isomer thereof. (+)-furofuran lignan and (?)-furofuran lignan, as well as an optical isomer thereof, can be selectively prepared by means of the method.
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-
Page/Page column 0026; 0027
(2015/03/16)
-
- Total synthesis of (±)-sacidumlignans D and A through Ueno-Stork radical cyclization reaction
-
Efficient synthesis of (±)-sacidumlignan D (4) has been successfully achieved employing Ueno-Stork radical cyclization of α-bromo acetal 21 as a key step. Two synthetic approaches for the symmetrical diaryl ketone 19 have been discussed in detail. Notably, sacidumlignan A (1) can be also efficiently synthesized in only 7 steps with 25% overall yield, where acid triggered tandem reaction starting from analogous Ueno-Stork cyclization product 27 played an important role. Moreover, potentially biomimetic conversion from (±)-sacidumlignan D (4) to sacidumlignan A (1) could be realized. The Royal Society of Chemistry 2013.
- Zhang, Jian-Jian,Yan, Chang-Song,Peng, Yu,Luo, Zhen-Biao,Xu, Xiao-Bo,Wang, Ya-Wen
-
p. 2498 - 2513
(2013/06/26)
-
- Chemoselective metal-free aerobic alcohol oxidation in lignin
-
An efficient organocatalytic method for chemoselective aerobic oxidation of secondary benzylic alcohols within lignin model compounds has been identified. Extension to selective oxidation in natural lignins has also been demonstrated. The optimal catalyst system consists of 4-acetamido-TEMPO (5 mol %; TEMPO = 2,2,6,6-tetramethylpiperidine-N-oxyl) in combination with HNO3 and HCl (10 mol % each). Preliminary studies highlight the prospect of combining this method with a subsequent oxidation step to achieve C-C bond cleavage.
- Rahimi, Alireza,Azarpira, Ali,Kim, Hoon,Ralph, John,Stahl, Shannon S.
-
supporting information
p. 6415 - 6418
(2013/06/05)
-
- Compound
-
The present invention provides compounds of the formula Formula I or a salt thereof: and the uses of such compounds for the treatment of a disease or disorder involving oxidative damage, for preventing UV damage to the skin of a mammal and for preventing
- -
-
Paragraph 0190
(2013/10/22)
-
- C-C or C-O bond cleavage in a phenolic lignin model compound: Selectivity depends on vanadium catalyst
-
The aerobic oxidation of a phenolic lignin model compound with a vanadium catalyst results in the oxidative cleavage of the C-C bond between the aryl ring and the adjacent hydroxy-substituted carbon atom (see scheme). Labeling experiments indicate key mechanistic differences to a previously reported related C-O bond cleavage reaction. The selectivity in C-C versus C-O bond cleavage depends on the choice of the vanadium catalyst. Copyright
- Hanson, Susan K.,Wu, Ruilian,Silks, Louis A. Pete
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supporting information; experimental part
p. 3410 - 3413
(2012/06/30)
-
- Design, synthesis, and pharmacological evaluation of novel tetrahydroprotoberberine derivatives: Selective inhibitors of dopamine D 1 receptor
-
A series of new tetrahydroprotoberberine (THPB) derivatives were designed, synthesized, and tested for their binding affinity towards dopamine (D 1 and D2) and serotonin (5-HT1A and 5-HT 2A) receptors. Many of the THPB compounds exhibited high binding affinity and activity at the dopamine D1 receptor, as well as high selectivity for the D1 receptor over the D2, 5-HT 1A, and 5-HT2A receptors. Among these, compound 19c exhibited a promising D1 receptor binding affinity (Ki = 2.53 nM) and remarkable selectivity versus D2R (inhibition = 81.87%), 5-HT1AR (inhibition = 61.70%), and 5-HT2AR (inhibition = 24.96%). Compared with l-(S)-stepholidine (l-SPD) (D1 Ki = 6.23 nM, D2 Ki = 56.17 nM), compound 19c showed better binding affinity for the D1 receptor (2.5-fold higher) and excellent D2/D1 selectivity. Functional assays found compounds 18j, 18k, and 19c are pure D1 receptor antagonists. These results indicate that removing the C10 hydroxy group and introducing a methoxy group at C11 of the pharmacophore of l-SPD can reverse the function of THPB compounds at the D1 receptor. These results are in accord with molecular docking studies.
- Qian, Wangke,Lu, Weijian,Sun, Haifeng,Li, Zeng,Zhu, Liyuan,Zhao, Rui,Zhang, Lei,Zhou, Shengbin,Zhou, Yu,Jiang, Hualiang,Zhen, Xuechu,Liu, Hong
-
experimental part
p. 4862 - 4871
(2012/09/05)
-
- COMPOUND
-
The present invention provides compounds of the formula Formula I or a salt thereof: and the uses of such compounds for the treatment of a disease or disorder involving oxidative damage, for preventing UV damage to the skin of a mammal and for preventing or reversing the effects of ageing, or for treating or preventing dry skin.
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Page/Page column 44
(2012/05/04)
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- Synthesis of (1R,2S)-2-(4'-allyl-2',6'-dimethoxyphenoxyl)-1-(4''-hydroxy- 3'', 5''-dimethoxyphenyl)propan-1-ol
-
The asymmetric synthesis of the natural neolignan (1R,2S)-2-(4'-allyl-2', 6'-dimethoxyphenoxyl)-1-(4''-hydroxy-3'',5''- dimethoxyphenyl)propan-1-ol based on an asymmetric dihydroxylation as a key reaction using AD-mix-β to preparing the chiral threo-(1R,2R)-glycerol. The reaction, threo-alcohols were inverted by an SN2 reaction into erythro-(1R,2S)-isomers.
- Ding, Junwei,Qi, Rongwei,Zhou, Haitang,Jiao, Bin,Xia, Yamu
-
p. 519 - 521
(2011/11/29)
-
- NOVEL POLYSPIRANE COMPOUNDS, APPLICATION THEREOF IN THE TREATMENT OF MALARIA OR TOXOPLASMOSIS AND METHOD FOR PREPARING SAME
-
Novel polyspirane compounds used in the treatment of diseases involving parasites that belong to the phylum of apicomplexae, and a method for preparing the same.
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Page/Page column 24
(2010/12/29)
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- General approach to 2, 3-dibenzyl-γ-butyrolactone lignans: application to the total synthesis of (±)-5'-methoxyyatein, (±)-5'-methoxyclusin, and ( ± )-4' -hydroxycubebinone
-
The total synthesis of natural lignans 5'-methoxyyatein (1), 5'-methoxyclusin (2), and 4'-hydroxycubebmone (3), inracemic form, has been achieved by a newly developed strategy, wherein lithium, naphthalenide induced decyanation was employed as a key opera
- Amancha, Prashanth K.,Liu, Hsing-Jang,Wei Ly, Tai,Shia, Kak-Shan
-
experimental part
p. 3473 - 3480
(2010/09/07)
-
- Synthesis of diketopiperazine-based carboline homodimers and in vitro growth inhibition of human carcinomas
-
Starting from d- or l-tryptophan, we have synthesized and characterized six compounds 2.29-2.31a and b that belong to a class of nitrogen heterocycles: the carboline-based homodimers. Each individual homodimer features a 1,3-trans relationship on each side of the central diketopiperazine core, but differs in absolute stereochemistry and also in substitution on the 4′ and 4″ oxygens (-Bn, -CH3, or -H). The in vitro cytotoxicity of the six compounds was evaluated by measuring the growth inhibition in NCI-H520 and PC-3 human carcinoma cells. Phenol 2.30a inhibited cancer cell growth approximately three times better than its enantiomer 2.30b and possessed a GI50 comparable to the clinically used agent etoposide in both cell lines. We have concluded that both the stereochemistry imparted by l-tryptophan and the presence of hydroxy substituents at the 4′ and 4″ positions are necessary to generate cytotoxic properties in the homodimer class. We are now employing 2.30a as a new lead compound in our efforts to discover improved indole-based cancer chemotherapeutics.
- Deveau, Amy M.,Costa, Nancy E.,Joshi, Elizabeth M.,Macdonald, Timothy L.
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supporting information; experimental part
p. 3522 - 3525
(2009/04/06)
-
- Discovery and SAR of hydrazide antagonists of the pituitary adenylate cyclase-activating polypeptide (PACAP) receptor type 1 (PAC1-R)
-
Potent small molecule antagonists for the PAC1-R have been discovered. Previously known antagonists for the PAC1-R were slightly truncated peptide ligands. The hydrazides reported here are the first small molecule antagonists ever reported for this class B GPCR.
- Beebe, Xenia,Darczak, Daria,Davis-Taber, Rachel A.,Uchic, Marie E.,Scott, Victoria E.,Jarvis, Michael F.,Stewart, Andrew O.
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p. 2162 - 2166
(2008/09/20)
-
- Design, synthesis, and SAR analysis of cytotoxic sinapyl alcohol derivatives
-
Five series totalling 51 of sinapyl alcohol derivatives were designed and synthesized. Their cytotoxicity analyses were performed on six human tumor cell lines such as PC-3, CNE, KB, A549, BEL-7404, and HeLa. Certain sinapyl alcohol derivatives showed significant cytotoxic activities. Compound 14d exhibited especially potent cytotoxicity against the BEL-7404 cell line with an IC 50 value of 0.7 μM, which showed more cytotoxic activity than the positive control, cisplatin. The structure-cytotoxicity relationships were discussed and the CoMFA analysis was performed using the cytotoxic data against HeLa cells as a template.
- Zou, Hong Bin,Dong, Sheng Yi,Zhou, Chang Xin,Hu, Li Hong,Wu, Yi Hang,Li, Hai Bo,Gong, Jing Xu,Sun, Lian Li,Wu, Xiu Mei,Bai, Hua,Fan, Bo Tao,Hao, Xiao Jiang,Stoeckigt, Joachim,Zhao, Yu
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p. 2060 - 2071
(2007/10/03)
-
- Synthesis of lyoniresinol with combined utilization of synthetic chemistry and biotechnological methods
-
We have synthesized lyoniresinol with the combined utilization of synthetic chemistry and biotechnological methods, specifically using plant cell cultures as an "enzyme source."
- Takemoto, Masumi,Fukuyo, Ayako,Aoshima, Yoichi,Tanaka, Kiyoshi
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p. 226 - 229
(2007/10/03)
-
- Antioxidant and antimicrobial activity evaluation of polyhydroxycinnamic acid ester derivatives
-
Polyhydroxycinnamic acid esters 5a-p have been synthesized starting from the appropriately substituted benzaldehydes. The antioxidant activity of these esters has been determined by superoxide free radical scavenging activity and DPPH free radical scavenging activity. The SAR studies reveal that pyrogallol, catechol moieties are essential for good antioxidant activity and an increase in the length of alkyl chain of the ester decreases the activity. Butyl hydroxycinnamates exhibit higher antibacterial activity among the synthesized hydroxycinnamates 5a-p, but, none of these show significant antifungal activity.
- Venkateswarlu, Somepalli,Ramachandra, Mareullapudi S.,Krishnaraju, Alluri V.,Trimurtulu, Golakoti,Subbaraju, Gottumukkala V.
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p. 252 - 257
(2007/10/03)
-
- Synthesis of Ether Oligomers
-
(Equation presented) Hydroxyaromatic aldehydes and ketones were used as building blocks to prepare ether oligomers. An iterative two-step protocol involving Mitsunobu coupling and carbonyl reduction provided a protecting-group-free route with high yields. Activity screening of an 84-member library against proteases led to the discovery of micromolar inhibitors for trypsin, chymotrypsin, and subtilisin.
- Renaudet, Olivier,Reymond, Jean-Louis
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p. 397 - 400
(2007/10/03)
-
- Potential therapeutic antioxidants that combine the radical scavenging ability of myricetin and the lipophilic chain of vitamin E to effectively inhibit microsomal lipid peroxidation
-
The flavonol myricetin, reacts with oxygen-centred galvinoxyl radicals 28 times faster than d-α-tocopherol (vitamin E), the main lipid-soluble antioxidant in biological membranes. Moreover, each myricetin molecule reduces twice as many such radicals as vitamin E. However, myricetin fails to protect vitamin E-deficient microsomes from lipid peroxidation as assessed by the formation of thiobarbituric acid reactive substances (TBARS). Novel and potentially therapeutic antioxidants have been prepared that combine the radical-scavenging ability of a myricetin-like head group with a lipophilic chain similar to that of vitamin E. C6-C12 alkyl chains are attached to the A-ring of either a 3,3′,4 ′,5′-tetrahydroxyflavone or a 3,2 ′,4′,5′-tetrahydroxyflavone head group to give lipophilic flavonoids (ClogP=4 to 10) that markedly inhibit iron-ADP catalysed oxidation of microsomal preparations. Orientation of the head group as well as total lipophilicity are important determinants of antioxidant efficacy. MM2 models indicate that our best straight chain 7-alkylflavonoids embed to the same depth in the membrane as vitamin E. The flavonoid head groups are prepared by aldol condensation followed by Algar-Flynn-Oyamada (AFO) oxidation or by Baker-Venkataraman rearrangement. The alkyl tails are introduced by Suzuki or Negishi palladium-catalysed cross-coupling or by cross-metathesis catalysed by first generation Grubbs catalyst, which tolerate phenolic hydroxyl and ketone groups.
- Bennett, Christopher J.,Caldwell, Stuart T.,McPhail, Donald B.,Morrice, Philip C.,Duthie, Garry G.,Hartley, Richard C.
-
p. 2079 - 2098
(2007/10/03)
-
- FLAVONOID COMPOUNDS AS THERAPEUTIC ANTIOXIDANTS
-
Novel flavonoid compounds having anti-oxidant activity are described. The compounds have been shown to exhibit anti-oxidative properties in biological systems and their utility in a sunscreen or skincare composition or to treat conditions involving oxidative damage, especially curative or prophylactic treatment of Alzheimer's disease or ischaemia-reperfusion injury, is described.
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-
-
- Compositions containing aromatic aldehydes and their use in treatments
-
Disclosed are pharmaceutical and cosmetic compositions containing aromatic aldehyde compounds. Some of the disclosed compositions are useful as topical therapeutics for treating inflammatory dermatologic conditions. Some of the compositions are useful in transdermal and other systemic dose forms for treating other inflammatory conditions in mammals.
- -
-
-
- Synthesis and antibacterial activity of amoenylin, a metabolite of Dendrobium amoenum
-
Amoenylin 6, a dihydrostilbene from Dendrobium amoenum, has been synthesised from syringaldehyde 1, in three steps with an overall yield of 40%. The spectral data of synthetic 6 are in good agreement with those of natural product. Amoenylin 6 shows weak a
- Venkateswarlu, Somepalli,Ramachandra, Marellapudi S.,Subbaraju, Gottumukkala V.
-
p. 1779 - 1781
(2007/10/03)
-
- Biosynthesis of yatein in Anthriscus sylvestris.
-
Little is known about the biosynthesis of yatein, in spite of its importance as a typical heartwood lignan and a key biosynthetic intermediate of the antitumor lignan podophyllotoxin. The present study, based on individual administration of [13C]phenylalanine and deuterium labelled lignans and simultaneous administration of two distinct lignans labelled with deuterium atoms to Anthriscus sylvestris, established the two independent branch pathways from matairesinol, one to afford yatein via thujaplicatin, 5-methylthujaplicatin, and 4,5-dimethylthujaplicatin and the other to bursehernin via pluviatolide. The latter pathway did not lead to yatein, eliminating the presence of a metabolic grid from matairesinol to yatein.
- Sakakibara, Norikazu,Suzuki, Shiro,Umezawa, Toshiaki,Shimada, Mikio
-
p. 2474 - 2485
(2007/10/03)
-
- Syntheses of two cytotoxic sinapyl alcohol derivatives and isolation of four new related compounds from Ligularia nelumbifolia
-
Phytochemical reinvestigation on Ligularia nelumbifolia afforded four novel sinapyl alcohol analogues named nelumols B-E (1-4) and three known sinapyl alcohol derivatives (5-7). Their structures were elucidated by NMR techniques. Total syntheses of cytotoxic geranyloxy sinapyl alcohol (6) and geranyloxy sinapyl aldehyde (7) were carried out via two different paths. The 4-O-benzyl-substituted analogues (20 and 27) as well as the 4-O-(2-methylbutenyl) derivatives (34 and 35) were also synthesized. The cytotoxicities of 6 and 7 were measured using A-549, HL-60, and KB cancer cell lines.
- Zhao, Yu,Hao, Xiaojiang,Lu, Wei,Cai, Junchao,Yu, Hong,Sevenet, Thierry,Gueritte, Francoise
-
p. 902 - 908
(2007/10/03)
-
- Synthesis and antimicrotubule activity of combretatropone derivatives.
-
Combretatropone is a hybrid of combretastatin and colchicine in which the o-methoxyphenol of dihydrocombretastatin A-4 is replaced by an alpha-methoxytropone. Derivatives of combretatropone have been synthesized and evaluated for antimicrotubule activity.
- Janik, Mark E,Bane, Susan L
-
p. 1895 - 1903
(2007/10/03)
-
- Synthesis of α-hydroxyacetosyringone
-
A phytoalexin from papaya fruit has been synthesized in four steps; this procedure involved a Pummerer- type reaction.
- Echeverri, Fernando,Quinones, Winston,Torres, Fernando,Duque, Mario,Archbold, Rosendo
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p. 1287 - 1290
(2007/10/03)
-
- Studies on the Synthesis of highly substituted naphthol: Preparation of 6-Hydroxy-5,7-Dimethoxy-2-Naphthoic Acid, Isolated From Ulmus Thomasii
-
An improvement of a known procedure, affording substituted 4-hydroxy-2-naphthoic acid derivatives from aromatic aldehydes is described and its general applicability is shown through the preparation of a natural naphthalene derivative isolated from Ulmus thomasii.
- Fuganti, Claudio,Serra, Stefano
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p. 2769 - 2782
(2007/10/03)
-
- Synthesis and biological evaluation of flavanones and flavones related to podophyllotoxin
-
A series of novel flavonoids comprising structural elements present in the antineoplastic agents podophyllotoxin and etoposide was synthesized. These oxygen-containing analogues of antiproliferative quinolones exhibited moderate cytotoxicity towards L1210 and HT-29 cell lines.
- De Peredo, Anne Gonzalez,Léonce, Stéphane,Monneret, Claude,Dauzonne, Daniel
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- New recurrent synthetic method for the synthesis of functionalized oligomeric β-O-4 lignin model compounds
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β-O-4-lignin model compounds have been synthesized using a new recurrent method affording dimers and trimers with controlled stereochemistry and bearing an aldehyde group.
- Roblin,Duran,Duran,Banuls,Gorrichon
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p. 2355 - 2358
(2007/10/03)
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- Stilbene derivatives as anticancer agents
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The present invention relates to stilbene derivatives which possess utility as anti-cancer agents. The compounds can be used to treat cancers which are susceptible to treatment therewith, and can be utilized in a method of treating such cancers. Pharmaceu
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- STUDIES WITH PLANT CELL CULTURES OF PODOPHYLLUM PELTATUM L. II. BIOTRANSFORMATION OF DIBENZYLBUTANOLIDES TO LIGNANS. DEVELOPMENT OF A "BIOLOGICAL FACTORY" FOR LIGNAN SYNTHESIS
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An efficient and versatile synthetic route to appropriate dibenzylbutanolides suitable for biotransformation to lignans as potential intermediates for the syntheses of the clinical anti-cancer drug etoposide has been developed.Biotransformation of such substrates, for example 10, with cell cultures of Podophyllum peltatum affords a potentially exciting route to this drug.Of particular significance is the development of a semi-continuous fermentation process with these plant cells wherein successive additions of substrate and isolation of end products can be pursued with a given batch of cells and over a period of several months.Biotransformation times for the conversion of 10 to 11 and 12 are short (usually 24-48 h).Although conditions have not yet optimized, this "biological factory" for lignan synthesis provides a novel approach for the use of plant cells, in combination with chemistry, for continuous and large scale production of such metabolites.
- Kutney, James P.,Chen, Yung Ping,Gao, Shixiang,Hewitt, Gary M.,Kuri-Brena, Francisco,et al.
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- Intramolecular Oxidative Coupling of Aromatic Compounds. I Oxidation of Diphenolic Substrates
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The synthesis of (2RS,3SR)-1-(3,5-dihydroxy-4-methoxyphenyl)-(4-hydroxy-3,5-dimethoxyphenyl)2,3-dimethylbutan-1-one (26) is described.Diphenolic oxidative coupling of (26) did not produce a eupodienone-type product.An aryltetralin derivative was formed in
- Krauss, Adrian S.,Taylor, Walter C.
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p. 1307 - 1333
(2007/10/02)
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- Studies on the Constituents of the Seeds of Hernandia ovigera L. VII. Syntheses of (+/-)-Hernolactone and (+/-)-Hernandin
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Two new lignans, hernolactone (1) and hernandin (2), isolated from the seeds of Hernandia ovigera L. were synthesized in racemic forms.Firstly, (+/-)-1 was obtained by utilizing the conjugate addition reaction of 4 with butenolide followed by alkylation with trimethoxybenzyl bromide and subsequent removal of the protecting groups.Synthesis of 2 was pursued using the corresponding 4-phenyl-1,2-dihydronaphthalene lactone (18).The cleavage of the lactone moiety of 18 afforded an unsaturated hydroxy acid (22).Subsequent hydrogenation of 22 followed by acidification with concentrated hydrochloric acid gave isopicrohernandin (21), leaving the 2,3-trans, 3,4-cis hydroxy acid (23), which was lactonized by means of N,N-dicyclohexylcarbodiimide to afford (+/-)-2.Keywords: Hernandia ovigera; hernolactone; hernandin; lignan; dibenzylbutyrolactone lignan; phenyltetralin lignan; isopicrohernandin; Diels-Alder reaction
- Tanoguchi, Mariko,Kashima, Tatsuhiko,Saika, Hideyuki,Inoue, Taishi,Arimoto, Masao,Yamaguchi, Hideo
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- Oxidative Coupling of Lignans. IV. Monophenolic Oxidative Coupling
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Oxidative coupling of the monophenolic monoester (6) gives an aryltetralin (12) which is a potential intermediate for the synthesis of clinically active monophenolic lignan lactones.In contrast, oxidative couplings of the monophenols (32) and (35), derived from matairesinol (29), give mixtures of diastereoisomeric cyclooctadiene lignans while 4'-demethyldeoxypodorhizon (26) does not cyclize.These results show that the degree of aromatic substitution in monophenolic diarylbutanes plays an important role in determining the outcome of oxidative coupling.An alternative synthesis of the lactone (57) from piperonal has been investigated.
- Burden, Jonathan K.,Cambie, Richard C.,Craw, Peter A.,Rutledge, Peter S.,Woodgate, Paul D.
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p. 919 - 933
(2007/10/02)
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- THE SYNTHESES OF (R)-(+)-β-VANILLYL-γ-BUTYROLACTONE AND OF CHIRAL LIGNANS THEREFROM
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(R)-(+)-β-vanillyl-γ-butyrolactone was obtained in 4 steps including a resolution, from vanillin and dimethyl succinate, and was used for the total syntheses of 5 naturally occurring and optically active lignans such as (+)-isolariciresinol 20.
- Brown, Eric,Daugan, Alain
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p. 1169 - 1172
(2007/10/02)
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- Synthesis along Biosynthetic Pathways. Part 2. Synthesis of Protostephanine
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The dienone protostephanone (3) is synthesised by phenol coupling or by Pschorr cyclisation from readily prepared tetrahydroisoquinolines, and the corresponding dienols (17) and (18) are converted by rearrangement, fragmentation, and reduction into protostephanine (4).This sequence mimics the natural pathway to the alkaloid.
- Battersby, Alan R.,Bhatnagar, Akil K.,Hackett, Peter,Thornber, Craig W.,Staunton, James
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p. 2002 - 2009
(2007/10/02)
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