- Methyl 3,4,5-trimethoxycinnamate suppresses inflammation in RAW264.7 macrophages and blocks macrophage–adipocyte interaction
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Methyl 3,4,5-trimethoxycinnamate (MTC) is a bioactive natural phenylpropanoid. We evaluated anti-inflammatory effects of synthetic MTC in RAW264.7 macrophages and RAW264.7–3T3-L1 adipocytes co-culture. Levels of cytokines and chemokines, as well as NO and
- Olajide, Olumayokun A.,Akande, Idowu S.,da Silva Maia Bezerra Filho, Carlos,Lepiarz-Raba, Izabela,de Sousa, Dami?o Pergentino
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Read Online
- Synthesis, antiepileptic effects, and structure-activity relationships of α-asarone derivatives: In vitro and in vivo neuroprotective effect of selected derivatives
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In the present study, we compared the antiepileptic effects of α-asarone derivatives to explore their structure-activity relationships using the PTZ-induced seizure model. Our research revealed that electron-donating methoxy groups in the 3,4,5-position on phenyl ring increased antiepileptic potency but the placement of other groups at different positions decreased activity. Besides, in allyl moiety, the optimal activity was reached with either an allyl or a 1-butenyl group in conjugation with the benzene ring. The compounds 5 and 19 exerted better neuroprotective effects against epilepsy in vitro (cell) and in vivo (mouse) models. This study provides valuable data for further exploration and application of these compounds as potential anti-seizure medicines.
- Zhang, Jian,Mu, Keman,Yang, Peng,Feng, Xinqian,Zhang, Di,Fan, Xiangyu,Wang, Qiantao,Mao, Shengjun
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- Design, Antileishmanial Activity, and QSAR Studies of a Series of Piplartine Analogues
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Piplartine is an alkamide found in different Piper species and possesses several biological activities, including antiparasitic properties. Thus, the aim of the present study was to evaluate a series of 32 synthetic piplartine analogues against the Leishmania amazonensis promastigote forms and establish the structure-activity relationship and 3D-QSAR of these compounds. The antileishmanial effect of the compounds was determined using the MTT method. Most compounds were found to be active against L. amazonensis. Among 32 assayed derivatives, compound (E)-(-)-bornyl 3-(3,4,5-trimethoxyphenyl)-acrylate exhibited the most potent antileishmanial activity (IC50 = 0.007 ± 0.008 μM, SI > 10), followed by benzyl 3,4,5-trimethoxybenzoate (IC50 = 0.025 ± 0.009 μM, SI > 3.205) and (E)-furfuryl 3-(3,4,5-trimethoxyphenyl)-acrylate (IC50 = 0.029 ± 0.007 μM, SI > 2.688). It was found that the rigid substituents contribute to increasing antiparasitic activity against L. amazonensis promastigotes. The presence of the unsaturated heterocyclic substituent in the phenylpropanoid chemical structure (furfuryl group) resulted in a bioactive derivative. Molecular simplification of benzyl 3,4,5-trimethoxybenzoate by omitting the spacer group contributed to the bioactivity of this compound. Furthermore, bornyl radical appears to be important for antileishmanial activity, since (E)-(-)-bornyl 3-(3,4,5-trimethoxyphenyl)-acrylate exhibited the most potent antileishmanial activity. These results show that some derivatives studied would be useful as prototype molecules for the planning of new derivatives with profile of antileishmanial drugs.
- Nóbrega, Flávio R.,Silva, Larisse V.,Bezerra Filho, Carlos Da Silva M.,Lima, Tamires C.,Castillo, Yunierkis P.,Bezerra, Daniel P.,Lima, Tatjana K. Souza,Sousa, Dami?o P. De
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- Synthesis and biological evaluation of celastrol derivatives as anti-ovarian cancer stem cell agents
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Ovarian cancer is associated with a high percentage of recurrence of tumors and resistance to chemotherapy. Cancer stem cells (CSCs) are responsible for cancer progression, tumor recurrence, metastasis, and chemoresistance. Thus, developing CSC-targeting therapy is an urgent need in cancer research and clinical application. In an attempt to achieve potent and selective anti-CSC agents, a series of celastrol derivatives with cinnamamide chains were synthesized and evaluated for their anti-ovarian cancer activities. Most of the compounds exhibited stronger antiproliferative activity than celastrol, and celastrol derivative 7g with a 3,4,5-trimethoxycinnamamide side chain was found to be the most potent antiproliferative agent against ovarian cancer cells with an IC50 value of 0.6 μM. Additionally, compound 7g significantly inhibited the colony formation ability and reduced the number of tumor spheres. Furthermore, compound 7g decreased the percentage of CD44+, CD133+ and ALDH+ cells. Thus, compound 7g is a promising anti-CSC agent and could serve as a candidate for the development of new anti-ovarian cancer drugs.
- Li, Xiaojing,Ding, Jie,Li, Ning,Liu, Wenxia,Ding,Zheng, Huijuan,Ning, Yanyan,Wang, Hongmin,Liu, Renmin,Ren, Shaoda
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p. 667 - 679
(2019/07/05)
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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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- Piplartine analogues and cytotoxic evaluation against glioblastoma
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Piplartine (1) is an alkamide extracted from plants of the genus Piper which shows several pharmacological properties, including antitumor activity. To improve this activity, a series of analogues based on 1 have been synthesized by esterification and amidation using the 3,4,5-trimethoxycinnamic acid-like starting material. During the study, the moieties 3-(3,4,5-trimethoxyphenyl)acrylate and 3-(3,4,5-trimethoxyphenyl)acrylamide were maintained on esters and amides respectively. Meanwhile, functional changes were exploited, and it was revealed that the presence of two aromatic rings in the side-chain was important to improve the cytotoxic activity against the U87MG cell line, such as the compound (E)-benzhydryl 3-(3,4,5-trimethoxyphenyl)acrylate (10), an ester that exhibited strong cytotoxicity and a similar level of potency to that of paclitaxel, a positive control. Compound 10 had a marked concentration-dependent inhibitory effect on the viability of the U87MG cell line with apoptotic and oxidative processes, showing good potential for altering main molecular pathways to prevent tumor development. Moreover, it has strong bioavailability with non-genotoxic and non-cytotoxic properties on human blood cells. In conclusion, the findings of the present study demonstrated that compound 10 is a promising agent that may find applications combatting diseases associated with oxidative stress and as a prototype for the development of novel drugs used in the treatment of glioblastoma.
- da Nóbrega, Flávio Rogério,Ozdemir, Ozlem,Nascimento Sousa, Sheila Cristina S.,Barboza, Joice Nascimento,Turkez, Hasan,de Sousa, Dami?o Pergentino
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- Antifungal activity of cinnamic acid and benzoic acid esters against Candida albicans strains
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Candida albicans is an important opportunistic fungal pathogen capable of provoking infection in humans. In the present study, we evaluated the antifungal effect of 23 ester derivatives of the cinnamic and benzoic acids against 3 C. albicans strains (ATCC-76645, LM-106 and LM-23), as well as discuss their Structure–Activity Relationship (SAR). The antifungal assay results revealed that the screened compounds exhibited different levels of activity depending on structural variation. Among the ester analogues, methyl caffeate (5) and methyl 2-nitrocinnamate (10) were the analogues that presented the best antifungal effect against all C. albicans strains, presenting the same MIC values (MIC?=?128?μg/mL), followed by methyl biphenyl-2-carboxylate (21) (MIC?=?128, 128 and 256?μg/mL for C. albicans LM-106, LM-23, and ATCC-76645, respectively). Our results suggest that certain molecular characteristics are important for the antifungal action.
- Lima, Tamires C.,Ferreira, Alana R.,Silva, Daniele F.,Lima, Edeltrudes O.,de Sousa, Dami?o P.
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p. 572 - 575
(2017/09/30)
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- Microwave-Assisted Synthesis of Phenylpropanoids and Coumarins: Total Synthesis of Osthol
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Herein we describe a one-pot microwave-assisted method for the synthesis of cinnamic acid and coumarin derivatives. The synthesis begins with an aldehyde synthon, and the chosen reaction conditions determine whether a cinnamic acid or coumarin derivative is formed. A regioselective Claisen rearrangement was also efficiently incorporated into the synthetic sequence to further increase the complexity of the product. Notably, this approach provides high product yields and selectivities without the need of a phenol protecting group.
- Konrádová, Daniela,Kozubíková, Hana,Dole?al, Karel,Pospí?il, Ji?í
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supporting information
p. 5204 - 5213
(2017/09/29)
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- An in Situ Generated Palladium on Aluminum Oxide: Applications in Gram-Scale Matsuda-Heck Reactions
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In situ generated palladium on aluminum oxide provides an active catalytic system for Matsuda-Heck reactions in gram-scale. The novel catalyst proceeded through a significantly higher catalytic activity compared to the classical Pd/C system. Based on the high catalytic activity the first α,β,β-triarylation of methyl acrylate in good yields could be provided in one-step.
- Pape, Simon,Dauk?ait?, Lauryna,Lucks, Sandra,Gu, Xiaoting,Brunner, Heiko
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supporting information
p. 6376 - 6379
(2016/12/23)
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- A kind of carboxylic acid with malonic acid method of esterification reaction of dimethyl ester (by machine translation)
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The invention belongs to the field of chemical synthesis and particularly relates to a carboxyl acid compound methyl etherification method. The carboxyl acid compound methyl etherification method comprises the following steps: in a polar solvent, using a carboxyl acid compound and dimethyl malonate as reactants, under the catalysis of a catalyst, and preparing an acid methyl ester compound through the methyl etherification reaction of the carboxyl acid. The method has the advantages of cheap raw materials, easiness in raw material acquisition, low toxicity, high safety, simple neutral salt catalyst and low dosage and is suitable for industrial application.
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Paragraph 0050; 0051
(2017/02/28)
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- Copper Hydride Catalyzed Reductive Claisen Rearrangements
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An efficient reductive Claisen rearrangement, catalyzed by in situ generated copper hydride and stoichiometric in diethoxymethylsilane, has been developed. Yields of up to 95 ;% with good to excellent diastereoselectivities were observed in this reaction. Mechanistic studies showed that the stereospecific rearrangement proceeded via a chair transition state of (E)-silyl ketene acetals as intermediates and not via the copper enolates.
- Wong, Kong Ching,Ng, Elvis,Wong, Wing-Tak,Chiu, Pauline
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supporting information
p. 3709 - 3712
(2016/03/08)
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- Solvolysis, Electrochemistry, and Development of Synthetic Building Blocks from Sawdust
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Either aldehyde or cinnamyl ether products can be selectively extracted from raw sawdust by controlling the temperature and pressure of a solvolysis reaction. These materials have been used as platform chemicals for the synthesis of 15 different synthetic substrates. The conversion of the initial sawdust-derived materials into electron-rich aryl substrates often requires the use of oxidation and reduction chemistry, and the role electrochemistry can play as a sustainable method for these transformations has been defined.
- Nguyen, Bichlien H.,Perkins, Robert J.,Smith, Jake A.,Moeller, Kevin D.
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p. 11953 - 11962
(2016/01/09)
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- A practical, chemoselective approach to O-methylation of carboxylic acids with dimethyl malonate
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A practical and chemoselective method is described for the O-methylation of carboxylic acids. Dimethyl malonate, a low toxic and commercially available compound was found to be an effective methylating reagent for a variety of carboxylic acids affording methyl ester products in good to high yields and with excellent chemoselectivity, without the use of strong bases as additives. A mechanism involving the utilization of potassium bromide is tentatively proposed.
- Mao, Jincheng,Liu, Defu,Li, Yongming,Zhao, Jinzhou,Rong, Guangwei,Yan, Hong,Zhang, Guoqi
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p. 9067 - 9072
(2015/11/09)
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- Heck-Matsuda arylation of olefins through a bicatalytic approach: Improved procedures and rationalization
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The scope of the palladium-catalyzed Heck-Matsuda reaction, proceeding through the catalytic activation of anilines into the corresponding diazonium salts, has been considerably extended and is now working with deactivated electrophiles. Two different procedures, using catalytic amounts of both palladium and acid, have been optimized allowing the concept of bicatalysis to cover the complete electronic range of anilines. These environmentally friendly procedures proceed under very mild conditions, at room temperature in methanol, and only generate tert-butyl alcohol, water and nitrogen as by-products. Rationalization of reaction outcomes encountered in this work has been discussed with the support of computational studies.
- Oger, Nicolas,Le Callonnec, Francois,Jacquemin, Denis,Fouquet, Eric,Le Grognec, Erwan,Felpin, Francois-Xavier
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supporting information
p. 1065 - 1071
(2014/04/03)
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- Synthesis and DPPH radical scavenging activity of novel compounds obtained from tyrosol and cinnamic acid derivatives
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Tyrosol, a naturally occurring phenolic compound poorly attractive as an antioxidant because of its weak efficacy, was used as starting material to obtain novel compounds. The synthesis is based on a trifluoroacetic acid-mediated hydroarylation of cinnamic esters with tyrosol to produce 4-aryl-3,4-dihydrocoumarins, molecules of biological interest, followed by a basic hydrolysis to give the corresponding ring opening products. Unreported mechanistic investigations confirmed that the first step resulted from an electrophilic aromatic substitution and an intramolecular transesterification. Final products exhibited DPPH radical scavenging activity significantly higher than tyrosol.
- Barontini, Maurizio,Bernini, Roberta,Carastro, Isabella,Gentili, Patrizia,Romani, Annalisa
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p. 809 - 816
(2014/02/14)
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- Synthesis and Evaluation of a Series of 3,4,5-Trimethoxycinnamic Acid Derivatives as Potential Antinarcotic Agents
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A series of 3,4,5-trimethoxycinnamic acid derivatives was prepared and evaluated for antinarcotic effects on morphine dependence in mice and binding affinities on serotonergic receptors. The key synthetic strategies involve generation of ketones 6-7, esters 9-12 through condensation reaction, and amides 13-19 via coupling reaction using 1-hydroxybenzotriazole/ethyl(dimethylaminopropryl)carbodiimide system in high yield. We found that the naloxone-induced morphine withdrawal syndrome was significantly suppressed by new synthetic 3,4,5-trimethoxycinnamic acid derivatives (20mg/kg/day). Most of 3,4,5-trimethoxycinnamic acid derivatives were found to have high affinity to 5-HT1A receptor. The naloxone-induced morphine withdrawal syndrome was attenuated by (+)8-OH-DPAT (0.1mg/kg/day, i.p.), a 5-HT1A receptor agonist. In cortical neuronal cells, (+)8-OH-DPAT (1μm) produced an elevation of the pERK 1/2 expression, and the elevated pERK levels were inhibited by WAY 100635, a 5-HT1A receptor-specific antagonist. Interestingly, the pERK levels were increased by the 3,4,5-trimethoxycinnamic acid derivatives and the derivatives-mediated changes in pERK levels were blocked by the WAY 100635. These results suggested that new synthetic 3,4,5-trimethoxycinnamic acid derivatives have a potential antinarcotic effect through acting as a 5-HT1A receptor agonist in mice.
- Jung, Jae-Chul,Moon, Sohyeon,Min, Dongguk,Park, Woo Kyu,Jung, Mankil,Oh, Seikwan
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p. 389 - 398
(2013/04/10)
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- Biologically active bergenin derivatives from bergenia stracheyi
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New bergenin derivatives, bergecins A and B (1 and 2, resp.), have been isolated from the AcOEt-soluble fraction of Bergenia stracheyi, along with bergenin (3), and their structures were elucidated on the basis of 1H- and 13C-NMR spectra, and by COSY, HMQC, and HMBC experiments. Compound 2 showed potent inhibitory potential against the enzyme lipoxygenase, while 1 was moderately active. On the other hand, both compounds exhibited significant antioxidant activities in 1,1-diphenyl-2-picrylhydrazyl (DPPH) scavenging assay. Copyright
- Siddiq, Farah,Fatima, Itrat,Malik, Abdul,Afza, Nighat,Iqbal, Lubna,Lateef, Mehreen,Hameed, Saira,Khan, Sher Wali
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body text
p. 91 - 98
(2012/04/10)
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- Synthesis and biological evaluation of new piplartine analogues as potent aldose reductase inhibitors (ARIs)
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As a continuation of our efforts directed towards the development of anti-diabetic agents from natural sources, piplartine was isolated from Piper chaba, and was found to inhibit recombinant human ALR2 with an IC50 of 160 μM. To improve the efficacy, a series of analogues have been synthesized by modification of the styryl/aromatic and heterocyclic ring functionalities of this natural product lead. All the derivatives were tested for their ALR2 inhibitory activity, and results indicated that adducts 3c, 3e and 2j prepared by the Michael addition of piplartine with indole derivatives displayed potent ARI activity, while the other compounds displayed varying degrees of inhibition. The active compounds were also capable of preventing sorbitol accumulation in human red blood cells.
- Rao, Vidadala Ramasubba,Muthenna, Puppala,Shankaraiah, Gundeti,Akileshwari, Chandrasekhar,Babu, Kothapalli Hari,Suresh, Ganji,Babu, Katragadda Suresh,Chandra Kumar, Rotte Sateesh,Prasad, Kothakonda Rajendra,Yadav, Potharaju Ashok,Petrash, J. Mark,Reddy, Geereddy Bhanuprakash,Rao, Janaswamy Madhusudana
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p. 344 - 361
(2013/01/15)
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- ALR2 INHIBITORS AND THEIR SYNTHESIS FROM A NATURAL SOURCE
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A Michael adduct of piplartine, to provide inhibition of ALR2 in vitro (supported by molecular docking) and their potential to suppress the accumulation of sorbitol in erythrocytes when incubated under high glucose conditions; a treatment method using a Michael adduct; and a process for preparing a Michael adduct are provided.
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Page/Page column 10
(2012/10/08)
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- Stereoselective olefination of N-sulfonyl imines with stabilized phosphonium ylides for the synthesis of electron-deficient alkenes
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An unprecedented protocol has been developed for thestereoselective synthesis of structurally diverse electron-deficient alkenes in moderate to excellent yields from readily accessible N-sulfonyl imines and stabilized phosphonium ylides. Significantly, the olefination reaction of N-sulfonylimines with nitrile-stabilized phosphonium ylides affords an array of α,β-unsaturated nitriles with high Z selectivity, and the reactions with ester-, amide-, and ketone-stabilized phosphonium ylides afford α,β-unsaturated esters, amides, and ketones with high E selectivity, respectively. Spectroscopic analysis of the reaction mixtures and trapping of the intermediates allow plausible mechanisms to be proposed. Initialimine/ylide addition leads to the formation of betaines that cyclize to form 1,2-azaphosphetanes that subsequently eliminate iminophosphoranes to yield alkenes. For the synthesis of electron-deficient 1,2-disubstituted alkenes, the presence of an electron-withdrawing group in the betaine allows rapid interconversion between its two diastereomers through proton transfer. The Z/E selectivity for alkene synthesis is determined by the different rates at which the two betaine diastereomers form the corresponding 1,2-azaphosphetane diastereomers. In contrast, the Z/E selectivity for the synthesis of electron-deficient trisubstituted alkenes originates from the diastereoselective addition of stabilized phosphonium ylides to N-sulfonyl imines.
- Fang, Fan,Li, Yuan,Tian, Shi-Kai
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scheme or table
p. 1084 - 1091
(2011/04/15)
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- An efficient chemoselective strategy for the preparation of (E)-cinnamic esters from cinnamaldehydes using heterogeneous catalyst and DDQ
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An efficient chemoselective protocol is developed for the synthesis of (E)-cinnamic esters from substituted cinnamaldehydes or cinnamyl alcohols using a combination of DDQ and heterogeneous catalyst under microwave irradiation. The method showed remarkable selectivity for cinnamaldehydes over aliphatic and aromatic aldehydes, which is a novel finding. The results demonstrate that the developed protocol can be a useful synthetic tool for chemoselective esterification in total synthesis of complex organic compounds.
- Sinha, Arun K.,Sharma, Anuj,Swaroop, Anand,Kumar, Vinod
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p. 1000 - 1007
(2007/10/03)
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- Caulerpenyne-colchicine hybrid: Synthesis and biological evaluation
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The synthesis of an analog of caulerpenyne having a trimethoxyaryl moiety was achieved in 11% overall yield over 11 steps. Its biological activity has been evaluated as inhibitor of in vitro tubulin polymerization or angiogenesis.
- Bourdron, Julien,Commeiras, Laurent,Barbier, Pascale,Bourgarel-Rey, Veronique,Pasquier, Eddy,Vanthuyne, Nicolas,Hubaud, Jean-Claude,Peyrot, Vincent,Parrain, Jean-Luc
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p. 5540 - 5548
(2007/10/03)
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- Isolation of α-glusosidase inhibitors from hyssop (Hyssopus officinalis)
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α-Glucosidase inhibitory activity was found in aqueous methanol extracts of dried hyssop (Hyssopus officinalis) leaves. Active principles against α-glucosidase, prepared from rat small intestine acetone powders, were isolated and characterized. The structures of these isolated compounds were determined to be (7S, 8S)-syringoylglycerol-9-O-(6′-O-cinnamoyl)- β-D-glucopyranoside and (7S, 8S)-syringoylglycerol 9-O-β-D- glucopyranoside by analysis of physical and spectroscopic data (FDMS, 1H NMR, 13C NMR, HMQC, and HMBC experiments) together with chemical syntheses.
- Matsuura, Hideyuki,Miyazaki, Hiroyuki,Asakawa, Chikako,Amano, Midori,Yoshihara, Teruhiko,Mizutani, Junya
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- The asymmetric synthesis of β-aryl-α-hydroxy esters from β-aryl-α,β-dihydroxy esters
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α,β-Dihydroxy-β-aryl esters obtained via Sharpless asymmetric dihydroxylation (AD) of substituted cinnamate esters are reduced by sequential reaction with trimethyl orthoacetate and acetyl bromide followed by catalytic hydrogenolysis in methanol to give enantiomerically enriched β-aryl-α-hydroxy esters.
- Lawrence, Nicholas J,Brown, Stephen
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p. 613 - 619
(2007/10/03)
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- Application of a new combination of palladium and CaCo3 for an aerobic heck reaction using arenediazonium-salts
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Efficient Heck reactions under aerobic conditions were carried out using Pd-catalyst in the presence of CaCO3. Under these conditions a neat Heck Reaction rising arenediazonium salts bearing functional groups including nitro functionalities can generally take place in good yields tip to 95%.
- Brunner, Heiko,De Courcy, Nathalie Le Cousturier,Genet, Jean-Pierre
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p. 4815 - 4818
(2007/10/03)
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- A new synthesis of podophyllum lignans by Weitz' aminium salt-induced free radical cycloaddition reaction of a doubly unsaturated ester
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(±)-Isopodophyllotoxin (1e) and related lactones 12, 13, 14 were synthesized by a biomimetic procedure from the doubly unsaturated esters 11a and 11b by means of an oxidative free radical cycloaddition reaction utilizing a stable cation radical salt, Weitz' aminium salt, in one step. (±)-Isopicropodophyllin (1g), the trans-fused lactones, 12, 13, and 16, and the cis-fused lactone 17 were also synthesized from the esters 11c and 11d by the reaction with the same reagent.
- Ara,Takeya,Tobinaga
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p. 1977 - 1984
(2007/10/03)
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- Process for the preparation of polycyclic compounds using ferric perchlorate and acid trifluoroacidic
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Polycyclic compounds (I) can be prepared in accordance with the following reaction formula: STR1 wherein R1 -R8 each represents a hydrogen atom, a hydroxyl group, an alkoxyl group or a substituted or unsubstituted benzyloxy group or
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- Polycyclic compounds, their preparation and their use as phosphodiesterases inhibitors
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Polycyclic compounds (I) can be prepared in accordance with the following reaction formula: wherein R1-R8 each represents a hydrogen atom, a hydroxyl group, an alkoxyl group or a substituted or unsubstituted benzyloxy group or neighb
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- Fully Regiocontrolled Synthesis of (+/-)-12a,12b-Secocolchicine and Studies Concerning its Cyclisation to the Alkaloid Colchicine
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A fully regiocontrolled synthesis of the title compound 6, an AC-ring analogue of the alkaloid colchicine 1, is reported.The key step associated with the sequence used was condensation of lithium halogenocarbenoid 10 - a synthetic equivalent for the inaccessible 7-methoxytropon-3-yl anion 12-with 3,4,5-trimethoxycinnamaldehyde 17 to produce the 1,2-addition product 18 as a mixture of diastereoisomers.Elaboration of compound 18 provided benzoate 23 which, on treatment with base, underwent ring-expansion to give troponoid 24 in excellent yield.Replacement of the C-7 benzoate group in compound 24 by an acetamido moiety was readily achieved and produced compound 6 in good overall yield.Unsuccessful attempts to convert compound 6 and the deacetamido analogue 38 into colchinine and deacetamidocolchicine 3, respectively, are described.
- Banwell, Martin G.,Lambert, John N.,Gravatt, G. Lance
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p. 2817 - 2830
(2007/10/02)
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- Four new phenolic glycosides from Polygala tenuifolia
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Four new phenolic glycosides, tenuifolisides A (1), B (2), C (3), and D (4) together with a known phenolic glycoside, β-D-(3-O-sinapoyl)-fructofuranosyl-α-D-(6-O-sinapoyl)-glucopyranoside (5) were isolated from the roots of Polygala tenuifolia. The structures of these new compounds were characterized as β-D-[3-O-(3,4,5-trimethoxycinnamoyl)]fructofuranosyl-α-D-[6-O-(p-hydr oxybenzoyl)]-glucopyranoside (1), β-D-(3-O-sinapoyl)-fructofuranosyl-α-D-[6-O-(p-hydroxybenzoyl)]-gluco pyranoside (2), β-D-[3-O-(3,4,5-trimethoxycinnamoyl)]-fructofuranosyl-α-D-(6-O-sinapo yl)glucopyranoside (3), and 1,5-anhydro-[6-O-(3,4,5-trimethoxycinnamoyl)]-D-glucitol (4), respectively, on the basis of chemical and spectral evidence including two dimensional nuclear magnetic resonance (2D-NMR) studies.
- Ikeya,Sugama,Okada,Mitsuhashi
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p. 2600 - 2605
(2007/10/02)
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- Synthesis and Experimental Ionization Energies of Certain (E)-3-Arylpropenoic Acids and Their Methyl Esters
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Ionization energies for several methoxy-substituted (E)-3-arylpropenoic acids and methyl (E)-3-arylpropenoates were experimentally determined by mass spectroscopy.The title compounds were prepared in excellent yield by Knoevenagel condensation of an aromatic aldehyde with malonic acid and by Fischer esterification of the acid with methanol.
- Peterson, John R.,Russell, Morley E.,Surjasasmita, Irawan B.
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p. 534 - 537
(2007/10/02)
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- 1-(3,4-DIHYDROXY-5-METHOXYPHENYL)-3-METHYLBUT-2-ENE FROM THE LIVERWORT PLAGIOCHILA RUTILANS
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Extraction of the liverwort Plagiochila rutilans afforded 1-(3,4-dihydroxy-5-methoxyphenyl)-3-methylbut-2-ene, the structure of which was confirmed by synthesis. - Key Word Index: Plagiochila rutilans; Hepaticae; 1-(3,4-dihydroxy-5-methoxyphenyl)-3-methyl
- Huneck, Siegfried,Connolly, Joseph D.,Harrison, Leslie J.,Joseph, Robert S. I.,Pocs, Thomas
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p. 2396 - 2397
(2007/10/02)
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- Studies on the Constituents of Hedysarum polybotrys Hand.-Mazz.
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Thirteen phenolic compounds were isolated from Hedysarum polybotrys Hand.-Mazz., and their structures were determined by spectroscopic studies.Among the thirteen, 5-hydroxy-2-(2-hydroxy-4-methoxyphenyl)-6-methoxybenzofuran (X) is a new compound, and 6-hyd
- Miyase, Toshio,Fukushima, Seigo,Akiyama, Yoshihiko
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p. 3267 - 3270
(2007/10/02)
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- Pyrazolopyrimidine Ribonucleosides as Anticoccidials. 3. Synthesis and Activity of Some Nucleosides of 4-pyrazolopyrimidines
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Ribonucleosides of 4-(alkylthio)-1H-pyrazolopyrimidines have been shown to be useful anticoccidial agents .In that study, the unsaturated 4-allylthio and 4-crotylthio derivatives (19 and 20) were shown to be more active in vivo against Eimeria tenella than their saturated congeners; therefore, some unsaturated (arylalkyl)thio derivatives were synthesized and investigated as anticoccidial agents.The novel compounds in this study (2 to 18) were prepared by the alkylation of 4-mercapto-1-β-D-ribofuranosyl-1H-pyrazolopyrimidine (1), which was prepared by an enzymatic method.The (E)-4-cinnamylthio derivative (2) and the 5'-monophosphate (18) were the most active compounds against E. tenella in vivo.None of the analogues with substituents in the aryl moiety (3 to 13) was more active than 2 in vivo.The geometry about the double bond was important, since the (Z)-4-cinnamylthio derivative (14) was inactive both in vitro and in vivo.The 4-(3-phenylpropynyl)thio and 4-(5-phenyl-2,4-pentadienyl)thio derivatives (15 and 16) were at least as active as 2 in vitro; however, they were less active than 2 in vivo.Compound 2 was effective in vivo against E. tenella, E. necatrix, E. maxima, and E. brunetti; these species of Eimeria were controlled when 2 was given in the diet at levels up to 100 ppm.Infections in vivo due to E. acervulina were controlled by 2 only at about 800 ppm.The broad spectrum of anticoccidial activity shown by 2 represents a significant improvement over the activities reported for related compounds .
- Rideout, Janet L.,Krenitsky, Thomas A.,Chao, Esther Y.,Elion, Gertrude B.,Williams, Raymond B.,Latter, Victoria S.
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p. 1489 - 1494
(2007/10/02)
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