- First synthesis of tabamides A–C and their derivatives: In vitro nitric oxide inhibitory activity
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The first synthesis of natural phenolic amides, tabamides A–C (1–3), and their derivatives (4–12) was accomplished using Stobbe condensation and amide coupling reactions as key steps. The in vitro nitric oxide (NO) inhibitory effects of these compounds in LPS-induced RAW-264.7 macrophages were evaluated as an indicator of anti-inflammatory activity. All compounds tested had a concentration-dependent inhibitory effect on NO production by RAW-264.7 macrophages without significant cytotoxicity. Compound 6, a tabamide A derivative (IC50 = 82.6 μM), followed by tabamide A (1, IC50 = 100.7 μM), was the most potent from the series. The present study revealed that tabamide A (1) could be considered as a lead structure to develop NO production-targeted anti-inflammatory agents.
- Damodar, Kongara,Jeon, Sung Ho,Lee, Jeong Tae,Shin, Sooyong
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supporting information
(2021/11/10)
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- Synthesis, mitochondrial localization of fluorescent derivatives of cinnamamide as anticancer agents
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Mitochondria are considered as a therapeutic target for new drug design toward all kinds of cancer. Hence in order to enhance the dosage in mitochondrial fraction of cinnamamides, the mitochondria-targeted derivatives were designed by the incorporation of cinnamamides into a fluorophore carrier of coumarin-3-carboxamide with a 1:1 stoichiometry. Using the amide linkers, twenty-one compounds were synthesized and the cytotoxicity against a panel of cancer cells (MCF-7, Hela, HepG2, HL-60) was tested. In particular, compound 18c displayed the potent cytotoxicity toward HL-60 leukaemia cells, which could quickly and efficiently entry into HL-60 cells and specifically localize within mitochondria. And 18c preferred enrichment in HL-60 cells than in PBMC normal cells, accounting for the higher toxicity to cancer cells than to normal cells. Moreover, the dissipations of mitochondrial membrane potential and enhancement of cellular ROS level were also preceded upon 18c treatment, leading to cell cycle arrest and apoptosis/necrosis in HL-60 cells. Besides, acted as a Michael acceptor, 18c initiated a thia-Michael addition reaction toward cysteamine (1:2 stoichiometry), detecting by the UV-Vis spectrum and HRMS analysis. This could result in the blue emission of 18c in mitochondria after the procedure of cell fixation, owing to the formation of covalent bond with mitochondrial thiols. Our study reported 18c might be useful for the further development into a mitochondria-targeted anti-leukemia agent and the Michael acceptor might be a versatile functional group.
- Yang, Kun,Li, Yuanyuan,Tang, Qun,Zheng, Lifang,He, Dian
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- Paired Electrochemical Reactions and the On-Site Generation of a Chemical Reagent
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While the majority of reported paired electrochemical reactions involve carefully matched cathodic and anodic reactions, the precise matching of half reactions in an electrolysis cell is not generally necessary. During a constant current electrolysis almost any oxidation and reduction reaction can be paired, and in the presented work we capitalize on this observation by examining the coupling of anodic oxidation reactions with the production of hydrogen gas for use as a reagent in remote, Pd-catalyzed hydrogenation and hydrogenolysis reactions. To this end, an alcohol oxidation, an oxidative condensation, intramolecular anodic olefin coupling reactions, an amide oxidation, and a mediated oxidation were all shown to be compatible with the generation and use of hydrogen gas at the cathode. This pairing of an electrolysis reaction with the production of a chemical reagent or substrate has the potential to greatly expand the use of more energy efficient paired electrochemical reactions.
- Wu, Tiandi,Nguyen, Bichlien H.,Daugherty, Michael C.,Moeller, Kevin D.
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supporting information
p. 3562 - 3565
(2019/02/20)
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- Modular synthesis and biological investigation of 5-hydroxymethyl dibenzyl butyrolactones and related lignans
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Dibenzyl butyrolactone lignans are well known for their excellent biological properties, particularly for their notable anti-proliferative activities. Herein we report a novel, efficient, convergent synthesis of dibenzyl butyrolactone lignans utilizing the acyl-Claisen rearrangement to stereoselectively prepare a key intermediate. The reported synthetic route enables the modification of these lignans to give rise to 5-hydroxymethyl derivatives of these lignans. The biological activities of these analogues were assessed, with derivatives showing an excellent cytotoxic profile which resulted in programmed cell death of Jurkat T-leukemia cells with less than 2% of the incubated cells entering a necrotic cell death pathway.
- Davidson, Samuel J.,Pilkington, Lisa I.,Dempsey-Hibbert, Nina C.,El-Mohtadi, Mohamed,Tang, Shiying,Wainwright, Thomas,Whitehead, Kathryn A.,Barker, David
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- Synthesis, in vitro and in silico evaluation of diaryl heptanones as potential 5LOX enzyme inhibitors
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A new series of diaryl heptanones (12a-q) were synthesized and their structures were confirmed by its 1H, 13C NMR and Mass spectral data. These analogs were evaluated for their anti-oxidant activity and potential to inhibit 5-lipoxygenase. Compounds 12k and 12o showed potent in vitro 5-lipoxygenase enzyme inhibitory activity with IC50 values of 22.2, 21.5 μM, which are comparable to curcumin (24.4 μM). Further they also have shown significant antioxidant activity. Molecular docking studies clearly showed correlation between binding energy and potency of these compounds.
- Meka, Bharani,Ravada, Suryachandra Rao,Muthyala, Murali Krishna Kumar,Kurre, Purna Nagasree,Golakoti, Trimurtulu
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p. 408 - 421
(2018/07/13)
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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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- Synthesis, biological evaluation and mechanism study of chalcone analogues as novel anti-cancer agents
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A series of novel chalcone analogues were designed, synthesized and evaluated as anticancer agents. The results of antiproliferative activity tests showed that most of the analogues exhibited moderate to very good antiproliferative activities with GI50 values in the micromol to sub-micromol range. Especially compound 10a gave 0.026 μM to 0.035 μM GI50 for five cancer cell lines. The mechanistic studies including tubulin polymerization inhibition, disruption of microtubule dynamics and cell cycle arrest assay demonstrated that compound 10a could effectively inhibit in vitro cellular tubulin polymerization, interfere with the mitosis, resulting in a prolonged G2/M cell cycle arrest and ultimately lead to cell apoptosis of cancer cells. Taken together, these results suggested that 10a may became a promising lead compound for development of new anticancer drugs.
- Chen, Jie,Yan, Jun,Hu, Jinhui,Pang, Yanqing,Huang, Ling,Li, Xingshu
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p. 68128 - 68135
(2015/08/24)
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- Synthesis, biological evaluation and mechanism study of a class of benzylideneindanone derivatives as novel anticancer agents
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A series of new benzylideneindanone derivatives were designed, synthesized and evaluated as antitumor agents. Structure-activity relationship (SAR) studies showed that derivatives with 4,5,6-trimethoxyl on an indanone moiety displayed good anti-proliferative activities. Especially, compound 5a demonstrated the most potent inhibitory activity, with GI50 values from 0.172 to 0.57 μM for five kinds of cancer cell lines. Further investigation showed that 5a could inhibit microtubule polymerization and thus induce G2/M phase arrest and apoptosis in A549 cells. Our findings revealed the benzylideneindanone moiety as a new attractive scaffold for mitosis-targeting drug discovery.
- Hu, Jinhui,Yan, Jun,Chen, Jie,Pang, Yanqing,Huang, Ling,Li, Xingshu
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p. 1318 - 1327
(2015/07/15)
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- A biocompatible alkene hydrogenation merges organic synthesis with microbial metabolism
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Organic chemists and metabolic engineers use orthogonal technologies to construct essential small molecules such as pharmaceuticals and commodity chemicals. While chemists have leveraged the unique capabilities of biological catalysts for small-molecule production, metabolic engineers have not likewise integrated reactions from organic synthesis with the metabolism of living organisms. Reported herein is a method for alkene hydrogenation which utilizes a palladium catalyst and hydrogen gas generated directly by a living microorganism. This biocompatible transformation, which requires both catalyst and microbe, and can be used on a preparative scale, represents a new strategy for chemical synthesis that combines organic chemistry and metabolic engineering. Reduction to practice: A hydrogenation reaction has been developed that employs hydrogen generated in situ by a microorganism and a biocompatible palladium catalyst to reduce alkenes on a synthetically useful scale. This type of transformation, which directly combines tools from organic chemistry with the metabolism of a living organism for small-molecule production, represents a new strategy for chemical synthesis.
- Sirasani, Gopal,Tong, Liuchuan,Balskus, Emily P.
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supporting information
p. 7785 - 7788
(2014/08/05)
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- Synthesis and antitumor activity evaluation of 2-arylisoquinoline-1,3(2H, 4H)-diones in vitro and in vivo
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Six 2-(2-acylaminobenzothiazol-6-yl)isoquinoline-1,3(2H,4H)-diones (1a-1f) and five 2-arylisoquinoline-1,3(2H,4H)-diones (1g-1k) were synthesized by refluxing homophthalic anhydrides with 2-acylaminobenzothiazolyl-6-amine or substituted aniline in glacial acetic acid. The cytotoxic activities of 1a-1k were evaluated via MTT method against A431, A549, and PC3. Compound 1b relatively displayed a higher cytotoxic activity than the others. The antitumor effect of 1b were evaluated in established nude mice PANC-1 xenograft model. The results suggest that compound 1b could potentially inhibit tumor growth.
- Kang, Bo-Rui,Wang, Juan,Li, Huan,Li, Yan,Mei, Qi-Bing,Zhang, San-Qi
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p. 1340 - 1349
(2014/03/21)
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- First total synthesis of two new amide alkaloids from Piper boehmeriaefolium
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3-(3,4,5-Trimethoxyphenyl)propanoylpyrrole and 3-(3,5-dimethoxy-4- hydroxyphenyl)propanoylpyrrole, two new amide alkaloids, were prepared from 3,4,5-trimethoxybenzaldehyde via 3,4,5-trimethoxycinnamic acid and the corresponding dihydroacid. This route is simple and the reaction conditions are mild.
- Shan, Shao-Jun,Zhang, Hong,Wang, Xiao-Dan
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experimental part
p. 56 - 57
(2012/04/04)
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- FLAVAN-3-OL CONTAINING FOODSTUFFS
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The use of a compound for the reduction or elimination of bitterness caused by flavan-3-ols is provided. Compositions having greater than 0.01 wt % flavan-3-ols and that comprise an effective amount of the compound are also provided. The compound conforms to the general formula (I): wherein R1 represents C2-C3 saturated or unsaturated divalent hydrocarbon radical, n is an integer from 0 to 3, and each X is independently selected from C1-C3 alkyloxy and OH; and wherein if n is 0 then R1 is C3 saturated divalent hydrocarbon radical or C2-C3 unsaturated divalent hydrocarbon radical; and wherein if n is greater than 0 then the compound has formula (II)
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- Microwave induced process for the preparation of substituted 4-vinylphenols
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The present invention relates to “a microwave induced process for the preparation of 4-vinylphenols or its derivatives” in which commercially important FEMA GRAS approved perfumery and flavouring vinylphenols (i.e. hydroxystyrenes) namely 4-vinylguaiacol (FEMA GRAS No. 2675) and 4-vinylphenol (FEMA GRAS No. 3739) as well as other useful vinylphenols such as 2,6-dimethoxy-4-vinylphenol, 2-hydroxy-4-vinylphenol, 3-hydroxy-4-vinylphenol etc. by condensation of malonic acid and 4-hydroxyphenylaldehydes or its derivatives.
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- A Rapid and Efficient Microwave-Assisted Synthesis of Substituted 3-Phenylpropionic Acids from Benzaldehydes in Minutes
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A convenient, inexpensive, and efficient synthesis of 3-phenylpropionic acids (1a-1f) by reacting benzaldehyde (2a-2f) and malonic acid in acetic acid and piperidine into cinnamic acid (3a-3f) in 77 to 89% followed by its reduction with PdCl2 in the biphase of formic acid and aqueous sodium hydroxide is reported under microwave irradiation which utilizes short reaction time ranging 5 to 7 min to provide 1a-1f in moderate to high yield (69-86%) depending upon methoxy, methylenedioxy, and hydroxy groups present at the phenyl ring.
- Sharma, Anuj,Joshi, Bhupendra P.,Sinha, Arun K.
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p. 1186 - 1187
(2007/10/03)
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- Tricyclic compounds
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Novel tricyclic compounds of formula I as defined in the specification, a process for their preparation and their use for the preparation of optically active or racemic colchicine and thiocolchicine derivatives.
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- Simple, safe, large scale synthesis of 5-arylmethyl-2,2-dimethyl-1,3-dioxane-4,6-diones and 3-aryl-propanoic acids
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Reaction of aryl aldehydes with Meldrum's acid 2 in the presence of formic acid and triethylamine with 5-arylmethyl Meldrum's acid derivatives 4 at room temperature, whereas at 80-100°C 3-arylpropanoic acids 5 are formed.
- Toth,Kover
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p. 3067 - 3074
(2007/10/03)
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- Process for the preparation of carboxylic acids and derivatives of them
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The subject matter of the invention is a process for the preparation of carboxylic acids and derivatives of them of the general formula STR1 wherein R means hydrogen, or a C1-4 alkyl or a (C1-5 alkoxy)carbonyl group, R1 is as defined in claim 1, R7 stands for hydrogen or a C1-7 alkyl group and R8 means hydrogen or a carboxyl group, by reacting a 1,3-dioxane-4,6-dione derivative of the general formula STR2 wherein R9 stands for a C1-4 alkyl group or a phenyl group, optionally monosubstituted by halogen and R10 stands for hydrogen or a C1-5 alkyl group or R9 and R10 together form a pentamethylene group, and an aldehyde or ketone of the general formula STR3 in the presence of formic acid.
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- Process for the preparation of carboxylic acids and derivatives of them
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The subject matter of the invention is a process for the preparation of carboxylic acids and derivatives of them of the general formula wherein Rmeans hydrogen, or a C1 4alkyl or a (C1 5alkoxy)carbonyl group, R1is as defined in claim 1, R7stands for hydrogen or a C1 7alkyl group and R8means hydrogen or a carboxyl group, by reacting a 1,3-dioxane-4,6-dione derivative of the general formula wherein R9stands for a C1 4alkyl group or a phenyl group, optionally monosubstituted by halogen and R10stands for hydrogen or a C1 5alkyl group or R9 and R10together form a pentamethylene group, and an aldehyde or ketone of the general formula in the presence of formic acid and of [a] amine(s) and, if desired, of an alcohol of the general formula, , R7 - OH VI,, , wherein R7is a C1 7alkyl group, at a temperature of 20 to 140°C, and/or, reducing an unsaturated 1,3-dioxane-4,6-dione derivative of the general formula and/or, a 1,3-dioxane-4,6-dione derivative of the general formula with formic acid in the presence of [a] amine(s) and, if desired, of an alcohol as above defined.
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- Method of inhibiting sweetness
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The sweetness of an ingestible product containing a sweetening sugar or sugar alcohol in large quantities can be reduced by incorporating therein a sweetness-reducing amount of at least one compound of the general formula: STR1 in which m represents 0 or 1, and when m represents 0, n represents 1, 2 or 3, and p represents 1, 2, 3 or 4, and when m represents 1, n represents 1 or 2 and p represents 0, 1, 2, 3 or 4; the substituents R, which may be the same or different, each represent a lower alkoxy group, e.g. with 1 to 5 carbon atoms, phenoxy group or a lower alkyl or trifluoromethyl group; and/or two substituents R together represent an aliphatic chain linked to the phenyl ring at two positions, either directly or via an oxa-group, e.g. an alkylenedioxy, alkenylenedioxy, alkylenoxy or alkenylenoxy group; and/or one substituent R represents a hydroxy group while at least one other substituent R represents an alkoxy group; and X+ represents a physiologically acceptable cation.
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- BIOSYNTHESIS OF PIPERLONGUMINE
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The incorporation of L-lysine and L-phenylalanine into piperlongumine has been demonstrated in Piper longum.The subsequent stepwise degradation to methyl-(3,4,5-trimethoxyphenyl)-propanoate and δ-aminovaleric acid revealed that the C6-C3 moiety of the alkamide arises from phenylalanine; the heterocyclic ring is biosynthesized from lysine.It has also been shown that DL-tyrosine and sodium acetate are poor precursors for piperlongumine. Key Word Index - Piper longum; Piperaceae; alkamides; piperlongumine; biosynthesis.
- Prabhu, Bharathi R.,Mulchandani, Newand B.
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p. 2589 - 2592
(2007/10/02)
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