- Br?nsted Acid Catalyzed Tandem Defunctionalization of Biorenewable Ferulic acid and Derivates into Bio-Catechol
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An efficient conversion of biorenewable ferulic acid into bio-catechol has been developed. The transformation comprises two consecutive defunctionalizations of the substrate, that is, C?O (demethylation) and C?C (de-2-carboxyvinylation) bond cleavage, occurring in one step. The process only requires heating of ferulic acid with HCl (or H2SO4) as catalyst in pressurized hot water (250 °C, 50 bar N2). The versatility is shown on a variety of other (biorenewable) substrates yielding up to 84 % di- (catechol, resorcinol, hydroquinone) and trihydroxybenzenes (pyrogallol, hydroxyquinol), in most cases just requiring simple extraction as work-up.
- Bal, Mathias,Bomon, Jeroen,Liao, Yuhe,Maes, Bert U. W.,Sels, Bert F.,Sergeyev, Sergey,Van Den Broeck, Elias,Van Speybroeck, Veronique
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supporting information
p. 3063 - 3068
(2020/02/05)
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- Sesquiterpene lactone-cinnamic acid derivative and salt, pharmaceutical composition and application thereof
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The invention provides application of sesquiterpene lactone-cinnamic acid derivatives shown as a formula (I) and salts thereof in preparation of medicines for treating cancers and auxiliary medicinesfor treating cancers.
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Paragraph 0095-0096; 0106-0108
(2020/08/09)
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- Design, synthesis and biological evaluation of (E)-5-styryl-1,2,4-oxadiazoles as anti-tubercular agents
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Cinnamic acid and its derivatives are known for anti-tubercular activity. The present study reports the synthesis of cinnamic acid derivatives via bioisosteric replacement of terminal carboxylic acid with “oxadiazole”. A series of cinnamic acid derivatives (styryl oxadiazoles) were designed and synthesized in good yields by reaction of substituted cinnamic acids (2, 15a-15s) with amidoximes. The synthesized styryl oxadiazoles were evaluated in vitro for anti-tubercular activity against Mycobacterium tuberculosis (Mtb) H37Ra strain. The structure-activity relationship (SAR) study has identified several compounds with mixed anti-tubercular profiles. The compound 32 displayed potent anti-tubercular activity (IC50 = 0.045 μg/mL). Molecular docking studies on mycobacterial enoyl-ACP reductase enzyme corroborated well with the experimental findings providing a platform for structure based hit-to-lead development.
- Atmaram Upare, Abhay,Gadekar, Pradip K.,Sivaramakrishnan,Naik, Nishigandha,Khedkar, Vijay M.,Sarkar, Dhiman,Choudhari, Amit,Mohana Roopan
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supporting information
p. 507 - 512
(2019/02/19)
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- Synthesis and structure-activity relationship studies of parthenolide derivatives as potential anti-triple negative breast cancer agents
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Triple-negative breast cancer (TNBC) is the most aggressive cancers with a high recurrence rate and rapidly acquired drug resistance among various breast cancer subtypes. There is no specific drug for treatment of TNBC. Discovery of therapeutic agents with unique modes of actions is urgently needed. In this study, a series of seventy parthenolide derivatives was designed, synthesized, and evaluated for their anti-TNBC activities. Compound 7d exhibited the most potent activity against different breast cancer cells with IC50 values ranging from 0.20 μM to 0.27 μM, which demonstrated 11.6- to 18.6-fold improvement comparing to that of the parent compound parthenolide with IC50 values of 2.68–4.63 μM. It is worth to note that 7d was more active than the positive control drug ADR. Moreover, compound 7d could induce apoptosis of SUM-159 cells through mitochondria pathway and cause G1 phase arrest of SUM-159 cells. These findings indicate that compound 7d deserves further studies as a lead compound for ultimate discovery of effective anti-TNBC drug.
- Ge, Weizhi,Hao, Xin,Han, Fangzhi,Liu, Zhongquan,Wang, Tianpeng,Wang, Mengmeng,Chen, Ning,Ding, Yahui,Chen, Yue,Zhang, Quan
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p. 445 - 469
(2019/02/12)
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- Design, synthesis and cytotoxic evaluation of novel imatinib amide derivatives that target Abl kinase
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Novel imatinib amide derivatives (a1-28, b1-9) were synthesized and evaluated for their biological activities. All compounds were characterized by 1H NMR, MS and elemental analysis. Among all the derivatives, compounds a4, a10, a21, b1 and b2 displayed the most significant ability of inhibiting K562 cell proliferation with the IC50 values of 0.67, 0.66, 0.65, 0.59 and 0.62 μM, respectively, indicating that these compounds were potent inhibitors of Bcr-Abl in leukemic K562 cells, comparable to the reference compound imatinib. Molecular docking study was performed to position compounds a21 and b1 into the active site of Abl to determine the probable binding modes
- Yao, Ri-Sheng,Guan, Qiu-Xiang,Lu, Xiao-Qin,Ruan, Ban-Feng
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- Synthesis and leishmanicidal activity of cinnamic acid esters: Structure-activity relationship
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Several cinnamic acid esters were obtained via Fischer esterification of cinnamic acids derivatives with aliphatic alcohols. Structures of the products were elucidated by spectroscopic analysis. The synthesized compounds were evaluated for antileishmanial activity against L. (V) panamensis amastigotes and cytotoxic activity was evaluated against mammalian U-937 cells. The compounds 11, 15-17, and 23, were active against Leishmania parasite and although toxic for mammalian cells, they still are potential candidates for antileishmanial drug development. A SAR analysis indicates that first, while smaller alkyl chains lead to higher selectivity indices (10, 11 vs. 12-17); second, the degree of oxygenation is essential for activity, primarily in positions 3 and 4 (17 vs. 18-20 and 22); and third, hydroxyl groups increase both activity and cytotoxicity (14 vs. 23). On the other hand, the presence of a double bond in the side chain is crucial for cytotoxicity and leishmanicidal activity (12 vs. 21). However, further studies are required to optimize the structure of the promising molecules and to validate the in vitro activity against Leishmania demonstrated here with in vivo studies.
- Otero, Elver,Robledo, Sara M.,Diaz, Santiago,Carda, Miguel,Munoz, Diana,Panos, Julian,Velez, Ivan D.,Cardona, Wilson
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p. 1378 - 1386
(2014/03/21)
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- A practical and convenient protocol for the synthesis of (E)-α,β-unsaturated acids
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α,β-Unsaturated acids are very useful and versatile reagents in organic synthesis. A novel, practical, and convenient catalytic protocol comprising FeCl3·6H2O (0.5 mol %) and H 2O (1 equiv) in CH3NO2 is described for the rapid synthesis of α,β-unsaturated acids with high E-stereoselectivity under both microwave and conventional heating conditions with high TON and TOF values. This powerful approach efficiently demonstrated the utility of biomass derived aldehydes to build chemical agents used as fuel additives. The method proved to be scalable to gram scale synthesis.
- Mohite, Amar R.,Bhat, Ramakrishna G.
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p. 4564 - 4567
(2013/09/24)
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- Synthesis of trans-cinnamic acids from aryl aldehydes and aryl aldehyde bisulfite adducts with malonic acid using piperazine
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Piperazine as a new reagent for the condensation of aryl aldehydes and their bisulfite adducts with malonic acid are described which afford the corresponding cinnamic acids in excellent yields and short reaction times in the absence of solvents under microwave irradiation.
- Khosropour, Ahmad Reza,Khodaei, Mohammad Mehdi,Moghanian, Hassan
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p. 364 - 365
(2007/10/03)
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- Competitive formation of β-amino acids, propenoic, and ylidenemalonic acids by the Rodionov reaction from malonic acid, aldehydes, and ammonium acetate in alcoholic medium
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The Rodionov reaction of 49 available aliphatic and aromatic aldehydes with malonic acid and ammonium acetate in alcoholic medium, resulting in formation of β-amino acids, propenoic, and ylidenemalonic acids, was studied. Certain regioselectivity regularities of the reaction were revealed. Among the variety of ketones studied, cyclohexanone is the only whose reaction yields a β-amino acid. Unusual dehydrofluorination of 6-chloro-2-fluorocinnamic acid under the Rodionov reaction was discovered. 2005 Pleiades Publishing, Inc.
- Lebedev,Lebedeva,Sheludyakov,Kovaleva,Ustinova,Kozhevnikov
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p. 1113 - 1124
(2007/10/03)
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- A one-pot synthesis of 3-amino-3-arylpropionic acids
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3-Aminopropionic acids (β-amino acids) are biologically active compounds of interest in medicinal and pharmaceutical chemistry. Twenty-one 3-amino-3-arylpropionic acids were synthesized via a facile one-pot synthesis. In addition, a series of mechanistic studies have been performed to optimize the production of these β-amino acids. The reaction mechanism of this one-pot synthesis of β-amino acids, as well as the electronic effect of para-substitution and the influence of solvent polarity on the proposed reaction mechanism are discussed.
- Tan,Weaver
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p. 7449 - 7461
(2007/10/03)
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- Solid state behaviour of vinyl quinones
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2,5-Bisvinyl-1,4-benzoquinones 1 and 2-vinyl-1,4-benzoquinones 2 substituted with aryl or ester end groups have been synthesized. The 2,5-bisstyryl-1,4-benzoquinones 1 (R=phenyl, p-tolyl, o-tolyl) crystallize with a 7 angstrom-stacking axis. But only for the o-tolyl derivative the contacts between the vinyl groups are close enough to allow a four-center type photopolymerization. The ester derivative 1 (R=COOEt) has a layer structure and can be photooligomerized in the crystal. The generated cyclobutane subgroups have twofold symmetry. The vinylquinones 2 (R=aryl) may be dimerized photochemically in the crystal at the vinyl groups to centrosymmetric cyclobutanes. Crystals with 4 angstrom stacking axis are also photoreactive.
- Irngartinger,Lichtenthaeler,Herpich,Stadler
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p. 349 - 360
(2007/10/03)
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- SYNTHESIS OF RIGIDLY LINKED TRIAD MOLECULES BASED ON OCTAALKYLPORPHYRIN, CAPABLE OF MULTISTEP ELECTRON TRANSFER
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We have designed and carried out the synthesis of triad model systems containing octaalkylporphyrin, benzoquinone, and trichlorobenzoquinone with an oxidation-reduction potential gradient in the molecule.The quinone moieties are fixed relative to the porphyrin using spirononane and methylene spacers.
- Gribkov, A.A.,Borovkov, V.V.,Evstigneeva, R.P.,Sakata, Y.
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p. 905 - 915
(2007/10/02)
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- Phenylalkan(en)oic acid
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The phenylalkan(en)oic acids of the formula: STR1 wherein A is i) --NHCO--, ii) --O-- iii) --NHSO2 --, iv) --CO-- v) --CH2 -- or vi) --CH(OH)--; W is i) C1-13 alkylene, ii) phenylene or iii) STR2 R1 is i) hydrogen, ii) C1-4 alkyl, iii) --COOH, iv) saturated or unsaturated, 4-7 membered mono-cyclic hetero ring containing one nitrogen as a hetero atom or saturated or unsaturated, 4-7 member mono-cyclic hetero ring containing one nitrogen as a hetero atom substituted by an oxo group, v) STR3 vi) --CH2 OH; or A, taken together with W and R1, is i) STR4 ii) STR5 iii) --N--(SO2 R6)2, iv) STR6 or v) STR7 two R2 are, same or different, i) hydrogen, ii) C1-4 alkyl or iii) 4-7 membered saturated or unsaturated, mono-cyclic hetero ring containing two or three of nitrogen and sulfur in total, or two R2, taken together with a nitrogen to which they are attached, form saturated or unsaturated, i) 7-14 membered, bi- or tri-cyclic hetero ring containing one nitrogen as a hetero atom, or ii) 4-7 mebered, mono-cyclic hetero ring containing two or three of nitrogen and oxygen in total; Y is ethylene or vinylene; D is i) --Z--B or ii) STR8 Z is C3-11 alkylene or alkenylene R is STR9 or Z taken together with B, is C3-22 alkyl; R3 is i) hydrogen, ii) halogen, iii) C1-8 alkyl, alkoxy or alkylthio, or iv) C2-8 alkenyl, alkenyloxy or alkenylthio; n is 1-3; R4 is C1-7 alkylene; R5 is i) C1-12 alkyl, ii) C2-12 alkenyl, iii) C5-7 cycloalkyl or pp2 iv) phenethyl or phenethyl wherein the ring is substituted by one C1-4 alkoxy; Two R6 are, same or different, i) C1-7 alkyl, ii) benzyl or iii) phenyl or phenyl wherein the ring is substituted by one C1-4 alkyl; and Two R7 are, same or different, C1-4 alky; with the proviso that i) --A--W--R1 should bind to 3- or 4- carbon in benzene ring, and ii) when W phenylene or STR10 A should not represent --O--, --CO--, --CH2 -- or --CH(OH)--; and non-toxic salts thereof, possess an antagonistic activity on leukotriene B4, and therefore, are useful for the prevention and treatment of several diseases induced by leukotriene B4.
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- Substituent Effects in the Reaction of t-Butylmagnesium Chloride with Substituted Ethyl Cinnamates. A Correlation with 13C NMR Chemical Shifts
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The reaction of t-butylmagnesium chloride with some substituted ethyl (E)-cinnamates gave mainly 1,3-, 1,4-, 1,2- and 1,4-addition products and minor amounts of 1,2- and 1,3-addition products.The relative amounts of 1,3-addition products has been shown to correlate with 13C NMR chemical shifts of C-α of the ethyl cinnamates.The correlation indicates that the regio selectivity of the reactions is to a great extent dependent of polar effects and that the t-butyl radical has a nucleophilic character.
- Jalander, Lars
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p. 419 - 428
(2007/10/02)
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