cas 1866-38-2, 3-Chlorocinnamic acid | Articles data

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Design, Synthesis, and Anticancer Activity of Cinnamoylated Barbituric Acid Derivatives
This work deals with the design and synthesis of 18 barbituric acid derivatives bearing 1,3-dimethylbarbituric acid and cinnamic acid scaffolds to find potent anticancer agents. The target molecules were obtained through Knoevenagel condensation and acylation reaction. The cytotoxicity was assessed by the MTT assay. Flowcytometry was performed to determine the cell cycle arrest, apoptosis, ROS levels and the loss of MMP. The ratios of GSH/GSSG and the MDA levels were determined by using UV spectrophotometry. The results revealed that introducing substitutions (CF3, OCF3, F) on the meta- of the benzyl ring of barbituric acid derivatives led to a considerable increase in the antiproliferative activities compared with that of corresponding ortho- and para-substituted barbituric acid derivatives. Mechanism investigation implied that the 1c could increase the ROS and MDA level, decrease the ratio of GSH/GSSG and MMP, and lead to cell cycle arrest. Further research is needed for structural optimization to enhance hydrophilicity, thereby improve the biological activity of these compounds.
Li, Peng-Xiao,Liu, Guo-Yun,Liu, Ren-Min,Liu, Yue,Mu, Wen-Wen,Sun, Ya-Lei,Yang, Jie
(2022/01/13)

A novel phenylalanine ammonia-lyase from Pseudozyma antarctica for stereoselective biotransformations of unnatural amino acids
A novel phenylalanine ammonia-lyase of the psychrophilic yeast Pseudozyma antarctica (PzaPAL) was identified by screening microbial genomes against known PAL sequences. PzaPAL has a significantly different substrate binding pocket with an extended loop (26 aa long) connected to the aromatic ring binding region of the active site as compared to the known PALs from eukaryotes. The general properties of recombinant PzaPAL expressed in E. coli were characterized including kinetic features of this novel PAL with L-phenylalanine (S)-1a and further racemic substituted phenylalanines rac-1b-g,k. In most cases, PzaPAL revealed significantly higher turnover numbers than the PAL from Petroselinum crispum (PcPAL). Finally, the biocatalytic performance of PzaPAL and PcPAL was compared in the kinetic resolutions of racemic phenylalanine derivatives (rac-1a-s) by enzymatic ammonia elimination and also in the enantiotope selective ammonia addition reactions to cinnamic acid derivatives (2a-s). The enantiotope selectivity of PzaPAL with o-, m-, p-fluoro-, o-, p-chloro- and o-, m-bromo-substituted cinnamic acids proved to be higher than that of PcPAL.
Varga, Andrea,Csuka, Pál,Sonesouphap, Orlavanah,Bánóczi, Gergely,To?a, Monica Ioana,Katona, Gabriel,Molnár, Zsófia,Bencze, László Csaba,Poppe, László,Paizs, Csaba
p. 185 - 194
(2020/04/28)

Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C-H methylation
A practical and general iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabling aldehyde C-H methylation for the synthesis of methyl ketones has been developed. This mild, operationally simple method uses ambient air as the sole oxidant and tolerates sensitive functional groups for the late-stage functionalization of complex natural-product-derived and polyfunctionalized molecules.
Gong, Pei-Xue,Xu, Fangning,Cheng, Lu,Gong, Xu,Zhang, Jie,Gu, Wei-Jin,Han, Wei
supporting information
p. 5905 - 5908
(2021/06/18)

Synthesis, in vitro cytotoxicity, and molecular docking study of novel 3,4-dihydroisoquinolin-1(2H)-one based piperlongumine analogues
With the aim of expanding the scope of SAR on piperlongumine (PL), a naturally occurring anticancer molecule, we have designed a novel hybrid molecule bearing 3,4-dihydroisoquinolin-1(2H)-one and trans-cinnamic acids. The structure, based on hybridization strategy, is used for hybridization of naturally occurring scaffolds. We have synthesized 14 hybrid molecules by coupling 3,4-dihydroisoquinolin-1(2H)-one core with cinnamic acids using the mix anhydride approach. The newly synthesized inhibitors were evaluated for cell viability against breast cancer MCF-7 and cervical cancer HeLa cell lines. Furthermore, the active compounds were screened for their potential in breast cancer MDA-MB-231, cervical cancer C33A cell lines, prostate cancer DU-145, PC-3, and normal VERO cells. From the series, compound 10g was seen to inhibit MCF-7 cell growth significantly with GI50 50 = 20 μM) and C33A (GI50 = 3.2 μM). While the inhibitor 10i inhibits MCF-7 breast cancer cell growth GI50 = 3.42 μM along with inhibition of cell growth in MDA-MB-231 (GI50 = 30 μM), HeLa (GI50 = 7.67 μM), C33A (GI50 = 13 μM), DU-145 (GI50 = 6.45 μM), PC-3 (GI50 = 8.68 μM), and VERO (GI50 = 2.93 μM), respectively. Furthermore, molecular docking study demonstrated these compounds could bind tightly to the colchicine domain of tubulin through a network of favorable steric and electrostatic interactions and thus act as a tubulin polymerization inhibitor.
Kulkarni, Mahesh R.,Lad, Nitin P.,Khedkar, Vijay M.,Gaikwad, Nitin D.
p. 1359 - 1370
(2021/04/09)

Discovery of Novel Benzothiazepinones as Irreversible Covalent Glycogen Synthase Kinase 3β Inhibitors for the Treatment of Acute Promyelocytic Leukemia
Recently, irreversible inhibitors have attracted great interest in antitumors due to their advantages of forming covalent bonds to target proteins. Herein, some benzothiazepinone compounds (BTZs) have been designed and synthesized as novel covalent GSK-3β inhibitors with high selectivity for the kinase panel. The irreversible covalent binding mode was identified by kinetics and mass spectrometry, and the main labeled residue was confirmed to be the unique Cys14 that exists only in GSK-3β. The candidate 4-3 (IC50 = 6.6 μM) showed good proliferation inhibition and apoptosis-inducing ability to leukemia cell lines, low cytotoxicity on normal cell lines, and no hERG inhibition, which hinted the potential efficacy and safety. Furthermore, 4-3 exhibited decent pharmacokinetic properties in vivo and remarkably inhibited tumor growth in the acute promyelocytic leukemia (APL) mouse model. All the results suggest that these newly irreversible BTZ compounds might be useful in the treatment of cancer such as APL.
Zhang, Peng,Min, Zhihui,Gao, Yang,Bian, Jiang,Lin, Xin,He, Jie,Ye, Deyong,Li, Yilin,Peng, Chao,Cheng, Yunfeng,Chu, Yong
p. 7341 - 7358
(2021/06/28)

Design, synthesis, and evaluation of different scaffold derivatives against NS2B-NS3 protease of dengue virus
The number of deaths or critical health issues is a threat in the infection caused by Dengue virus, which complicates the situation, as only symptomatic treatment is the current solution. In this regard we have targeted the dengue protease NS2B-NS3 that is responsible for the replication. The series was designed with the help of molecular modeling approach using docking protocols. The series comprised of different scaffolds viz. cinnamic acid analogs (CA1–CA11), chalcone (C1–C10) and their molecular hybrids (Lik1–Lik10), analogs of benzimidazole (BZ1-BZ5), mercaptobenzimidazole (BS1-BS4), and phenylsulfanylmethylbenzimidazole (PS1-PS4). Virtual screening of various natural phytoconstituents was employed to determine the interactions of designed analogs with the residues of catalytic triad in the active site of NS2B-NS3. We have further synthesized the selected leads. The synthesized analogs were evaluated for the cytotoxicity and NS2B-NS3 protease inhibition activity and compared with known anti-dengue natural phytoconstituent quercetin as the standard. CA2, BZ1, and BS2 were found to be more potent and efficacious than the standard quercetin as evident from the protease inhibition assay.
Ganji, Lata R.,Gandhi, Lekha,Musturi, Venkataramana,Kanyalkar, Meena A.
p. 285 - 301
(2020/11/19)

Metal-Free Hydropyridylation of Thioester-Activated Alkenes via Electroreductive Radical Coupling
An electrochemical hydropyridylation of thioester-activated alkenes with 4-cyanopyridines has been developed. The reactions experience a tandem electroreduction of both substrates on the cathode surface, protonation, and radical cross-coupling process, resulting in a variety of valuable pyridine variants, which contain a tertiary and even a quaternary carbon at the α-position of pyridines, in high yields. The employment of thioesters to the conjugated alkenes enables no requirement of catalyst and high temperature, representing a highly sustainable synthetic method.
Xu, Hehuan,Liu, Jiayu,Nie, Feiyun,Zhao, Xiaowei,Jiang, Zhiyong
p. 16204 - 16212
(2021/10/25)

Design and synthesis of bitopic 2-phenylcyclopropylmethylamine (pcpma) derivatives as selective dopamine d3 receptor ligands
2-Phenylcyclopropylmethylamine (PCPMA) analogues have been reported as selective serotonin 2C agonists. On the basis of the same scaffold, we designed and synthesized a series of bitopic derivatives as dopamine D3R ligands. A number of these new compounds show a high binding affinity for D3R with excellent selectivity. Compound (1R,2R)-22e and its enantiomer (1S,2S)-22e show a comparable binding affinity for the D3R, but the former is a potent D3R agonist, while the latter acts as an antagonist. Molecular docking studies revealed different binding poses of the PCPMA moiety within the orthosteric binding pocket of the D3R, which might explain the different functional profiles of the enantiomers. Compound (1R,2R)-30q shows a high binding affinity for the D3R (Ki = 2.2 nM) along with good selectivity, as well as good bioavailability and brain penetration properties in mice. These results reveal that the PCPMA scaffold may serve as a privileged scaffold for the design of aminergic GPCR ligands.
Tan, Liang,Zhou, Qingtong,Yan, Wenzhong,Sun, Jian,Kozikowski, Alan P.,Zhao, Suwen,Huang, Xi-Ping,Cheng, Jianjun
p. 4579 - 4602
(2020/06/08)

Design, synthesis, and evaluation of novel cinnamic acid-tryptamine hybrid for inhibition of acetylcholinesterase and butyrylcholinesterase
Background: Acetylcholine deficiencies in hippocampus and cortex, aggregation of β-amyloid, and β-secretase over activity have been introduced as main reasons in pathogenesis of Alzheimer’s disease. Methods: Colorimetric Ellman’s method was used for determination of IC50 value in AChE and BChE inhibitory activity. The kinetic studies, neuroprotective and β-secretase inhibitory activities, evaluation of inhibitory potency on β-amyloid (Aβ) aggregations induced by AChE, and docking study were performed for prediction of the mechanism of action. Result and discussion: A new series of cinnamic acids-tryptamine hybrid was designed, synthesized, and evaluated as dual cholinesterase inhibitors. These compounds demonstrated in-vitro inhibitory activities against acetyl cholinesterase (AChE) and butyryl cholinesterase (BChE). Among of these synthesized compounds, (E)-N-(2-(1H-indol-3-yl)ethyl)-3-(3,4-dimethoxyphenyl)acrylamide (5q) demonstrated the most potent AChE inhibitory activity (IC50 = 11.51?μM) and (E)-N-(2-(1H-indol-3-yl)ethyl)-3-(2-chlorophenyl)acrylamide (5b) were the best anti-BChE (IC50 = 1.95?μM) compounds. In addition, the molecular modeling and kinetic studies depicted 5q and 5b were mixed type inhibitor and bound with both the peripheral anionic site (PAS) and catalytic sites (CAS) of AChE and BChE. Moreover, compound 5q showed mild neuroprotective in PC12 cell line and weak β-secretase inhibitory activities. This compound also inhibited aggregation of β-amyloid (Aβ) in self-induced peptide aggregation test at concentration of 10?μM. Conclusion: It is worth noting that both the kinetic study and the molecular modeling of 5q and 5b depicted that these compounds simultaneously interacted with both the catalytic active site and the peripheral anionic site of AChE and BChE. These findings match with those resulted data from the enzyme inhibition assay. [Figure not available: see fulltext.]
Ghafary, Shahrzad,Ghobadian, Roshanak,Mahdavi, Mohammad,Nadri, Hamid,Moradi, Alireza,Akbarzadeh, Tahmineh,Najafi, Zahra,Sharifzadeh, Mohammad,Edraki, Najmeh,Moghadam, Farshad Homayouni,Amini, Mohsen
p. 463 - 477
(2020/05/25)

Synthesis process of indoxacarb
The invention discloses a synthesis process of indoxacarb. The method comprises the following steps: reacting m-chlorobenzaldehyde serving as a raw material with malonic acid to remove monomolecular water and carbon dioxide to generate an intermediate SRCA, performing a hydrogenation reduction on the intermediate SRCA in an autoclave in the presence of a catalyst to obtain an intermediate SRCH, and cyclizing the SRCH by using hydrogen fluoride as a dehydrating agent to obtain the final product indoxacarb. The synthesis process is simple and easy to implement, energy is saved, consumption is reduced, the yield is increased, and good economic and environmental benefits are obtained.
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Paragraph 0015-0017

(2020/05/30)

Cinnamic acid derivative and preparation method and application thereof
The invention provides a cinnamic acid derivative. The cinnamic acid derivative is of the structure as shown in the formula I. The invention also provides two methods for preparing the cinnamic acid derivative. The two methods depend on a single bond or double bonds in the structure shown in the formula I. The invention further provides a pesticide. The pesticide comprises the cinnamic acid derivative. In addition, the invention provides a sterilization method. The sterilization method includes the step of applying the cinnamic acid derivative or the pesticide to crops. The crops include rice,wheat, fruit trees and vegetables. The low-toxicity, low-residue-content and high-activity environment-friendly cinnamic acid derivative is developed, and the cinnamic acid derivative pesticide can replace traditional high-toxicity and high-residue-content pesticides.
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Paragraph 0131-0133

(2019/10/22)

Structure-aided drug development of potential neuraminidase inhibitors against pandemic H1N1 exploring alternate binding mechanism
Abstract: The rate of mutability of pathogenic H1N1 influenza virus is a threat. The emergence of drug resistance to the current competitive inhibitors of neuraminidase, such as oseltamivir and zanamivir, attributes to a need for an alternative approach. The design and synthesis of new analogues with alternate approach are particularly important to identify the potential neuraminidase inhibitors which may not only have better anti-influenza activity but also can withstand challenge of resistance. Five series of scaffolds, namely aurones (1a–1e), pyrimidine analogues (2a–2b), cinnamic acid analogues (3a–3k), chalcones (4a–4h) and cinnamic acid linkages (5a–5c), were designed based on virtual screening against pandemic H1N1 virus. Molecular modelling studies revealed that the designed analogues occupied 430-loop cavity of neuraminidase. Docking of sialic acid in the active site preoccupied with the docked analogues, i.e. in 430-loop cavity, resulted in displacement of sialic acid from its native pose in the catalytic cavity. The favourable analogues were synthesized and evaluated for the cytotoxicity and cytopathic effect inhibition by pandemic H1N1 virus. All the designed analogues resulting in displacement of sialic acid suggested alternate binding mechanism. Overall results indicated that aurones can be measured best among all as potential neuraminidase inhibitor against pandemic H1N1 virus. Graphical abstract: [Figure not available: see fulltext.].
Malbari, Khushboo D.,Chintakrindi, Anand S.,Ganji, Lata R.,Gohil, Devanshi J.,Kothari, Sweta T.,Joshi, Mamata V.,Kanyalkar, Meena A.
p. 927 - 951
(2019/02/07)

Novel morpholine containing cinnamoyl amides as potent tyrosinase inhibitors
Tyrosinase enzyme plays a crucial role in melanin biosynthesis and enzymatic browning process of vegetables and fruits. Hence, tyrosinase inhibitors are important in the fields of medicine, cosmetics and agriculture. In this study, novel N-(2-morpholinoethyl)cinnamamide derivatives bearing different substituents on phenyl ring were designed, synthesized and evaluated for their tyrosinase diphenolase inhibitory activity. The compounds were found to be better tyrosinase inhibitors (IC50s were in micro molar range) than cinnamic acid. (E)-3-(3-chlorophenyl)-N-(2-morpholinoethyl)acrylamide (B6) exhibited the highest inhibition with IC50 value of 15.2 ± 0.6 μM which was comparable to that of kojic acid. The inhibition kinetic analysis of B6 indicated that the compound was a mixed-type tyrosinase inhibitor. In silico ADME prediction indicated that B6 might show more skin penetration than kojic acid. Molecular docking analysis confirmed that the active inhibitors well accommodated in the mushroom tyrosinase active site and it was also revealed that B6 formed the most stable drug-receptor complex with the target protein. Therefore, cinnamamide B6 could be introduced as a potent tyrosinase inhibitor that might be a promising lead in cosmetics, medicine and food industry.
Ghafari, Shahrzad,Ranjbar, Sara,Larijani, Bagher,Amini, Mohsen,Biglar, Mahmood,Mahdavi, Mohammad,Bakhshaei, Maryam,Khoshneviszadeh, Mahsima,Sakhteman, Amirhossein,Khoshneviszadeh, Mehdi
p. 978 - 985
(2019/06/13)

Synthesis, Crystallization Studies, and in vitro Characterization of Cinnamic Acid Derivatives as SmHDAC8 Inhibitors for the Treatment of Schistosomiasis
Schistosomiasis is a neglected parasitic disease that affects more than 265 million people worldwide and for which the control strategy relies on mass treatment with only one drug: praziquantel. Based on the 3-chlorobenzothiophene-2-hydroxamic acid J1075, a series of hydroxamic acids with different scaffolds were prepared as potential inhibitors of Schistosoma mansoni histone deacetylase 8 (SmHDAC8). The crystal structures of SmHDAC8 with four inhibitors provided insight into the binding mode and orientation of molecules in the binding pocket as well as the orientation of its flexible amino acid residues. The compounds were evaluated in screens for inhibitory activity against schistosome and human HDACs. The most promising compounds were further investigated for their activity toward the major human HDAC isotypes. The most potent inhibitors were additionally screened for lethality against the schistosome larval stage using a fluorescence-based assay. Two of the compounds showed significant, dose-dependent killing of the schistosome larvae and markedly impaired egg laying of adult worm pairs maintained in culture.
Bayer, Theresa,Chakrabarti, Alokta,Lancelot, Julien,Shaik, Tajith B.,Hausmann, Kristin,Melesina, Jelena,Schmidtkunz, Karin,Marek, Martin,Erdmann, Frank,Schmidt, Matthias,Robaa, Dina,Romier, Christophe,Pierce, Raymond J.,Jung, Manfred,Sippl, Wolfgang
p. 1517 - 1529
(2018/08/01)

Polystyrene supported palladium nanoparticles catalyzed cinnamic acid synthesis using maleic anhydride as a substitute for acrylic acid
Maleic anhydride was explored as a substitute for acrylic acid to synthesize cinnamic acids from aryl halides under heterogeneous palladium catalyzed conditions. The combined role of surface and impregnated catalyst together performed an upright engineering to hold in situ generated molecules on the surface and subsequently facilitate their interaction for the desired product synthesis. Overall, a surface mediated approach for cinnamic acid synthesis from maleic anhydride following a major unexplored pathway through catalyst promoted decarboxylation was critically investigated.
Thakur, Vandna,Kumar, Sandeep,Das, Pralay
p. 3692 - 3697
(2017/09/07)

Chiral phosphoric acid catalyzed enantioselective annulation of acyclic enecarbamates to: In situ -generated ortho -quinone methides
The first organocatalytic asymmetric reaction of acyclic enecarbamates with o-quinone methides is disclosed. BINOL-based phosphoric acid catalysts were found to be suitable for the annulation reaction. With 10 mol% of the TRIP catalyst, high yields as well as excellent diastereo- and enantioselectivities are achieved for a variety of 2,3,4-trisubstituted chroman products.
Gharui, Chandan,Singh, Shreya,Pan, Subhas Chandra
supporting information
p. 7272 - 7276
(2017/09/25)

Palladium nanoparticles immobilized on amphiphilic and hyperbranched polymer-functionalized magnetic nanoparticles: An efficient semi-heterogeneous catalyst for Heck reaction
To address the obstacles facing the use of palladium-based homogeneous and heterogeneous catalysts in C─C cross-coupling reactions, a novel semi-heterogeneous support was developed based on hyperbranched poly(ethylene glycol)-block-poly(citric acid)-functionalized Fe3O4 magnetic nanoparticles (Fe3O4@PCA-b-PEG). Because of the surface modification of the Fe3O4 nanoparticles with amphiphilic and hyperbranched polymers (PCA-b-PEG), these hybrid materials are not only soluble in a wide range of solvents (e.g. water, ethanol and dimethylformamide) but also are able to trap Pd2+ ions via complex formation of free carboxyl groups of the PCA dendrimer with metal ions. The reduction of trapped palladium ions in the dendritic shell of Fe3O4@PCA-b-PEG leads to immobilized palladium nanoparticles. The morphology and structural features of the catalyst were characterized using various microscopic and spectroscopic techniques. The catalyst was effectively used in the palladium-catalysed Mizoroki–Heck coupling reaction in water as a green solvent. In addition, the catalyst can be easily recovered from the reaction mixture by applying an external magnetic field and reused for more than ten consecutive cycles without much loss in activity, exhibiting an example of a sustainable and green methodology.
Tabatabaei Rezaei, Seyed Jamal,Shamseddin, Azin,Ramazani, Ali,Mashhadi Malekzadeh, Asemeh,Azimzadeh Asiabi, Pegah
(2017/09/01)

Tert-Butyl Nitrite-Mediated Synthesis of N-Nitrosoamides, Carboxylic Acids, Benzocoumarins, and Isocoumarins from Amides
This work reports tert-butyl nitrite (TBN) as a multitask reagent for (1) the controlled synthesis of N-nitrosoamide from N-alkyl amides, (2) hydrolysis of N-methoxyamides to carboxylic acids, (3) metal- and oxidant-free benzocoumarin synthesis from ortho-aryl-N-methoxyamides via N-H, C-N, and C-H bond activation, and (4) isocoumarin synthesis using Ru(II)/PEG as a recyclable catalytic system via ortho-C-H activation and TBN as an oxygen source. The sequential functional group interconversion of amide to acid has also been examined using IR spectroscopic analysis. Additionally, this methodology is highly advantageous due to short reaction time, gram scale synthesis, and broad substrate scope.
Yedage, Subhash L.,Bhanage, Bhalchandra M.
p. 5769 - 5781
(2017/06/07)

Influence of the aromatic moiety in α- And β-arylalanines on their biotransformation with phenylalanine 2,3-aminomutase from: Pantoea agglomerans
In this study enantiomer selective isomerization of various racemic α- and β-arylalanines catalysed by phenylalanine 2,3-aminomutase from Pantoea agglomerans (PaPAM) was investigated. Both α- and β-arylalanines were accepted as substrates when the aryl moiety was relatively small, like phenyl, 2-, 3-, 4-fluorophenyl or thiophen-2-yl. While 2-substituted α-phenylalanines bearing bulky electron withdrawing substituents did not react, the corresponding substituted β-aryl analogues were converted rapidly. Conversion of 3- and 4-substituted α-arylalanines happened smoothly, while conversion of the corresponding β-arylalanines was poor or non-existent. In the range of pH 7-9 there was no significant influence on the conversion of racemic α- or β-(thiophen-2-yl)alanines, whereas increasing the concentration of ammonia (ammonium carbonate from 50 to 1000 mM) inhibited the isomerization progressively and decreased the amount of the by-product (i.e. (E)-3-(thiophen-2-yl)acrylic acid was detected). In all cases, the high ee values of the products indicated excellent enantiomer selectivity and stereospecificity of the isomerization except for (S)-2-nitro-α-phenylalanine (ee 92%) from the β-isomer. Substituent effects were rationalized by computational modelling revealing that one of the main factors controlling biocatalytic activity was the energy difference between the covalent regioisomeric enzyme-substrate complexes.
Varga, Andrea,Bánóczi, Gergely,Nagy, Botond,Bencze, László Csaba,To?a, Monica Ioana,Gellért, ákos,Irimie, Florin Dan,Rétey, János,Poppe, László,Paizs, Csaba
p. 56412 - 56420
(2016/07/06)

Synthesis and bioactivities of novel piperazine-containing 1,5-Diphenyl-2-penten-1-one analogues from natural product lead
A series of novel 1,5-Diphenyl-2-penten-1-one analogues (7a–h, 8a–h) with piperazine moiety have been designed and synthesized on the basis of natural product 1,5-Diphenyl-2-penten-1-one (I). All the synthesized compounds were evaluated in vitro for anti-plant pathogenic fungi activities and insecticidal activities. The results indicated that most of these analogues exhibited moderate antifungal activities and moderate to good insecticidal activities. Amongst them, the most potent 7c, 7e and 7h keep a mortality of 100% against larva of mosquito at the concentration of 1?mg/L. Initial structure–activity relationship (SAR) analysis showed that, a methyl group can influence the biological activities of these compounds significantly, the compounds with N′-unsubstituted piperazine showed much better antifungal activities and larvicidal activity against mosquito than the compounds with N′-methylated piperazine. In addition, the larvicidal activity against mosquito had sharply decline when the substituent on benzene ring was changed from 4-position to 2 or 3-position.
Xu, Gaofei,Yang, Xinling,Jiang, Biaobiao,Lei, Peng,Liu, Xili,Wang, Qingmin,Zhang, Xuebo,Ling, Yun
p. 1849 - 1853
(2016/07/27)

Telescopic one-pot condensation-hydroamination strategy for the synthesis of optically pure L-phenylalanines from benzaldehydes
A chemo-enzymatic telescopic approach was designed for the synthesis of L-arylalanines in high yield and optical purity, starting from commercially available and inexpensive substituted benzaldehydes. The method exploits a chemical Knoevenagel–Doebner condensation (optimised to give complete conversions in a short reaction time, employing microwave irradiation) and a biocatalytic phenylalanine ammonia lyase mediated hydroamination (for the stereoselective addition of ammonia). The two reactions can be run sequentially in one pot, bringing together the advantages of chemical and biological catalysis. The preparative applicability was demonstrated with the synthesis of five L-dihalophenylalanines (71–84% yield, 98–99% ee) of relevance as molecular probes, for medicinal chemistry and for the synthesis of pharmaceutical ingredients.
Parmeggiani, Fabio,Ahmed, Syed T.,Weise, Nicholas J.,Turner, Nicholas J.
p. 7256 - 7262
(2016/10/26)

Palladium-Catalyzed Two-Component Domino Coupling Reaction of (Z)-β-Bromostyrenes with Norbornenes: Synthesis of 1,5-Enynes
Polyfunctional molecules, 1,5-enynes, have been achieved via a palladium(0)-catalyzed domino coupling reaction of (Z)-β-bromostyrenes with norbornenes in the presence of cesium carbonate and N,N-dimethylformamide. The process involves a double Heck-type procedure, two-fold C(sp2) H activation and formation of two carbon-carbon bonds. There are possibilities of diversified transformation for the domino coupling of (Z)-β-bromostyrenes with norbornenes, the procedure is successfully driven to 1,5-enynes via accurate adjustment of the reaction conditions. (Figure presented.) .
Mao, Jiangang,Li, Huifang,Wen, Herui,Li, Min,Fan, Xiaolin,Bao, Weiliang
supporting information
p. 1873 - 1879
(2016/07/06)

Copper catalyzed oxygen assisted C(CNOH)-C(alkyl) bond cleavage: A facile conversion of aryl/aralkyl/vinyl ketones to aromatic acids
A novel copper-catalyzed aerobic oxidative C(NOH)-C(alkyl) bond cleavage reaction of aryl/aralkyl/vinyl ketones for the synthesis of aromatic/acrylic acids is described. A series of ketones having aryl/aralkyl/vinyl at the one end and methyl to any higher alkyl at the other end can be selectively cleaved and converted into the corresponding acids via oxime intermediates.
Sathyanarayana, Pochampalli,Ravi, Owk,Muktapuram, Prathap Reddy,Bathula, Surendar Reddy
supporting information
p. 9681 - 9685
(2015/09/28)

Design, synthesis and cytotoxic evaluation of novel imatinib amide derivatives that target Abl kinase
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
p. 20 - 28
(2015/03/31)

Chiral Cyclopentadienyl Iridium(III) Complexes Promote Enantioselective Cycloisomerizations Giving Fused Cyclopropanes
The cyclopentadienyl (Cp) group is a very important ligand for many transition-metal complexes which have been applied in catalysis. The availability of chiral cyclopentadienyl ligands (Cpx) lags behind other ligand classes, thus hampering the investigation of enantioselective processes. We report a library of chiral CpxIrIII complexes equipped with an atropchiral Cp scaffold. A robust complexation procedure reliably provides CpxIrIII complexes with tunable counterions. In a proof-of-concept application, the iodide-bearing members are shown to be highly selective for enyne cycloisomerization reactions. The dehydropiperidine-fused cyclopropane products are formed in good yields and enantioselectivities.
Dieckmann, Michael,Jang, Yun-Suk,Cramer, Nicolai
supporting information
p. 12149 - 12152
(2015/10/12)

Palladium(0)-Catalyzed Methylcyclopropanation of Norbornenes with Vinyl Bromides and Mechanism Study
An unusual methylcyclopropanation from [2 + 1] cycloadditions of vinyl bromides to norbornenes catalyzed by Pd(OAc)2/PPh3 in the presence of CH3ONa and CH3OH has been established. A methylcyclopropane subunit was installed by a 3-fold domino procedure involving a key protonation course. Preliminary deuterium-labeling studies revealed that the proton came from methyl of CH3OH and also exposed an additional hydrogen/deuterium exchange process. These two proton-concerned reactions were fully chemoselective.
Mao, Jiangang,Xie, Hujun,Bao, Weiliang
supporting information
p. 3678 - 3681
(2015/08/18)

Cu/Fe-Cocatalyzed Formation of β-Ketophosphonates by a Domino Knoevenagel-Decarboxylation-Oxyphosphorylation Sequence from Aromatic Aldehydes and H-Phosphonates
A domino Knoevenagel-decarboxylation-alkene difunctionalization sequence has been developed for the conversion of benzaldehydes into β-ketophosphonates, catalyzed by a cooperative Cu/Fe system, whereby CP and CO bonds are formed simultaneously in a one-pot reaction. The reaction proceeds in good yields and with a broad substrate scope and environmentally benign conditions.
Zhou, Mingxin,Zhou, Yao,Song, Qiuling
supporting information
p. 10654 - 10658
(2015/07/20)

Multifunctional novel Diallyl disulfide (DADS) derivatives with β-amyloid-reducing, cholinergic, antioxidant and metal chelating properties for the treatment of Alzheimer's disease
A series of novel Diallyl disulfide (DADS) derivatives were designed, synthesized and evaluated as chemical agents, which target and modulate multiple facets of Alzheimer's disease (AD). The results showed that the target compounds 5a-l and 7e-m exhibited significant anti-Aβ aggregation activity, considerable acetylcholinesterase (AChE) inhibition, high selectivity towards AChE over butyrylcholinesterase (BuChE), potential antioxidant and metal chelating activities. Specifically, compounds 7k and 7l exhibited highest potency towards self-induced Aβ aggregation (74% and 71.4%, 25 μM) and metal chelating ability. Furthermore, compounds 7k and 7l disaggregated Aβ fibrils generated by Cu2+-induced Aβ aggregation by 80.9% and 78.5%, later confirmed by transmission electron microscope (TEM) analysis. Besides, 7k and 7l had the strongest AChE inhibitory activity with IC50 values of 0.056 μM and 0.121 μM, respectively. Furthermore, molecular modelling studies showed that these compounds were capable of binding simultaneously to catalytic active site (CAS) and peripheral anionic site (PAS) of AChE. All the target compounds displayed moderate to excellent antioxidant activity with ORAC-FL values in the range 0.546-5.86 Trolox equivalents. In addition, absorption, distribution, metabolism and excretion (ADME) profile and toxicity prediction (TOPKAT) of best compounds 7k and 7l revealed that they have drug like properties and possess very low toxic effects. Collectively, the results strongly support our assertion that these compounds could provide good templates for developing new multifunctional agents for AD treatment.
Manral, Apra,Saini, Vikas,Meena, Poonam,Tiwari, Manisha
p. 6389 - 6403
(2015/10/05)

Aromatic diacylhydrazine derivatives as a new class of polo-like kinase 1 (PLK1) inhibitors
A novel class of aromatic diacylhydrazine derivatives was designed as PLK1 inhibitors. All the 19 new synthesized compounds were assayed for antitumor activity against the respective cervical cancer cells. In which, nine compounds with better antitumor activities were further tested for their PLK1 inhibitory activity. Last, we have successfully found that compound 7k showed both the promising antitumor activity with IC50 of 0.17 μM against the cervical cancer cells, and also processed the most potent PLK1 inhibitory activity with IC50 of 0.03 μM. In addition, docking simulation also carried out in this study to give a potent prediction binding mode between the small molecule and PKL1 (PDB code: 1umw) protein.
Sun, Juan,Lv, Peng-Cheng,Guo, Feng-Jiao,Wang, Xin-Yi,Han, Xiao-,Zhang, Yang,Sheng, Gui-Hua,Qian, Shao-Song,Zhu, Hai-Liang
p. 420 - 426
(2014/06/09)

Palladium(0)-catalyzed methylenecyclopropanation of norbornenes with vinyl bromides
Highly strained methylenecyclopropane derivatives have been achieved via a novel and efficient Pd(0)-catalyzed domino reaction. The formal [2 + 1] cycloaddition reaction of vinyl bromides to norbornenes involves a Heck-type coupling and a C(sp2)-H bond activation.
Mao, Jiangang,Bao, Weiliang
supporting information
p. 2646 - 2649
(2014/06/09)

Palladium-catalyzed [2+1+1] annulation of norbornenes with (z)-bromostyrenes: Synthesis of bismethylenecyclobutanes via twofold C(sp2)-H bond activation
The first Pd-catalyzed intermolecular [2+1+1] annulation reaction of (Z)-bromostyrene derivatives and norbornenes has been realized. Bismethylenecyclobutane derivatives were obtained with high yields. The domino coupling reaction involves a double Heck-type coupling process, twofold C(sp2)-H bond activation and formation of three carbon-carbon bonds.
Mao, Jiangang,Bao, Weiliang
supporting information
p. 15726 - 15729
(2015/01/08)

Synthesis and sar study of diarylpentanoid analogues as new anti-inflammatory agents
A series of ninety-seven diarylpentanoid derivatives were synthesized and evaluated for their anti-inflammatory activity through NO suppression assay using interferone gamma (IFN-γ)/lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages. Twelve compounds (9, 25, 28, 43, 63, 64, 81, 83, 84, 86, 88 and 97) exhibited greater or similar NO inhibitory activity in comparison with curcumin (14.7 ± 0.2 μM), notably compounds 88 and 97, which demonstrated the most significant NO suppression activity with IC50 values of 4.9 ± 0.3 μM and 9.6 ± 0.5 μM, respectively. A structure-activity relationship (SAR) study revealed that the presence of a hydroxyl group in both aromatic rings is critical for bioactivity of these molecules. With the exception of the polyphenolic derivatives, low electron density in ring-A and high electron density in ring-B are important for enhancing NO inhibition. Meanwhile, pharmacophore mapping showed that hydroxyl substituents at both meta- and para-positions of ring-B could be the marker for highly active diarylpentanoid derivatives.
Leong, Sze Wei,Mohd Faudzi, Siti Munirah,Abas, Faridah,Mohd Aluwi, Mohd Fadhlizil Fasihi,Rullah, Kamal,Wai, Lam Kok,Abdul Bahari, Mohd Nazri,Ahmad, Syahida,Tham, Chau Ling,Shaari, Khozirah,Lajis, Nordin H.
p. 16058 - 16081
(2015/01/08)

The [RPPhPd as a catalyst precursor for the heck cross-coupling reaction by in situ formation of stabilized Pd(0) nanoparticles
Pd(II) anionic, square planar complexes of the type [RPPhPdl, where X = Cl, Br, have been applied for the first time as a catalyst precursor for the Heck reaction carried out in DMF at 140 °C. The highest yield was obtained for the most reducible ones, [MePPhPdrl, in DMF in the presence of NaHCOas a base. It was found that during the reaction, phosphonium halide stabilized Pd(0) nanoparticles of about 10 nm, which have been formed in situ from the palladium(II) precursor and Pd(0) colloidal nanoparticles acts as the reservoir for Pd(II) species via activation of the metal surface through the oxidative addition of aryl halides. Georg Thieme Verlag Stuttgart New York.
Hajipour, Abdol Reza,Azizi, Ghobad
supporting information
p. 254 - 258
(2013/03/13)

Sodium tetraborate/benzyltriethylammonium chloride-mediated synthesis of substituted cinnamic acids from aromatic aldehydes and aliphatic carboxylic acids
A simple, efficient, and cost-effective method has been developed for the synthesis of some cinnamic acid derivatives in moderate to high yields (63-86%) by a one-pot condensation reaction of benzaldehyde and aliphatic carboxylic acids in the presence of sodium tetraborate and benzyltriethylammonium chloride, and N-methyl-pyrrolidinone as solvent. The reaction requires high temperatures (reflux at 180-190°C) and strong basic conditions, which have been generated by pyridine and 4-dimethylaminopyridine added to the reaction medium.
Nechifor, Marioara,Chiriac, Constantin I.,Tanasa, Fulga
p. 161 - 164
(2014/04/03)

Design, synthesis and biological evaluation of cinnamic acyl shikonin derivatives
Inducing apoptosis is an important and promising therapeutic approach to overcome cancer. Here, we described a series of novel synthesized compounds, cinnamic acyl shikonin derivatives (1b-19b), which were synthesized starting from shikonin and cinnamic acids, which exhibit anticancer activity via inducing apoptosis in vitro. Our flow cytometry results showed that compound 8b((E)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent -3-enyl-3-(3-(trifluoromethyl) phenyl)acrylate) (IC50=0.69, 0.65, 1.62 μm for human SW872-s, A875 and A549 cell lines, respectively) exhibited conspicuous anticancer activities and has low cell toxicity in vitro. Therefore, we considered that compound 8b is potentially to be a candidate of anticancer agent. The proliferation inhibitory effect of compound 8b was associated with its apoptosis-inducing effect by activating caspase-3, caspase-7, caspase-9, and PARP. When the level of cleaved caspase-3, cleaved caspase-7, cleaved caspase-9, and cleaved PARP are rise, apoptosis of cancer cells will be induced.
Lin, Hong-Yan,Chen, Wei,Shi, Jing,Kong, Wen-Yao,Qi, Jin-Liang,Wang, Xiao-Ming,Yang, Yong-Hua
p. 275 - 283
(2013/03/13)

Sodium tetraborate-dibenzo-18-crown ether-6 complex as reagent in the synthesis of cinnamic acids from aromatic aldehydes and aliphatic carboxylic acids
Cinnamic acids have been prepared in 74-81% yields by a new synthesis from aromatic aldehydes and aliphatic carboxylic acids in the presence of anhydrous sodium tetraborate-dibenzo-18-crown ether-6 complex as reagent, 4-dimethylaminopyridine as activating agent, pyridine as base, and N-methyl-2-pyrolidinone as solvent, at reflux (180-190°C) for 10-12 hours.
Chiriac, Constantin I.,Tanasa, Fulga,Nechifor, Marioara
experimental part
p. 419 - 423
(2012/01/03)

Regioselective addition of thiophenol to α,β-unsaturated N-acylbenzotriazoles
Regioselective addition of thiophenol to α,β-unsaturated N-acylbenzotriazoles has been achieved by controlling the conditions. Thus, three types of products, namely α,β-unsaturated thioesters, β-thiophenoxy substituted N-acylbenzotriazoles, and β-thiophenoxy substituted thioesters were selectively obtained in good to excellent yields.
Xia, Ziming,Lv, Xin,Wang, Wencun,Wang, Xiaoxia
supporting information; experimental part
p. 4906 - 4910
(2011/10/07)

Environmentally benign and energy efficient methodology for condensation: An interesting facet to the classical Perkin reaction
We have reported use of biodegradable deep eutectic solvent (DES) based on choline chloride and urea, for the synthesis of cinnamic acid and its derivatives via Perkin reaction. The reaction proceeds efficiently under mild condition without use of additional catalyst with better yields. Ease of recovery and reusability of solvent with consistent activity makes this method efficient and environmentally benign. This method is also energy efficient and easy to handle.
Pawar, Poonam Mahadev,Jarag, Krishna Jagannath,Shankarling, Ganapati Subray
experimental part
p. 2130 - 2134
(2011/10/03)

Synthesis and anticancer activity of 13-membered cyclic enediynes
We herein describe the synthesis of 15 novel 13-membered cyclic enediyne derivatives using simple and straightforward approach. Representative examples were screened for their anticancer activities on 60 different human tumor cell lines representing various histologies viz. leukemia, melanoma, and cancers of lung, colon, kidney, ovary, breast, prostate, and central nervous system. The enediyne derivatives with halogen substitutions, especially fluorides were found to be active against most of the cell lines. The initial results indicates marginal to good inhibition for the growth of tumor cells for several cell lines, which shows the potential of these class of compound towards anticancer application. 15 novel 13-membered cyclic enediyne derivatives using a simple and straightforward approach are synthesized. The initial results show the potential of this class of compounds towards anticancer application. Copyright
Sharma, Mukul,Joshi, Mukesh C,Kumar, Vineet,Malhotra, Sanjay V.,Rawat, Diwan S.
scheme or table
p. 567 - 571
(2012/06/30)

A novel direct boron-mediated synthesis of cinnamic acids from aromatic aldehydes and aliphatic carboxylic acids
Cinnamic acids have been prepared in 64-85% yields by a new direct synthesis from aromatic aldehydes and aliphatic carboxylic acids in the presence of anhydrous sodium tetraborate and lithium chloride, bases as pyridine (Py) and 4-dimethylaminopyridine (DMAP), and N-methyl-2-pyrolidinone (NMP) as solvent, at reflux (180-190°C), for 8-12 hours. Without sodium tetraborate-lithium chloride this reaction is not possible.
Chiriac, Constantin I.,Tanasa, Fulga,Nechifor, Marioara
experimental part
p. 987 - 991
(2011/06/21)

Phenylalanine aminomutase-catalyzed addition of ammonia to substituted cinnamic acids: A route to enantiopure α- and β-amino acids
(Chemical Equation Presented) An approach is described for the synthesis of aromatic α- and β-amino acids that uses phenylalanine aminomutase to catalyze a highly enantioselective addition of ammonia to substituted cinnamic acids. The reaction has a broad scope and yields substituted α- and β-phenylalanines with excellent enantiomeric excess. The regioselectivity of the conversion is determined by substituents present at the aromatic ring. A box model for the enzyme active site is proposed, derived from the influence of the hydrophobicity of substituents on the enzyme affinity toward various substrates.
Szymanski, Wiktor,Wu, Bian,Weiner, Barbara,De Wildeman, Stefaan,Feringa, Ben L.,Janssen, Dick B.
supporting information; experimental part
p. 9152 - 9157
(2010/03/01)

Synthesis and structure-activity relationships of substituted cinnamic acids and amide analogues: A new class of herbicides
In the present investigation, substituted cinnamic acids (3-hydroxy, 4-hydroxy, 2-nitro, 3-nitro, 4-nitro, 3-chloro, and 4-methoxy) and their amide analogues with four different types of substituted anilines have been synthesized. The synthesized compounds have been screened for their germination inhibition activity on radish (Raphanus sativus L. var. Japanese White) seeds at 50, 100, and 200 ppm concentrations, and the activity was compared with standard herbicide, metribuzin formulation (sencor). Significant activity was exhibited by all of the compounds. It was observed that with the increase in concentration of the test solution, the activity also increased. All of the compounds showed more than 70% inhibition at 100 ppm concentration except 4-hydroxy cinnamanilide. The compound, 2-chloro (4′-hydroxy) cinnamanilide was the best among the tested compounds, and it was found to be at par with the standard, metribuzin at all concentrations. Thus, it can be concluded that substituted cinnamic acids and their amide analogues may be developed as potential herbicides.
Vishnoi, Shipra,Agrawal, Vikash,Kasana, Virendra K.
experimental part
p. 3261 - 3265
(2010/06/14)

A new alternative method for the synthesis of cinnamic acids from aromatic aldehydes and zinc acetate
Cirmamic acids have been prepared in 58-85% yields by a new synthetic route from aromatic aldehydes and zinc acetate in acetic acid and N-methyl-2-pyrrolidinone (NMP) as solvents, at reflux (185-195°C), for 8-12 hours.
Chiriac, Constantin I.,Tanasa, Fulga,Nechifor, Marioara
experimental part
p. 833 - 836
(2009/12/24)

A new synthesis of cinnamic acids from aromatic aldehydes and N,N-dimethylacetamide hydrochloride
Cinnamic acids have been prepared in 61-85% yields by a new synthesis from aromatic aldehydes and N, Ndimethylacetamide hydrochloride as reagent and solvent, at reflux (190-200°C), for 8-12 hours. Without N,N- dimethylacetamide hydrochloride this reaction is not possible.
Chiriac, Constantin I.,Tanasa, Fulga,Nechifor, Marioara
experimental part
p. 949 - 952
(2009/09/29)

A novel approach in cinnamic acid synthesis: Direct synthesis of cinnamic acids from aromatic aldehydes and aliphatic carboxylic acids in the presence of boron tribromide
Cinnamic acids have been prepared in moderate to high yields by a new direct synthesis using aromatic aldehydes and aliphatic carboxylic acids, in the presence of boron tribromide as reagent, 4-dimethylaminopyridine (4-DMAP) and pyridine (Py) as bases and N-methyl-2-pyrolidinone (NMP) as solvent, at reflux (180-190°C) for 8-12 hours.
Chiriac, Constantin I.,Tanasa, Fulga,Onciu, Marioara
p. 481 - 487
(2007/10/03)

Synthesis of trans-cinnamic acids from aryl aldehydes and aryl aldehyde bisulfite adducts with malonic acid using piperazine
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
p. 364 - 365
(2007/10/03)

New boron reagents for designed organic synthesis. 2 cinnamic acids synthesis in the presence of sodium tetramethoxyborate-lithium chloride
Cinnamic acids were prepared in good to high yields by Perkin reaction between aromatic aldehydes and aliphatic anhydrides in the presence of a boron compound, namely sodium tetramethoxyborate-lithium chloride, as a novel catalyst for this synthesis and N-methyl-pyrrolidin-2-one (NMP) as a solvent, at reflux (170-180°C) for 9-12 hours.
Chiriac, Constantin I.,Tanasǎ, Fulga,Onciu, Marioara
p. 627 - 631
(2007/10/03)

A new direct synthesis of cinnamic acids from aromatic aldehydes and aliphatic carboxylic acids in the presence of sodium borohydride
Cinnamic acids have been prepared in 59-86% yields by a new direct synthesis from aromatic aldehydes and aliphatic carboxylic acids in the presence of sodium borohydride and N-methyl-2-pyrrolidinone (NMP) as solvent, at reflux (185-190°C), for 9-12 hours. Without sodium borohydride, this reaction is not possible.
Chiriac, Constantin I.,Tanasa, Fulga,Onciu, Marioara
p. 3579 - 3580
(2007/10/03)

Synthesis, and biological evaluation of new 1,3,4-thiadiazolium-2-phenylamine derivatives against Leishmania amazonensis promastigotes and amastigotes
1,3,4-Thiadiazolium-2-aminide, which is a class of mesoionic compounds, were tested against promastigote and amastigote forms of Leishmania amazonensis. Parasites were assayed with or without the drugs in axenic media, using pentamidine isethionate as a reference drug. The very promising results showed us the most active compounds were the 4′- and 3′-methoxy derivatives against promastigote forms, while the highest activity against the amastigote forms was obtained with the 4′-fluor and 3′-bromo derivatives.
Da Silva, Edson F.,Canto-Cavalheiro, Marilene M.,Braz, Viviane R.,Cysne-Finkelstein, Lea,Leon, Leonor L.,Echevarria, Aurea
p. 979 - 984
(2007/10/03)

Process for acyloxylating side chains of alkyl-substituted aromatic compounds and catalysts used therefor
The present invention is a method for acyloxylating an alkyl group substituted aromatic compound at the side chain, by letting the alkyl group substituted aromatic compound and a carboxylic acid and/or a carboxylic anhydride react with each other in the presence of an oxygen containing gas. In this case, if (1) a solid catalyst in which at least one selected from cobalt, cerium and manganese is supported on a solid material or (2) a catalyst containing at least one selected from cobalt oxides, cerium oxides and manganese oxides is used, an alkali group substituted aromatic compound and a carboxylic acid and/or a carboxylic anhydride can be caused to react with each other efficiently in the presence of an oxygen containing gas, and in addition the catalyst can be easily separated from the reaction solution. Furthermore, (3) a compound diacyloxylated at the side chains can be highly selectively produced if a cerium compound is used as a catalyst in the absence of a cobalt compound and a manganese compound. Moreover, the present invention relates to a method for producing a cinnamic acid by letting a benzylidene diacetate react in the presence of a basic catalyst. The alkyl group substituted aromatic compounds acyloxylated and diacyloxylated at the side chain obtained in the present invention are useful for perfumes, and the benzyl alcohols and benzaldehydes obtained by hydrolyzing them are useful for intermediate products of agricultural chemicals, drugs and perfumes and also for resin additives. The cinnamic acids produced according to the present invention are useful for intermediate products of agricultural chemicals, drugs and perfumes.
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(2008/06/13)