cas 20583-78-2, ETHYL 3-(3,4-DIMETHOXYPHENYL)ACRYLATE

Articles about 20583-78-2Total 59 be found

Article title
Article abstract
Author
Journal number and time
Download

Electrochemical reduction of a bromo propargyloxy ester at silver cathodes in dimethylformamide
Cyclic voltammograms for the reduction of ethyl 2-bromo-3-(3',4'-dimethoxyphenyl)-3-(propargyloxy)propanoate (1) at a silver cathode in dimethylformamide (DMF) containing 0.10 M tetraethylammonium tetrafluoroborate (TEABF4) exhibit several cathodic peaks,
Henderson, Robert J.,Buehler, Nathan R.,Pasciak, Erick M.,Mubarak, Mohammad S.,Peters, Dennis G.
p. G128 - G132
(2014)
Read Online

S,O-Ligand-Promoted Pd-Catalyzed C?H Olefination of Anisole Derivatives
The C?H olefination of substituted anisole derivatives by a Pd/S,O-ligand catalyst is reported. The reaction proceeds under mild conditions with a broad range of substituted aryl ethers bearing both electron donating and withdrawing substituents at ortho,
Fernández-Ibá?ez, M. ángeles,Jia, Wen-Liang,Sukowski, Verena,van Borselen, Manuela,van Diest, Rianne
supporting information
p. 4132 - 4135
(2021/08/24)

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)

In silico design and synthesis of N-arylalkanyl 2-naphthamides as a new class of non-purine xanthine oxidase inhibitors
A series of N-arylalkanyl 2-naphthamides (Xa~e), which were predicted from virtual molecular docking on a built xanthine oxidase template as potential inhibitors, were synthesized. Their inhibitory activity against xanthine oxidase was assayed. Among these prepared, compounds Xb (IC50 13.6?μM), Xc (IC50 13.1?μM), and Xd (IC50 12.5?μM) showed comparable inhibitory activity to allopurinol (IC50 22.1?μM). The in vitro assay result correlated well with molecular docking scores, ΔG?=??16.99, ?17.66, and ?17.13 Kcal/mol, respectively. On the potassium oxonate-induced hyperuricemic mice model, oral administration of Xc-Ac (40 mg/ Kg), the per-O-acetylated Xc, could reduce the blood uric acid level by 60% in comparison to the normal control group and is statistically significant (p .01) while compared with the hyperuricemic mice group.
Ho, Sheau Ling,Lin, Ching-Ting,Lee, Shoei-Sheng
p. 789 - 801
(2021/01/12)

Hypervalent iodine(iii) induced oxidative olefination of benzylamines using Wittig reagents
We have developed hypervalent iodine(iii) induced oxidative olefination of primary and secondary benzylamines using 2C-Wittig reagents, which provides easy access to α,β-unsaturated esters. Mild reaction conditions, good to excellent yields with high (E) selectivity, and a broad substrate scope are the key features of this reaction. We have successfully carried out the gram-scale synthesis of α,β-unsaturated esters.
Ramavath, Vijayalakshmi,Rupanawar, Bapurao D.,More, Satish G.,Bansode, Ajay H.,Suryavanshi, Gurunath
p. 8806 - 8813
(2021/05/26)

Synthesis of Bidentate Nitrogen Ligands by Rh-Catalyzed C-H Annulation and Their Application to Pd-Catalyzed Aerobic C-H Alkenylation
A new class of bidentate ligands was prepared by a modular approach involving Rh-catalyzed C-H annulation reactions. The resulting conformationally constrained ligands enabled the Pd-catalyzed C-H alkenylation at electron-rich and sterically less hindered positions of electron-rich arenes while promoting the facile oxidation of Pd(0) intermediates by oxygen. This newly introduced ligand class is complementary to the ligands developed for Pd-catalyzed oxidative reactions and may find broad application in transition-metal-catalyzed reactions.
Kim, Hyun Tae,Kang, Eunsu,Kim, Minkyu,Joo, Jung Min
supporting information
p. 3657 - 3662
(2021/05/10)

Iron-Catalyzed Cross-Coupling of Bis-(aryl)manganese Nucleophiles with Alkenyl Halides: Optimization and mechanistic investigations
Various substituted bis-(aryl)manganese species were prepared from aryl bromides by one-pot insertion of magnesium turnings in the presence of LiCl and in situ trans-metalation with MnCl2 in THF at ?5 ?C within 2 h. These bis-(aryl)manganese reagents undergo smooth iron-catalyzed cross-couplings using 10 mol% Fe(acac)3 with various functionalized alkenyl iodides and bromides in 1 h at 25 ?C. The aryl-alkenyl cross-coupling reaction mechanism was thoroughly investigated through paramagnetic 1H-NMR, which identified the key role of tris-coordinated ate-iron(II) species in the catalytic process.
Rousseau, Lidie,Desaintjean, Alexandre,Knochel, Paul,Lefèvre, Guillaume
supporting information

(2020/02/18)

Br?nsted Acid Catalyzed Tandem Defunctionalization of Biorenewable Ferulic acid and Derivates into Bio-Catechol
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
p. 3063 - 3068
(2020/02/05)

Regioselective Br?nsted Acid-Catalyzed Annulation of Cyclopropane Aldehydes with N′-Aryl Anthranil Hydrazides: Domino Construction of Tetrahydropyrrolo[1,2- a]quinazolin-5(1 H)ones
A highly regioselective synthesis of tetrahydropyrrolo[1,2-a]quinazolin-5(1H)one derivatives was achieved by reacting cyclopropane aldehydes with N′-aryl anthranil hydrazides in the presence of p-toluene sulfonic acid (PTSA). The transformation involves domino imine formation and intramolecular cyclization to form 2-arylcyclopropyl-2,3-dihydroquinolin-4(1H)-one, followed by nucleophilic ring opening of the cyclopropyl ring to form desired tetrahydropyrrolo[1,2-a]quinazolin-5(1H)one in good to excellent yield with complete regioselectivity. This protocol tolerates a great variety of functional groups and thus provides a simple and step-efficient method for pyrroloquinazolinone synthesis.
Banerjee, Prabal,Kaur, Navpreet,Singh, Priyanka
p. 3393 - 3406
(2020/03/23)

Accessing dihydro-1,2-oxazine via cloke-wilson-type annulation of cyclopropyl carbonyls: application toward the diastereoselective synthesis of pyrrolo[1,2- b][1,2]oxazine
A convenient additive-free synthesis of dihydro-4H-1,2-oxazines via a Cloke-Wilson-type ring expansion of the aryl-substituted cyclopropane carbaldehydes with the hydroxylamine salt is introduced. Comparatively less active cyclopropyl ketones also follow a similar protocol if supplemented by catalytic p-toluene sulfonic acid monohydrate. The transformation is performed in an open-to-air flask as it shows negligible sensitivity toward air/moisture. Dihydro-4H-1,2-oxazines when subjected to cycloaddition with the cyclopropane diester afford a trouble-free formulation of the valued hexahydro-2H-pyrrolo[1,2-b][1,2]oxazine derivatives. A cascade one-pot variant of this two-step strategy offers a comparable overall yield of the final product.
Banerjee, Prabal,Kumar, Pankaj,Kumar, Rakesh
supporting information
p. 6535 - 6550
(2020/06/09)

Synthesis and biological evaluation of 4-arylcoumarins as potential anti-Alzheimer's disease agents
Alzheimer's disease (AD) is a progressive neurological degenerative disease that has complex pathogenesis. A variety of studies in humans indicate that several enzymes inhibitors can be useful in the treatment of AD, including acetylcholinesterase (AchE), butyrylcholinesterase (BuChE) and monoamine oxidase (MAO). Various substituted 4-arylcoumarin derivatives were synthesised, and their activity in vitro were investigated, including AChE/BuChE inhibitory activity, MAO inhibitory activity, and antioxidant activity. Most of the compounds were found to exhibit high inhibitory activity, and individual compounds have extremely excellent activities. Therefore 4-arylcoumarins provides an idea for drugs design for the development of therapeutic or preventive agents for AD.
Miao, Yuhang,Sun, Jie,Wang, Xiaojing,Yang, Jie,Yun, Yinling
(2020/01/03)

Discovery of an Orally Bioavailable and Central Nervous System (CNS) Penetrant mGlu7 Negative Allosteric Modulator (NAM) in Vivo Tool Compound: N-(2-(1 H-1,2,4-triazol-1-yl)-5-(trifluoromethoxy)phenyl)-4-(cyclopropylmethoxy)-3-methoxybenzamide (VU6012962)
Herein, we report the discovery of a new, orally bioavailable and CNS-penetrant metabotropic glutamate receptor 7 (mGlu7) negative allosteric modulator (NAM) that achieves exposure in cerebral spinal fluid (CSF) 2.5× above the in vitro IC50 at minimum effective doses (MEDs) of 3 mg/kg in preclinical anxiety models.
Reed, Carson W.,Yohn, Samantha E.,Washecheck, Jordan P.,Roenfanz, Hanna F.,Quitalig, Marc C.,Luscombe, Vincent B.,Jenkins, Matthew T.,Rodriguez, Alice L.,Engers, Darren W.,Blobaum, Anna L.,Conn, P. Jeffrey,Niswender, Colleen M.,Lindsley, Craig W.
p. 1690 - 1695
(2019/02/24)

In-vitro and in-vivo antimalarial activity of caffeic acid and some of its derivatives
Objectives: To explore the in-vitro and in-vivo antimalarial potential of caffeic acid and derivatives. Methods: Two common phenolic acids (caffeic acid and chlorogenic acid) were evaluated for in-vitro and in-vivo antiplasmodial activity in comparison with some semi-synthetic derivatives that were synthesized. An in-vitro assay based on plasmodial lactate dehydrogenase activity, and the classical in-vivo 5-day suppressive test from Peters on an artemisinin-resistant Plasmodium berghei strain was used. Parasitic stage sensitivity to ethyl caffeate was determined in this work. Key findings: Phenolic acid esters derivatives showed better antiplasmodial activity than corresponding phenolic acids. The derivative with the highest in-vitro activity being caffeic acid ethyl ester, exhibiting an IC50?=?21.9?±?9.4?μm. Ethyl caffeate and methyl caffeate were then evaluated for antimalarial activity in?vivo and ethyl caffeate showed a growth inhibition of 55% at 100?mg/kg. Finally, it seems that ethyl caffeate blocks the growth of young parasitic forms. Conclusions: Our study provides evidence for an antimalarial potential of caffeic acid derivatives which are common in several medicinal plants traditionally used against malaria. It also demonstrates the possibility to use such derivatives in the treatment of malaria.
Alson, Sylvain G.,Jansen, Olivia,Cieckiewicz, Ewa,Rakotoarimanana, Hajatiana,Rafatro, Herintsoa,Degotte, Gilles,Francotte, Pierre,Frederich, Michel
p. 1349 - 1356
(2018/07/31)

Dual Ligand-Enabled Nondirected C?H Olefination of Arenes
The application of the Pd-catalyzed oxidative C?H olefination of arenes, also known as the Fujiwara–Moritani reaction, has traditionally been limited by the requirement for directing groups on the substrate or the need to use the arene in large excess, ty
Chen, Hao,Wedi, Philipp,Meyer, Tim,Tavakoli, Ghazal,van Gemmeren, Manuel
supporting information
p. 2497 - 2501
(2018/02/06)

Lewis Acid Catalyzed Annulation of Cyclopropane Carbaldehydes and Aryl Hydrazines: Construction of Tetrahydropyridazines and Application Toward a One-Pot Synthesis of Hexahydropyrrolo[1,2- b]pyridazines
In this report, a facile synthesis of tetrahydropyridazines via a Lewis acid catalyzed annulation reaction of cyclopropane carbaldehydes and aryl hydrazines has been demonstrated. Moreover, the generated tetrahydropyridazine further participated in a cycloaddition reaction with donor-acceptor cyclopropanes to furnish hexahydropyrrolo[1,2-b]pyridazines. We also performed these two steps in one pot in a consecutive manner. In addition, a monodecarboxylation reaction of hexahydropyrrolo[1,2-b]pyridazine was achieved with a good yield.
Dey, Raghunath,Kumar, Pankaj,Banerjee, Prabal
p. 5438 - 5449
(2018/05/28)

Exploitation of Cyclopropane Carbaldehydes to Prins Cyclization: Quick Access to (E)-Hexahydrooxonine and Octahydrocyclopenta[ b]pyran
A single-step TiX4-mediated Prins-type cyclization of cyclopropane carbaldehydes with 3-buten-1-ol for the highly stereoselective construction of relatively strained (E)-hexahydrooxonines is reported. Switching the alcohol to 3-butyn-1-ol prompted a similar route, augmented by another cyclization within a nine-membered ring to afford a bicyclized product (4,4-dihalo-5-aryloctahydrocyclopenta[b]pyran). Easy transformation of the resulting geminal dihalide to a vinyl halide and a ketone further supplemented the substance of this approach.
Kumar, Pankaj,Dey, Raghunath,Banerjee, Prabal
supporting information
p. 5163 - 5166
(2018/09/13)

Gold-Catalyzed [2,3]-Sigmatropic Rearrangement: Reaction of Aryl Allyl Alcohols with Diazo Compounds
A gold-catalyzed [2,3]-sigmatropic rearrangement reaction has been developed. The intermolecular rearrangement occurs between in situ generated donor-acceptor gold-carbenes and cinnamyl alcohols via tandem oxonium ylide formation. The desired rearranged product has been accomplished selectively over more conventional O-H insertion, cyclopropanation, cycloaddition, and C-H functionalization products under mild, open-air conditions. The scope of the work has been illustrated by synthesizing a new class of substrates that can be used for constructing complex molecular targets.
Rao, Santhosh,Prabhu, Kandikere Ramaiah
supporting information
p. 846 - 849
(2017/02/26)

Bu 4 N + -Controlled Addition and Olefination with Ethyl 2-(Trimethylsilyl)acetate via Silicon Activation
Catalytic Bu 4 NOAc as silicon activator of ethyl 2-(trimethylsilyl)acetate, in THF, was utilized for the synthesis of β-hydroxy esters, whereas employing catalytic Bu 4 NOTMS gave α,β-unsaturated esters. The established reaction conditions were applicable to a diverse range of aromatic, heteroaromatic, aliphatic aldehydes and ketones. Reactions were achieved at room temperature without taking any of the specialized precautions that are in place for other organometallics. A stepwise olefination pathway via silylated β-hydroxy esters with subsequent elimination to form the α,β-unsaturated ester has been demonstrated. The key to selective product formation lies in use of the weaker acetate activator which suppresses subsequent elimination whereas stronger TMSO - activator (and base) facilitates both addition and elimination steps. The use of tetrabutyl ammonium salts for both acetate and trimethylsilyloxide activators provide enhanced silicon activation when compared to their inorganic cation counterparts.
Das, Manas,Manvar, Atul,Fox, Ian,Roberts, Dilwyn J.,O'Shea, Donal F.
supporting information
p. 2401 - 2406
(2017/09/30)

Bioactivity and structure-activity relationship of cinnamic acid esters and their derivatives as potential antifungal agents for plant protection
A series of cinnamic acid esters and their derivatives were synthesized and evaluated for antifungal activities in vitro against four plant pathogenic fungi by using the mycelium growth rate method. Structure-activity relationship was derived also. Almost all of the compounds showed some inhibition activity on each of the fungi at 0.5 mM. Eight compounds showed the higher average activity with average EC50 values of 17.4-28.6 μg/mL for the fungi than kresoxim-methyl, a commercial fungicide standard, and ten compounds were much more active than commercial fungicide standards carbendazim against P. grisea or kresoxim-methyl against both P. grisea and Valsa Mali. Compounds C1 and C2 showed the higher activity with average EC50 values of 17.4 and 18.5 μg/mL and great potential for development of new plant antifungal agents. The structure-activity relationship analysis showed that both the substitution pattern of the phenyl ring and the alkyl group in the alcohol moiety significantly influences the activity. There exists complexly comprehensive effect between the substituents on the phenyl ring and the alkyl group in the alcohol moiety on the activity. Thus, cinnamic acid esters showed great potential the development of new antifungal agents for plant protection due to high activity, natural compounds or natural compound framework, simple structure, easy preparation, low-cost and environmentally friendly.
Zhou, Kun,Chen, Dongdong,Li, Bin,Zhang, Bingyu,Miao, Fang,Zhou, Le
(2017/04/26)

Efficient synthesis of functionalized olefins by Wittig reaction using Amberlite resin as a mild base
A convenient procedure for the synthesis of olefins by the reaction of stabilized, semistabilized, and nonstabilized phosphorous ylides with various aldehydes or ketone using Amberlite resin as a mild base is described. Our developed method offers facile and racemization-free synthesis of α,β-unsaturated amino esters and chiral allylic amine. The developed methodology offers mild reaction conditions, high efficiency, and facile isolation of the final products, a practical alternative to known procedures.
Valkute, Tushar R.,Aratikatla, Eswar K.,Bhattacharya, Asish K.
p. 581 - 589
(2017/03/15)

Preparation method of neoflavonoids
The invention relates to the field of chemical synthesis, in particular to a preparation method of neoflavonoids. The preparation method is characterized by comprising the following steps of using substituted benzaldehyde as an initial raw material to be reacted with malonic acid to generate a substituted phenylacrylic acid compound; performing an addition reaction, an elimination reaction and the like on the substituted phenylacrylic acid compound, or performing acetylation so as to protect a phenolic hydroxyl group, then performing a bromination reaction and the elimination reaction so as to synthesize the substituted phenylpropiolic acid compound ; and using montmorillonite K-10 after being acidulated by sulfuric acid as a catalyst, enabling the substituted phenylpropiolic acid compound and a phenolic compound to perform a heating reaction so as to generate the neoflavonoids. Compared with the prior art, the preparation method of the neoflavonoids, disclosed by the invention, has the characteristics that raw materials are cheap, and easy to obtain, the operation is simple, the catalyst can be recovered for use, and the method is environmentally-friendly, the post-treatment is simple, and the production cost is low, and the method has a high popularization and application value.
-
(2017/04/26)

A 3,4-dimethoxy-method for preparation of propionic acid (by machine translation)
The invention belongs to the technical field of chemical synthesis, in particular relates to a key intermediate donepezil hydrochloride 3,4-dimethoxy-method for preparation of propionic acid. The method comprises the following steps: to 3,4-dimethoxy-benzaldehyde as a raw material, sodium in ethanol and ethyl acetate under the action of the reaction, the intermediate 3,4-di-methoxy cinnamic acid ethyl ester; 3,4-di-methoxy cinnamic acid ethyl ester hydrolysis under alkaline conditions after the, re-hydrogenation reduction to obtain 3,4-dimethoxy-propionic acid. The preparation method of this invention has is friendly to the environment, the product has high purity, high yield, low cost of raw materials, and the like. (by machine translation)
-
Paragraph 0005; 0024

(2016/11/14)

Solvent-free, one-pot synthesis of α,β-unsaturated esters in the presence of a C3-symmetric arsine
An efficient synthesis of α, β-unsaturated esters is achieved via a one-pot reaction in the presence of a C3-symmetric arsine. The key advantages are the short reaction time, simple workup, mild reaction conditions, and high yields.
Wang, Changqing,Yang, Liu,Zhou, Rong,Mei, Guangquan
supporting information
p. 1074 - 1079
(2016/07/16)

Design and synthesis of a series of serine derivatives as small molecule inhibitors of the SARS coronavirus 3CL protease
Synthesis of serine derivatives having the essential functional groups for the inhibitor of SARS 3CL protease and evaluation of their inhibitory activities using SARS 3CL R188I mutant protease are described. The lead compounds, functionalized serine derivatives, were designed based on the tetrapeptide aldehyde and Bai's cinnamoly inhibitor, and additionally performed with simulation on GOLD softwear. Structure activity relationship studies of the candidate compounds were given reasonable inhibitors ent-3 and ent-7k against SARS 3CL R188I mutant protease. These inhibitors showed protease selectivity and no cytotoxicity.
Konno, Hiroyuki,Wakabayashi, Masaki,Takanuma, Daiki,Saito, Yota,Akaji, Kenichi
supporting information
p. 1241 - 1254
(2016/03/01)

Ethyl cinnamate derivatives as promising high-efficient acaricides against Psoroptes cuniculi: Synthesis, bioactivity and structure-activity relationship
This paper reported the synthesis, structure-activity relationship (SAR) and acaricidal activity in vitro against Psoroptes cuniculi, a mange mite, of 25 ethyl cinnamate derivatives. All target compounds were synthesized and elucidated by means of MS, 1H- and 13C-NMR analysis. The results showed that 24 out of 25 tested compounds at 1.0 mg/mL demonstrated acaricidal activity in varying degrees. Among them, 6, 15, 26, 27 and 30 showed significant activity with median lethal concentration values (LC50) of 89.3, 119.0, 39.2, 29.8 and 41.2 μg/mL, respectively, which were 2.1- to 8.3-fold the activity of ivermectin (LC50=247.4 μg/mL), a standard drug in the treatment of Psoroptes cuniculi. Compared with ivermectin, with a median lethal time value (LT50) of 8.9 h, 27 and 30 showed smaller LTM50 values of 7.9 and 1.3 h, respectively, whereas 6, 15 and 26 showed slightly larger LT50 values of 10.6, 11.0 and 10.4 h at 4.5 μmol/mL. SARs showed that the presence of o-NO2 or m-NO2 on the benzene ring significantly improved the activity, whereas the introduction of a hydroxy, methoxy, acetoxy, methylenedioxy, bromo or chloro group reduced the activity. (E)-Cinnamates were more effective than their (Z)-isomer. Nevertheless, the carbon-carbon double bond in the acrylic ester moiety was proven not to be essential to improve the activity of cinnamic acid esters. Thus, the results strongly indicate that cinnamate derivatives, especially their dihydro derivatives, should be promising candidates or lead compounds for the development of novel acaricides for the effective control of animal or human acariasis.
Zhang, Bingyu,Lv, Chao,Li, Weibo,Cui, Zhiming,Chen, Dongdong,Cao, Fangjun,Miao, Fang,Zhou, Le
p. 255 - 262
(2015/04/22)

Divergent Gold(I)-Catalyzed Skeletal Rearrangements of 1,7-Enynes
The gold(I) complex catalyzed cycloisomerization and skeletal rearrangement of 1,n-enynes (n=5-7) is a powerful methodology for the efficient synthesis of complex molecular architectures. In contrast to 1,6-enynes, readily accessible homologous 1,7-enynes are largely unexplored in such transformations. Here, the divergent skeletal rearrangement of all-carbon 1,7-enynes by catalysis with a cationic gold(I) complex is reported. Depending on electronic and steric factors, differently substituted 1,7-enynes react via different carbocations formed from a common gold carbene intermediate to yield on the one hand novel exocyclic allenes and on the other hand tricyclic hexahydro-anthracenes through a novel dehydrogenative Diels-Alder reaction. Two birds with a gold-stone! Divergent gold(I) catalysis unraveled a novel cycloisomerization and a dehydrogenative Diels-Alder reaction of 1,7-enynes.
Mei?, Rebecca,Kumar, Kamal,Waldmann, Herbert
supporting information
p. 13526 - 13530
(2015/09/22)

Simple, copper(I)-catalyzed oxidation of benzylic/allylic alcohols to carbonyl compounds: Synthesis of functionalized cinnamates in one pot
An environmentally benign [Cu(I)]-catalyzed oxidation of activated (benzylic/allylic) alcohols to the corresponding carbonyl compounds is presented. Interestingly, the reaction was also compatible with benzylic alcohols containing ortho-bromo substituents on the aromatic ring without competing with the expected intermolecular Buchwald coupling. Significantly, the catalytic system enables the synthesis of cinnamate-esters in a sequential domino one-pot fashion via oxidation followed by Wittig-Horner protocol. Copyright
Reddy, Alavala Gopi Krishna,Mahendar, Lodi,Satyanarayana, Gedu
p. 2076 - 2087
(2014/07/07)

Improved synthesis of natural ester sintenin and its analogues via Wittig reaction
The synthesis of a cytotoxic natural ester sintenin (7a) and twenty eight of its analogues including nitrogen-containing heterocyclic indole moiety (7b-7t), saturated (10a-10d) and unsaturated (10e-10h) amides were carried out by convenient route via one-pot Wittig reaction in aqueous medium with improved yield. A systematic structure activity relationship of sintenin ester was designed by chemically modified derivatives in order to get better cytotoxicity.
Sharma, Mukul,Rajesh, U. Chinna,Rawat, Diwan S.
p. 1853 - 1860
(2014/01/17)

Inhibitory effects of substituted cinnamic acid esters on mushroom tyrosinase
A series of substituted cinnamic acid esters were synthesized and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were evaluated. Compound 8 was found to be the most potent inhibitor with IC 50 value of 5.60μM. Preliminary structure activity relationships (SARs) were concluded. The inhibition kinetics analyzed by Lineweaver-Burk plots revealed that compound 8 was anti-competitive inhibitor.
Zhang, Zhenghua,Liu, Jinbing,Wu, Fengyan,Zhao, Liangzhong
p. 529 - 534
(2013/07/26)

Synthesis of substituted nitroolefins: A copper catalyzed nitrodecarboxylation of unsaturated carboxylic acids
A novel, mild and convenient method for the nitrodecarboxylation of substituted cinnamic acid derivatives to their nitroolefins is achieved using a catalytic amount of CuCl (10 mol%) and tert-butyl nitrite (2 equiv.) as a nitrating agent in the presence of air. This reaction provides a useful method for the synthesis of β,β-disubstituted nitroolefin derivatives, which are generally difficult to access from other conventional methods. Additionally, this reaction is selective as the E-isomer of the acid derivatives furnishes the corresponding E-nitroolefins. One more salient feature of the method is, unlike other methods, no metal nitrates or HNO3 are employed for the transformation.
Rokade, Balaji V.,Prabhu, Kandikere Ramaiah
supporting information
p. 6713 - 6716
(2013/10/01)

Synthesis of melicodenines C, D and e
A synthesis of the unusual cyclobutane-quinolinone alkaloids melicodenines C, D and E by intermolecular [2+2] cycloaddition is described.
Holla, Harish,Jenkins, Ian D.,Neve, Juliette E.,Pouwer, Rebecca H.,Pham, Ngoc,Teague, Simon J.,Quinn, Ronald J.
supporting information
p. 7101 - 7103
(2013/01/15)

Synthesis of methoxylated goniothalamin, aza-goniothalamin and γ-pyrones and their in vitro evaluation against human cancer cells
The present work describes the preparation of three novel series of compounds based on the structure of goniothalamin, a natural styryl lactone which has been found to display cytotoxic and antiproliferative activities against a variety of cancer cell lines. A focused library of 29 novel goniothalamin analogues was prepared and evaluated against seven human cancer cell lines. While the γ-pyrones and the aza-goniothalamin analogues were less potent than the lead compound, 2,4-dimethoxy analogue 88 has shown to be more potent in vitro than goniothalamin against all cancer cell lines evaluated. Furthermore, it was more potent than doxorubicin against NCI-ADR/RES, OVCAR-03 and HT-29 while being less toxic to human keratinocytes (HaCat). The 3,5-dimethoxy analogue 90 and 2,4,5-trimethoxy analogue 92 also displayed promising antiproliferative activity when compared to goniothalamin (1). These results provide new elements for the design and synthesis of novel representatives of this family of natural compounds.
Barcelos, Rosimeire Coura,Pastre, Julio Cezar,Caixeta, Vanessa,Vendramini-Costa, Débora Barbosa,De Carvalho, Jo?o Ernesto,Pilli, Ronaldo Aloise
experimental part
p. 3635 - 3651
(2012/07/27)

NOVEL DXR INHIBITORS FOR ANTIMICROBIAL THERAPY
The present invention generally concerns particular methods and compositions for antimicrobial therapy. In particuarl embodiments, the compositions target DXR. In specific embodiments, the compositions are electron-deficient heterocyclic rings.
-
Page/Page column 67; 72

(2011/05/05)

Synthesis of some phenylpropanoid glycosides (PPGs) and their acetylcholinesterase/xanthine oxidase inhibitory activities
In this research, three categories of phenylpropanoid glycosides (PPGs) were designed and synthesized with PPGs isolated from Rhodiola rosea L. as lead compounds. Their inhibitory abilities toward acetylcholinesterase (AChE) and xanthine oxidase (XOD) were also tested. Some of the synthetic PPGs exhibited excellent enzyme inhibitory abilities.
Li, Xiao-Dong,Kang, Shuai-Tao,Li, Guo-Yu,Li, Xian,Wang, Jin-Hui
experimental part
p. 3580 - 3596
(2011/07/07)

Inhibitory effects of caffeic acid ester analogues on free radicals and human liver microsome CYP1A2 activities
Ethyl caffeate (EC), octyl caffeate(OC), benzyl caffeate(BC) and phenethyl caffeate(PC) were synthesized and evaluated for scavenging of superoxide anion, nitric oxide radical and 1,1-diphenyl-1-picrylhydrazyl radical(DPPH). Antioxidant activity was inves
Jaikang, Churdsak,Chaiyasut, Chaiyavat,Narongchai, Paitoon,Niwatananun, Kanokporn,Narongchai, Siripun,Kusirisin, Winthana
p. 99 - 105
(2013/01/10)

Synthesis, biological evaluation, and structure-activity relationship study of novel cytotoxic aza-caffeic acid derivatives
Three series of aza-caffeic acid derivatives with different linkers were designed and synthesized. Each of the synthesized derivatives was then used in cytotoxicity screening on either 8 or 12 human cancer cell lines. The structure-activity relationships on three structural regions A, B, and C are analyzed in detail, indicating that a nine bond linker B, containing a piperazine unit, is the most favorable linker leading to the generation of molecules with potent cytotoxicities. Compound (E)-1-(4-(3,4-dichlorobenzyl) piperazin-1-yl)-3-(4-(4-ethoxybenzyloxy)-3,5-dimethoxyphenyl)prop-2-en-1-one (80) exhibited the most significant and selective cytotoxicity to KB, BEL7404, K562, and Eca109 cell lines, with IC50 values of 0.2, 2.0, 1.7, and 1.1 μM, respectively, stronger than that seen for caffeic acid phenethyl ester (CAPE) and cisplatin (CDDP). Flow cytometric and western blot analysis indicate that compound 80 plays a role in mitochondria-dependent apoptosis activity by suppressing K562 cell proliferation in a concentration- and time-dependent manner.
Zou, Hongbin,Wu, Hao,Zhang, Xiangnan,Zhao, Yu,St?ckigt, Joachim,Lou, Yijia,Yu, Yongping
scheme or table
p. 6351 - 6359
(2010/10/19)

Coordination chemistry based approach to lipophilic inhibitors of 1-deoxy-D-xylulose-5-phosphate reductoisomerase
1-Deoxy-D-xylulose-5-phosphate reductoisomerase (DXR) in the non-mevalonate pathway found in most bacteria is a validated anti-infective drug target. Fosmidomycin, a potent DXR inhibitor, is active against Gram-negative bacteria. A coordination chemistry and structure based approach was used to discover a novel, lipophilic DXR inhibitor with an IC50 of 1.4 μM. It exhibited a broad spectrum of activity against Gram-negative and -positive bacteria with minimal inhibition concentrations of 20-100 μM (or 3.7-19 μg/mL).
Deng, Lisheng,Sundriyal, Sandeep,Rubio, Valentina,Shi, Zheng-Zheng,Song, Yongcheng
supporting information; experimental part
p. 6539 - 6542
(2010/04/04)

A concise enantioselective synthesis of 1-[(S)-3-(dimethylamino)-3,4-dihydro-6,7-dimethoxyquinolin-1(2H)-yl]propan-1-one, (S)-903
A concise enantioselective synthesis of (S)-903, an inotropic agent, is described in nine linear steps and 95% ee based on asymmetric dihydroxylation of cinnamate ester and Co-catalyzed multifunctional reduction of several functional groups leading to the
Jagdale, Arun R.,Reddy, R. Santhosh,Sudalai, Arumugam
experimental part
p. 335 - 339
(2009/09/05)

Ionic liquid promoted selective debromination of α-bromoketones under microwave irradiation
The debromination of α-bromoketones with an easily accessible ionic liquid, 1-methyl-3-pentylimidazolium tetrafluoroborate, [pmIm]BF4 under microwave irradiation has been investigated. By controlling the reaction time gem-α-dibromoketones are selectively debrominated to either monobromo or debromoketones. The α-monobromo- and α-monoiodoketones are dehalogenated while the corresponding chloroketones remain inert. The activated vic-bromoacetates are converted to the corresponding (E)-alkenes by the same procedure. These reactions do not require any organic solvent, any metal or any conventional reducing agent. The ionic liquid works here as catalyst as well as reaction medium and is recycled without any appreciable loss of its catalytic efficiency.
Ranu, Brindaban C.,Chattopadhyay, Kalicharan,Jana, Ranjan
p. 155 - 159
(2007/10/03)

Palladium-catalyzed cross-coupling reactions in one-pot multicatalytic processes
Palladium-catalyzed cross-coupling reactions have been investigated in multicatalytic processes to synthesize disubstituted alkenes and alkanes from carbonyl derivatives. The use of copper-catalyzed methylenation reactions is the key starting reaction to produce terminal alkenes which are not isolated, but submitted to further structure elongation. Not only is the isolation of the alkene intermediate unnecessary, but also the copper catalyst is a beneficial cocatalyst in the palladium-catalyzed cross-coupling reactions. The desired products are thus typically obtained in higher yields using this one-pot approach. We have used these processes to synthesize hydroxylated (E)-stilbenoids, which are known chemopreventive and chemotherapeutic agents, odorant-substituted indanes, and non-natural amino acids, such as homophenylalanine.
Lebel, Helene,Ladjel, Chehla,Brethous, Lise
p. 13321 - 13326
(2008/09/17)

Synthesis of phenylalanine analogs
A straight forward synthesis of phenylalanine analogs is described. Cerium ammonium nitrate (CAN) mediated addition of azide to cinnamicester, followed by reaction with sodium acetate aff orded the α-azidocinnamate in moderate yield. Hydrogenation of α-azidocinnamate, followed by BOC, CBZ or Fmoc protection gave phenylalanine analogs. A new approach for synthesizing racemic p-boronophenylalanine analog was also explored.
Chang, Meng-Yang,Lin, Chun-Yu,Sun, Pei-Pei
p. 1061 - 1067
(2007/10/03)

Two variations of solvent-reduced wittig olefination reactions - Comparison of solventless wittig reactions to wittig reactions under ultrasonication with minimal work-up
Stabilized and semi-stabilized phosphoranes can be subjected to solventless Wittig reactions with carbaldehydes. Simple heating of a mixture of added components at 100°C in an electric oven gives the corresponding olefins in good yield. Alternatively, the Wittig reactions can be carried out in a biphasic medium under ultrasonication. In this case, the Wittig products can be isolated by simple evaporation of the organic phase without additional work-up.
Watanabe, Masataka,Morais, Goreti Ribeiro,Mataka, Shuntaro,Ideta, Keiko,Thiemann, Thies
p. 909 - 915
(2007/10/03)

A microwave-accelerated esterification of α,β-unsaturated acids with alkyl or aryl carbonochloridate and triethylamine in acetonitrile as a novel esterifying reagent mixture
An efficient synthesis of α,β-unsaturated esters by treatment of the corresponding acids with alkyl or aryl carbonochloridate, triethylamine, and acetonitrile was accomplished for the first time under microwave irradiation for 10 min. The esters 1b-24b were isolated in 71-97% yield.
Pathania, Vinod,Sharma, Anuj,Sinha, Arun K.
p. 811 - 816
(2007/10/03)

Solvent-free Wittig olefination with stabilized phosphoranes - Scope and limitations
Neat mixtures of arene/hetarenecarbaldehydes, alkanals as well as alkenals with alkyl (triphenylphosphoranylidene)acetates react exothermally to furnish the corresponding alkenes. In certain cases, heating has to be provided externally. Reaction times are short and yields are generally very high. Neat mixtures of ketones and alkyl (triphenylphosphoranylidene)acetates react preferentially under microwave irradiation. The better stabilized phosphoranes do not react in the solid state with aldehydes or ketones under conventional heating, but necessitate microwave irradiation, although not all of the phosphoranes have been found to be stable under microwave irradiation at 500 W (2450 MHz).
Thiemann, Thies,Watanabe, Masataka,Tanaka, Yasuko,Mataka, Shuntaro
p. 578 - 584
(2007/10/03)

Pd(OAc)2-Catalyzed Oxidative Coupling Reaction of Benzenes with Olefins in the Presence of Molybdovanadophosphoric Acid under Atmospheric Dioxygen and Air
The direct oxidative coupling reaction of benzenes with alkenes bearing an electron-withdrawing group was successfully achieved by the use of Pd(OAc) 2/molybdovanadophosphoric acid (HPMoV) as the key catalyst under O2 or air atmosphere. Thus, the reaction of benzene with ethyl acrylate under air (1 atm) assisted by Pd(OAc)2/HPMoV afforded ethyl cinnamate as a major product in satisfactory yield (74%). This catalytic system could be extended to the coupling reactions between various substituted benzenes and alkenes through the direct aromatic C-H bond activation. In the reaction of benzene with ethyl acrylate under O2 (1 atm), the best turn-over number (TON) of Pd(OAc)2 reached was 121. This reaction provides a green route to cinnamate derivatives, which are important precursors of a variety of pharmaceuticals.
Tani, Masayuki,Sakaguchi, Satoshi,Ishii, Yasutaka
p. 1221 - 1226
(2007/10/03)

1,8-Diazabicyclo[5.4.0]undec-7-ene: A remarkable base in the debromination of 4- or 5-substituted N-benzyl α-bromo-α-p- toluenesulfonylglutarimide
Debromination of N-benzyl 4- or 5-substituted α-bromo-α-p- toluenesulfonylglutarimides is achieved with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) to give the N-benzyl 4- or 5-substituted α-p- toluenesulfonylglutarimides. The DBU/THF system is applied to a new methodology for the synthesis of bicyclic glutarimide skeleton in moderate yields.
Chang, Meng-Yang,Lin, John Yi-Chung,Chen, Shui-Tein,Chang, Nein-Chen
p. 1015 - 1024
(2007/10/03)

Radical cyclisation based approach to lignans. Synthesis of 4-arylmethyldihydrofuran-2-ones
Bromoacetalisation of the cinnamyl alcohols 7a-d, obtained from the corresponding benzaldehydes, generated the bromoacetals 10a-d. The 5-exo trig radical cyclisation of the bromoacetals 10a-d followed by one step hydrolysis-oxidation of the resulting cyclic acetals 11a-d furnished the title compounds 6a-d, respectively, well-established intermediates of a variety of lignans.
Srikrishna,Danieldoss
p. 2357 - 2364
(2007/10/03)

An efficient synthesis of neoflavonoid antioxidants based on Montmorillonite K-10 catalysis
A new approach to synthesis of neoflavonoids, based on a high yielding Montmorillonite K-10 catalyzed lactone ring forming cyclization process, is described. The utility of this methodology is exemplified by its employment in the preparation of the substituted 4-phenylneoflavonoids 1-8. The free radical scavenging properties of these substances were evaluated. The neoflavonoids 1 and 5, which mimic esculetin-type antioxidants, were observed to quench hydrazyl free radicals.
Lee,Tseng,Lee
p. 2247 - 2254
(2007/10/03)

Enolethers and their use as a fungicide
Enolethers and thioenolethers of formula I STR1 are disclosed. The compounds are useful for combatting phytopathogenic fungi.
-
(2008/06/13)

Inhibition of uridine phosphorylase: Synthesis and structure-activity relationships of aryl-substituted 5-benzyluracils and 1-[(2- hydroxyethoxy)methyl]-5-benzyluracils
A series of 1-[(2-hydroxyethoxy)methyl]-5-benzyluracils were synthesized and tested for inhibition of murine liver uridine phosphorylase (UrdPase). Inhibitors of UrdPase are reported to enhance the chemotherapeutic utility of 5-fluoro-2'-deoxyuridine and 5-fluorouracil and to ameliorate zidovudine- induced anemia in animal models. We prepared a series of 5-aryl-substituted analogues of 5-benzylacyclouridine (BAU), a good inhibitor of UrdPase (IC50 of 0.46 μM), to develop a compound with enhanced potency and improved pharmacokinetics. The first phase of structure-activity relationship studies on a series of 32 aryl-substituted 5-benzyluracils found several 5-(3- alkoxybenzyl) analogues of 5-benzyluracil with enhanced potency. The acyclovir side chain, the (2-hydroxyethoxy)methyl group, was substituted on the more potent aryl-substituted 5-benzyluracils. The two most potent compounds, 10y (3-propoxy) and 10dd (3-sec-butoxy), were inhibitors of UrdPase with IC50s of 0.047 and 0.027 μM, respectively. Six compounds were tested in vivo for effects on steady-state concentrations of circulating uridine in rats. Plasma uridine levels were elevated 3-9-fold by compound levels that ranged from 8 to 50 μM.
Orr,Musso,Boswell,Kelley,Joyner,Davis,Baccanari
p. 3850 - 3856
(2007/10/02)