101-97-3Relevant articles and documents
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Ogata et al.
, p. 794 (1969)
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Photocatalytic acyl azolium-promoted alkoxycarbonylation of trifluoroborates
Scheidt, Karl A.,Zhu, Joshua L.
, (2021)
Despite recent advancements in the selective generation and coupling of organic radical species, the alkoxycarbonyl radical remains underexplored relative to other carbon-containing radical species. Drawing inspiration from new strategies for generating acyl radical equivalents utilizing dual N-heterocyclic carbene catalysis and photocatalysis, we have prepared dimethylimidazolium esters that can function as an alkoxycarbonyl radical surrogate under photocatalytic conditions. We demonstrate the synthetic utility of these azolium-based partners through the preparation of esters arising from the coupling of this radical surrogate with an oxidatively generated alkyl radical.
Chemoenzymatic synthesis and antileukemic activity of novel C9- and C14-functionalized parthenolide analogs
Tyagi, Vikas,Alwaseem, Hanan,O'Dwyer, Kristen M.,Ponder, Jessica,Li, Qi Ying,Jordan, Craig T.,Fasan, Rudi
, p. 3876 - 3886 (2016)
Parthenolide is a naturally occurring terpene with promising anticancer properties, particularly in the context of acute myeloid leukemia (AML). Optimization of this natural product has been challenged by limited opportunities for the late-stage functionalization of this molecule without affecting the pharmacologically important α-methylene-γ-lactone moiety. Here, we report the further development and application of a chemoenzymatic strategy to afford a series of new analogs of parthenolide functionalized at the aliphatic positions C9 and C14. Several of these compounds were determined to be able to kill leukemia cells and patient-derived primary AML specimens with improved activity compared to parthenolide, exhibiting LC50values in the low micromolar range. These studies demonstrate that different O–H functionalization chemistries can be applied to elaborate the parthenolide scaffold and that modifications at the C9 or C14 position can effectively enhance the antileukemic properties of this natural product. The C9-functionalized analogs 22a and 25b were identified as the most interesting compounds in terms of antileukemic potency and selectivity toward AML versus healthy blood cells.
Trimethylamine N-oxide: A novel reagent for the promotion of the retro- aldol reaction of R106-1 (LY295337)
Rodriguez,Zweifel
, p. 4301 - 4304 (1996)
The retro-aldol reaction of R106-1 (LY295337), 1 using trimethylamine N- oxide (TNO) facilitates the removal of the tertiary hydroxy group generating R106-sarcosine, 2 a key synthetic intermediate. The reagent is highly reproducible and provides high yields with no major side products. A side by side comparison of TNO vs. traditional bases is described.
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Brown,Rogic
, p. 4304 (1969)
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Structure activity relationship of organic alcohol and esters for antidepressant-like activity
Perveen, Shahnaz,Yasmeen, Arfa,Khan, Muhammad Aitmaud,Dar, Ahsana,Jafri, Rehana,Ahmed, Amir
, p. 14 - 17 (2010)
The synthesized compounds 1-7 were evaluated for their antidepressant activity, among which 2-phenylethyl alcohol 1 and isoamyl phenylacetate 3 showed 43 % and 37 % reduction in immobility time in mice using forced swim test, thereby, displaying antidepressant-like activity. Compound 1 and 3 were equipotent and both these compounds were 2x effective than the standard drug phenelzine. Considering other esters it appears that a decrease in alkyl chain length or addition of either NO2 or OH groups to the phenyl ring caused a marked decline in the antidepressant-like activity.
Pd-catalyzed synthesis of arylacetic acid derivatives from boronic acids
Goossen
, p. 669 - 670 (2001)
A palladium(0)-catalyzed cross-coupling reaction between arylboronic acids or esters and α-bromoacetic acid derivatives is described which allows the synthesis of various functionalized arylacetic acid derivatives under mild conditions.
Synthesis, Structural Analysis, and Screening of Some Novel 5-Substituted Aryl/Aralkyl-1,3,4-Oxadiazol-2-Yl 4-(Morpholin-4-Ylsulfonyl)Benzyl Sulfides As Potential Antibacterial Agents
Aziz-Ur-Rehman,Gul, Samreen,Abbasi, Muhammad Athar,Nafeesa, Khadija,Akhtar, Muhammad Nadeem,Ahmad, Irshad,Afzal, Saira
, p. 1045 - 1055 (2015)
A series of new 5-substituted aryl/aralkyl-1,3,4-oxadiazol-2-yl 4-(morpholin-4-ylsulfonyl)benzyl sulfides 6a-k were synthesized by converting multifarious aryl/aralkyl organic acids 1a-k successively into corresponding esters 2a-k, hydrazides 3a-k, and 5-substituted aryl/aralkyl-1,3,4-oxadiazole-2-thiols 4a-k. Finally, the target compounds, 6a-k were prepared by stirring 5-substituted-1,3,4-oxadiazole-2-thiols with 4-(4-(bromomethyl)phenylsulfonyl) morpholine (5) in the presence of N,N-dimethylformamide (DMF) and sodium hydride (NaH). The structures of the newly synthesized compounds were elucidated by spectroscopic techniques. In addition, the antibacterial activity of all the synthesized compounds was investigated in vitro against Gram-positive and Gram-negative bacteria by using ciprofloxacin as reference standard drug and the results showed that some of the tested compounds possessed good antibacterial activity.
Palladium-Catalyzed C(sp3)-C(sp2) Cross-Couplings of O -(α-Bromoacyl) Cyanohydrins with Boronic Acids: An Entry to Enantioenriched N -Acylated β-Amino Alcohols
Hertzberg, Robin,Dinér, Peter,Moberg, Christina
, p. 3175 - 3182 (2016)
Suzuki-type cross-coupling of enantiomerically enriched O-(α-bromoacyl) cyanohydrins with aromatic boronic acids substituted with electron-withdrawing or electron-donating groups gave the expected coupling products in high yields without racemization. These substrates exhibit higher reactivities than analogous substrates lacking the nitrile function, probably as a result of π-coordination of the nitrile to palladium. Reduction of the nitrile group of the products, with accompanying intramolecular acyl transfer, provides access to biologically interesting N-acylated β-amino alcohols.
Trans-esterification in dry media using ferric perchlorate adsorbed on silica gel
Parmar, Anupama,Goyal, Rita,Kumar, Baldev,Kumar, Harish
, p. 139 - 143 (1999)
Adsorption of Fe(ClO4)3(H2O)6 onto chromatographic grade silica gel in the presence of ethyl acetate (to be used for trans-esterification) produces a supported reagent, Fe(ClO4)3(EtOAc)6/SiO2. This reagent, has been found effective for the rapid and high yield of esters via trans- esterification on grinding in the presence of alcohols/carboxylic acids using pestle and mortar in the solid state.
Targeting malaria and leishmaniasis: Synthesis and pharmacological evaluation of novel pyrazole-1,3,4-oxadiazole hybrids. Part II
Verma, Garima,Khan, Mohemmed Faraz,Mohan Nainwal, Lalit,Ishaq, Mohd,Akhter, Mymoona,Bakht, Afroz,Anwer, Tariq,Afrin, Farhat,Islamuddin, Mohammad,Husain, Ibraheem,Alam, Mohammad Mumtaz,Shaquiquzzaman, Mohammad
, (2019)
In continuance with earlier reported work, an extension has been carried out by the same research group. Mulling over the ongoing condition of resistance to existing antimalarial agents, we had reported synthesis and antimalarial activity of certain pyrazole-1,3,4-oxadiazole hybrid compounds. Bearing previous results in mind, our research group ideated to design and synthesize some more derivatives with varied substitutions of acetophenone and hydrazide. Following this, derivatives 5a–r were synthesized and tested for antimalarial efficacy by schizont maturation inhibition assay. Further, depending on the literature support and results of our previous series, certain potent compounds (5f, 5n and 5r) were subjected to Falcipain-2 inhibitory assay. Results obtained for these particular compounds further strengthened our hypothesis. Here, in this series, compound 5f having unsubstituted acetophenone part and a furan moiety linked to oxadiazole ring emerged as the most potent compound and results were found to be comparable to that of the most potent compound (indole bearing) of previous series. Additionally, depending on the available literature, compounds (5a–r) were tested for their antileishmanial potential. Compounds 5a, 5c and 5r demonstrated dose-dependent killing of the promastigotes. Their IC50 values were found to be 33.3 ± 1.68, 40.1 ± 1.0 and 19.0 ± 1.47 μg/mL respectively. These compounds (5a, 5c and 5r) also had effects on amastigote infectivity with IC50 of 44.2 ± 2.72, 66.8 ± 2.05 and 73.1 ± 1.69 μg/mL respectively. Further target validation was done using molecular docking studies. Acute oral toxicity studies for most active compounds were also performed.
Selective transesterification of aliphatic acids in the presence of aromatic acids using silica gel supported NaHSO4 catalyst
Das,Venkataiah
, p. 1671 - 1672 (2000)
Acidolysis of EtOAc in the presence of silica gel supported NaHSO4 catalyst has been applied for the protection of aliphatic nonconjugated carboxylic acids through the formation of esters.
Kumulierte Ylide; XIII1: Diethoxyvinylidentriphenylphosphoran als Reagenz zur Herstellung von Carbonsaeure-ethylestern in aprotischen Loesungmitteln
Bestmann, Hans Juergen,Roth, Kurt
, p. 998 - 999 (1981)
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Selective synthesis of arylacetic acid esters from ethyl acetoacetate and aryl halides in the presence of copper(II) on 4 ? molecular sieves
Zsolczai, Dávid,Németh, János,Hell, Zoltán
, p. 6389 - 6392 (2015)
A heterogeneous catalyst, copper(II) on 4 ? molecular sieves has successfully been used in the arylation of ethyl acetoacetate, selectively forming arylacetic esters in high yields. The air stable and easily handled catalyst can be simply filtered off during purification thus avoiding significant metal contamination of the product.
Synthesis and anti-inflammatory activity of hydrazide-hydrazones bearing anacardic acid and 1,2,3-triazole ring based hybrids
Kumar Reddy,Kathale, Niren E
, p. 2930 - 2936 (2017)
A novel series of hydrazide-hydrazone derivatives 39-50, linked with anacardic acid motif and 1,2,3-triazole ring were synthesized by reacting 4-(1-(2-methoxy-6-pentadecylbenzyl)-1H-1, 2, 3-triazol-4-yl)benzaldehyde with 2-phenyl-acetohydrazides and benzohydrazides. The structures of the newly synthesized hydrazide-hydrazone derivatives 39-50 were confirmed by 1H NMR, MS and IR spectroscopic tools. These compounds were also evaluated for their anti-inflammatory activity by carrageenan paw edema method.
Palladium supported on triphenylphosphine functionalized porous organic polymer: A highly active and recyclable catalyst for alkoxycarbonylation of aryl iodides
Lei, Yizhu,Wu, Linjuan,Zhang, Xuefeng,Mei, Hui,Gu, Yanlong,Li, Guangxing
, p. 164 - 169 (2015)
An efficient method for the alkoxycarbonylation of aryl iodides using palladium supported on triphenylphosphine functionalized porous organic polymer (Pd@KAPs(Ph-PPh3)) as the catalyst is reported. Under balloon pressure of CO, various aryl iodides on carbonylation with alcohols and phenols give the corresponding products in moderate to excellent yields (74-96%). The catalyst can be easily separated by simple filtration process and recycled up to ten times without significant decrease in activity. The salient features of this protocol are the simplicity in handling of the catalyst, low CO pressure, negligible palladium leaching and good catalyst recyclability.
Oxadiazole mannich bases: Synthesis and antimycobacterial activity
Ali, Mohamed Ashraf,Shaharyar, Mohammad
, p. 3314 - 3316 (2007)
A series of oxadiazole mannich bases were synthesized by reacting oxadiazole derivatives, dapsone and appropriate aldehyde in the presence of methanol. The synthesized compounds were evaluated for antimycobacterial activity against M. tuberculosis H37Rv and INH resistant M. tuberculosis. Among the synthesized compounds, compound (4) 3-{2-furyl[4-(4-{2-furyl[5-(2-naphthyloxymethyl)-2-thioxo-2,3-dihydro-1,3,4-oxadiazol-3-yl]methylamino}phenylsulfonyl)anilino]methyl}-5-(2-naphthyloxymethyl)-2,3-dihydro-1,3,4-oxadiazole-2-thione was found to be the most promising compound active against M. tuberculosis H37Rv and isoniazid (INH) resistant M. tuberculosis with Minimum inhibitory concentration (MIC) 0.1 μM & 1.10 μM respectively.
Intermetallic coinage metal-catalyzed functionalization of alkanes with ethyl diazoacetate: Gold as a ligand
Fuentes, M. ángeles,Rodríguez-Castillo, María,Monge, Miguel,Olmos, M. Elena,López-De-Luzuriaga, Jose M.,Caballero, Ana,Pérez, Pedro J.
, p. 146 - 149 (2011)
The complexes [Au2M2(C6F5) 4(NCMe)2]n (M = Cu, 1; M = Ag, 2) have been tested as catalysts for the functionalization of alkanes by the carbene insertion methodology, using ethyl diazoacetate as the carbene source. Moderate to high conversions have been obtained. The observed selectivities seem to favor the proposal that the active metal for catalysis is the Cu/Ag center, the Au(C6F5)2 unit acting as a spectator ligand in both cases.
Aromatization and hydrogen-shift of 7-substituted 1,3,5-cycloheptatrienes in the presence of palladium(II) acetate
Saito,Kozaki,Takahashi
, p. 2187 - 2189 (1993)
Reaction of 7-ethoxycarbonyl-1,3,5-cycloheptatriene with palladium(II) acetate afforded 2- and 4-formylbenzoic acid ethyl ester and diethyl maleate via aromatization, and a mixture of position isomers of the cycloheptatriene through hydrogen-shift. The reaction with 7-cyano-1,3,5-cycloheptatriene was also investigated. The reactions are considered to proceed through palladium complexes of the cycloheptatrienes and their norcaradiene isomers.
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Izawa et al.
, p. 211,212,214,215 (1972)
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Synthese electrochemique d'esters arylacetique et arylpropionique via des complexes du nickel
Folest, J. C.,Perichon, J.,Fauvarque, J. F.,Jutand, A.
, p. 259 - 262 (1988)
Aryl acetic and aryl propionic esters are obtained by an electrochemical process.The ?-arylnickel complex ArNiXL2 (L = PPh3) obtained in the presence of an aromatic halide with THF/HMPT or THF/NMP as solvent reacts with α halide aliphatic esters to give the corresponding aryl-substituted esters.
Copper(I) iodide-catalysed arylation of acetoacetate to yield 2-arylacetic acid esters
Zeevaart, Jacob G.,Parkinson, Christopher J.,de Koning, Charles B.
, p. 3289 - 3293 (2007)
The C-C coupling reaction between ethyl acetoacetate and aryl halides in the presence of CuI is described. The effects of solvent, ligands such as vicinal diamines and amino acids, base and temperature are reported. The arylated acetoacetate ester is deacylated under the reaction conditions resulting in the generation of 2-arylacetic acid esters, constituting a mild alternative to direct arylation of carboxylate esters.
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Bailey,W.J.,Daly,J.J.
, p. 1249 - 1251 (1964)
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Remarkable co-catalysis by copper(I) oxide in the palladium catalyzed cross-coupling of arylboronic acids with ethyl bromoacetate
Liu, Xing-Xin,Deng, Min-Zhi
, p. 622 - 623 (2002)
Copper(I) oxide can effectively co-catalyze the Suzuki type cross-coupling reactions of arylboronic acids with ethyl bromoacetate. As an alternative protocol for introducing the methylenecarboxy group into functionalized molecules, this reaction occurs in
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Fauvarque,Jutand
, p. C17 (1977)
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A Convenient and Stable Heterogeneous Nickel Catalyst for Hydrodehalogenation of Aryl Halides Using Molecular Hydrogen
Anwar, Muhammad,Beller, Matthias,Dastgir, Sarim,Junge, Kathrin,Leonard, David K.,Ryabchuk, Pavel
, (2022/02/03)
Hydrodehalogenation is an effective strategy for transforming persistent and potentially toxic organohalides into their more benign congeners. Common methods utilize Pd/C or Raney-nickel as catalysts, which are either expensive or have safety concerns. In this study, a nickel-based catalyst supported on titania (Ni-phen@TiO2-800) is used as a safe alternative to pyrophoric Raney-nickel. The catalyst is prepared in a straightforward fashion by deposition of nickel(II)/1,10-phenanthroline on titania, followed by pyrolysis. The catalytic material, which was characterized by SEM, TEM, XRD, and XPS, consists of nickel nanoparticles covered with N-doped carbon layers. By using design of experiments (DoE), this nanostructured catalyst is found to be proficient for the facile and selective hydrodehalogenation of a diverse range of substrates bearing C?I, C?Br, or C?Cl bonds (>30 examples). The practicality of this catalyst system is demonstrated by the dehalogenation of environmentally hazardous and polyhalogenated substrates atrazine, tetrabromobisphenol A, tetrachlorobenzene, and a polybrominated diphenyl ether (PBDE).
Photoinduced Diverse Reactivity of Diazo Compounds with Nitrosoarenes
Roy, Sourav,Kumar, Gourav,Chatterjee, Indranil
, p. 6709 - 6713 (2021/09/08)
A diverse reactivity of diazo compounds with nitrosoarene in an oxygen-transfer process and a formal [2 + 2] cycloaddition is reported. Nitosoarene has been exploited as a mild oxygen source to oxidize an in situ generated carbene intermediate under visible-light irradiation. UV-light-mediated in situ generated ketenes react with nitosoarenes to deliver oxazetidine derivatives. These operationally simple processes exemplify a transition-metal-free and catalyst-free protocol to give structurally diverse α-ketoesters or oxazetidines.
Expedient discovery for novel antifungal leads: 1,3,4-Oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment
Chai, Jianqi,Chen, Min,Jin, Fei,Kong, Xiangyi,Wang, Xiaobin,Xue, Wei,Yang, Chunlong
, (2021/08/03)
Developing novel fungicide candidates are intensively promoted by the rapid emergences of resistant fungi that outbreak on agricultural production. Aiming to discovery novel antifungal leads, a series of 1,3,4-oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment were constructed for evaluating their inhibition effects against phytopathogenic fungi in vitro and in vivo. Systematically structural optimizations generated the bioactive molecule I32 that was identified as a promising inhibitor against Rhizoctonia solani with the in vivo preventative effect of 58.63% at 200 μg/mL. The observations that were captured by scanning electron microscopy and transmission electron microscopy demonstrated that the bioactive molecule I32 could induce the sprawling growth of hyphae, the local shrinkage and rupture on hyphal surfaces, the extreme swelling of vacuoles, the striking distortions on cell walls, and the reduction of mitochondria numbers. The above results provided an indispensable complement for the discovery of antifungal lead bearing a quinazolin-4(3H)-one and 1,3,4-oxadiazole fragment.