- 1,2-Dibutoxyethane-Promoted Oxidative Cleavage of Olefins into Carboxylic Acids Using O2 under Clean Conditions
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Herein, we report the first example of an effective and green approach for the oxidative cleavage of olefins to carboxylic acids using a 1,2-dibutoxyethane/O2 system under clean conditions. This novel oxidation system also has excellent functional-group tolerance and is applicable for large-scale synthesis. The target products were prepared in good to excellent yields by a one-pot sequential transformation without an external initiator, catalyst, and additive.
- Ou, Jinhua,Tan, Hong,He, Saiyu,Wang, Wei,Hu, Bonian,Yu, Gang,Liu, Kaijian
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p. 14974 - 14982
(2021/10/25)
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- Potent arylamide derivatives as dual-target antifungal agents: Design, synthesis, biological evaluation, and molecular docking studies
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Fungal infections have become a serious medical problem due to the high infection rate and the frequent emergence of drug resistance. Ergosterol is an important structural component of the fungal cell membrane, its synthetases (squalene epoxidase (SE) and 14α-demethylase (CYP51)) are considered as the key points to block the ergosterol synthesis. In this study, we designed a series of dual-target arylamides derivatives based on the analysis of active sites (SE, CYP51). Subsequently, these target compounds were synthesized, and their antifungal activity was evaluated. Most of compounds demonstrate the potent antifungal activity against multiple Candida spp. and A. fum. In particular, the antifungal activities of compounds 10b and 11c are not only superior to positive control drugs, but also have significant inhibitory effects on drug-resistant fungi (C.alb. Strain100, C.alb. Strain103). Therefore, their action mechanism was further studied. Cellular uptake and electron microscopy observation showed that target compounds were able to enter fungal cytoplasmic region through free diffusion, and destroyed cell membrane structure. At the same time, preliminary mechanisms have demonstrated that they can affect the synthesis of ergosterol by inhibiting the activity of dual targets. It is worth noting that they also can exhibit excellent antifungal activity and low toxic side effects in vivo. Their ADMET properties and binding models were established will be useful for further lead optimization.
- An, Yunfei,Dong, Yue,Han, Jun,Liu, Min,Liu, Xinyong,Sun, Bin
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- Bis(methoxypropyl) ether-promoted oxidation of aromatic alcohols into aromatic carboxylic acids and aromatic ketones with O2 under metal- and base-free conditions
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We describe an eco-friendly, practical and operationally simple procedure for the bis(methoxypropyl) ether-promoted oxidation of aromatic alcohols into aromatic carboxylic acids and aromatic ketones with atmospheric dioxygen as the sole oxidant. This chemical process is clean with high conversion and good selectivity, and an external initiator, catalyst, additive and base are not required. The virtue of this reaction is highlighted by its easily available and economical raw materials and excellent functional group tolerance (acid-, base- and oxidant-labile groups).
- Liu, Kai-Jian,Jiang, Si,Lu, Ling-Hui,Tang, Ling-Li,Tang, Shan-Shan,Tang, Hai-Shan,Tang, Zilong,He, Wei-Min,Xu, Xinhua
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supporting information
p. 3038 - 3043
(2018/07/13)
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- Preparation method of 2,3-dihydro-1,4-benzodioxane-6-carboxylic acid compound
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The invention relates to a preparation method of a 2,3-dihydro-1,4-benzodioxane-6-carboxylic acid compound. The method comprises the following steps: carrying out a ring closing reaction on a raw material 3,4-dihydroxy benzaldehyde and 1,2-dibromoethane under alkaline conditions to obtain an intermediate 2,3-dihydro-1,4-benzodioxane-6-carboxaldehyde, purifying the intermediate, and carrying out an oxidation reaction on the purified intermediate in an aqueous potassium permanganate solution to obtain the 2,3-dihydro-1,4-benzodioxane-6-carboxylic acid compound. The method has the advantages of cheap and easily available raw materials, mild reaction conditions, simple post-treatment process, simple operation, high chemical yield, good application prospect, and suitableness for industrial production.
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Paragraph 0006; 0015; 0016; 0017
(2016/11/21)
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- Direct carboxylation of simple arenes with CO2 through a rhodium-catalyzed C-H bond activation
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Direct carboxylation of simple arenes under atmospheric pressure of CO2 is achieved through a rhodium-catalyzed C-H bond activation without the assistance of a directing group. Various arenes such as benzene, toluene, xylene, electron-rich or electron-deficient benzene derivatives, and heteroaromatics are directly carboxylated with high TONs. This journal is
- Suga, Takuya,Mizuno, Hajime,Takaya, Jun,Iwasawa, Nobuharu
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supporting information
p. 14360 - 14363
(2015/02/19)
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- Synthesis, structure, and urease inhibitory activities of three binuclear copper(II) complexes with protocatechuic acid derivative
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Three Cu(II) complexes, [CuII2(L1) 4(L2)2] (1), [CuII 2(L1)4(H2O)2]·HL (2), and [CuII2(L1)
- Sheng, Gui-Hua,Zhou, Quan-Cheng,Sun, Juan,Cheng, Xiao-Shan,Qian, Shao-Song,Zhang, Chun-Yang,You, Zhong-Lu,Zhu, Hai-Liang
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p. 1265 - 1278
(2014/06/10)
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- Effective palladium-catalyzed hydroxycarbonylation of aryl halides with substoichiometric carbon monoxide
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A protocol for the Pd-catalyzed hydroxycarbonylation of aryl iodides, bromides, and chlorides has been developed using only 1-5 mol % of CO, corresponding to a pCO as low as 0.1 bar. Potassium formate is the only stoichiometric reagent, acting as a mildly basic nucleophile and a reservoir of CO. The substoichiometric CO could be delivered to the reaction from an acyl-Pd(II) precatalyst, which provides both the CO and an active catalyst, and thereby obviates the need for handling a toxic gas.
- Korsager, Signe,Taaning, Rolf H.,Skrydstrup, Troels
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supporting information
p. 2891 - 2894
(2013/04/10)
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- N-acylaminophenylcyclopropanes in reaction with nitrous acid generated in situ
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The reaction of N-acylaminophenylcyclopropanes with HNO2 proceeds regioselectively with introduction of an N=O fragment into the three-membered ring and formation of the corresponding Δ2-isoxazolines. For ortho-substituted N-acylaminophenylcyclopropanes side processes were observed, caused by the intramolecular participation of the N-acyl group in conversions of the carbenium ions formed on opening the cyclopropane ring under the action of the nitrosating reagent, and by direct insertion of the modified ortho substituent into the three-membered ring.
- Mochalov,Gazzaeva,Kadzhaeva,Fedotov,Trofimova
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p. 1415 - 1429
(2014/07/21)
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- Application of plant allylpolyalkoxybenzenes in synthesis of antimitotic phenstatin analogues
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Phenstatin and its derivatives with the modified ring A have been synthesized, using plant allylpolyalkoxybenzenes as a starting material. The targeted molecules were evaluated in a phenotypic sea urchin embryo assay for antiproliferative activity. It was found that phenstatin ring A modifications yielded antimitotic compounds. The most effective myristicin derivative 7d (combretastatin A-2 analogue) was determined to be ca. 10 times more potent than phenstatin, displaying antimitotic tubulin-destabilizing activity at the same concentration range as combretastatins. In contrast to combretastatins, 7d featured the steric stability with potential for further design as anticancer agent.
- Titov, Ilia Y.,Sagamanova, Irina K.,Gritsenko, Roman T.,Karmanova, Irina B.,Atamanenko, Olga P.,Semenova, Marina N.,Semenov, Victor V.
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supporting information; experimental part
p. 1578 - 1581
(2011/05/04)
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- Copper-catalyzed aerobic oxidative synthesis of aromatic carboxylic acids
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A simple, practical and efficient copper-catalyzed method for synthesis of aromatic carboxylic acids has been developed. The protocol uses inexpensive CuI/l-proline as the catalyst/ligand, and readily available aryl halides and malononitrile as the starting materials, and the corresponding aromatic carboxylic acids were obtained in moderate to good yields. The method is of tolerance towards functional groups in the substrates.
- Yang, Daoshan,Yang, Haijun,Fu, Hua
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supporting information; experimental part
p. 2348 - 2350
(2011/03/21)
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- Design, synthesis, structure-activity relationship, and in vivo activity of azabicyclic aryl amides as α7 nicotinic acetylcholine receptor agonists
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A novel set of azabicyclic aryl amides have been identified as potent and selective agonists of the α7 nAChR. A two-pronged approach was taken to improve the potential hERG liability of previously disclosed α7 nAChR agonist, PNU-282,987, while maintaining the compound's other desirable pharmacological properties. The first approach involved further exploration of the aryl carboxylic acid fragment of PNU-282,987, while the second approach focused on modification of the azabicyclic amine portion of PNU-282,987. The best compounds from each series are characterized by rapid brain penetration, good oral bioavailability in rat, and demonstrate in vivo efficacy in a rat P50 auditory sensory gating assay. At least one analog from each series (1h, 1o, 2a, 9a, and 18a) shows an improved hERG safety profile over PNU-282,987.
- Walker, Daniel P.,Wishka, Donn G.,Piotrowski, David W.,Jia, Shaojuan,Reitz, Steven C.,Yates, Karen M.,Myers, Jason K.,Vetman, Tatiana N.,Margolis, Brandon J.,Jacobsen, E. Jon,Acker, Brad A.,Groppi, Vincent E.,Wolfe, Mark L.,Thornburgh, Bruce A.,Tinholt, Paula M.,Cortes-Burgos, Luz A.,Walters, Rodney R.,Hester, Matthew R.,Seest, Eric P.,Dolak, Lester A.,Han, Fusen,Olson, Barbara A.,Fitzgerald, Laura,Staton, Brian A.,Raub, Thomas J.,Hajos, Mihaly,Hoffmann, William E.,Li, Kai S.,Higdon, Nicole R.,Wall, Theron M.,Hurst, Raymond S.,Wong, Erik H.F.,Rogers, Bruce N.
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p. 8219 - 8248
(2007/10/03)
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- Structure-activity relationship studies on unifiram (DM232) and sunifiram (DM235), two novel and potent cognition enhancing drugs
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Structure-activity relationships on two novel potent cognition enhancing drugs, unifiram (DM232, 1) and sunifiram (DM235, 2), are reported. Although none of the compounds synthesised reached the potency of the parent drugs, some fairly active compounds have been identified that may represent new leads to develop other cognition enhancing drugs. An interesting result of this research is the identification of two compounds (13 and 14) that are endowed with amnesing activity (the opposite of the activity of the original molecules) and are nearly equipotent to scopolamine. Moreover, two compounds of the series (5 and 6) were found endowed with analgesic activity on a rat model of neuropathic pain at the dose of 1 mg/kg.
- Scapecchi, Serena,Martini, Elisabetta,Manetti, Dina,Ghelardini, Carla,Martelli, Cecilia,Dei, Silvia,Galeotti, Nicoletta,Guandalini, Luca,Romanelli, Maria Novella,Teodori, Elisabetta
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- HETEROCYCLICALLY SUBSTITUTED INDOLINONES, THEIR PRODUCTION AND USE AS MEDICAMENTS
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The invention relates to heterocyclically substituted indolinones of general formula (I), in which R1 to R5 and X are defined as cited in claim 1, to their tautomers, diastereomers, enantiomers and to their mixtures, prodrugs and salts, in particular their physiologically compatible salts. Said compounds exhibit valuable pharmacological characteristics, in particular an inhibiting action on various receptor tyrosine kinases and cyclin-CDK complexes and on the proliferation of endothelial cells and various tumour cells. The invention also relates to medicaments containing said compounds, to the use of the latter and to a method for producing the same.
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Page/Page column 76-77
(2008/06/13)
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- Effect of a-ring modifications on the DNA-binding behavior and cytotoxicity of pyrrolo[2,1-c][1,4]benzodiazepines
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Several A-ring-modified analogues of the DNA-binding antitumor agent DC- 81 (5) have been synthesized in order to study structure- reactivity/cytotoxicity relationships. For two molecules (23 and 30) the modifications required the addition of a fourth rin
- Thurston, David E.,Bose, D. Subhas,Howard, Philip W.,Jenkins, Terence C.,Leoni, Alberto,Baraldi, Pier G.,Guiotto, Andrea,Cacciari, Barbara,Kelland, Lloyd R.,Foloppe, Marie-Paule,Rault, Sylvain
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p. 1951 - 1964
(2007/10/03)
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- Insecticidal N'-substituted-N,N'-diacylhydrazines
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Insecticidal compounds having the formula N-(2-Ra -3-Rb -4-Rh -benzoyl)-N'-(2-Rc -3-Rd -4-Re -5-Rf -benzoyl)-N'-Rg -hydrazine wherein Ra is a halo or lower alkyl; R b is lower alkoxy, optionally substituted with halo (preferably fluoro); Rc is selected from hydrogen, halo, lower alkyl, lower alkoxy, lower alkoxy lower alkyl, and nitro; Rd, Re and Rf are each independently selected from hydrogen, bromo, chloro, fluoro, lower alkyl, lower alkoxy, and lower alkoxy lower alkyl; Rg is a (C4 -C6)alkyl; Rh is hydrogen, lower alkoxy, lower alkyl, or when taken together with Rb is methylenedioxy (--OCH2 O--), 1,2-ethylenedioxy (--OCH2 CH2 O--), 1,2-ethyleneoxy (--CH2 CH2 O--) or 1,3-propyleneoxy (--CH2 CH2 CH2 O--) wherein an oxo atom is located at the Rb position; and the substituents Rc and Rd, or Rd and Re, or Re and Rf when taken together can be methylenedioxy or 1,2-ethylenedioxy as well as compositions comprising an agronomically acceptable carrier and an insecticidally effective amount of such compounds; and methods of using such compounds and compositions. Also, methods for the production of the compounds and their intermediates, which methods comprise either admixing a 3-amino-2-(substituted)-benzoic acid, sodium nitrite and methanol under acidic conditions or admixing a 3,4-fused heterocyclic benzoic acid and an alkyl lithium reagent followed by subsequent reaction with an electrophilic reagent.
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