2157-52-0Relevant academic research and scientific papers
Oxime esters of anthraquinone as photo-induced DNA-cleaving agents for single- and double-strand scissions
Hwu, Jih Ru,Tsay, Shwu-Chen,Hong, Shih Chin,Leu, Yi-Jing,Liu, Chih-Fen,Chou, Shang-Shing P.
, p. 2957 - 2960 (2003)
Anthraquinone-O-9-(4-cyanobenzoyl)oxime (13) with binding constant of 4.49×104 M-1 exhibited single-strand scission of DNA at the concentration of 10 μM and double-strand scission at 50 μM upon UV irradiation.
Nickel-Catalyzed NO Group Transfer Coupled with NOxConversion
Padmanaban, Sudakar,Choi, Jonghoon,Vazquez-Lima, Hugo,Ko, Donghwi,Yoo, Dagyum,Gwak, Jinseong,Cho, Kyung-Bin,Lee, Yunho
supporting information, p. 4585 - 4593 (2022/03/02)
Nitrogen oxide (NOx) conversion is an important process for balancing the global nitrogen cycle. Distinct from the biological NOx transformation, we have devised a synthetic approach to this issue by utilizing a bifunctional metal catalyst for producing value-added products from NOx. Here, we present a novel catalysis based on a Ni pincer system, effectively converting Ni-NOx to Ni-NO via deoxygenation with CO(g). This is followed by transfer of the in situ generated nitroso group to organic substrates, which favorably occurs at the flattened Ni(I)-NO site via its nucleophilic reaction. Successful catalytic production of oximes from benzyl halides using NaNO2 is presented with a turnover number of >200 under mild conditions. In a key step of the catalysis, a nickel(I)-?NO species effectively activates alkyl halides, which is carefully evaluated by both experimental and theoretical methods. Our nickel catalyst effectively fulfills a dual purpose, namely, deoxygenating NOx anions and catalyzing C-N coupling.
Novel phenanthridine amide analogs as potential anti-leishmanial agents: In vitro and in silico insights
Aggarwal, Himanshu,Bala?a-Fouce, Rafael,Chandra Sekhar, Kondapalli Venkata Gowri,Karan Kumar, Banoth,Melcón-Fernandez, Estela,Murugesan, Sankaranarayanan,Nandikolla, Adinarayana,Pérez-Pertejo, Yolanda,Srinivasarao, Singireddi
supporting information, (2021/11/01)
In the current work, sixteen novel amide derivatives of phenanthridine were designed and synthesized using 9-fluorenone, 4-Methoxy benzyl amine, and alkyl/aryl acids. The characterization of the title compounds was performed using LCMS, elemental analysis, 1HNMR, 13CNMR and single crystal XRD pattern was also developed for compounds A8. All the final analogs were screened in vitro for anti-leishmanial activity against promastigote form of L. infantum strain. Among the tested analogs, four compounds (A-06, A-11, A-12, and A-15) exhibited significant anti-leishmanial activity with EC50 value ranges from 8.9 to 21.96 μM against amastigote forms of tested L. infantum strain with SI ranges of 1.0 to 4.3. From the activity results it was found that A-11 was the most active compound in both promastigote and amastigotes forms with EC50 values 8.53 and 8.90 μM respectively. In-silico ADME prediction studies depicted that the titled compounds obeyed Lipinski's rule of five as that of the approved marketed drugs. The predicted in-silico toxicity profile also confirmed that the tested compounds were non-toxic. Finally, molecular docking and molecular dynamics study was also performed for significantly active compound (A-11) in order to study it's putative binding pattern at the active site of the selected leishmanial trypanothione reductase target as well as to understand the stability pattern of target-ligand complex for 100 ns. Single crystal XRD of compound A-08 revealed that the compound crystallizes in monoclinic C2/c space group and showed interesting packing arrangements.
Synthesis of hydroxyethyl methyl morpholinium azide (HEM Morph)N3: A highly efficient new task specific azide-based ionic liquid and its dual application as an azide source and media for synthesis of some novel aromatic O-oxime ethers-1,2,3-triazole conjugates as a potential antihistaminic agents
Rad, Mohammad Navid Soltani,Behrouz, Somayeh,Saremi, Hossein,Mohammadtaghi-Nezhad, Javad
, (2019/12/27)
The synthesis, characterization and application of hydroxyethyl methyl morpholinium azide (HEM Morph)N3 as a new azide-based ionic liquid (ABIL) has been described. (HEM Morph)N3 is used as a source of azide and reaction media for three components ‘Click’ Huisgen cycloaddition reaction between O-propargyl oxime ether and alkyl bromide to acquire novel aromatic O-oxime ethers-1,2,3-triazole conjugates as potential antihistaminic agents in good yields. The influence of parameters like temperature, amount of IL, type of azide-based ionic liquids and its reusability is investigated. The (HEM Morph)N3 is proved to be an efficient, thermally stable, inexpensive and recyclable azide-based ionic liquid which can be easily synthesized and used as both azide's source and reaction media for ‘Click’ Huisgen cycloaddition reaction.
Arylboronic Acid-Catalyzed C-Allylation of Unprotected Oximes: Total Synthesis of N-Me-Euphococcine
Kürti, László,Kattamuri, Padmanabha V.,Siitonen, Juha H.,Yousufuddin, Muhammed
supporting information, (2020/03/24)
O-Unprotected keto-and aldoximes are readily C-allylated with allyl diisopropyl boronate in the presence of arylboronic acid catalysts to yield highly substituted N-α-secondary and tertiary homoallylic hydroxylamines. The method was used in the total synthesis of the trace alkaloid N-Me-Euphococcine.
Access to Cyanoimines Enabled by Dual Photoredox/Copper-Catalyzed Cyanation of O-Acyl Oximes
Wei, Ziyan,Yu, Shouyun,Zhang, Ai Hua,Zhang, Hao
supporting information, p. 7315 - 7320 (2020/10/02)
An efficient strategy for the synthesis of pharmaceutically important and synthetically useful cyanoimines, as well as cyanamides, has been described. This strategy is enabled by dual photoredox/copper-catalyzed cyanation of O-acyl oximes or O-acyl hydroxamides. This state of the art protocol for cyanoimines and cyanamides features readily available starting materials, mild reaction conditions, good functional group tolerance, and operational simplicity. The resultant cyanoimines can be transformed into structurally diverse and functionally important N-containing heterocycles.
The impact of cation structure upon the acidity of triazolium salts in dimethyl sulfoxide
Konstandaras, Nicholas,Dunn, Michelle H.,Guerry, Max S.,Barnett, Christopher D.,Cole, Marcus L.,Harper, Jason B.
supporting information, p. 66 - 75 (2019/12/26)
A series of triazolium salts, selected for their varying electronic and steric properties, were prepared and their pKa values were determined in DMSO at 25 °C using the bracketing indicator method. The effect of each systematic structural variation upon the acidity of the triazolium cation has been considered, in particular examining the effects of systematically altering electronic properties, quantified through the use of Hammett σ parameters. The first pKa value for an azolium salt that generates a mesionic carbene is also reported. These new data allow for the selection of appropriate bases for the deprotonation of such triazolium salts and the potential to correlate the pKa values determined herein with the nucleophilicity of the corresponding carbenes.
Application of phenanthridine compounds to pesticides
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Paragraph 0020; 0029; 0030, (2019/10/01)
The invention relates to an application of phenanthridine compounds shown in general formula (1) to pesticides. Part of the compounds is used as a plant virus agent and can well inhibit the tobacco mosaic virus; when used as a bactericide, the compounds have good inhibitory activity on tomato early blight, wheat scab, potato late blight, phytophthora capsici, rape sclerotinia rot, cucumber gray mould, rice sheath blight disease, cucumber fusarium wilt, cercospora brown spot of peanut, apple ring rot, wheat sharp eyespot, corn southern leaf blight, watermelon anthracnose and rice bakanae disease; when used as an insecticide, the compounds have poisonous activity on armyworms, mosquito larvae, cotton bollworms, ostrinia nubilalis, aphids, adult mites and plutella xylostella. In the formula,when molecular nitrogen is not imine, R can represent hydrogen atoms, methyl, acetyl and benzoyl; R and R represent a hydrogen atom or an oxygen atom simultaneously; R and R can represent hydroxyl, acetoxyl, methoxyl, methyleneoxy, a fluorine atom and the hydrogen atom; R is a bromine atom or the fluorine atom; R is the hydrogen atom or vinyl. When nitrogen is imine, R doesnot represent any group; one of R and R does not represent any group, and the other can represent the hydrogen atom, methoxyl, ethyoxyl, benzyloxy and a chlorine atom; R, R, R and Rrepresent the hydrogen atom.
Copper(ii)-promoted direct conversion of methylarenes into aromatic oximes
Yu, Jiatao,Lu, Ming
supporting information, p. 7397 - 7401 (2015/07/15)
A simple and efficient catalytic system for direct conversion of methylarenes into aromatic oximes has been developed, with Cu(OAc)2 as catalyst, NHPI (N-Hydroxyphthalimide) as additive, TBN (tert-butyl nitrite) as both the nitrogen source and the oxidant. This process proceeds under mild conditions, tolerates a wide range of substrates, affording the targeted aromatic oximes in 63-86% yields.
Copper(II)-promoted direct conversion of methylarenes into aromatic oximes
Yu, Jiatao,Lu, Ming
supporting information, p. 7397 - 7401 (2015/11/27)
A simple and efficient catalytic system for direct conversion of methylarenes into aromatic oximes has been developed, with Cu(OAc)2 as catalyst, NHPI (N-Hydroxyphthalimide) as additive, TBN (tert-butyl nitrite) as both the nitrogen source and the oxidant. This process proceeds under mild conditions, tolerates a wide range of substrates, affording the targeted aromatic oximes in 63-86% yields.
