136918-14-4Relevant articles and documents
Redox-Mediated Decarboxylative Photo-Phenylselenenylation of N-Acyloxyphthalimides
Okada, Keiji,Okubo, Katsura,Morita, Naoto,Oda, Masaji
, p. 2021 - 2024 (1993)
Decarboxylative phenylselenenylation of N-acyloxyphthalimides by visible light irradiation in aqueous solvents using catalytic amount of Ru(bpy)3Cl2 as a sensitizer in the presence of one equivalent of BNAH and 0.5 equivalent of diphenyl diselenide effici
Exploratory studies probing the intermediacy of azomethine ylides in the photochemistry of N-phthaloyl derivatives of α-amino acids and β-amino alcohols
Yoon, Ung Chan,Lee, Chan Woo,Oh, Sun Wha,Mariano, Patrick S.
, p. 11997 - 12008 (1999)
Exploratory photochemical studies with N-phthaloyl derivatives of glutamic acid, aspartic acid, serine, threonine and analogous carboxylic acids and alcohols have been conducted to determine the generality of azomethine ylide forming decarboxylation and retro-aldol fragmentation reactions. Preferences in the competition between these excited state reaction pathways have been determined by studies with phthalimides which contain both α-amino acid and β-aminoethanol groups.
Utilization of cyanoacetohydrazide and 2-(1,3-dioxoisoindolin-2-yl) acetyl chloride in the synthesis of some novel anti-proliferative heterocyclic compounds
Hekal, Mohamed H.,Ali, Yasmeen M.,Abu El-Azm, Fatma S. M.
, p. 2839 - 2852 (2020)
Owing to its high reactivity and commercial availability, 2-cyanoacetohydrazide can be utilized as a versatile and appropriate intermediate for synthesis of a broad variety of heterocyclic compounds. Thus, 2-cyanoacetohydrazide and 2-(1,3-dioxoisoindolin-2-yl) acetyl chloride were used as starting materials for construction of new heterocyclic compounds bearing 1,3-dioxoisoindoline moiety. The newly synthesized compounds were recognized by elemental analyses and spectral data (IR, 1H-NMR, and 13C-NMR spectra). The synthesized compounds were screened for their anti-proliferative activity against two human epithelial cell lines; breast (MCF-7) and liver (HepG2) as well as to normal fibroblasts (WI-38). The data showed distinctly that compounds 1 and 12 presented promising in-vitro anti-proliferative activity against two cell lines (MCF-7 and HepG2) without harming normal fibroblasts.
Spectroscopic and analysis of the hydrolytic process of folpet and its interaction with DNA
Zhang, Yepeng,Zhang, Guowen
, p. 1388 - 1401 (2014)
Hydrolysis of the pesticide folpet [N-(trichloromethylthio) phthalimide] in aqueous solution in the absence or presence of calf thymus DNA (ctDNA) was investigated using UV-Vis absorption spectroscopy, and the interactions of folpet and its hydrolyzates with ctDNA were determined by fluorescence and circular dichroism spectroscopy, coupled with viscosity and melting temperature measurements. The absorption spectra data was further analyzed by alternate least squares, a chemometrics method, and the concentration profiles of the reacting species (folpet, unstable intermediate, phthalimide and phthalic acid) and their pure component spectra were simultaneously extracted to monitor the hydrolytic process. It was found that the hydrolytic process consists of at least two steps, generation of an unstable intermediate and production of its end hydrolyzates, phthalimide and phthalic acid. Addition of ctDNA significantly affects the hydrolysis of folpet. The results from the competitive binding with intercalator ethidium bromide, ctDNA melting and viscosity measurements, and circular dichroism studies indicate that folpet and the intermediate can intercalate into the double-helix of DNA, phthalic acid is bound to DNA by a partial intercalation, while phthalimide does not show binding to ctDNA. Moreover, the binding of folpet (or the intermediate) and phthalic acid to ctDNA induced structural changes of the DNA.
Investigations of reactions of selected azaarenes with radicals in water. 2. Chlorine and bromine radicals
Beitz, Toralf,Bechmann, Wolfgang,Mitzner, Rolf
, p. 6766 - 6771 (1998)
The halogen radicals that react with azaarenes are produced by the photooxidation of halogenide anions with hydroxyl and sulfate radicals and exist as complexes of the radical and the respective halogenide anion in the aqueous phase. The main reaction products of the reactions are identified, and in the case of the bromine radicals, the second order rate constants are determined. Oxidation takes place according to the different redox potentials of the two reactants and is especially observed for chlorine radicals. A typical product spectrum comparable with that in reactions with hydroxyl and sulfate radicals has been found. The formation of some oxidation products in reactions of bromine radicals is in contradistinction to the oxidation potentials of the azaarenes and can be understood only by the reaction of their excited states. The halogenation is the main reaction of the azaarenes. Halogenation products of both, the benzene and the pyridine/diazine rings, have been found. The halogenation of the pyridine/diazine ring again requires the reaction of excited states. The majority of derivatives is halogenated in substitution reactions, but in the reaction of benzo[h]quinoline, addition is also observed. The resonance energy per electron is responsible for the change in the halogenation mechanism from substitution to addition.
Photochemical Chlorodecarboxylation via an Electron Transfer Mechanism
Okada, Keiji,Okamoto, Kazushige,Oda, Masaji
, p. 1636 - 1637 (1989)
A new method of chlorodecarboxylation of carboxylic acids via N-acyloxyphthalimides is developed; the reaction proceeds upon irradiation of N-acyloxyphthalimides in the presence of 1,4-diazabicyclooctane in ButOH-CCl4-H2O (53:42:5 v/v) in moderate to high yields.
Use of Standard Addition to Quantify in Situ FTIR Reaction Data
Hutchinson, George,Welsh, Calum D. M.,Burés, Jordi
, p. 2012 - 2016 (2021)
FTIR spectroscopy is a common in situ reaction monitoring technique used in modern academic and industrial environments. The FTIR signals collected during the course of a reaction are proportional to the concentration of the reaction components but not intrinsically quantitative. To make FTIR data quantitative, precalibration or offline analyses of reaction samples are required, which diminishes the unique benefits of in situ reaction monitoring techniques. Herein, we report the use of standard addition as a convenient method to obtain quantitative FTIR data.
Electrochemical reduction of N,N′-thiobisphthalimide and N,N′-dithiobisphthalimide: Ejection of diatomic sulfur through an autocatalytic mechanism
Hamed, Emad M.,Koczkur, Kallum M.,Houmam, Abdelaziz
, p. 22600 - 22610 (2014)
The electrochemical reduction of N,N′-dithiobisphthalimide and N,N′-thiobisphthalimide is investigated using electrochemical techniques and theoretical calculations. The results are rationalized using adequate electron transfer theories. The reduction leads to the ejection of diatomic sulfur and involves an interesting autocatalytic mechanism. This mechanism is dependent on the concentration of the initial compound and the cyclic voltammetric scan rate. The starting material is reduced both at the electrode and through homogeneous electron transfer from the produced sulfur. The initial electron transfer follows a stepwise mechanism involving the formation of the corresponding radical anion. This is supported by both the electrochemical data and the theoretical calculation results. The radical anion of the N,N′-dithiobisphthalimide dissociates through cleavage of the N-S chemical bond and not the S-S chemical bond. Application of the extension of the dissociative electron transfer theory to the dissociation of radical anions shows that the N-S chemical bond dissociates despite being stronger than the S-S chemical bond. This is due to the large difference in the oxidation potentials of the two potential anions (the phthalimidyl anion and the phthalimidyl thiyl anion). The electrochemical reduction of N,N′-thiobisphthalimide involves the intermediate formation of N,N′-dithiobisphthalimide and hence the autocatalytic process is less efficient.
Oxidative C-O cross-coupling of 1,3-dicarbonyl compounds and their heteroanalogues with N-substituted hydroxamic acids and N-hydroxyimides
Terent'Ev, Alexander O.,Krylov, Igor B.,Timofeev, Vladimir P.,Starikova, Zoya A.,Merkulova, Valentina M.,Ilovaisky, Alexey I.,Nikishin, Gennady I.
, p. 2375 - 2390 (2013)
The oxidative C-O cross-coupling of 1,3-dicarbonyl compounds and their heteroanalogues, 2-substituted malononitriles and cyanoacetic esters, with N-substituted hydroxamic acids and N-hydroxy- imides was realized. The best results were obtained with the use of manganese (III) acetate [Mn (OAc) 3] or the cobalt(II) acetate catalyst [Co (OAc)2cat.]/ potassium permanganate [KMnO4] system as the oxidant. The synthesis can be scaled up to gram quantities of coupling products; yields are 30-94%. The reaction proceeds via a radical mechanism through the formation of nitroxyl radicals from N-substituted hydroxamic acids and N-hydroxyimides.
Photoinduced electron-transfer chemistry of the bielectrophoric N-phthaloyl derivatives of the amino acids tyrosine: Histidine and tryptophan
Griesbeck, Axel G.,Neudoerfl, Joerg,Kiff, Alan De
, p. 518 - 524 (2011)
The photochemistry of phthalimide derivatives of the electron-rich amino acids tyrosine, histidine and tryptophan 8-10 was studied with respect to photoinduced electron-transfer (PET)induced decarboxylation and Norrish II bond cleavage. Whereas exclusive photodecarboxylation of the tyrosine substrate 8 was observed, the histidine compound 9 resulted in a mixture of histamine and preferential Norrish cleavage. The tryptophan derivative 10 is photochemically inert and shows preferential decarboxylation only when induced by intermolecular PET.
