- Exploring symmetry-based logic for a synthesis of Palau'amine
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(Chemical Equation Presented) A synthetic approach to palau'amine is described that exploits veiled symmetry in the structure. Bis-alkylidenes i have been prepared and found susceptible to halogenative desymmetrization using t-BuOCl. This oxidation forms
- Li, Qingyi,Hurley, Paul,Ding, Hui,Roberts, Andrew G.,Akella, Radha,Harran, Patrick G.
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Read Online
- Aromatic Linkers Unleash the Antiproliferative Potential of 3-Chloropiperidines Against Pancreatic Cancer Cells
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In this study, we describe the synthesis and biological evaluation of a set of bis-3-chloropiperidines (B?CePs) containing rigid aromatic linker structures. A modification of the synthetic strategy also enabled the synthesis of a pilot tris-3-chloropiperidine (Tri-CeP) bearing three reactive meta-chloropiperidine moieties on the aromatic scaffold. A structure–reactivity relationship analysis of B?CePs suggests that the arrangement of the reactive units affects the DNA alkylating activity, while also revealing correlations between the electron density of the aromatic system and the reactivity with biologically relevant nucleophiles, both on isolated DNA and in cancer cells. Interestingly, all aromatic 3-chloropiperidines exhibited a marked cytotoxicity and tropism for 2D and 3D cultures of pancreatic cancer cells. Therefore, the new aromatic 3-chloropiperidines appear to be promising contenders for further development of mustard-based anticancer agents aimed at pancreatic cancers.
- Helbing, Tim,Carraro, Caterina,Francke, Alexander,Sosic, Alice,De Franco, Michele,Gandin, Valentina,G?ttlich, Richard,Gatto, Barbara
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- Cooperative induction in double H-bonding donor/acceptor compounds: Chains vs. ribbons
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Two different types of monodimensional crystalline aggregates formed by squaramides, chains and ribbons, have been studied both in the solid state and ab initio with four model compounds. Although ribbons are a priori possible, only covalently forced syn conformations have been observed. Cooperative induction is postulated to explain the preference for chains instead of ribbons in squaramide crystals.
- Prohens, Rafel,Portell, Anna,Puigjaner, Cristina,Barbas, Rafael,Alcobe, Xavier,Font-Bardia, Merce,Tomas, Salvador
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- Convenient semihydrogenation of azoarenes to hydrazoarenes using H2
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The high atom-economical and eco-benign nature of hydrogenation reactions make them much more superior to conventional reduction and transfer hydrogenation. Herein, a convenient and highly selective hydrogenation reaction of azoarenes using molecular hydrogen to access diverse hydrazoarenes is reported. The present catalytic method is general and operationally simple, and it operates under exceedingly mild conditions (room temperature and 1 atm of hydrogen pressure). The reusability of catalysts used in this method is also successfully demonstrated.
- Sahoo, Manoj K.,Sivakumar, Ganesan,Jadhav, Sanjay,Shaikh, Samrin,Balaraman, Ekambaram
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supporting information
p. 5289 - 5293
(2021/06/30)
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- Chemoselective reduction of nitro and nitrile compounds using an Fe3O4-MWCNTs?PEI-Ag nanocomposite as a reusable catalyst
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Multi-walled carbon nanotubes (MWNTs) were modified with carboxylic acid functional groups (MWCNTs-(COOH)n) prior to decoration with Fe3O4 nanoparticles. A further modification step by polyethyleneimine (PEI) resulted in Fe3O4-MWCNTs?PEI which provided a suitable platform for coordination and in situ reduction of silver ions to obtain an Fe3O4-MWCNTs?PEI-Ag nanocomposite with highly dispersed Ag nanoparticles. The Fe3O4-MWCNTs?PEI-Ag hybrid material was characterized by various techniques such as Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), transmission electron microscopy (TEM), vibrating sample magnetometry (VSM), X-ray photoelectron spectroscopy (XPS) and thermogravimetric analysis (TGA), and was used as an efficient catalyst for chemoselective reduction of nitroaromatic and nitrile compounds to their corresponding amines in aqueous solution at ambient temperature. Nitrofurazone, a cytotoxic antibiotic, as a non-aromatic example was also reduced selectively at the nitro group without reduction of the other functionalities in the presence of Fe3O4-MWCNTs?PEI-Ag. The catalyst was magnetically recoverable and maintained its activity for at least six cycles without considerable loss of efficiency.
- Ansari, Sara,Khorshidi, Alireza,Shariati, Shahab
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p. 3554 - 3565
(2020/02/04)
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- Green and convenient protocols for the efficient reduction of nitriles and nitro compounds to corresponding amines with NaBH4 in water catalyzed by magnetically retrievable CuFe2O4 nanoparticles
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Abstract: In this study, firstly, CuFe2O4 nanoparticles were prepared by a simple operation. The structure of the mentioned nanoparticles was characterized by Fourier transform infrared spectroscopy, X-ray diffraction, scanning electron microscopy, transmission electron microscopy, energy-dispersive X-ray spectroscopy, inductively coupled plasma-optical emission spectrometry, vibrating sample magnetometer and also Brunauer–Emmett–Teller and Barrett–Joyner–Halenda analyses. The prepared magnetically copper ferrite nanocomposite was successfully applied as a simple, cost-effective, practicable, and recoverable catalyst on the green, highly efficient, fast, base-free, and ligand-free reduction of nitriles and also on the affordable and eco-friendly reduction of nitro compounds with the broad substrate scope to the corresponding amines with NaBH4 in water at reflux in high to excellent yields. Graphical abstract: [Figure not available: see fulltext.].
- Zeynizadeh, Behzad,Mohammad Aminzadeh, Farkhondeh,Mousavi, Hossein
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- MERCAPTOAMIDINE DERIVATIVES AND METHODS OF USE
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Compounds of formula (I) are useful in treating conditions or disorders prevented by or ameliorated by histamine-3 receptor ligands. Also disclosed are pharmaceutical compositions of compounds of formula (I), methods for using such compounds and compositi
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Paragraph 0168
(2013/03/26)
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- Diversity-oriented synthesis of polycyclic diazinic scaffolds
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An efficient and versatile synthesis of a polycyclic diazinic system starting from oxazine has been developed using a two-step Michael/retro Michael and cyclization sequence. The substrates were synthesized with good to high yields giving rapid access to molecular diversity.
- Gigant, Nicolas,Claveau, Elise,Bouyssou, Pascal,Gillaizeau, Isabelle
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supporting information; experimental part
p. 844 - 847
(2012/03/26)
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- New synthetic route to [bis-1,2-(aminomethyl)benzene]dichloroplatinum(II) complexes, screening for cytotoxic activity in cisplatin-sensitive and resistant human cancer cell lines, and reaction with glutathione
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A new synthetic route to [bis-1,2-(aminomethyl)benzene]dichloroplatinum(II) complexes is described. o-Xylene and the 4-methoxy substituted derivative were used as starting points for the synthesis: benzylic bromination with N-bromosuccinamide /benzoylperoxide followed by the substitution of the benzyl bromides for azide and finally a catalytic hydrogenation with Pd/C of the diazides gave the desired diamines ligands. An attempt to synthesize the 4,6-dimethoxy derivative was unsuccessful due to the bromination of the aromatic ring. The diamines were complexed with K2PtCl4 to give the target Pt(II) complexes: [1,2-bis(aminomethyl)benzene]dichloroplatinum(II) (4a) and [1,2-bis(aminomethyl)-4-methoxy-benzene]dichloroplatinum(II) (4b). Screening for cytotoxic activity was done in comparison to cisplatin in a panel of eight human cancer cell lines; in all cases, the 4-methoxy derivative 4b was less active than the unsubstituted analog, 4a. In four cell lines 4a was as potent as cisplatin, while in the other four lines cisplatin was considerably more potent then 4a. The 5637 bladder cancer cell line was made 4-5 fold resistant to either cisplatin or [d,l-trans-1,2-diaminocyclohexane]dichloroplatinum(II); 4a showed some cross resistance (2-3 fold) to both resistant cell lines. The reactivity of 4a towards substitutions with glutathione (GSH), a biological thiol involved in intrinsic and acquired resistance to Pt-complexes, was measured by a RP-HPLC method. It was found that the second-order rate constant for the reaction of 4a with GSH was similar to that that reported for CDDP, indicating that reactivity towards GSH does not explain the different levels of cross resistance.
- Rinke,Gruenert,Bednarski
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p. 763 - 769
(2007/10/03)
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- Regulated apoptosis
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We have developed a general procedure for the regulated (inducible) dimerization or oligomerization of intracellular proteins and disclose methods and materials for using that procedure to regulatably initiate cell-specific apoptosis (programmed cell death) in genetically engineered cells.
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- Regulated transcription of targeted genes and other biological events
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Dimerization and oligomerization of proteins are general biological control mechanisms that contribute to the activation of cell membrane receptors, transcription factors, vesicle fusion proteins, and other classes of intra- and extracellular proteins. We
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- One-pot preparation of o-xylylene diamine and its related amines
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A method for one-pot preparation of o-xylylene diamine, 1,8-diaminomethylnaphthalene, and 1,2,4,5-tetrakis(aminomethyl)benzene has been developed. The procedure is simpler and the yield of the reaction is higher than by the conventional method.
- Kawahara, Shun-Ichi,Uchimaru, Tadafumi
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p. 985 - 987
(2007/10/03)
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- Regulated transcription of targeted genes and other biological events
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Dimerization and oligomerization of proteins are general biological control mechanisms that contribute to the activation of cell membrane receptors, transcription factors, vesicle fusion proteins, and other classes of intra- and extracellular proteins. We
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- N,N-bis (quinolin-4-yl)-diamine derivatives, their preparation and their use as antimalarials
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Disclosed are N,N'-bis(quinolin-4-yl)diamine derivatives of general formula I wherein R1 signifies halogen or trifluoromethyl, R2 signifies hydrogen or halogen, A signifies cyclohexane-1,3-diyl, 2-methyl-cyclohexane-1,3-diyl, cyclohexane-1,4-diyl, dicyclohexylmethane-4,4'-diyl, cyclopentane-1,3-diyl, phenylene-1,4, phenylene-1,3 and phenylene-1,2; n is 1 or 2; m is 1 or 2, as well as their pharmaceutically acceptable salts. These products are useful as agents for preventing malaria and for treating it, especially where the pathogens are resistant to chloroquine. STR1
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- Cosmetic composition containing an amide-amine type condensate, and a cosmetic treating process using said condensate
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A cosmetic composition for improving the suppleness of the skin or hair and for protecting the keratin of the skin or hair from degradation by atmospheric agents or light comprises in a cosmetic or dermatologic acceptable vehicle a saturated condensate resulting from the polyaddition of a bis-acrylamide and a sterically hindered primary diamine, the condensate being saturated by hydrogenation or by addition of a thiol or an amine on the double bonds of the acrylamide residue.
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- Reduction of Heterocycles with Nickel-Aluminum Alloy
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Pyrazines, pyridazines, isoxazoles, oxazole, 4-methylpyrimidine, and indole are reduced by nickel-aluminum alloy in potassium hydroxide solution.The reaction is simple to carry out and does not require special apparatus or hydrogen atmospheres.The products were the fully hydrogenated species although benzene rings were not attacked. 4-Methylpyrimidine gave 1,3-diaminobutane and oxazole gave 2-(methylamino)ethanol.It was found that the reaction frequently exhibited an induction period.
- Lunn, George
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p. 1043 - 1046
(2007/10/02)
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