- Asymmetric hydrogenation of the C-C double bond of 1- and 1,2-methylated maleimides with cultured suspension cells of Marchantia polymorpha
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Suspension cultured cells of Marchantia polymorpha have the potential to hydrogenate the C-C double bonds of 2-methyl- and 2,3-dimethylmaleimide derivatives to give enantiomerically pure (2R)-2-methyl- and (2R,3R)-2,3-dimethylsuccinimide derivatives, resp
- Hegazy, Mohamed-Elamir F.,Shishido, Kozo,Hirata, Toshifumi
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- Modification of Poly(vinyl chloride) by N -Phenyl Itaconimides for the Improvement of Its Thermal Stability
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Poly(vinyl chloride) (PVC) is modified by N-phenyl itaconimide derivatives (N-(RPh)IM) as modifying agents or graft comonomers. The resulting modified polymers or graft copolymers were characterized using FTIR and UV/Vis spectrophotometry. The thermal pro
- Elsharif, Asma M.,Al-Ghamdi, Azza A.,Abdel-Naby, Abir S.
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- N-Aryl-3-mercaptosuccinimides as Antivirulence Agents Targeting Pseudomonas aeruginosa Elastase and Clostridium Collagenases
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In light of the global antimicrobial-resistance crisis, there is an urgent need for novel bacterial targets and antibiotics with novel modes of action. It has been shown that Pseudomonas aeruginosa elastase (LasB) and Clostridium histolyticum (Hathewaya histolytica) collagenase (ColH) play a significant role in the infection process and thereby represent promising antivirulence targets. Here, we report novel N-Aryl-3-mercaptosuccinimide inhibitors that target both LasB and ColH, displaying potent activities in vitro and high selectivity for the bacterial over human metalloproteases. Additionally, the inhibitors demonstrate no signs of cytotoxicity against selected human cell lines and in a zebrafish embryo toxicity model. Furthermore, the most active ColH inhibitor shows a significant reduction of collagen degradation in an ex vivo pig-skin model.
- Konstantinovi?, Jelena,Yahiaoui, Samir,Alhayek, Alaa,Haupenthal, J?rg,Sch?nauer, Esther,Andreas, Anastasia,Kany, Andreas M.,Müller, Rolf,Koehnke, Jesko,Berger, Fabian K.,Bischoff, Markus,Hartmann, Rolf W.,Brandstetter, Hans,Hirsch, Anna K. H.
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p. 8359 - 8368
(2020/09/16)
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- Iterative Arylation of Itaconimides with Diazonium Salts through Electrophilic Palladium Catalysis: Divergent β-H-Elimination Pathways in Repetitive Matsuda-Heck Reactions
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N-Arylitaconimides, accessible from maleic anhydride, anilines, and paraformaldehyde, react with arene diazonium salts in Pd-catalyzed Matsuda-Heck arylation to the pharmacologically relevant E-configured 3-arylmethylidene pyrrolidine-2,5-diones (also kno
- Riemer, Nastja,Shipman, Michael,Wessig, Pablo,Schmidt, Bernd
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p. 5732 - 5746
(2019/05/10)
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- A highly efficient and stereoselective cycloaddition of nitrones to N-arylitaconimides
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The 1,3-dipolar cycloaddition of keto- and aldonitrones with N-arylitaconimides proceeds regioselectively giving only 5-spiroisoxazolidines. In the case of aldonitrones the reaction proceeds with high diastereoselectivity. A range of the obtained adducts
- Teterina, Polina S.,Efremova, Mariia M.,Sirotkina, Ekaterina V.,Novikov, Alexander S.,Khoroshilova, Olesya V.,Molchanov, Alexander P.
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supporting information
(2019/08/26)
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- Synthesis of cyclic imides (methylphtalimides, carboxylic acid phtalimides and itaconimides) and evaluation of their antifungal potential
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Background: This paper describes the synthesis of three different subfamilies of cyclic imides: methylphtalimides, carboxyl acid phtalimides and itaconimides. Methods: Fifteen compounds (five of each sub-family) were obtained by the reaction of appropriat
- Stiz, Dorimar,Corrêa, Rogério,D'Auria, Felicia D.,Simonetti, Giovanna,Cechinel-Filho, Valdir
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p. 647 - 654
(2016/10/18)
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- Synthesis, characterization, and computational study of potential itaconimide-based initiators for atom transfer radical polymerization
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Atom transfer radical polymerization (ATRP) has been a promising technique to provide polymers with well-defined composition, architecture, and functionality. In most of the ATRP processes, alkyl halides are used as an initiator. We report the synthesis o
- Deoghare, Chetana,Baby,Nadkarni, Vishnu S.,Behera, Raghu Nath,Chauhan, Rashmi
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p. 48163 - 48176
(2015/01/08)
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- Solid-state photochemistry of crystalline pyrazolines: Reliable generation and reactivity control of 1,3-biradicals and their potential for the green chemistry synthesis of substituted cyclopropanes
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To expand on the limited number of examples that exist in the literature for the solid-state photodenitrogenation of azoalkanes, a series of crystalline 7-alkyl-2,3,7-triazabicyclo[3.3.0]oct-2-ene-6,8-diones with varying 4,4-substituents were prepared. Th
- Shiraki, Saori,Vogelsberg, Cortnie S.,Garcia-Garibay, Miguel A.
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p. 1929 - 1937
(2013/01/16)
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- 1-AKAN-2-OL SUBSTITUTED PIPERAZINE AND PIPERIDINE COMPOUNDS
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Disclosed are novel substituted heterocyclic derivatives having the structure of Formula (I): The compounds are useful for the treatment of various disease states, in particular cardiovascular diseases such as atrial and ventricular arrhythmias, intermitt
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Page/Page column 69
(2008/06/13)
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- Photoreactions of 2-(N-alkylarylamino) succinimides and related compounds
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On irradiation (254 nm), 2-(N-methylanilino)-N-phenylsuccinimide (6a) underwent homolysis of the C(2)-N bond to yield fission products N-methylaniline and N-phenylsuccinimide (12), along with the products of ortho- and para-rearrangement 2-[2-(N-methylamino)phenyl]-N-phenylsuccinimide (13) and 2-[4- (N-methylamino)phenyl]-N-phenylsuccinimide (14a) respectively. Similarly, irradiation of 2-(N-methyl- anilino)succinimide (6b) and N-benzyl-2-(N-methylanilino)succinimide (6c) gave N-methylaniline and the corresponding products of para-rearrangement. In contrast, both fission and type II cyclisation photo-products 12 and 17 respectively were formed from N-phenyl-2-(1,2,3,4-tetrahydroquinolin-1-yl)succinimide (16) and only the type II cyclisation product 1-hydroxy-2,7-diphenyl-2,7-diazabicyclo-[3.3.0]octan-3-one (21) was obtained from 2-(N-methylanilinomethyl)-N-phenylsuccinimide (20).
- Ashraf, Syed A.,Hill, John,M'Hamedi, Ahmed,Zerizer, Hafiza
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p. 6747 - 6756
(2007/10/02)
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- Thermolysis of 7-Phenyl-2,3,7-triazabicyclooct-2-ene-6,8-dione
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Thermolysis of the title compound in boiling xylene (138 deg) produces a 7.7/10.1/1.0 mixture of the N-phenylimides of cis-1,2-cyclopropanedicarboxylic acid, citraconic acid, and itaconic acid.The imides of citraconic and itaconic acids are produced by hydrogen shifts.A completely concerted mechanism involving simultaneous hydrogen shift and cleavage of both C-N bonds is unlikely in the present case because both hydride-shift products are formed and because the optimal arrangement for the hydrogen shift requires deformation of the imide ring and loss of imide resonance.The C-N bond strengths in the title compound should be quite different.The products can arise either from two parallel pathways involving nitrogen-containing dipoles or from a single nitrogen-free trimethylene fragment.
- Majchrzak, Michael W.,Kotelko, Antoni
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p. 1475 - 1477
(2007/10/02)
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- NOVEL SYNTHESIS AND 1,3-DIPOLAR CYCLOADDITION REACTION OF PYRIDINIUM N-METHYLIDE
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Pyridinium N-methylide, generated in situ by treating N-(trimethylsilylmethyl)pyridinium triflate with fluoride ion, was found to react with dimethyl acetylenedicarboxylate to give dimethyl indolizine-1,2-dicarboxylate.Similarly, the N-methylides derived
- Miki, Yasuyoshi,Hachiken, Hiroko,Takemura, Shoji,Ikeda, Masazumi
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p. 701 - 703
(2007/10/02)
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- NEW C-C BOND FORMATION WITH PYRIDINIUM METHYLIDE: HYDROMETHYLENATION OF OLEFIN
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New C-C bond formation with pyridinium methylide is presented: Pyridinium methylide reacts with electron-deficient olefins providing the next higher homologs of olefins, in which the double bond of starting olefin is saturated and, instead, a C=C double bond is newly formed.This reaction mode has been never reported before in the study of nitrogen ylide and is to be referred to as hydromethylenation of olefin.In the presence of base, 1,2-double bond migration occurs leading to the methylated derivatives of starting olefins.
- Tsuge, Otohiko,Kanemasa, Shuji,Kuraoka, Satoru,Takenaka, Shigeori
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p. 281 - 284
(2007/10/02)
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