- Substrate promiscuity of ortho-naphthoquinone catalyst: Catalytic aerobic amine oxidation protocols to deaminative cross-coupling and n-nitrosation
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ortho-Naphthoquinone-based organocatalysts have been identified as versatile aerobic oxidation catalysts. Primary amines were readily cross-coupled with primary nitroalkanes via deaminative pathway to give nitroalkene derivatives in good to excellent yields. Secondary and tertiary amines were inert to ortho-naphthoquinone catalysts; however, secondary nitroalkanes were readily converted by ortho-naphthoquinone catalysts to the corresponding nitrite species that in situ oxidized the amines to the corresponding N-nitroso compounds. Without using harsh oxidants in a stoichiometric amount, the present catalytic aerobic oxidation protocol utilizes the substrate promiscuity feature to provide a facile access to amine oxidation products under mild reaction conditions.
- Kim, Hun Young,Oh, Kyungsoo,Si, Tengda
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p. 9216 - 9221
(2019/10/08)
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- Rhodium(III)-Catalyzed Directed C?H Amidation of N-Nitrosoanilines and Subsequent Formation of 1,2-Disubstituted Benzimidazoles
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An efficient rhodium-catalyzed direct C?H amidation of N-nitrosoanilines with 1,4,2-dioxazol-5-ones as amidating agents has been developed. This method featured mild reaction conditions, a wide substrate scope and satisfactory yields. Besides, the amidated products could be readily converted to pharmaceutically valuable 1,2-disubstituted benzimidazoles via an HCl-mediated deprotection/cyclization process in one pot.
- Chen, Yanyu,Zhang, Rong,Peng, Qiujun,Xu, Lanting,Pan, XianHua
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supporting information
p. 2804 - 2808
(2017/10/20)
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- Diaza [1,4] Wittig-type rearrangement of N-allylic-N-Boc-hydrazines into γ-amino- N -Boc-enamines
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Diaza [1,4] Wittig-type rearrangement of N-allylic-N-Boc-hydrazines into γ-amino-N-Boc-enamines was demonstrated. The scope and limitation, experimental mechanistic studies, and a proposed reaction mechanism were also described.
- Tayama, Eiji,Kobayashi, Yoshiaki,Toma, Yuka
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supporting information
p. 10570 - 10573
(2016/09/02)
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- 1-[(imidazolin-2-yl)amino]indoline and 1-[(imidazolin-2-yl)amino]1,2,3,4-tetrahydroquinoline derivatives: New insights into their circulatory activities
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N-[(Imidazolin-2-yl)amino]indolines and N-[(imidazolin-2-yl)amino]-1,2,3,4-tetrahydroquinolines, previously described in patent literature as hypertensive agents, were synthesized and tested in vitro for their affinities to α1- and α2-adrenoceptors as well as imidazoline I1 and I2 receptors. The compounds most potent at either α1- or α2-adrenoceptors were administered intravenously to normotensive Wistar rats to determine their effects on mean arterial blood pressure and heart rate. Upon intravenous administration at dose of 0.1 mg/kg to normotensive male Wistar rats, the initial transient pressor effect was followed by long-lasting hypotension and bradycardia. In view of the above results the 1-[(imidazolin-2-yl)amino]indolines and [(imidazolin-2-yl)amino]-1,2,3,4-tetrahydroquinolines are now found to possess circulatory profile characteristic of the centrally acting clonidine-like hypotensive imidazolines.
- S?czewski, Franciszek,Wasilewska, Aleksandra,Hudson, Alan L.,Ferdousi, Mehnaz,Rybczyńska, Apolonia,Boblewski, Konrad,Lehmann, Artur
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p. 277 - 287
(2015/04/22)
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- 3-(Hetero)aryl-4-indolylamino-α-tetralones by diastereoselective internal redox cyclization: An "azaenamine" conjugate addition
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(E)-3-(Hetero)aryl-1-(2-((E)-(indolin-1-ylimino)methyl)phenyl) prop-2-en-1-ones 1 undergo 6-exo-trig cyclization reactions upon treatment with BF3?Me2S in dichloromethane at low temperature to give the tetralones 10 in good yield. Th
- Ghavtadze, Nugzar,Narayan, Rishikesh,Wibbeling, Birgit,Wuerthwein, Ernst-Ulrich
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scheme or table
p. 5185 - 5197
(2011/08/09)
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- Bismuth chloride-sodium nitrite: A novel reagent for chemoselective N-nitrosation
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Bismuth(III) chloride-sodium nitrite was used as a mild and efficient reagent for N-nitrosation of various tetrazoles, secondary amines, and amides under ambient conditions. Nitrosation took place chemoselectively at the nitrogen atom, giving corresponding N-nitroso derivatives in good to excellent yield. Copyright Taylor & Francis Group, LLC.
- Chaskar, Atul C.,Langi, Bhushan P.,Deorukhkar, Amol,Deokar, Hrushikesh
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experimental part
p. 604 - 612
(2009/07/04)
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- 1H-Indole-Pyridinecarboxamide and 1H-Indole-Piperidinecarboxamide Compounds
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Compounds of formula (I): wherein: A represents a divalent radical: wherein: Z represents an oxygen atom or a sulphur atom,R6 represents a hydrogen atom, an alkyl, alkenyl, arylalkyl or polyhaloalkyl group or a substituted, linear or branched alkyl chain, represents a single bond or a double bond,R1, R2, R3 and R4 represent a hydrogen or halogen atom,an alkyl, alkoxy, hydroxy, cyano, nitro, polyhaloalkyl or optionally substituted amino group, or a linear or branched alkyl chain substituted by one or more groups,R5 represents a hydrogen atom or an alkyl, aminoalkyl or hydroxyalkyl group,X and Y represent a hydrogen atom or an alkyl group,Ra, Rb, Rc and Rd represent a hydrogen or halogen atom, an alkyl, hydroxy, alkoxy, cyano, nitro, polyhaloalkyl, optionally substituted amino group, or a substituted, linear or branched alkyl chain,Re represents a hydrogen atom or an alkyl, arylalkyl or alkenyl group or a substituted, linear or branched alkyl chain, their enantiomers, diastereoisomers, and N-oxides, and also addition salts thereof with a pharmaceutically acceptable acid or base.
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Page/Page column 7
(2009/10/21)
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- COMPOSITIONS AND METHODS FOR TREATMENT OF CANCER
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The present invention relates to pyrrolidine-2,5-dione compounds, and methods of preparation of these compounds. The present invention also relates to pharmaceutical compositions comprising pyrrolidine-2,5-dione compounds. The present invention provides methods of treating a cell proliferative disorder, such as a cancer, by administering to a subject in need thereof a therapeutically effective amount of a compound or pyrrolidine-2,5-dione compound of the present invention.
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Page/Page column 52
(2009/03/07)
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- Efficient procedure for chemoselective N-nitrosation of secondary amines with trichloromelamine-NaNO2
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A combination of trichloromelamine and sodium nitrite in the presence of wet silica gel was used as an effective nitrosating agent for the transformation of secondary amines into the corresponding N-nitroso derivatives under mild and heterogeneous conditions in good to excellent yields.
- Bamoniri,Zolfigol,Mirjalili,Fallah
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p. 1393 - 1396
(2008/03/27)
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- Alumina-methanesulfonic acid (AMA)/NaNO2 as an efficient procedure for the chemoselectivite N-nitrosation of secondary amines
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A combination of alumina/methanesulfonic acid (AMA) and sodium nitrite was used as an effective nitrosating agent for the nitrosation of secondary amines under mild and heterogeneous conditions in good to excellent yields. Copyright Taylor & Francis Group, LLC.
- Niknam, Khodabakhsh,Zolfigol, Mohammad Ali
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p. 2311 - 2319
(2007/10/03)
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- Synthesis of secondary and tertiary aminofurazans
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Reactions of nitrofurazans with primary and secondary amines were studied. Conditions were found which allow the efficient replacement of the nitro group with these nucleophiles. Transformations of the amidoxime fragment, which is bound to the furazan ring and contains an amino substituent, enable one to substantially expand the spectrum of polyfunctional derivatives. The structures of the amines synthesized were studied by X-ray diffraction analysis.
- Sheremetev,Andrianov,Mantseva,Shatunova,Aleksandrova,Yudin,Dmitriev,Averkiev,Antipin
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p. 596 - 614
(2007/10/03)
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- Selective N-nitrosation of amines, N-alkylamides and N-alkylureas by N2O4 supported on cross-linked polyvinylpyrrolidone (PVP-N2O4)
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N2O4 was supported on the cross-linked polyvinylpyrrolidone (PVP) to afford a solid, stable and recyclable nitrosating agent. This reagent shows excellent selectivity for N-nitrosation of dialkyl amines in the presence of diaryl-, arylalkyl-, trialkylamines and also for secondary amides in dichloromethane at room temperature under mild and heterogeneous conditions. Also N-nitroso-N-alkyl amides can be selectively prepared in the presence of primary amides and N-phenylamides under similar reaction conditions. Selective N-nitrosation or dealkylation and N-nitrosation of tertiary amines can also be performed by this reagent.
- Iranpoor, Nasser,Firouzabadi, Habib,Pourali, Ali-Reza
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p. 1591 - 1597
(2007/10/03)
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- The use of Nafion-H/NaNO2 as an efficient procedure for the chemoselective N-nitrosation of secondary amines under mild and heterogeneous conditions
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A combination of Nafion-H and sodium nitrite in the presence of wet SiO2 was used as an effective agent for the N-nitrosation of secondary amines under mild and heterogeneous conditions in good to excellent yields.
- Zolfigol, Mohammad Ali,Habibi, Davood,Mirjalili, BiBi Fatemeh,Bamoniri, Abdolhamid
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p. 3345 - 3349
(2007/10/03)
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- N-aminoindoline derivatives as inhibitors of 5-lipoxygenase
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N-Aminoindoline derivatives were prepared and their 5-lipoxygenase inhibitory activities were evaluated in vitro and compared with those of phenidone and NDGA. Compound 4 presents the most effective 5-LO inhibition.
- Audouin, Corinne,Mestdagh, Nathalie,Lassoie, Marie-Agnes,Houssin, Raymond,Henichart, Jean-Pierre
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p. 845 - 848
(2007/10/03)
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- Structural features of aliphatic N-nitrosamines of 7-azabicyclo[2.2.1]heptanes that facilitate N-NO bond cleavage
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N-Nitrosamines can be considered as potential nitric oxide (NO)/nitrosonium ion (NO+) donors. However, the relation of the structures of N-nitrosamines, in particular of aliphatic N-nitrosamines, to the characteristics of release of NO or NO+ remains unclear. Here we show that aliphatic N-nitrosoamines of 7-azabicyclo[2.2.1]heptanes can undergo heterolytic N-NO bond cleavage. On the basis of the observation of reduced rotational barriers of the N-NO bonds in solution and nitrogen-pyramidal structures of the N-nitroso group in the solid state, we postulate that N-NO bond cleavage of N-nitrosamines is enhanced by a reduction of the resonance in the N-NO group. Computational studies suggest that these structural features of the N-nitrosamines of 7-azabicyclo[2.2.1]heptane are derived from angle strain imposed on the CNC angles.
- Ohwada,Miura,Tanaka,Sakamoto,Yamaguchi,Ikeda,Inagaki
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p. 10164 - 10172
(2007/10/03)
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- Transnitrosation by N-aryl-N-nitrosoureas; NO-carrying O-nitrosoisourea
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Transfer of nitroso groups, so-called transnitrosation, from aromatic N-nitroso compounds such as N-nitrosoureas, N-nitrosamides and N-nitrosamines, to aromatic amines or ureas was observed under non-acidic conditions at room temperature. Sterically hindered 3,3-dibenzyl-1-(4-tolyl)-1-nitrosourea (1a) rapidly nitrosates indoline, N-alkylanilines or 3-methyl-1-(4-tolyl)urea to give their N-nitroso derivatives. In the case of N,N-dimethylanilines, nitrosative demethylation occurs to give N-methyl-N-nitrosanilines. The transnitrosation is accelerated by electron-releasing groups on the nitroso acceptors, N-alkylanilines. The transnitrosation mechanism is considered to be as follows: N-nitrosourea (1) thermally decomposes to nitric oxide and ureidyl radical followed by formation of an O-nitrosoisourea intermediate (10), which acts as an NO-carrying agent and nitrosates anilines or ureas.
- Tanno,Sueyoshi,Miyata
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p. 1760 - 1767
(2007/10/02)
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- Development of high-affinity 5-HT3 receptor antagonists. Structure- affinity relationships of novel 1,7-annelated indole derivatives. 1
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On the basis of the structures of ondansetron and GR 65,630, its ring- opened C-linked methylimidazole analogue, novel 1,7-annelated indole derivatives were synthesized as potential 5-HT3 antagonists. Receptor binding studies show that all compounds display a high affinity for the 5- HT3 receptors. In both series annelation results in compounds being 7 and 4 times more potent than the references ondansetron and GR 65,630, respectively. Similar to ondansetron, the 1,7-annelated indoles show little stereoselectivity. The (-)-isomers are only slightly more potent than the (+)-isomers. The receptor binding profile of l-10-[(2-methyl-1H-imidazol-1- yl)methyl]-5,6,8,9,10,11-hexahydro-4H-pyrido[3,2,1-jk]carbazol-11-one hydrochloride (24b) (INN cilansetron) shows that the compound displays, besides a high affinity for 5-HT3 receptors (K(i) = 0.19 nM), a weak affinity for σ-receptors (K(i) = 340 nM), muscarine M1 receptors (K(i) = 910 nM), and 5-HT4 receptors (K(i) = 960 nM) and no affinity (K(i) ≥ 5000 nM) for all the other receptor types tested (n = 37). The new compounds fit the proposed necessary chemical template for binding: a heteroaromatic ring system, a coplanar carbonyl group, and a nitrogen center at well-defined distances. The enhanced potency of the annelated 1,7-indole derivatives indicates that the extra ring provides a favorable hydrophobic area for interaction with the 5-HT3 receptor site. In vivo cilansetron is more potent and induces less central side effects than ondansetron. At present cilansetron is in clinical trials.
- Van Wijngaarden,Hamminga,Van Hes,Standaar,Tipker,Tulp,Mol,Olivier,De Jonge
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p. 3693 - 3699
(2007/10/02)
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- 7-(α-Acetylbenzyl)indoline
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The preparation of compounds of the formula SPC1 Wherein R is selected from the group consisting of hydrogen and chlorine is described. The compounds are useful as chemical intermediates and as anti-inflammatory agents.
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