- I2-Promoted Intramolecular Oxidative Cyclization of Butenyl Anilines: A Facile Route to Benzo[b]azepines
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A metal-free approach for the synthesis of seven-membered N-heterocycles has been developed by the I2-promoted intramolecular cross-coupling/annulation of butenyl anilines. This cyclization reaction involves C?H activation and C?C bond formation and exhibits good functional group tolerance. A series of benzo[b]azepine derivatives are obtained in moderate to good yields.
- An, Zhenyu,Ren, Yi,Liu, Yafeng,Yan, Rulong
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supporting information
p. 2614 - 2617
(2021/08/06)
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- Synthesis and Evaluation of 2-Azetidinone and 1H-Pyrrole-2,5-dione Derivatives as Cholesterol Absorption Inhibitors for Reducing Inflammation Response and Oxidative Stress
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Excess lipid accumulation can initiate the development and progression of atherosclerotic lesions, thus eventually leading to cardiovascular disease. Lipid-lowering medication therapy is one of the cornerstones of cardiovascular disease therapy. On the basis of the cholesterol absorption inhibitor ezetimibe, we successfully synthesized seven 2-azetidinone derivatives and eighteen 1H-pyrrole-2,5-dione derivatives. Most of the new compounds significantly inhibited cholesterol uptake in vitro. In addition, one of the most active inhibitors, 3-(4-fluorophenyl)-1-[(3S)-3-hydroxy-3-(4-hydroxyphenyl)propyl]-4-(4-hydroxyphenyl)-1H-pyrrole-2,5-dione (14q), showed no cytotoxicity in L02 and HEK293T cell lines. Further evaluation indicated that 14q inhibited considerably the amount of TNF-α, ROS, MDA, and LDH in vitro. Therefore, 14q might be a novel cholesterol absorption inhibitor.
- Xia, Yineng,Zhu, Lijuan,Yuan, Xinrui,Wang, Yubin
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- Asymmetric Hydrogenation of β-Secondary Amino Ketones Catalyzed by a Ruthenocenyl Phosphino-oxazoline-ruthenium Complex (RuPHOX-Ru): The Synthesis of γ-Secondary Amino Alcohols
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A ruthenocenyl phosphino-oxazoline-ruthenium complex (RuPHOX-Ru) was applied successfully to the asymmetric hydrogenation of β-secondary amino ketones, directly affording the corresponding chiral γ-secondary amino alcohols in up to 99% yield and with 99% ee. Reaction with β-(benzylamino)-1-phenylpropan-1-one could be performed on a gram-scale with a relatively low catalyst loading (up to 2000 S/C). The resulting hydrogenated product could be used for the synthesis of synthetically useful compounds.
- Wang, Jianxia,Wang, Yanzhao,Liu, Delong,Zhang, Wanbin
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supporting information
p. 3262 - 3272
(2015/11/03)
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- PROTEIN CROSSLINKING INHIBITOR AND USE OF THE SAME
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The present invention relates to: a ketone compound having transglutaminase-inhibiting activity, which is represented by the following Formula 1, 2, or 3: wherein R1 is a substituted or unsubstituted aryl or heterocyclyl group, R2, R3, and R4 are hydrogen atoms, n is 2, X is halogen, R5 and R6 independently represent a hydrogen atom or a substituted or unsubstituted C1-C10 alkyl, aryl, or aralkyl group, wherein R5 and R6 are not hydrogen atoms at the same time, or R5 and R6 may be taken together to form a saturated or unsaturated and substituted or unsubstituted heterocyclyl group containing a nitrogen atom (N); an inhibitor of protein crosslinking comprising the compound; and a composition for preventing or treating a protein-crosslinking causative disease, which comprises the compound or the protein crosslinking inhibitor.
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Page/Page column 25
(2012/11/08)
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- Copper(II)-catalyzed hydrosilylation of ketones using chiral dipyridylphosphane ligands: Highly enantioselective synthesis of valuable alcohols
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In the presence of PhSiH3 as the reductant, the combination of enantiomeric dipyridylphosphane ligands and Cu(OAc)2·H 2O, which is an easy-to-handle and inexpensive copper salt, led to a remarkably practical and versatile chiral catalyst system. The stereoselective formation of a selection of synthetically interesting β-, γ- or δ-halo alcohols bearing high degrees of enantiopurity (up to 99.9 % enantiomeric excess (ee)) was realized with a substrate-to-ligand molar ratio (S/L) of up to 10 000. The present protocol also allowed the hydrosilylation of a diverse spectrum of alkyl aryl ketones with excellent enantioselectivities (up to 98 % ee) and exceedingly high turn-over rates (up to 50 000 S/L molar ratio in 50 min reaction time) in air, under very mild conditions, which offers great opportunities for the preparation of various physiologically active targets. The synthetic utility of the chiral products obtained was highlighted by the efficient conversion of optically enriched β-halo alcohols into the corresponding styrene oxide, β-amino alcohol, and β-azido alcohol, respectively.
- Yu, Feng,Zhou, Ji-Ning,Zhang, Xi-Chang,Sui, Yao-Zong,Wu, Fei-Fei,Xie, Lin-Jie,S. C. Chan, Albert,Wu, Jing
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supporting information; experimental part
p. 14234 - 14240
(2012/01/12)
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- Synthesis of enantiomerically pure γ-azidoalcohols by lipase-catalyzed transesterification
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An enantioselective synthesis of chiral γ-azidoalcohols via lipase-catalyzed resolution is described. The efficiency of various lipases and the effect of different solvents have been studied. Pseudomonas cepacia immobilized on diatomaceous earth (PS-D) in n-hexane catalyzed the transesterification process in an efficient manner providing γ-azidoalcohols in high enantiomeric excess.
- Kamal, Ahmed,Malik, M. Shaheer,Shaik, Ahmad Ali,Azeeza, Shaik
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p. 1078 - 1083
(2008/09/19)
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- 1-[(3-Aryloxy-3-aryl)propyl]-1H-imidazoles, new imidazoles with potent activity against Candida albicans and dermatophytes. Synthesis, structure-activity relationship, and molecular modeling studies
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New 1-[(3-aryloxy-3-aryl)propyl]-1H-imidazoles were synthesized and evaluated against Candida albicans and dermatophytes in order to develop structure-activity relationships (SARs). Against C. albicans the new imidazoles showed minimal inhibitory concentrations (MICs) comparable to those of ketoconazole, miconazole, and econazole, and were more potent than fluconazole. Several derivatives (10, 12, 14, 18-20, 24, 28, 29, 30, and 34) turned out to be potent inhibitors of C. albicans strains resistant to fluconazole, with MIC values less than 10 μg/mL. Against dermatophytes strains, compounds 20, 25, and 33 (MIC ≤ 5 μg/mL) were equipotent to ketoconazole, econazole, and miconazole. SARs of imidazoles 10-44 were rationalized with reasonable accuracy by a previously developed quantitative pharmacophore for antifungal agents.
- La Regina, Giuseppe,D'Auria, Felicia Diodata,Tafi, Andrea,Piscitelli, Francesco,Olla, Stefania,Caporuscio, Fabiana,Nencioni, Lucia,Cirilli, Roberto,La Torre, Francesco,De Melo, Nadja Rodrigues,Kelly, Steven L.,Lamb, David C.,Artico, Marino,Botta, Maurizio,Palamara, Anna Teresa,Silvestri, Romano
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scheme or table
p. 3841 - 3855
(2009/04/11)
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- Regio- and stereoselective ring opening of enantiomerically enriched 2-aryl oxetanes and 2-aryl azetidines with aryl borates
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(Chemical Equation Presented) The regioselective ring opening of 2-aryl-substituted four-membered heterocyclic rings with phenols, including catechol, was achieved by the use of aryl borates in mild and neutral reaction conditions without the aid of any transition metal catalysts. While β-alkyl azetidines were found not to be reactive, optically active N-tosyl azetidines gave the corresponding β-aryloxy amines in a racemic form, thus indicating the considerable carbocationic character of the transition state. The introduction of a hydroxyl group in the azetidine ring (i.e., an azetidinol), able to anchor the aryl borate and to direct the subsequent nucleophilic delivery, was shown to determine the ring-opening process with predominant inversion of configuration. When enantiomerically enriched 2-aryl oxetanes were used, the reduced extent of racemization observed (up to 93:7 er) was rationalized by an intramolecular delivery through a six-membered transition state, giving β-aryloxy alcohols with a predominant retention of configuration (i.e., a syn-stereoselective ring opening). The aryloxy alcohols obtained, endowed with suitable functionalities, can be cyclized to give access to enantiomerically enriched 2-aryl-1,5-benzodioxepins.
- Bertolini, Ferruccio,Crotti, Stefano,Di Bussolo, Valeria,Macchia, Franco,Pineschi, Mauro
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supporting information; experimental part
p. 8998 - 9007
(2009/04/11)
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- Imidazole analogues of fluoxetine, a novel class of anti-Candida agents
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Imidazole analogues of fluoxetine have been obtained by replacing the methylamino terminus of aminopropane chain with the imidazole ring. The newly designed imidazoles showed potent anti-Candida activity, superior to those of miconazole and other antifungal agents of clinical interest. 1-(4-Chlorophenyl)-l-(2,4-dichlorophenoxy)-3-(1H-imidazol-1-yl)propane (16), the most active among test imidazoles, Was about 2-fold more active and as much less cytotoxic than miconazole. High increase of activity was observed with methyl, nitro, fluorine, and chlorine (Cl > F > CH3 > NO2 > CF3).
- Silvestri, Romano,Artico, Marino,La Regina, Giuseppe,Di Pasquali, Alessandra,De Martino, Gabriella,D'Auria, Felicia Diodata,Nencioni, Lucia,Palamara, Anna Teresa
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p. 3924 - 3926
(2007/10/03)
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- N-phenyl-N′-phenylpopylpiperazine derivatives and process for the preparation
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The present invention is directed to an N-phenyl-N′-phenylpropylpiperazine derivative represented by formula (1): (wherein R1represents a lower alkyl group; R2represents a lower alkoxy group; and R3represents a cyano group
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- SCHWEFELVERBINDUNGEN DES ERDOELS XXII. ALKYL-10,11-DIHYDRODIINDENOTHIOPHENE
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The one-pot syntheses of alkyl-10,11-dihydrodiindenothiophenes (3) by bromination and sulfurization of alkylindan-1-ones without substituents at C-2 (1) has been studied with 14 1 with C1-C4-rests at the benzene and or the cyclopentane ring. 9 dialkyl-3 and 3 tetraalkyl-3 are prepared in yields of 7-66percent; an octamethyl-3 is detected by tlc and ms. 2 dialkyl-3 are prepared too by an independent syntheses from dimethyl 2,5-bis(methylphenyl)thiophene-3,4-dicarboxylates (13).The mechanism of the one-pot syntheses, which gives diindeno-1,4-dithiines too,is discussed.The oxidation of 4 3 has been studied.Key words: Alkylindan-1-ones, alkyl-10,11-dihydrodiindenothiophenes, alkyldiindeno-1,4-dithiines, one-pot syntheses of anellated thiophenes, oxidation of anellated thiophenes.
- Boberg, Friedrich,Deters, Karin,Schulz, Juergen,Torges, Karl-Franz
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- Modern Friedel-Crafts chemistry XIII. Intra- and intermolecular cyclization of some carbonyl derivatives under Friedel-Crafts conditions
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Carbonyl group deactivation in the cycloalkylation of aryl haloalkyl ketones was studied.Ketones 1-5 were prepared and subjected to treatment with AlCl3, AlCl3/H2SO4 and H2SO4 catalysts.Whereas AlCl3 catalyst gave no cyclization products, the use of AlCl3/H2SO4 and H2SO4 catalysts afforded the corresponding indanones and/or tetralones (6-11).The intermediate p-methylacrylophenone (12) was also obtained in the case of ketone 2.Furthermore intermolecular cyclizations of benzene, toluene and p-xylene with 3-chloropropionyl chloride (13) and 4-chlorobutyryl chloride (14) were investigated.In the presence of AlCl3/CH3NO2 catalyst, only the corresponding aryl haloalkyl ketones (1-5) were formed whereas the use of AlCl3 catalyst gave, in addition, some cyclic ketones.However, the use of AlCl3/H2SO4 catalyst gave only the corresponding cyclic ketones (6-11).Results are discussed and mechanisms are suggested.In conclusion, carbonyl group deactivation for ring closure is demonstrated in the investigated ketones and cyclization can only effected under strenuous conditions.
- Khalaf, Ali A.,Abdel-Wahab, Aboel-Magd A.,El-Khawaga, Ahmed M.,El-Zohry, Maher F.
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p. 285 - 291
(2007/10/02)
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