- Chemoselective reduction of α,β-unsaturated carbonyl compounds in the presence of CuPd alloy nanoparticles decorated on mesoporous graphitic carbon nitride as highly efficient catalyst
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Herein, we reported reductions of acid, amide, ester and ketone groups with selectivity (>99%) by the catalytic transfer hydrogenation of with CuPd alloy nanoparticles (NPs) decorated on mesoporous graphitic carbon nitride (Cu50Pd50/mpg-C3N4) catalyst under mild conditions in a water/methanol mixture. CuPd alloy NPs were synthesized by the co-reduction of palladium (II) acetylacetonate and copper(II) acetylacetonate in oleylamine (OAm) solution by the reduction of morpholine-borane solution and then assembled on mpg-C3N4 via liquid phase self‐assembly method. The α, β-unsaturated carbonyl compounds were obtained from the condensation reaction of the benzaldehyde derivatives with acetone derivatives. Cu50Pd50/mpg-C3N4 nanocatalyst was characterized by TEM, XRD, XPS, BET and ICP‐MS. Cu50Pd50/mpg-C3N4 nanocatalyst is highly active catalyst for the reduction of various organic groups and converted to high yield and 99% selectivity. The superior Cu50Pd50/mpg-C3N4 nanocatalyst is highly efficient and reusable catalyst which is reuse after 5 cycle with 98% conversion.
- Bayrak, Cetin,Menzek, Abdullah,Sevim, Melike
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- Manganese(I) Catalyzed α-Alkenylation of Amides Using Alcohols with Liberation of Hydrogen and Water
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Herein, unprecedented manganese-catalyzed direct α-alkenylation of amides using alcohols is reported. Aryl amides are reacted with diverse primary alcohols, which provided the α,β-unsaturated amides in moderate to good yields with excellent selectivity. Mechanistic studies indicate that Mn(I) catalyst oxidizes the alcohols to their corresponding aldehydes and also plays an important role in efficient C═C bond formation through aldol condensation. This selective olefination is facilitated by metal-ligand cooperation by the aromatization-dearomatization process operating in the catalytic system. Biorenewable alcohols are used as alkenylation reagents for the challenging α-alkenylation of amides with the highly abundant base metal manganese as a catalyst, which results in water and dihydrogen as the only byproduct, making this catalytic transformation attractive, sustainable, and environmentally benign.
- Pandia, Biplab Keshari,Gunanathan, Chidambaram
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p. 9994 - 10005
(2021/07/31)
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- Electron-Catalyzed Aminocarbonylation: Synthesis of α,β-Unsaturated Amides from Alkenyl Iodides, CO, and Amines
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Aminocarbonylation of alkenyl iodides with CO and amines proceeded under heating to produce α,β-unsaturated amides in good yields (23 examples, 71% average yield). This catalyst-free method exhibited good functional-group tolerance, and open a straightforward access to functionalized acrylamides, as illustrated by the synthesis of Ilepcimide. A hybrid radical/ionic mechanism involving chain electron transfer is proposed for this transformation.
- Picard, Baptiste,Fukuyama, Takahide,Bando, Takanobu,Hyodo, Mamoru,Ryu, Ilhyong
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supporting information
p. 9505 - 9509
(2021/12/09)
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- An Efficient Solvent-Free Microwave-Assisted Synthesis of Cinnamamides by Amidation Reaction Using Phenylboronic Acid/Lewis Base Co-catalytic System
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A microwave-assisted dehydrative amide condensation reaction is reported as an efficient access to cinnamamide derivatives under solvent-free conditions. This protocol between conjugated carboxylic acids and amines is based on the use of a co-catalytic system, including the presence of the commercially available phenylboronic acid and 4-(N, N-dimethylamino)pyridine N-oxide (DMAPO), with a complete chemoselectivity in favor of the corresponding α,β-unsaturated amides. The implementation of the reaction needs no special precaution, and less reactive amines, such as substituted anilines, are also efficient under these conditions. A series of novel conjugated amides have been evaluated for their cytotoxic activities against several human cancer cell lines.
- Carboni, Bertrand,Khaldoun, Khadidja,Safer, Abdelmounaim,Saidi-Besbes, Salima,Carreaux, Fran?ois,Le Guével, Rémy
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p. 3891 - 3900
(2019/10/11)
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- Substituted Hantzsch Esters as Versatile Radical Reservoirs in Photoredox Reactions
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Substituted Hantzsch esters can act as radical reservoirs in photoredox reactions, steadily releasing a carbon radical and a hydrogen atom radical in the absence of an additional electron acceptor. We propose that radical release by substituted Hantzsch esters occurs via a mechanism involving an internal redox cycle. Cinnamidecinnamides, styrenes, α,β-unsaturated acids, and diarylethenes could be alkylated smoothly with these reagents. (Figure presented.).
- Gu, Fangjun,Huang, Wenhao,Liu, Xu,Chen, Wenxin,Cheng, Xu
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supporting information
p. 925 - 931
(2018/01/04)
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- Palladium-Catalyzed Carbonylative Synthesis of α,β-Unsaturated Amides from Styrenes and Nitroarenes
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A procedure on palladium-catalyzed selective aminocarbonylation of styrenes with nitroarenes for the synthesis of α,β-unsaturated amides has been developed. A range of substituted α,β-unsaturated amides were synthesized in moderate to good yields. Interestingly, nitroarenes act as both a nitrogen source and oxidant, and Mo(CO)6 acts as a solid CO source and reductant in this catalytic system.
- Peng, Jin-Bao,Geng, Hui-Qing,Li, Da,Qi, Xinxin,Ying, Jun,Wu, Xiao-Feng
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supporting information
p. 4988 - 4993
(2018/08/24)
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- Boronic acid-DMAPO cooperative catalysis for dehydrative condensation between carboxylic acids and amines
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Arylboronic acid and 4-(N,N-dimethylamino)pyridine N-oxide (DMAPO) cooperatively catalyse the dehydrative condensation reaction between carboxylic acids and amines to give the corresponding amides under azeotropic reflux conditions. This cooperative use is much more effective than their individual use as catalysts, and chemoselectively promotes the amide condensation of (poly)conjugated carboxylic acids. The present method is practical and scalable, and has been applied to the synthesis of sitagliptin and a drug candidate.
- Ishihara, Kazuaki,Lu, Yanhui
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p. 1276 - 1280
(2016/02/05)
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- Design, synthesis and antibacterial activity of cinnamaldehyde derivatives as inhibitors of the bacterial cell division protein FtsZ
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In an attempt to discover potential antibacterial agents against the increasing bacterial resistance, novel cinnamaldehyde derivatives as FtsZ inhibitors were designed, synthesized and evaluated for their antibacterial activity against nine significant pathogens using broth microdilution method, and their cell division inhibitory activity against four representative strains. In the in vitro antibacterial activity, the newly synthesized compounds generally displayed better efficacy against Staphylococcus aureus ATCC25923 than the others. In particular, compounds 3, 8 and 10 exerted superior or comparable activity to all the reference drugs. In the cell division inhibitory activity, all the compounds showed the same trend as their in vitro antibacterial activity, exhibiting better activity against S. aureus ATCC25923 than the other strains. Additionally, compounds 3, 6, 7 and 8 displayed potent cell division inhibitory activity with an MIC value of below 1 1/4g/mL, over 256-fold better than all the reference drugs.
- Li, Xin,Sheng, Juzheng,Huang, Guihua,Ma, Ruixin,Yin, Fengxin,Song, Di,Zhao, Can,Ma, Shutao
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- Design, synthesis, and evaluation of caffeic acid amides as synergists to sensitize fluconazole-resistant Candida albicans to fluconazole
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A series of caffeic acid amides were designed, synthesized, and their synergistic activity with fluconazole against fluconazole-resistant Candida albicans was evaluated in vitro. The title caffeic acid amides 3-30 except 26 exhibited potent activity, and the subsequent SAR study was conducted. Compound 3, 5, 21, and 34c, at a concentration of 1.0 μg/ml, decreased the MIC80 of fluconazole from 128.0 μg/ml to 1.0-0.5 μg/ml against the fluconazole-resistant C. albicans. This result suggests that the caffeic acid amides, as synergists, can sensitize drug-resistant fungi to fluconazole. The SAR study indicated that the dihydroxyl groups and the amido groups linking to phenyl or heterocyclic rings are the important pharmacophores of the caffeic acid amides.
- Dai, Li,Zang, Chengxu,Tian, Shujuan,Liu, Wei,Tan, Shanlun,Cai, Zhan,Ni, Tingjunhong,An, Maomao,Li, Ran,Gao, Yue,Zhang, Dazhi,Jiang, Yuanying
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- Direct amidation of carboxylic acids with amines under microwave irradiation using silica gel as a solid support
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A highly improved and green methodology for the direct amidation of carboxylic acids with amines using silica gel as a solid support and catalyst is described. The scope of this method is exemplified by the use of several aliphatic, aromatic, unsaturated and fatty acids. The reaction is also applied to different primary and secondary amines. Typically, the amines should be aliphatic, but aromatic amines can be used as well, though with lower yields. Several experiments to illustrate the selectivity of this methodology were also carried out with several more functionalized acids and amines. This approach is a substantial improvement over other previously described methods in amide synthesis.
- Ojeda-Porras, Andrea,Hernández-Santana, Alejandra,Gamba-Sánchez, Diego
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supporting information
p. 3157 - 3163
(2015/05/27)
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- TMSCl-mediated synthesis of α,β-unsaturated amides via C-C bond cleavage and C-N bond formation of propargyl alcohols with trimethylsilyl azide
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A new method with high efficiency for the synthesis of α,β- unsaturated amides from the easily prepared propargyl alcohols and TMSN 3 using TMSCl as an acid promoter is developed. A wide variety of α,β-unsaturated amides were produced in moderate to excellent yields. Mechanistic studies indicate that this transformation involves TMSCl-mediated allenylazide intermediate formation, C-C bond cleavage, and C-N bond formation. Significantly, this reaction shows good functional group compatibility and high regioselectivity, with a relatively short reaction time and inexpensive reagents.
- Song, Xian-Rong,Song, Bo,Qiu, Yi-Feng,Han, Ya-Ping,Qiu, Zi-Hang,Hao, Xin-Hua,Liu, Xue-Yuan,Liang, Yong-Min
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p. 7616 - 7625
(2014/09/16)
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- Synthesis, structure, and biological assay of cinnamic amides as potential EGFR kinase inhibitors
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A series of derivatives of cinnamic amide (compounds 2a-2v) were synthesized and evaluated for antiproliferative activities against the human breast cancer cell line MCF-7- and EGFR-inhibitory activities. The structures of compounds 2b and 2i were determined by single-crystal X-ray diffraction analysis. Compounds 2f and 2j showed moderate EGFR inhibitory activity with IC50 values of 5.16 and 7.37 μM, respectively. Docking simulation of compound 2f was carried out to illustrate the binding mode of the molecule into the EGFR active site. Structure-activity relationship analysis found that the N-phenyl rings are required for enhancing the activities.
- Zhang, Mao,Lu, Xiang,Zhang, Hong-Jia,Li, Na,Xiao, Yu,Zhu, Hai-Liang,Ye, Yong-Hao
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p. 986 - 994
(2013/04/23)
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- Preparation of esters and amides from carboxylic acids and N-formylation of amines promoted by 1,3,5-triazo-2,4,6-triphosphorine-2,2,4,4,6,6-hexachloride (TAPC)
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A new method is described for the preparation of esters and amides promoted by TAPC from carboxylic acids using a solvent-free grinding technique. The solvent-free N-formylation of amines is also reported.
- Bahrami, Kiumars,Khodaei, Mohammad M.,Targhan, Homa,Sheikh Arabi, Mehdi
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supporting information
p. 5064 - 5068
(2013/09/02)
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- Synthesis and structure-activity relationship analysis of caffeic acid amides as selective matrix metalloproteinase inhibitors
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Four series of acid amides were synthesized, and through measurement using a fluorogenic substrate assay with human recombinant MMP-1, MMP-2 and MMP-9, compound 3f showed considerable inhibitory activities against MMP-2, MMP-9 and the best selectivity over MMP-1. Preliminary structure-activity relationship analysis indicated that caffeic acid amides with electron-donating groups at para-position of amino phenyl group showed better inhibitory activities and selectivity than those with electron-withdrawing groups, and the presence of adjacent dihydroxy in the caffeoyl group was very important for the MMP-2 and MMP-9 inhibitory activities.
- Shi, Zhi-Hao,Li, Nian-Guang,Shi, Qian-Ping,Tang, Hao,Tang, Yu-Ping,Li, Wei,Yin, Lian,Yang, Jian-Ping,Duan, Jin-Ao
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p. 1206 - 1211
(2013/03/14)
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- Phosphine-based redox catalysis in the direct traceless staudinger ligation of carboxylic acids and azides
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Redox catalysis: Aryl amides, imides, lactams, and dipeptides are obtained through a direct Staudinger ligation mediated by phosphine-based redox catalysis (see scheme). Mechanistic studies indicate the involvement of a phosphonium carboxylate intermediate that leads to a 1,3-acyl migration and thus results in C-N bond formation. Copyright
- Kosal, Andrew D.,Wilson, Erin E.,Ashfeld, Brandon L.
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supporting information
p. 12036 - 12040
(2013/01/16)
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- Iron-catalyzed C-H and C-C bond cleavage: A direct approach to amides from simple hydrocarbons
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Something functional: The title reaction proceeds in the presence of azide and water to deliver amides in high yields, and it can be used in a ring-expansion strategy to generate lactams. A mechanism is proposed based on experimental results. This reaction offers a new approach to functionalizing simple and readily available hydrocarbons. DDQ=2,3-dichloro-5,6-dicyano-1,4- benzoquinone. Copyright
- Qin, Chong,Zhou, Wang,Chen, Feng,Ou, Yang,Jiao, Ning
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supporting information; experimental part
p. 12595 - 12599
(2012/01/15)
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- Accessing the amide functionality by the mild and low-cost oxidation of imine
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Oxidation of imines using sodium chlorite under buffered conditions gave the corresponding amides in good to high yield. The reaction was generally fast and was completed within 5-40 min. As has been established in the corresponding oxidation of aldehyde, so-called Pinnick oxidation, the good functional group tolerance and the use of inexpensive reagents are the advantages of this protocol.
- Mohamed, Magdi A.,Yamada, Ken-ichi,Tomioka, Kiyoshi
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experimental part
p. 3436 - 3438
(2009/09/25)
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- 2-[3H-THIAZOL-2-YLIDINEMETHYL]PYRIDINES AND RELATED COMPOUNDS AND THEIR USE
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The present invention pertains to certain 2-[3H-thiazol-2-ylidinemethyl]pyridine compounds and analogs thereof, which, inter alia, inhibit cell proliferation, treat cancer, etc., and more specifically to compounds of the following formula, wherein RA1, RA2, RA3, RA4, RB1, RB2, RNA, RNB, and X? are as defined herein: The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit cell proliferation, and in the treatment of proliferative conditions such as cancer, etc.
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-
Page/Page column 27; 46
(2009/10/06)
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- SmI3-catalyzed addition of amines to α,β-unsaturated N-acylbenzotriazoles
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The addition of amines to α,β-unsaturated N-acylbenzotriazoles could be catalyzed by samarium triiodide (SmI3) at ambient temperature. α,β-Unsaturated aliphatic N-acylbenzotriazoles afforded bis-addition products (β-amino amides), whereas N-cinnamoylbenzo
- Wang, Xiaoxia,He, Liang,Li, Zhifang,Wang, Wencun,Liu, Junhua
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experimental part
p. 819 - 829
(2009/08/08)
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- Features and applications of reactions of α,β-unsaturated N-acylbenzotriazoles with amino compounds
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Promoted by triethylamine, α,β-unsaturated N-acylbenzotriazoles reacted with amino compounds in a variety of ways. Thus, N-cinnamoylbenzotriazoles reacting with aromatic amines afforded novel addition products β-benzotriazolyl amides 3, which might be normally formed from the alternative but unknown 1,4-addition of benzotriazole to N-cinnamoylamides. The type 3 compounds could also result from the reaction between N-crotonoylbenzotriazole and aliphatic amines. However, normal 1,4-addition could occur between α,β-unsaturated aliphatic N-acylbenzotriazoles and aromatic amines, leading to β-amino N-acylbenzotriazoles 4 in good yields. In addition, exclusive 1,2-addition of aliphatic amines to N-cinnamoylbenzotriazoles gave excellent yields of cinnamides 5. Accordingly, three possible routes were proposed to rationalize the formation of compounds 3-5. Finally, with o-phenylenediamine and o-aminothiophenol as the substrates, the 1,4- and 1,2-addition to α,β-unsaturated N-acylbenzotriazoles could take place concurrently and the corresponding heterocycles 1,5-benzodiazepine-2-one and 1,5-benzothiazepine-4-one were constructed, respectively.
- Wang, Xiaoxia,Li, Zhifang,Zhu, Xiangming,Mao, Hui,Zou, Xuefei,Kong, Lichun,Li, Xinsheng
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p. 6510 - 6521
(2008/09/21)
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- Metal-free synthesis of alkynyl imines using an oxophosphonium-mediated approach at ambient temperatures
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A metal-free approach was developed for the mild synthesis of N-aryl α-alkynyl imines from corresponding amide precursors for the first time. The electronic effects of substrates and the reaction mechanisms were investigated and discussed. This newly deve
- Dong, Qing-Li,Liu, Guan-Sai,Zhou, Hai-Bin,Chen, Lin,Yao, Zhu-Jun
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p. 1636 - 1640
(2008/09/18)
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- New procedure for the total synthesis of cilostamide
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An efficient route to synthesise a wide range of N,N-R,R-4-(2-oxo-1,2- dihydroquinolin-6-yloxy)butanamide, specially Cilostamide (R = methyl and R = cyclohexyl), one of the most selective inhibitors of phosphodiesterase3 (PDE3) enzyme, from 5-methoxy-2-ni
- Seyedi, Seyed Mohammad,Sadeghian, Hamid,Arghiani, Zahra
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experimental part
p. 183 - 186
(2009/04/06)
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- Esters, amides and substituted derivatives of cinnamic acid: Synthesis, antimicrobial activity and QSAR investigations
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A series of esters (Ia-k), substituted derivatives (II a-d) and amides (IIIa-q) of cinnamic acid were synthesized and evaluated as antibacterial and antifungal agents. All the derivatives belonging to the series I, II and III showed antimicrobial activity comparable to the standard. Compounds If and IIc proved to be the most effective compounds. Quantitative structure-activity relationship (QSAR) investigation with multiple linear regression analysis was applied to find a correlation between different calculated physicochemical parameters of the compounds and biological activity. The quantitative models relating the structural features of cinnamic acid derivatives Ia-k, II a-d and IIIa-q and their antimicrobial activity showed that Gram negative Escherichia coli and Candida albicans (fungus) were the most sensitive microorganisms.
- Narasimhan, Balasubramanian,Belsare, Deepak,Pharande, Devayani,Mourya, Vishnukant,Dhake, Avinash
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p. 827 - 834
(2007/10/03)
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- Photochemical debromination of vic-dibromides
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Photochemical debromination of dibromohydro cinnamamides gave the carbon-carbon double bond compounds.
- Aruna,Kalyanakumar,Ramakrishnan
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p. 3125 - 3130
(2007/10/03)
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- Unusual Regioselectivity of the Dipolar Cycloaddition Reactions of Nitrile Oxides and Tertiary Cinnamides and Crotonamides
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Benzonitrile oxides undergo 1,3-dipolar cycloaddition reactions with methyl cinnamate to produce the 5-phenyl and 4-phenyl regioisomers in approximately an 80:20 ratio. However, use of N,N-diethylcinnamide as the dipolarophile unexpectedly resulted in the formation of the 5-phenyl and 4-phenyl regioisomers in a 23:77 ratio. Studies have shown that this phenomena occurs only for tertiary cinnamides. In addition, it has been demonstrated that the phenyl group of tertiary cinnamides is not essential for the reversal of regioselectivity since crotonamides produce the same results and trends as the cinnamides. However, since acrylates and acrylamides both produce the 5-carbonyl regioisomers, it can be concluded that the β-substituent is playing a key role for the unexpected results by possibly increasing steric interactions between the dipole and dipolarophile in the transition state. Transition state energies were calculated for the regioisomeric cycloadduct pairs derived from several crotonamides as well as methyl crotonate. These calculations indicate that steric factors are indeed responsible for the reversal of regioselectivity.
- Weidner-Wells, Michele A.,Fraga-Spano, Stephanie A.,Turchi, Ignatius J.
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p. 6319 - 6328
(2007/10/03)
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- Lewis acid catalyzed reaction of cinnamanilides: Competition of intramolecular and intermolecular Friedel-Crafts reaction
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The first intermolecular Friedel-Crafts reaction of benzene leading to the formation of 3,3-diphenylpropionanilide 7 is described. 4-Methoxyaniline was reacted with cinnamoyl chloride to give 4-methoxycinnamanilide (5a), the treatment of which with aluminum (III) chloride in chlorobenzene at 120 °C or in benzene at 80 °C afforded exclusively 6-hydroxyquinolin-2(1H)-one (3a) or 4'-hydroxy-3,3-diphenylpropionanilide (7a), respectively. The formation of 7a rather than 3a in benzene indicated that an intermolecular Friedel-Crafts reaction occurred prior to the relatively more facile intramolecular ring cyclization. This intermolecular Friedel-Crafts reaction was observed during the attempted ring cyclization of cinnamanilide and its methoxy derivatives in aluminum (III) chloride/benzene. Preparation of 3a can also be achieved in 17% overall yield via the N-oxidation of 6-hydroxyquinoline followed by acetylation and hydrolysis.
- Wang, Tai-Chi,Chen, Yeh-Long,Lee, Kuan-Han,Tzeng, Cherng-Chyi
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- Synthesis and Biological Evaluation of 2-Styrylquinazolin-4(3H)-ones, a New Class of Antimitotic Anticancer Agents Which Inhibit Tubulin Polymerization
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A novel series of 2-styrylquinazolin-4(3H)-ones which inhibited tubulin polymerization and the growth of L1210 murine leukemia cells was discovered.Extensive structure-activity relationship studies suggest that the entire quinazolinone structure was requi
- Jiang, J. B.,Hesson, D. P.,Dusak, B. A.,Dexter, D. L.,Kang, G. J.,Hamel, E.
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p. 1721 - 1728
(2007/10/02)
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- Substituted carbostyrils as inhibitors of cyclic AMP phosphodiesterase
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A series of 6-substituted carbostyrils has been synthesized and tested as inhibitors of two vascular smooth muscle phosphodiesterases, one of them selective for cyclic AMP and the other calmodulin dependent and selective for cyclic GMP. The inhibitory act
- Lugnier,Bruch,Stoclet,et al.
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p. 121 - 125
(2007/10/02)
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- Formation of 2,3-Dihydro-4(1H)-quinolones and Related Compounds via Fries-type Acid-catalysed Rearrangement of 1-Arylazetidin-2-ones
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A variety of 1-arylazetidin-2-ones were treated with trifluoroacetic acid under reflux, methanesulphonic acid at 100 deg C, or conc. sulphuric acid to give the corresponding 2,3-dihydro-4(1H)-quinolones via acyl migration and N-CO fission.In the case of 1-(3-substituted phenyl)azetidin-2-ones, two positional isomeric products, 5- and 7-substituted 2,3-dihydro-4(1H)-quinolones were obtained. 4-Methyl, 4-ethoxycarbonyl, and 4-piperidin-2-yl-1-arylazetidin-2-ones and their analogues were also converted into the corresponding 2-substituted 2,3-dihydro-4(1H)-quinolones under acidic conditions.The 3-substituted 1-phenylazetidin-2-ones (36) and (37) were converted into the furoquinoline systems (38) and (40), respectively, by application of this method.
- Kano, Shinzo,Ebata, Tsutomu,Shibuya, Shiroshi
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p. 2105 - 2111
(2007/10/02)
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