- Catalytic activity of copper(II) benzenetricarboxylate (HKUST-1) in reactions of aromatic aldehydes condensation with nitromethane: Kinetic and diffusion study
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Catalytic activity of copper(II) 1,3,5-benzenetricarboxylate, HKUST-1, in reactions of condensation of aromatic aldehydes with nitromethane was studied. It was shown that HKUST-1 catalyzed condensation of salicylaldehyde with nitromethane leading to formation of trans-nitrovinylphenol, while 9-anthracenecarbaldehyde did not react in the same conditions. Catalytic activity of HKUST-1 was consistent with its sorption capacity in respect to the reagents. The difference in catalytic activity of HKUST-1 in reactions with salicylaldehyde and 9-anthracenecarbaldehyde can be caused by sieving effect (molecules discrimination by size). Kinetics of salicylaldehyde condensation with nitromethane, catalyzed by HKUST-1, as well as kinetics of salicylaldehyde sorption by HKUST-1 were studied. Accessibility of pores of HKUST-1 to salicylaldehyde and condensation product (trans-nitrovinylphenol) was evaluated by molecular mechanics. Catalytic activity (reaction rate and salicylaldehyde diffusion rate) of HKUST-1 is compared with FeIII analog, role of diffusion rate is shown.
- Sotnik, Svetlana A.,Gavrilenko, Konstantin S.,Lytvynenko, Anton S.,Kolotilov, Sergey V.
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Read Online
- Synthesis, characterization and crystal structure of trans-2-(2- Hydroxyphenyl)-1-nitroethylene
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The nitroalkene compound, namely trans-2-(2-hydroxyphenyl)-1-nitroethylene (I), has been successfully synthesized from the condensation of 2-hydroxybenzaladehyde with nitromethane. It was characterized by elemental analysis, 1H NMR spectrum and single-cry
- Liu, Yun-Feng,Liu, Sheng-Nan,Zhao, Pei-Hua,Li, Xin-Hang,Liang, Wen-Jun,Liu, Ya-Qing
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- Synthesis, crystal structure, and physicochemical properties of the new metal-organic framework - The iron(III) complex with benzene- 1,3,5-tricarboxylate
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A new iron(III) coordination compound with the benzene- 1,3,5-tricarboxylate anion of the composition [FeIII2(OH)0.3(H2O)1.7(btc)4/3]Cl1.7· 2.8DMF·1.9H2O (1) was synthesized. Its crystal structure was determined, and the M ? ssbauer spectra were analyzed. The adsorption of salicylaldehyde and nitromethane by compound 1 was studied. The adsorption kinetics of salicylaldehyde is described by the pseudo-second order equation. The diffusion of this aldehyde in particles of compound 1 is, most probably, the rate-limiting step in the Henry reaction.
- Sotnik,Kolotilov,Kiskin,Dobrokhotova,Gavrilenko,Novotortsev,Eremenko,Imshennik,Maksimov,Pavlishchuk
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Read Online
- Green sustainable approach for carbon–carbon bond-forming reactions using FeNPs/DETA@rGO nano-catalyst
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We have fabricated eccentric highly persuasive bifunctional FeNPs/DETA@rGO (where DETA = diethylenetriamine) nano-catalyst with a dual activation mechanism by presenting aliphatic amine on the basal and/or edges sites offering a base characteristic and Fe
- Kane, Sanjeev R.,Modi, Chetan K.,Patel, Dikin,Srivastava, Himanshu,Trivedi, Komal A.
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- Regio- and Stereoselective Cascade of β,γ-Unsaturated Ketones by Dipeptided Phosphonium Salt Catalysis: Stereospecific Construction of Dihydrofuro-Fused [2,3-b] Skeletons
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Chiral (dihydro)furo-fused heterocycles are significant structural motifs in numerous natural products, functional materials and pharmaceuticals. Therefore, developing efficient methods for preparing compounds with these privileged scaffolds is an important endeavor in synthetic chemistry. Herein, we develop an effective, modular method by a dipeptide-phosphonium salt-catalyzed regio- and stereoselective cascade reaction of readily available linear β,γ-unsaturated ketones with aromatic alkenes, affording a wide variety of structurally fused heterocyclic molecules in high yields with excellent stereoselectivities. Moreover, mechanistic investigations revealed that the bifunctional phosphonium salt controlled the regio- and stereoselectivities of this cascade reaction, particularly proceeding through the initial ketone α-addition followed by O-participated substitution; and the multiple hydrogen-bonding interactions between Br?nsted acid moieties of catalyst and nitro group of aromatic alkene were crucial in asymmetric induction. Given the generality, versatility, and high efficiency of this method, we anticipate that it will have broad synthetic utilities.
- Chen, Yayun,He, Jiajia,Jiang, Chunhui,Ren, Xiaoyu,Su, Zhishan,Wang, Tianli,Xiao, Kai,Zhang, Hongkui,Zhuang, Cheng
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supporting information
p. 19860 - 19870
(2021/08/06)
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- Strategies towards potent trypanocidal drugs: Application of Rh-catalyzed [2?+?2?+?2] cycloadditions, sulfonyl phthalide annulation and nitroalkene reactions for the synthesis of substituted quinones and their evaluation against Trypanosoma cruzi
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Rhodium-catalyzed [2 + 2 + 2] cycloadditions, sulfonyl phthalide annulations and nitroalkene reactions have been employed for the synthesis of 56 quinone-based compounds. These were evaluated against Trypanosoma cruzi, the parasite that causes Chagas disease. The reactions described here are part of a program that aims to utilize modern, versatile and efficient synthetic methods for the one or two step preparation of trypanocidal compounds. We have identified 9 compounds with potent activity against the parasite; 3 of these were 30-fold more potent than benznidazole (Bz), a drug used for the treatment of Chagas disease. This article provides a comprehensive outline of reactions involving over 120 compounds aimed at the discovery of new quinone-based frameworks with activity against T. cruzi.
- Wood, James M.,Satam, Nishikant S.,Almeida, Renata G.,Cristani, Vinicius S.,de Lima, Dênis P.,Dantas-Pereira, Luiza,Salom?o, Kelly,Menna-Barreto, Rubem F.S.,Namboothiri, Irishi N.N.,Bower, John F.,da Silva Júnior, Eufranio N.
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- Facile synthesis of chiral [2,3]-fused hydrobenzofuran: Via asymmetric Cu(i)-catalyzed dearomative 1,3-dipolar cycloaddition
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Intermolecular asymmetric dearomative 1,3-dipolar cycloaddition of 2-nitrobenzofurans with azomethine ylides was enabled by using a chiral Cu(i)/(S,Sp)-iPr-Phosferrox catalyst. As a result, a series of highly stereoselective chiral [2,3]-fused hydrobenzofurans possessing four contiguous stereogenic centers were obtained with good to high yields, diastereoselectivities and enantioselectivities. The reaction has broad substrate scope tolerating various functional groups.
- Liang, Lei,Niu, Hong-Ying,Wang, Dong-Chao,Yang, Xin-He,Qu, Gui-Rong,Guo, Hai-Ming
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supporting information
p. 553 - 556
(2019/01/10)
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- Enantioselective dearomative [3+2] cycloaddition of 2-nitrobenzofurans with aldehyde-derived Morita-Baylis-Hillman carbonates
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The phosphine-catalyzed asymmetric dearomative [3+2] cycloaddition of 2-nitrobenzofurans with aldehyde-derived Morita-Baylis-Hillman (MBH) carbonates or allenoate was developed. The reaction with MBH carbonates resulted in a series of cyclopentabenzofurans containing three contiguous stereocenters with good to high yields, diastereoselectivities and enantioselectivities. The use of allenoate also gave the target product with moderate enantioselectivity.
- Yang, Xin-He,Li, Jian-Ping,Wang, Dong-Chao,Xie, Ming-Sheng,Qu, Gui-Rong,Guo, Hai-Ming
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supporting information
p. 9144 - 9147
(2019/08/07)
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- Phosphine-Catalyzed Enantioselective Dearomative [3+2]-Cycloaddition of 3-Nitroindoles and 2-Nitrobenzofurans
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Over the past years, the metal-catalyzed dearomative cycloaddition of 3-nitroindoles and 2-nitrobenzofurans have emerged as a powerful protocol to construct chiral fused heterocyclic rings. However, organocatalytic dearomative reaction of these two classe
- Wang, Huamin,Zhang, Junyou,Tu, Youshao,Zhang, Junliang
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supporting information
p. 5422 - 5426
(2019/03/17)
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- Synthesis, antiproliferative and pro-apoptotic effects of nitrostyrenes and related compounds in Burkitt’s lymphoma
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Background: Cancers of the lymphatic cells (lymphomas) account for approximately 12% of malignant diseases worldwide. The nitrostyrene scaffold is identified as a lead target structure for the development of particularly effective compounds targeting Burkitt’s lymphoma (BL). Objectives: The aims of the curent study were to synthesise a panel of nitrostyrene compounds and to evaluate their activity in Burkitt’s lymphoma (BL). Methods: A panel of structurally varied compounds were designed and synthesised using Henry Knoevenagel condensation reactions. Single crystal X-Ray analysis confirmed the E configuration for six examples of these novel structures. A number of nitrostyrene-related compounds were also investigated including 1,3-bis(aryl)-2-nitropropenes together with heterocyclic scaffolds containing the nitrovinyl pharmacophore such as 3-nitro-2-phenyl-2H-chromenes. The antiproliferative activities of the compounds were evaluated using the BL cell lines EBV- MUTU-1 and EBV+ DG-75 (chemoresistant) to establish preliminary structure-activity relationships. Results: Lead compounds with optimized nitrostyrene scaffolds and 3-nitro-2-phenyl-2Hchromene structures were successfully established with typical IC50 values of 0.45 μM and 0.47 μM in MUTU-1 cells and 1.41 μM and 1.92 μM, respectively, in DG-75 cells. The mechanism of cell death was identified as apoptotic and the lead compound was found to elicit comparable apoptotic effects to Taxol in Burkitt’s lymphoma cell lines MUTU-1 and DG-75. Conclusion: This class of pharmaceutically active compounds with potential for the treatment of Burkitt’s lymphoma suggest a potential role for nitrostyrene based agents in chemotherapy.
- Byrne, Andrew J.,Bright, Sandra A.,Fayne, Darren,McKeown, James P.,McCabe, Thomas,Twamley, Brendan,Williams, Clive,Meegan, Mary J.
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p. 181 - 199
(2018/03/13)
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- Carboxylate Salt Bridge-Mediated Enamine Catalysis: Expanded Michael Reaction Substrate Scope and Facile Access to Antidepressant (R)-Pristiq
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We report broad guidance on how to catalyze enantioselective aldehyde additions to nitroalkene or maleimide Michael electrophiles in the presence of unprotected acidic spectator groups, e.g., carboxylic acids, acetamides, phenols, catechols, and maleimide
- Nugent, Thomas C.,Hussein, Hussein Ali El Damrany,Ahmed, Shahzad,Najafian, Foad Tehrani,Hussain, Ishtiaq,Georgiev, Tony,Aljoumhawy, Mahmoud Khalaf
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supporting information
p. 2824 - 2831
(2017/08/23)
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- Acid-Mediated Intermolecular [3 + 2] Cycloaddition toward Pyrrolo[2,1-a]isoquinolines: Total Synthesis of the Lamellarin Core and Lamellarin G Trimethyl Ether
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A novel one-pot reaction has been developed for the efficient synthesis of pyrrolo[2,1-a]isoquinolines and 1-dearyllamellarin core from (E)-(2-nitrovinyl)benzenes and azomethine ylides generated in situ. This strategy provides a concise total synthesis of
- Zheng, Kai-Lu,You, Min-Qi,Shu, Wen-Ming,Wu, Yan-Dong,Wu, An-Xin
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supporting information
p. 2262 - 2265
(2017/05/12)
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- Stereoselective reaction of 2-carboxythioesters-1,3-dithiane with nitroalkenes: An organocatalytic strategy for the asymmetric addition of a glyoxylate anion equivalent
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An efficient organocatalytic methodology has been developed to perform the stereoselective addition of 2-carboxythioesters-1,3-dithiane to nitroalkenes. Under mild reaction conditions γ-nitro-β-aryl-α-keto esters with up to 92% ee were obtained, realizing a formal catalytic stereoselective conjugate addition of the glyoxylate anion synthon. The reaction products are versatile starting materials for further synthetic transformations; for example, the simultaneous reduction of the nitro group and removal of the dithiane ring was accomplished, allowing the preparation of a GABAB receptor agonist baclofen.
- Massolo, Elisabetta,Benaglia, Maurizio,Genoni, Andrea,Annunziata, Rita,Celentano, Giuseppe,Gaggero, Nicoletta
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supporting information
p. 5591 - 5596
(2015/05/27)
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- Intermediates for macrocyclic compounds
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The present invention is directed to novel macrocyclic compounds of formula (I) and their pharmaceutically acceptable salts, hydrates or solvates: wherein R1, R2, R3, R4, R5, R6, n1, m, p Z1, Z2, and Z3 are as describe in the specification. The invention also relates to compounds of formula (I) which are antagonists of the motilin receptor and are useful in the treatment of disorders associated with this receptor and with or with motility dysfunction.
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Page/Page column 33; Sheet 7
(2015/11/30)
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- A high yield procedure for the preparation of 2-hydroxynitrostyrenes: Synthesis of imines and tetracyclic 1,3-benzoxazines
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Attempts to synthesize 2-hydroxynitrostyrenes by a Knoevenagel condensation of salicylaldehyde and subsequent elimination were unsuccessful because of the formation of a stable imine. This could be easily prevented by using secondary amines to catalyze the reaction, which then afforded 2-hydroxynitrostyrenes in high yields. In addition, the stable imine that was formed by employing ammonium acetate underwent a reaction with phosgene to allow the preparation of benzoxazines in good yields. Copyright
- Tena Perez, Victor,Fuentes De Arriba, Angel L.,Monleon, Laura M.,Simon, Luis,Rubio, Omayra H.,Sanz, Francisca,Moran, Joaquin R.
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p. 3242 - 3248
(2014/06/09)
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- Aldehyde-Assisted Ruthenium(II)-Catalyzed C-H Oxygenations
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Versatile ruthenium(II) complexes allow for site-selective C-H oxygenations with weakly-coordinating aldehydes. The challenging C-H functionalizations proceed with high chemoselectivity by rate-determining C-H metalation. The new method features an ample substrate scope, which sets the stage for the step-economical preparation of various bioactive heterocycles.
- Yang, Fanzhi,Rauch, Karsten,Kettelhoit, Katharina,Ackermann, Lutz
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supporting information
p. 11285 - 11288
(2016/02/18)
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- Preparation of indium nitronates and their Henry reactions
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Indium nitronates were readily prepared from commercially available nitroalkanes by transmetallation of the corresponding lithium nitronates with indium salts. The Henry reaction of this indium organometallics with aldehydes afforded β-nitroalkanols in moderate to high yields. The use of chiral sugar aldehydes furnished the corresponding carbohydrate-derived β-nitroalkanols with excellent stereoselectivity.
- Soengas, Raquel G.,Acrcio, Rita,Silva, Artur M. S.
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supporting information
p. 8593 - 8597
(2014/12/10)
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- Synthetic calanolides with bactericidal activity against replicating and nonreplicating mycobacterium tuberculosis
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It is urgent to introduce new drugs for tuberculosis to shorten the prolonged course of treatment and control drug-resistant Mycobacterium tuberculosis (Mtb). One strategy toward this goal is to develop antibiotics that eradicate both replicating (R) and
- Zheng, Purong,Somersan-Karakaya, Selin,Lu, Shichao,Roberts, Julia,Pingle, Maneesh,Warrier, Thulasi,Little, David,Guo, Xiaoyong,Brickner, Steven J.,Nathan, Carl F.,Gold, Ben,Liu, Gang
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supporting information
p. 3755 - 3772
(2014/05/20)
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- Synthesis of nitroalkenes involving a cooperative catalytic action of iron(III) and piperidine: A one-pot synthetic strategy to 3-alkylindoles, 2H-chromenes and N-arylpyrrole
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An efficient and simple strategy has been developed to synthesize various substituted nitroalkenes involving a cooperative catalytic system of FeCl 3 and piperidine. This dual catalytic protocol simultaneously activates both electrophile and nucleophile and works under mild reaction conditions so that many sensitive functional groups were tolerated. Moreover, this cooperative catalytic reaction is also suitable for various one-pot reactions involving nitroalkenes such as, 2H-chromenes, N-arylpyrrole and Michael reaction with indole. Notably, this method is low-cost, efficient and environmentally friendly. Copyright
- Jalal, Swapnadeep,Sarkar, Soumen,Bera, Krishnendu,Maiti, Sukhendu,Jana, Umasish
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supporting information
p. 4823 - 4828
(2013/08/23)
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- New approach to oximes through reduction of nitro compounds enabled by visible light photoredox catalysis
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A range of nitro compounds are smoothly reduced to their corresponding oximes under the synergistic effects of visible light irradiation, the Ru(bpy)3Cl2 photocatalyst, Hünig's base, Mg(ClO 4)2 activation, and MeCN solvent. This remarkably mild and environmentally benign protocol, when orchestrated with classical Beckmann rearrangement, enables such high-value industrial feedstock as caprolactam to be readily accessed from simple precursor nitrocyclohexane.
- Cai, Shunyou,Zhang, Shaolong,Zhao, Yaohong,Wang, David Zhigang
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supporting information
p. 2660 - 2663
(2013/07/11)
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- Monoligated Pd(0)-catalyzed intramolecular ortho- and para-arylation of phenols for the synthesis of aporphine alkaloids. Synthesis of (-)-lirinine
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An intramolecular palladium(0)-mediated ortho-arylation of phenols applied to the synthesis of various substituted aporphines is reported. Most significantly, the efficiency of the transformation was enhanced by the use of monoligated Pd(0) complexes. This methodology was extended to para-arylation of phenols and employed in the synthesis of the aporphine alkaloid (-)-lirinine.
- Hellal, Malik,Singh, Shambhavi,Cuny, Gregory D.
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scheme or table
p. 1674 - 1681
(2012/03/10)
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- Organocatalytic asymmetric synthesis of functionalized 4 H -chromenes via a one-pot Domino Michael-Hemiacetalization and dehydration sequence
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A one-pot thiourea-catalyzed enantioselective synthesis of polyfunctionalized 4H-chromenes via a domino Michael-hemiacetalization reaction and subsequent dehydration is reported. Starting from 2-nitrovinylphenols and -keto esters, the new protocol affords the 4H-chromenes bearing a variety of functional groups with good to excellent yields (76-95%) and enantioselectivities ranging from 30-99%ee. Both enantiomers are available at will depending on the ephedrine or pseudoephedrine-based thiourea catalyst used. Georg Thieme Verlag Stuttgart - New York.
- Enders, Dieter,Urbanietz, Gregor,Raabe, Gerhard
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body text
p. 1905 - 1911
(2011/07/31)
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- Optimization of the potency and pharmacokinetic properties of a macrocyclic ghrelin receptor agonist (Part I): Development of ulimorelin (TZP-101) from Hit to Clinic
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High-throughput screening of Tranzyme Phar-ma's proprietary macrocycle library using the aequorin Ca2+-bioluminescence assay against the human ghrelin receptor (GRLN) led to the discovery of novel agonists against this G-protein coupled receptor. Early hits such as 1 (Ki = 86 nM, EC50 = 134 nM) though potent in vitro displayed poor pharmacokinetic properties that required optimization. While such macrocycles are not fully rule-of-five compliant, principally due to their molecular weight and clogP, optimization of their pharmacokinetic properties proved feasible largely through conformational rigidification. Extensive SAR led to the identification of 2 (Ki = 16 nM, EC50 = 29 nM), also known as ulimorelin or TZP-101, which has progressed to phase III human clinical trials for the treatment of postoperative ileus. X-ray structure and detailed NMR studies indicated a rigid peptidomimetic portion in 2 that is best defined as a nonideal type-I′ β-turn. Compound 2 is 24% orally bioavailable in both rats and monkeys. Despite its potency, in vitro and in gastric emptying studies, 2 did not induce growth hormone (GH) release in rats, thus demarcating the GH versus GI pharmacology of GRLN. (Figure presented)
- Hoveyda, Hamid R.,Marsault, Eric,Gagnon, René,Mathieu, Axel P.,Vézina, Martin,Landry, Annick,Wang, Zhigang,Benakli, Kamel,Beaubien, Sylvie,Saint-Louis, Carl,Brassard, Martin,Pinault, Jean-Fran?ois,Ouellet, Luc,Bhat, Shridhar,Ramaseshan, Mahesh,Peng, Xiaowen,Foucher, Laurence,Beauchemin, Sophie,Bhérer, Patrick,Veber, Daniel F.,Peterson, Mark L.,Fraser, Graeme L.
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supporting information; experimental part
p. 8305 - 8320
(2012/01/15)
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- Biocatalytic enantioselective approach to 3-aryl-2-nitropropanols: Synthesis of enantioenriched (R)-5-methoxy-3-aminochroman, a key precursor to the antidepressant drug Robalzotan
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The results of our studies on the biocatalytic enantioselective synthesis of different 3-aryl-2-nitropropanols are presented. These compounds could be obtained in moderate to good ee both bybaker's yeast mediated reduction of (E)-2-nitro-3-arylprop-2-en-1-ol precursors and by lipase kinetic resolution of racemic 3-aryl-2-nitropropanols. The synthesis of enantioenriched (R)-5-methoxy-3-aminochroman is also achieved. This important moietyispresent in different molecules active toward the central nervous system and is also the precursor for the synthesis of Robalzotan (NAD299), a potent 5-HT1A antagonist.
- Fuganti, Claudio,Sacchetti, Alessandro
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experimental part
p. 276 - 284
(2010/11/18)
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- Platinum-catalyzed michael addition and cyclization of tertiary amines with nitroolefins by dehydrogenation of α,β-sp3 C-H bonds
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A mild platinum-catalyzed oxidative dehydrogenation of α,β- C(sp3)-H bonds of tertiary amines in the presence of ambient oxygen is revealed, and the in situ formed enamines subsequently reacting with various nitroolefins resulted in the development of two one-pot synthetic protocols involving Michael addition-elimination and Michael addition-cyclization. By using different functionalized nitroolefins compatible with the current oxidative conditions, two types of structurally divergent products, trisubstituted enamines and chromano[2,3-b]piperidines, could be expediently accessed, respectively.
- Xia, Xiao-Feng,Shu, Xing-Zhong,Ji, Ke-Gong,Yang, Yan-Fang,Shaukat, Ali,Liu, Xue-Yuan,Liang, Yong-Min
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supporting information; experimental part
p. 2893 - 2902
(2010/07/09)
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- Sequential combination of Michael and acetalization reactions: Direct catalytic asymmetric synthesis of functionalized 4-nitromethyl-chromans as drug intermediates
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Functionalized chiral 4-nitromethyl-chromans as drug intermediates were achieved for the first time through sequential combination of Michael and acetalization reactions on 2-(2-nitro-vinyl)-phenols with acetone and alcohols in the presence of a catalytic
- Ramachary, Dhevalapally B.,Sakthidevi, Rajasekar
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supporting information; experimental part
p. 4259 - 4265
(2010/11/18)
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- E-Combretastatin and E-resveratrol structural modifications: Antimicrobial and cancer cell growth inhibitory β-E-nitrostyrenes
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As part of a broad-based SAR investigation of E-resveratrol (strong sirtuin activator and antineoplastic) and the anticancer vascular-targeting combretastatin-type stilbenes, a series of twenty-three β-E-nitrostyrenes was synthesized in order to evaluate potential antineoplastic, antitubulin, and antimicrobial activities. The β-E-nitrostyrenes evaluated ranged from monosubstituted phenols to trimethoxy and 3-methoxy-4,5-methylenedioxy derivatives. Two of the β-nitrostyrenes were synthesized as water-soluble sodium phosphate derivatives (4t, 4v). All except four (4r, 4s, 4t, 4u) of the series significantly inhibited a minipanel of human cancer cell lines. All but eight led to an IC50 of 10 μM for inhibition of tubulin polymerization, and all except three (4l, 4t, 4v) displayed antimicrobial activity.
- Pettit, Robin K.,Pettit, George R.,Hamel, Ernest,Hogan, Fiona,Moser, Bryan R.,Wolf, Sonja,Pon, Sandy,Chapuis, Jean-Charles,Schmidt, Jean M.
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experimental part
p. 6606 - 6612
(2009/12/06)
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- Synthesis and biological evaluation of N-acetyl-β-aryl-1,2-didehydroethylamines as new HIV-1 RT inhibitors in vitro
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A variety of N-acetyl-β-aryl-1,2-didehydroethylamines were synthesized by direct reduction-acetylation of β-aryl-nitroolefins and assayed as HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) for the first time. Compound 7a exhibited a TI value of >13.2 with CC50 value of >0.787 mM in C8166 cells. This structure-activity relationship (SAR) study provided a new lead for design and discovery of more potent and selective analogues act as NNRTIs.
- Cheng, Pi,Jiang, Zhi-Yong,Wang, Rui-Rui,Zhang, Xue-Mei,Wang, Qian,Zheng, Yong-Tang,Zhou, Jun,Chen, Ji-Jun
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p. 4476 - 4480
(2008/02/09)
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- A new efficient method for the total synthesis of linear furocoumarins
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A new efficient method for the synthesis of linear furocoumarins by a Nef reaction and intramolecular cyclocondensation in one pot results in the construction of a benzofuran ring. This method provides a new strategy to furnish the benzofuran framework easily, and also allows the convenient synthesis of furocoumarin derivatives with different substituents on the coumarin ring by a subsequent Pechmann reaction. This strategy has also been applied to the preparation of four additional benzofuran derivatives. Georg Thieme Verlag Stuttgart.
- Zhang, Bang-Le,Wang, Fang-Dao,Yue, Jian-Min
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p. 567 - 570
(2007/10/03)
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- The rapid synthesis of β-nitrostyrenes under microwave irradiation without solvent
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The β-nitrostyrenes (3a-l) were prepared by condensation of benzaldehydes with nitromethane in the presence of K2CO3/Al2O3 under microwave irradiation without solvent. They were characterized by IR, 1H-NMR, and elemental analysis.
- Wang, Cunde,Wang, Song
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p. 3481 - 3486
(2007/10/03)
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- Intramolecular Oxidative Cyclisation of 1-(4-Hydroxyaryl)-2-ketoximes 4-HOArCH2C(=NOH) R with Phenyliodine(III) Bis(trifluoroacetate)
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Reaction of 1-(4-hydroxyaryl)-2-ketoximes, 4-HOArCH2C(=NOH)R, with phenyliodine(III) bis(trifluoroacetate) in acetonitrile at 0 deg C results in smooth intramolecular oxidative cyclisation and formation of 1-oxa-2-azaspirodeca-2,6,9-trien-8-ones in g
- Kacan, Mesut,Koyuncu, Demet,McKillop, Alexander
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p. 1771 - 1776
(2007/10/02)
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- SYNTHESES BASED ON β-PHENYLETHYLAMINES. I. PREPARATION OF SUBSTITUTED β-PHENYLETHYLAMINES
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A comparative study has been made of methods of synthesizing substituted β-phenylethylamines via the corresponding nitriles and via nitrostyrenes, and a superiority of the latter method has been established.The possibility has been shown for the first time of reducing nitrostyrenes to saturated amines with diisobutylaluminum hydride (DIBAH).The use of DIBAH as reducing agent enables amines to be obtained in high yields.
- Vinogradova, V. I.,Yunusov, M. S.,Kuchin, A. V.,Tolstikov, G. A.,Sagandykov, R. T.,et al.
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- Reaction of Biologically Active &β-Nitrostyrenes with o-Phenylenediamine: A New Route to the Synthesis of 2-Substituted Benzimidazoles
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β-Nitrostyrenes (1) react with o-phenylenediamine in ethanol to give exclusively 2-substituted benzimidazoles (2) regardless of the nature and position of substituents in the phenyl ring.The correspondnig 2,3-dihydroperimidines (4) are readily obtained by reacting 1,8-diaminonaphthalene with benzaldehydes.Possible routes for the formation of 2 have been discussed.The nitrostyrenes (1) have been found to be toxic to fresh water snails and phytopathogenic fungi in high dilutions.
- Latif, N.,Mishriky, N.,Assad, F. M.,Meguid, S. Abdel
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p. 872 - 874
(2007/10/02)
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