- Biological evaluation and SAR analysis of novel covalent inhibitors against fructose-1,6-bisphosphatase
-
Fructose-1,6-bisphosphatase (FBPase) is an attractive target for affecting the GNG pathway. In our previous study, the C128 site of FBPase has been identified as a new allosteric site, where several nitrovinyl compounds can bind to inhibit FBPase activity. Herein, a series of nitrostyrene derivatives were further synthesized, and their inhibitory activities against FBPase were investigated in vitro. Most of the prepared nitrostyrene compounds exhibit potent FBPase inhibition (IC50 3, CF3, OH, COOH, or 2-nitrovinyl were installed at the R2 (meta-) position of the benzene ring, the FBPase inhibitory activities of the resulting compounds increased 4.5–55 folds compared to those compounds with the same groups at the R1 (para-) position. In addition, the preferred substituents at the R3 position were Cl or Br, thus compound HS36 exhibited the most potent inhibitory activity (IC50 = 0.15 μM). The molecular docking and site-directed mutation suggest that C128 and N125 are essential for the binding of HS36 and FBPase, which is consistent with the C128-N125-S123 allosteric inhibition mechanism. The reaction enthalpy calculations show that the order of the reactions of compounds with thiol groups at the R3 position is Cl > H > CH3. CoMSIA analysis is consistent with our proposed binding mode. The effect of compounds HS12 and HS36 on glucose production in primary mouse hepatocytes were further evaluated, showing that the inhibition was 71% and 41% at 100 μM, respectively.
- Chen, Haifeng,Guo, Yanrong,Han, Xinya,Hu, Wei,Huang, Yunyuan,Ren, Yanliang,Tang, Zilong,Wang, Qi,Wei, Lin,Xia, Qinfei,Yan, Jufen
-
supporting information
(2020/07/23)
-
- Poly(ethylene glycol) supported metal nitrates as well-organized reagents for hunsdiecker conversion of α,β-unsaturated acids to β-nitrostyrenes under solvent and acid-free conditions
-
Poly(ethylene glycol) (PEG) supported metal nitrates such as ferric nitrate and manganese nitrate were accomplished as well-organized reagents for Hunsdiecker conversion of α,β-unsaturated acids to β-nitrostyrenes under acid-free and solvent free conditions using grindstone technique. However, in the case of unsaturated aliphatic acids, nitro alkene derivatives were obtained as products. PEG-400 was found the best among the other PEGs (PEG-200,300, 400, 600, 3000 and 6000) used in this protocol.
- Ramesh,Shylaja,Ramgopal,Rao, A. Sambashiva,Rajanna
-
p. 1798 - 1800
(2019/07/17)
-
- Iodine monobromide catalysed regioselective synthesis of 3-arylquinolines from α-aminoacetophenones and: Trans -β-nitrostyrenes
-
A simple and efficient method for regioselective synthesis of 3-arylquinolines is described from α-aminoacetophenones and trans-β-nitrostyrenes using 20 mol% iodine monobromide as a catalyst in acetonitrile solvent at 80 °C. The present method involves tandem reaction of α-aminoacetophenones and trans-β-nitrostyrenes, formation of two new C-C bonds and cleavage of one C-C bond in a single step. The salient features of the protocol are metal- and oxidant-free reaction conditions, broad substrate scope, and good yields.
- Gattu, Radhakrishna,Mondal, Santa,Ali, Saghir,Khan, Abu T.
-
supporting information
p. 347 - 353
(2019/01/10)
-
- NITROALKENE NON STEROIDAL ANTI-INFLAMMATORY DRUGS (NA-NSAIDS) AND METHODS OF TREATING INFLAMMATION RELATED CONDITIONS
-
Nitroalkene non-steroidal anti-inflammatory compounds, pharmaceutical compositions thereof, and methods of treating inflammation related conditions.
- -
-
Paragraph 0083-0085; 0086-0087
(2019/07/17)
-
- NITROALKENE NON STEROIDAL ANTI-INFLAMMATORY DRUGS (NA-NSAIDS) AND METHODS OF TREATING INFLAMMATION RELATED CONDITIONS
-
Nitroalkene non-steroidal anti-inflammatory compounds, pharmaceutical compositions thereof, and methods of treating inflammation related conditions.
- -
-
Paragraph 0080; 0081; 0082
(2019/07/10)
-
- Synthesis, antiproliferative and pro-apoptotic effects of nitrostyrenes and related compounds in Burkitt’s lymphoma
-
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.
-
p. 181 - 199
(2018/03/13)
-
- Electronic effect of substituents on anilines favors 1,4-addition to: Trans -β-nitrostyrenes: Access to N -substituted 3-arylindoles and 3-arylindoles
-
A simple and an efficient method for the regioselective synthesis of N-alkyl/aryl/H 3-arylindole derivatives from N-substituted anilines and trans-β-nitrostyrenes has been described using 10 mol% of bismuth(iii) triflate as a catalyst in acetonitrile at 80 °C. The present protocol profits from the formation of new C-C and C-N bonds, broad substrate scope and moderate to good yields.
- Gattu, Radhakrishna,Bhattacharjee, Suchandra,Mahato, Karuna,Khan, Abu T.
-
supporting information
p. 3760 - 3770
(2018/05/30)
-
- Carboxylate Salt Bridge-Mediated Enamine Catalysis: Expanded Michael Reaction Substrate Scope and Facile Access to Antidepressant (R)-Pristiq
-
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
-
supporting information
p. 2824 - 2831
(2017/08/23)
-
- Synthesis and biological evaluation of novel inhibitors against 1,3,8-trihydroxynaphthalene reductase from Magnaporthe grisea
-
1,3,8-Trihydroxynaphthalene reductase (3HNR) is an essential enzymes that is involved in fungal melanin biosynthesis. Based on the structural informations of active site of 3HNR, a series of β-nitrostyrene compounds were rationally designed and synthesized. The enzymatic activities of these compounds showed that most of them exhibited high inhibitory activities (50 = 0.29 μM). In particular, some of these compounds had moderate fungicidal activity against Magnaporthe grisea. Compound 3-4 showed high in vivo activities against M. grisea (EC50 = 9.5 ppm). Furthermore, compound 3-2 was selected as a representative molecule, and the probable binding mode of this compound and the surrounding residues in the active site of 3HNR was elucidated by using molecular dock. The positive results suggest that β-nitrostyrene derivatives are most likely to be promising leads toward the discovery of novel agent of rice blast.
- Chen, Haifeng,Han, Xinya,Qin, Nian,Wei, Lin,Yang, Yue,Rao, Li,Chi, Bo,Feng, Lingling,Ren, Yanliang,Wan, Jian
-
p. 1225 - 1230
(2016/03/01)
-
- Iron-Mediated One-Pot Synthesis of 3,5-Diarylpyridines from β-Nitrostyrenes
-
An operationally simple and mild one-pot protocol for the synthesis of a variety of 3,5-diarylpyridines from β-nitrostyrenes was achieved by using elemental iron. This reaction proceeds via reduction of the nitro group, resulting in in situ imine formation followed by trimolecular condensation with concomitant debenzylative aromatization. By employing this method, a series of symmetrical and unsymmetrical 3,5-diarylpyridines were synthesized with good to excellent yields. In addition, this method was also utilized for the synthesis of Sch-21418, an anti-inflammatory agent on gram scale.
- Sathish, Manda,Chetna, Jadala,Hari Krishna, Namballa,Shankaraiah, Nagula,Alarifi, Abdullah,Kamal, Ahmed
-
p. 2159 - 2165
(2016/03/15)
-
- Mild and efficient reductive deoxygenation of epoxides to olefins with tin(II) chloride/sodium iodide as a novel reagent
-
A highly efficient and green protocol is reported for the reductive deoxygenation of organic epoxides to olefins using tin(II) chloride/sodium iodide as a novel reagent. The reaction gives an excellent yield (85-96%) in ethanol under reflux within 2-10 minutes, without affecting other functional groups. The advantages of our method are the use of inexpensive reagents, the eco-friendly and green reaction conditions, and the short reaction times and high yields.
- Pathe, Gulab Khushalrao,Ahmed, Naseem
-
supporting information
p. 3542 - 3552
(2015/11/17)
-
- Straightforward synthesis of 1,2-dicyanoalkanes from nitroalkenes and silyl cyanide mediated by tetrabutylammonium fluoride
-
A straightforward synthesis of 1,2-dicyanoalkanes by reacting nitroalkenes with trimethylsilyl cyanide in the presence of tetrabutylammonium fluoride is described. The reaction proceeds through a tandem double Michael addition under mild conditions. Employing the hypervalent silicate generated from trimethylsilyl cyanide and tetrabutylammonium fluoride is essential for achieving this transformation. Mechanistic studies suggest that a small amount of water included in the reaction media plays a key role. This protocol is applicable to various types of substrates including electron-rich and electron-deficient aromatic nitroalkenes, and aliphatic nitroalkenes. Moreover, vinyl sulfones were found to be good alternatives, particularly for electron-deficient nitroalkenes. The broad substrate scope and functional group tolerance of the reaction makes this approach a practical method for the synthesis of valuable 1,2-dicyanoalkanes.
- Kiyokawa, Kensuke,Nagata, Takaya,Hayakawa, Junpei,Minakata, Satoshi
-
supporting information
p. 1280 - 1285
(2015/02/19)
-
- NOVEL SUICIDAL LSD1 INHIBITORS TARGETING SOX2-EXPRESSING CANCER CELLS
-
Disclosed are inhibitors of lysine-specific demethylase I (LSD1); synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of treating cancers characterized by the presence of Sox2 using the compounds a
- -
-
Paragraph 00541
(2014/12/12)
-
- Ethylenediamine: A highly effective catalyst for one-pot synthesis of aryl nitroalkenes via henry reaction and dehydration
-
Ethylenediamine (H2NCH2CH2NH2) was found to be a highly effective catalyst for the condensation of aryl aldehydes with nitromethane (or nitroethane). When 1%-2% (mol%) of ethylenediamine was used as the catalyst, the one-pot reaction of aryl aldehydes with nitromethane (or nitroethane) by refluxing for 3-10 h efficiently afforded various arylnitroalkenes 1a-1y in 85%-97% yields. Ethylenediamine (H 2NCH2CH2NH2) was found to be a highly effective catalyst for the condensation of aryl aldehydes with nitromethane (or nitroethane). When 1-2 mol% of ethylenediamine was used as the catalyst, the one-pot reaction of aryl aldehydes with nitromethane (or nitroethane) by refluxing for 3-10 h efficiently afforded various aryl nitroalkenes 1a-1y in 85%-97% yields. Copyright
- Yang, Jianxin,Dong, Jing,Lue, Xia,Zhang, Qiang,Ding, Wei,Shi, Xiaoxin
-
p. 2827 - 2833
(2013/08/23)
-
- Synthesis of vinylphosphonates and its first exploration of bioactivity
-
Phosphonation of β-nitro-alkene with triethyl phosphite was achieved under microwave irradiation using CH2Cl2 as the solvent in the absence of catalyst with moderate to high yields (up to 90%). This method of formation of carbonphosphor bonds is simple, mild, convenient and effective. Synchronously, a number of vinylphosphonates derivatives were synthesized and evaluated biologically preliminary.
- Li, Sheng-Nan,Xu, Lan-Ting,Chenb, Yue,Lia, Ju-Lian,He, Ling
-
experimental part
p. 416 - 422
(2012/05/04)
-
- Silica grafted polyethylenimine as heterogeneous catalyst for condensation reactions
-
Primary amine groups were attached to a silica surface by using α,ω-diamines derivatives and (3-glycidyloxypropyl)-trimethoxysilane activation. The same activation was used to graft polyethylenimine, which also contains secondary and tertiary amine groups. These silica aminated structures were tested as heterogeneous catalysts in nitroaldol condensation with nitromethane, the derivative with the polyethylenimine moiety being the more active catalyst. This catalyst also showed efficiency in the Knoevenagel condensation of benzaldehydes with ethyl cyanoacetate under very mild reaction conditions and showed much the same efficiency when used in consecutive reaction runs. A reaction mechanism with participation of the several amine groups of the catalysts is discussed.
- Ribeiro, Sonia M.,Serra, Arménio. C.,Gonsalves, A.M. D'A. Rocha
-
experimental part
p. 126 - 133
(2012/02/01)
-
- E-Combretastatin and E-resveratrol structural modifications: Antimicrobial and cancer cell growth inhibitory β-E-nitrostyrenes
-
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.
-
experimental part
p. 6606 - 6612
(2009/12/06)
-
- Metal nitrate driven nitro Hunsdiecker reaction with α,β-unsaturated carboxylic acids under solvent-free conditions
-
Hunsdiecker reactions with α,β-unsaturated carboxylic acids were conducted under solvent-free conditions in the presence of a few drops of HNO3 together with a variety of metal nitrates [Mg(NO3)2, Sr(NO3)2], Al(NO3)3, Ca(NO3)2, Ni(NO3)2, Cd(NO3)2, Zn(NO3)2, Hg(NO3)2, AgNO3, ZrO(NO3)2, UO2(NO3)2, Th(NO3)2] or ammonium nitrate. α,β-Unsaturated aromatic carboxylic acids underwent nitro decarboxylation to afford β-nitro styrenes in moderate to good yields, while α,β-unsaturated aliphatic carboxylic acids underwent decarboxylation to yield the corresponding nitro derivatives.
- Ramgopal,Ramesh,Chakradhar,Reddy, N. Maasi,Rajanna
-
p. 4043 - 4045
(2008/02/04)
-
- Synthesis and biological evaluation of N-acetyl-β-aryl-1,2-didehydroethylamines as new HIV-1 RT inhibitors in vitro
-
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
-
p. 4476 - 4480
(2008/02/09)
-
- Investigation of pore-size effects on base catalysis using amino-functionalized monodispersed mesoporous silica spheres as a model catalyst
-
The effects of pore size on base catalysis have been studied using amino-functionalized monodispersed mesoporous silica spheres (NH2-MMSS). By changing the surfactant that is used for the template and also the synthetic conditions, NH2/su
- Suzuki, Tomiko M.,Yamamoto, Masami,Fukumoto, Keiko,Akimoto, Yusuke,Yano, Kazuhisa
-
p. 249 - 257
(2008/09/17)
-
- Cold microwave chemistry: synthesis using pre-cooled reagents
-
A novel experimental procedure for chemical reactions has been devised that involves mixing and then freezing the reagents (organic solvent-free) to a sub-zero temperature such as -30 °C. This frozen mixture is exposed to microwave irradiation for a brief period of time. The use of pre-cooled reagents may give a single product not obtained by traditional microwave irradiation at room temperature. Interestingly, such a product may provide information about mechanisms by identifying the first step of a multiple step reaction.
- Bose, Ajay K.,Ganguly, Subhendu N.,Manhas, Maghar S.,He, William,Speck, Jeffrey
-
p. 3213 - 3215
(2007/10/03)
-
- Microwave promoted rapid nitration of phenolic compounds with calcium nitrate
-
Highly accelerated and safe nitration of phenolic compounds has been found to be feasible with a mixture of calcium nitrate and acetic acid as an efficient nitration agent under brief microwave irradiation. This method is compatible with the green chemistry approach because calcium salts-the inorganic byproducts-can be useful agrochemicals rather than waste chemicals. Commercially available 15N-labeled calcium nitrate is convenient for the preparation of 15N-labeled compounds for metabolic studies and mass spectrometry. This safe nitration method can be included in laboratory experiments for high school and college students.
- Bose, Ajay K.,Ganguly, Subhendu N.,Manhas, Maghar S.,Rao, Sheetal,Speck, Jeffrey,Pekelny, Uri,Pombo-Villars, Esteban
-
p. 1885 - 1888
(2007/10/03)
-
- A modification of the Hammett equation for predicting ionisation constants of p-vinyl phenols
-
Currently there are several compounds used as drugs or studied as new chemical entities, which have an electron withdrawing group connected to a vinylic double bond in a phenolic or catecholic core structure. These compounds share a common feature - current computational methods utilizing the Hammett type equation for the prediction of ionisation constants fail to give accurate prediction of pKa's for compounds containing the vinylic moiety. The hypothesis was that the effect of electron-withdrawing substituents on the pKa of p-vinyl phenols is due to the delocalized electronic structure of these compounds. Thus, this effect should be additive for multiple substituents attached to the vinylic double bond and quantifiable by LFER-based methods. The aim of this study was to produce an improved equation with a reduced tendency to underestimate the effect of the double bond on the ionisation of the phenolic hydroxyl. To this end a set of 19 para-substituted vinyl phenols was used. The ionisation constants were measured potentiometrically, and a training set of 10 compounds was selected to build a regression model (r2 = 0.987 and S.E. = 0.09). The average error with an external test set of six compounds was 0.19 for our model and 1.27 for the ACD-labs 7.0. Thus, we have been able to significantly improve the existing model for prediction of the ionisation constants of substituted p-vinyl phenols.
- Sipilae, Julius,Nurmi, Harri,Kaukonen, Ann Marie,Hirvonen, Jouni,Taskinen, Jyrki,Yli-Kauhaluoma, Jari
-
p. 417 - 425
(2007/10/03)
-
- Nitration of cinnamic acids using cerium (IV) ammonium nitrate immobilized on silica
-
Treatment of cinnamic acids with cerium (IV) ammonium nitrate supported on silica (CAN/SiO2) was used to synthesize nitro derivative and ipso substitution products. The position of the substituents defines the type and the yields of the product
- Messere, Anna,Gentili, Alessandra,Garella, Isidoro,Temussi, Fabio,Di Blasio, Benedetto,Fiorentino, Antonio
-
p. 3317 - 3324
(2007/10/03)
-
- Catalytic activity of aminopropyl xerogels in the selective synthesis of (E)-nitrostyrenes from nitroalkanes and aromatic aldehydes
-
Various aminopropyl-functionalized silicas (APS) were prepared by the sol-gel technique using different tetraethyl orthosilicate/ aminopropyltriethoxysilane (TEOS/ATS) ratios and tested as base catalysts for the nitroaldol reaction. The solids were fully characterized. It was proved that the amount of organic component strongly influences the composition and textural properties of the hybrid organic-inorganic materials. In particular, when ATS was increased to more than 40%, pore volume collapse was observed and a significant decrease in interaction with benzaldehyde reagent was revealed by FT-IR. Catalytic activity in the nitroaldol reaction was correlated with chemical composition and textural properties, suggesting that the catalyst efficiency depends on accessibility to the catalytic sites. In all cases, (E)-nitrostyrene was selectively obtained.
- Sartori,Bigi,Maggi,Sartorio,Macquarrie,Lenarda,Storaro,Coluccia,Martra
-
p. 410 - 418
(2007/10/03)
-
- Morpholine adsorbed on silica gel: A novel and mild basic catalyst for the synthesis of α,β-unsaturated nitroalkenes
-
Syntheses of α,β-unsaturated nitroalkenes have been carried out under mild condition using morpholine adsorbed on silica gel as a novel catalyst.
- Bandgar, Babasaheb P.,Uppalla, Lav S.,Sadavarte, Vaibhav S.
-
p. 949 - 952
(2007/10/03)
-
- Microwave-Assisted Henry Reaction: Solventless Synthesis of Conjugated Nitroalkenes
-
In a solventless system and under microwave irradiation, nitroalkanes react with arylaldehydes in the presence of a catalytic amount of ammonium acetate to afford, in one step, conjugated nitroalkenes without the isolation of intermediary β-nitro alcohols. - Key Words: Arylaldehydes; Nitroalkanes; Ammonium acetate; Conjugated nitroalkenes; Henry reaction; Microwave irradiation
- Varma, Rajender S.,Dahiya, Rajender,Kumar, Sudhir
-
p. 5131 - 5134
(2007/10/03)
-
- Synthesis of a unique tripeptide L-Glu-Gly-4-hydroxystyrylamine
-
In the synthesis of the title tripeptide 1, the methodology of conjugate addition-elimination of thiophenol on suitable nitrostyrene derivative to construct trans-styrylamino unit, has been used.
- Gurjar,Tripathy, Sasmita
-
p. 1244 - 1247
(2007/10/03)
-
- Isolation and Structure of Thalictoside
-
Thalictoside (1), a novel glycoside containing a nitro group, was isolated from Thalictrum aquilegifolium and the structure was shown to be 4-hydroxy-1-(2-nitroethyl)benzene 4-O-β-D-glucopyranoside on the basis of chemical transformations, spectral analys
- Ina, Hiroji,Iida, Hideo
-
p. 726 - 729
(2007/10/02)
-
- Synthese d'aryl nitronorbornenes par cycloaddition de Diels-Alder entre les aryl-nitroethylenes et le cyclopentadiene. Justification de la stereochimie et de la reactivite relative observees par la methode CNDO/II. Obtention d'aryl aminonorbornenes
-
Syntheses of numerous 2-aryl nitroethylenes (nitrostyrenes) have been optimized.The nitrostyrenes have been reacted with cyclopentadiene in Diels-Alder cycloadditions and the 3-aryl 2-nitronorbornenes obtained have been reduced into 3-aryl 2-aminonorbornenes.These compounds are potentially dopaminergic molecules.The stereochemistry of the adducts obtained in the Diels-Alder reaction has been determined by 1H nmr.The stereochemistry and the relative reactivity of the nitrostyrenes versus cyclopentadiene have been confirmed by theoretical calculations based on the CNDO/II method.
- Bourguignon, Jean,Le Nard, Gilles,Queguiner, Guy
-
p. 2354 - 2361
(2007/10/02)
-