- Nickel-Catalyzed Reductive Cross-Coupling of N-Acyl and N-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides
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Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to afford the corresponding sulfonamides.
- Qu, Erdong,Li, Shangzhang,Bai, Jin,Zheng, Yan,Li, Wanfang
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supporting information
p. 58 - 63
(2021/12/27)
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- Red-shifted tetra-ortho-halo-azobenzenes for photo-regulated transmembrane anion transport
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Photo-responsive synthetic ion transporters are of interest as tools for studying transmembrane transport processes and have potential applications as targeted therapeutics, due to the possibility of spatiotemporal control and wavelength-dependent function. Here we report the synthesis of novel symmetric and non-symmetric red-shifted tetra-ortho-chloro- and tetra-ortho-fluoro azobenzenes, bearing pendant amine functionality. Functionalisation of the photo-switchable scaffolds with squaramide hydrogen bond donors enabled the preparation of a family of anion receptors, which act as photo-regulated transmembrane chloride transporters in response to green or red light. The subtle effects of chlorine/fluorine substitution,meta/parapositioning of the anion receptors, and the use of more flexible linkers are explored. NMR titration experiments on the structurally diverse photo-switchable receptors reveal cooperative binding of chloride in theZ, but notEisomer, by the two squaramide binding sites. These results are supported by molecular dynamics simulations in explicit solvent and model membranes. We show that this intramolecular anion recognition leads to effective switching of transport activity in lipid bilayer membranes, in which optimalZisomer activity is achieved using a combination of fluorine substitution andpara-methylene spacer units.
- Bo, Zonghua,Duarte, Fernanda,Kerckhoffs, Aidan,Langton, Matthew J.,Penty, Samuel E.
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supporting information
p. 9058 - 9067
(2021/11/04)
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- Targeting Her2-insYVMA with Covalent Inhibitors - A Focused Compound Screening and Structure-Based Design Approach
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Mutated or amplified Her2 serves as a driver of non-small cell lung cancer or mediates resistance toward the inhibition of its family member epidermal growth factor receptor with small-molecule inhibitors. To date, small-molecule inhibitors targeting Her2 which can be used in clinical routine are lacking, and therefore, the development of novel inhibitors was undertaken. In this study, the well-established pyrrolopyrimidine scaffold was modified with structural motifs identified from a screening campaign with more than 1600 compounds, which were applied against wild-type Her2 and its mutant variant Her2-A775_G776insYVMA. The resulting inhibitors were designed to covalently target a reactive cysteine in the binding site of Her2 and were further optimized by means of structure-based drug design utilizing a set of obtained complex crystal structures. In addition, the analysis of binding kinetics and absorption, distribution, metabolism, and excretion parameters as well as mass spectrometry experiments and western blot analysis substantiated our approach.
- Lategahn, Jonas,Hardick, Julia,Grabe, Tobias,Niggenaber, Janina,Jeyakumar, Kirujan,Keul, Marina,Tumbrink, Hannah L.,Becker, Christian,Hodson, Luke,Kirschner, Tonia,Kl?vekorn, Philip,Ketzer, Julia,Baumann, Matthias,Terheyden, Susanne,Unger, Anke,Weisner, J?rn,Müller, Matthias P.,Van Otterlo, Willem A. L.,Bauer, Sebastian,Rauh, Daniel
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p. 11725 - 11755
(2020/11/26)
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- Locking the Dynamic Axial Chirality of Biphenyl Crown Ethers through Threading
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This paper describes the syntheses of [2]rotaxanes comprising 23- and 26-membered biphenyl crown ethers as the macrocyclic components and secondary ammonium ions as the dumbbell-shaped components, and the locking of the dynamic axial chirality of the biph
- Kimura, Tomoya,Miyagawa, Shinobu,Takaya, Hikaru,Naito, Masaya,Tokunaga, Yuji
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supporting information
p. 3897 - 3903
(2020/10/28)
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- Discovery of phthalimide derivatives as novel inhibitors of a soluble epoxide hydrolase
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Soluble epoxide hydrolase (sEH) inhibitors are effective in reducing blood pressure, inflammation, and pain in a number of mammalian disease models. As most classical urea-based sEH inhibitors suffer from poor solubility and pharmacokinetic properties, the development of novel sEH inhibitors with an improved pharmacokinetic specification has received a great deal of attention. In this study, a series of amide-based sEH inhibitors bearing a phthalimide ring as the novel secondary pharmacophore (P2) was designed, synthesized, and evaluated. Docking results illustrated that the amide group as the primary pharmacophore (P1) was placed at a suitable distance from the three key amino acids (Tyr383, Tyr466, and Asp335) for an effective hydrogen bonding. In agreement with these findings, most of the newly synthesized compounds demonstrated moderate?to?high sEH inhibitory activities, relative to 12-(3-adamantan-1-yl-ureido)dodecanoic acid as the reference standard. Compound 12e with a 4-methoxybenzoyl substituent exhibited the highest sEH inhibitory activity, with an IC50 value of 1.06 nM. Moreover, the ADME properties of the compounds were evaluated in silico, and the results revealed appropriate predictions.
- Mahlooji, Iman,Shokri, Maryam,Manoochehri, Rana,Mahboubi-Rabbani, Mohammad,Rezaee, Elham,Tabatabai, Sayyed Abbas
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- Compound and application thereof in resistance to arenavirus infection
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The invention provides a compound and application thereof in resistance to arenavirus infection. The structural formula of the compound is as shown in the figure (I) in the specification, wherein Ar is selected from an aromatic ring or aromatic heterocyct
- -
-
Paragraph 0040-0043
(2019/04/04)
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- Tri(pentaflurophenyl)borane-catalyzed reduction of cyclic imides with hydrosilanes: Synthesis of pyrrolidines
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B(C6F5)3-catalyzed hydrosilylation of cyclic imides afforded an efficient synthetic method of pyrrolidines. In the presence of 5 mol% B(C6F5)3, various aromatic, aliphatic and polycyclic imides were smoothly reduced by PhSiH3 to generate the corresponding pyrrolidines in high yields. The reaction profiles monitored by 1H NMR spectroscopy disclosed the reduction process of cyclic imides and the effect of difference structure of the hydrosilanes on the hydrosilylation.
- Ding, Guangni,Wu, Xiaoyu,Lu, Bin,Lu, Wenkui,Zhang, Zhaoguo,Xie, Xiaomin
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supporting information
p. 1144 - 1150
(2018/02/17)
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- Mechanochemical N-alkylation of imides
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The mechanochemical N-alkylation of imide derivatives was studied. Reactions under solvent-free conditions in a ball mill gave good yields and could be put in place of the classical solution conditions. The method is general and can be applied to various imides and alkyl halides. Phthalimides prepared under ball milling conditions were used in a mechanochemical Gabriel synthesis of amines by their reaction with 1,2-diaminoethane.
- Bri?, Anamarija,Dud, Mateja,Margeti?, Davor
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supporting information
p. 1745 - 1752
(2017/09/27)
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- Novel sulfonamide compound, preparation method, and use of novel sulfonamide compound as protein tyrosine phosphatase 1B inhibitor
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The invention relates to a novel sulfonamide compound in a structure of a general formula I as shown in the specification, or pharmaceutically acceptable salt and a preparation method of the novel sulfonamide compound, and further relates to a drug composition containing the compound as shown as the general formula I or the pharmaceutically acceptable salt of the compound, and a use of the compound or the pharmaceutically acceptable salt for preparing a drug for preventing and/or treating symptoms or diseases such as hyperglycemia and diabetes mellitus type 2 since the compound as shown as the general formula I or the pharmaceutically acceptable salt of the compound has activity of inhibiting a protein tyrosine phosphatase 1B (PTP 1B).
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- Synthetic method for N-substituted imide
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The invention provides a synthetic method for N-substituted imide. According to the method, aromatic ketone and amine are used as substrates, air or oxygen is used as an oxygen source, and cyclic imide is produced under liquid phase conditions under the action of a catalyst. The method is mild in conditions, high in oxidation efficiency and high in product yield; and since the method uses air or oxygen as the oxygen source, the method is economic and environment-friendly and has good application prospect.
- -
-
Paragraph 0016; 0028; 0029; 0030; 0031
(2017/04/20)
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- 3. 4 - diphenyl - 4H - 1, 2, 4 - triazole derivative and its preparation method and application (by machine translation)
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The invention discloses 3, 4 - diphenyl - 4H - 1, 2, 4 - triazole derivative and its preparation method and application. In particular, the invention relates to the formula (I) structure of 3, 4 - diphenyl - 4H - 1, 2, 4 - triazole derivatives, its stereoisomers or its pharmaceutically acceptable salt, formula (I) in the definition of each substituent is as defined in the specification. These structure of novel compound with heat shock protein HSP90 inhibitory activity, can be used for treating cancer, neurodegenerative diseases, inflammatory diseases, autoimmune diseases, ischemic brain injury and the like, it has broad application prospects. (by machine translation)
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-
Paragraph 0243; 0244; 0245; 0246
(2017/07/01)
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- Characterization of a selective inverse agonist for estrogen related receptor α as a potential agent for breast cancer
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The estrogen-related receptor α (ERRα) is an orphan nuclear receptor that plays a primary role in the regulation of cellular energy homeostasis and osteogenesis. It is reported that ERRα is widely expressed in a range of tissues and accumulating evidence has supported that the high expression of ERRα correlates with poor prognosis of various human malignancies, including breast, endometrium, colon, prostate and ovary cancers. Herein is described the discovery of a novel selective inverse agonist (HSP1604) of ERRα, but not of ERRβ and ERRγ, as determined using transient transfection luciferase reporter assay and a time-resolved fluorescence resonance energy transfer (TR-FRET) co-activator assay. HSP1604 potently inhibits ERRα transcriptional activity with IC50=1.47±0.17?μM in cell-based luciferase reporter assay and also decreases the protein level of ERRα and the mRNA levels of its downstream target genes such as pyruvate dehydrogenase kinase 4 (PDK4), pS2 and osteopontin. HSP1604 has also suppressed the proliferation of different human cancer cell lines and the migration of breast cancer cells with high expression of ERRα. Representative in vivo results show that HSP1604 suppresses the growth of human breast cancer xenograft in nude mice as doses at 30?mg/kg or 100?mg/kg administered every other day during 28-day period. HSP1604 thus has the potential both as a new agent to inhibit the growth of tumors and as a chemical probe of ERRα biology.
- Zhang, Liudi,Liu, Peihong,Chen, Haifei,Li, Qunyi,Chen, Lu,Qi, Huijie,Shi, Xiaojin,Du, Yongli
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p. 439 - 448
(2016/08/17)
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- Novel, potent, selective and cellular active ABC type PTP1B inhibitors containing (methanesulfonyl-phenyl-amino)-acetic acid methyl ester phosphotyrosine mimetic
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Protein tyrosine phosphatase 1B (PTP1B) which plays an important role in the negative regulation of insulin and leptin pathway has emerged as a novel promising therapeutic target for the treatment of type 2 diabetes mellitus and obesity. Upon careful study, a series of novel scaffold and simple synthesis method inhibitors were discovered based on the analysis of X-ray crystal structures of PTP1B/inhibitor complexes and docking simulations. Among them, compound P7 exhibited high inhibitory activity (IC50 = 222 nM) with moderate selectivity (8-fold) over T-cell PTPase (TCPTP) through interacting with the A, B and C binding sites of PTP1B enzyme. Further studies on cellular activities revealed that compound P7 could enhance insulin-mediated IRβ phosphorylation and insulin-stimulated glucose uptake.
- Liu, Peihong,Du, Yongli,Song, Lianhua,Shen, Jingkang,Li, Qunyi
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p. 7079 - 7088
(2015/11/11)
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- An unprecedented approach to the Gabriel amine synthesis utilizing tosylhydrazones as alkylating agents
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A new and one-pot version of the Gabriel phthalimide amine synthesis utilizing carbonyl compounds as alkylating agents via their tosylhydrazone surrogates is disclosed. The alkylation involves copper catalysed carbene insertion into the N-H bond of phthalimide. Basically, the protocol also offers a powerful tool for deoxygenative hydroamination of carbonyl compounds.
- Yadav, Arvind K.,Yadav, Lal Dhar S.
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p. 34764 - 34767
(2014/11/08)
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- AMINE SUBSTITUTED METHANESULFONAMIDE DERIVATIVES AS VANILLOID RECEPTOR LIGANDS
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The invention relates to amine substituted methanesulfonamide derivatives of formula (I) as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
- -
-
Page/Page column 87
(2013/04/13)
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- Substituted Methanesulfonamide Derivatives as Vanilloid Receptor Ligands
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The invention relates to substituted methanesulfonamide derivatives as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseas
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- SUBSTITUTED PYRAZOLYL-BASED CARBOXAMIDE AND UREA DERIVATIVES BEARING A PHENYL MOIETY SUBSTITUTED WITH AN N-CONTAINING GROUP AS VANILLOID RECEPTOR LIGANDS
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The invention relates to substituted pyrazolyl-based carboxamide and urea derivatives of formula (R) bearing a phenyl moiety substituted with an N-containing group as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
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- ARYL OR N-HETEROARYL SUBSTITUTED METHANESULFONAMIDE DERIVATIVES AS VANILLOID RECEPTOR LIGANDS
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The invention relates to aryl or N-heteroaryl substituted methanesulfonamide derivatives of Formula (I) as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
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- SUBSTITUTED METHANESULFONAMIDE DERIVATIVES AS VANILLOID RECEPTOR LIGANDS
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The invention relates to substituted methanesulfonamide derivatives as vanilloid receptor ligands of formula (I), to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and
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- Aryl or N-heteroaryl Substituted Methanesulfonamide Derivatives as Vanilloid Receptor Ligands
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The invention relates to aryl or N-heteroaryl substituted methanesulfonamide derivatives as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
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-
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- Amine Substituted Methanesulfonamide Derivatives as Vanilloid Receptor Ligands
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The invention relates to amine substituted methanesulfonamide derivatives as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
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- Thiourea derived troeger's bases as molecular cleft receptors and colorimetric sensors for anions
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Thiourea-functionalized Troeger's base receptors 1 and 2 have been synthesized and evaluated as novel for the recognition of anions. Receptor 2 gave rise to significant changes in the absorption spectrum upon titration with AcO- and H2/su
- Boyle, Elaine M.,Comby, Steve,Molloy, Jennifer K.,Gunnlaugsson, Thorfinnur
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p. 8312 - 8319
(2013/09/24)
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- 2,4,6-Trichloro-1,3,5-triazine/dimethylformamide as an efficient reagent for one-pot conversion of alcohols into N-alkylphthalimides
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An efficient and mild method for the direct conversion of alcohols into N-alkylphthalimides using 2,4,6-trichloro-1,3,5-triazine and dimethylformamide was described. The reaction was preceded via (alcoxymethylene) dimethylammonium chloride intermediate an
- Mokhtari, Babak,Azadi, Roya,Azhdari, Aseieh
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experimental part
p. 171 - 174
(2010/11/18)
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- Structure-based design and synthesis of the first weak non-phosphate inhibitors for IspF, an enzyme in the non-mevalonate pathway of isoprenoid biosynthesis
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In this paper, we describe the structure-based design, synthesis, and biological evaluation of cytosine derivatives and analogues that inhibit IspF, an enzyme in the non-mevalonate pathway of isoprenoid biosynthesis. This pathway is responsible for the biosynthesis of the C5 precursors to isoprenoids, isopentenyl diphosphate (IPP, 1) and dimethylallyl diphosphate (DMAPP, 2; Scheme 1). The non-mevalonate pathway is the sole source for 1 and 2 in the protozoan Plasmodium parasites. Since mammals exclusively utilize the alternative mevalonate pathway, the enzymes of the non-mevalonate pathway have been identified as attractive new drug targets in the fight against malaria. Based on computer modeling (cf. Figs. 2 and 3), new cytosine derivatives and analogues (Fig. 1) were selected as potential drug-like inhibitors of IspF protein, and synthesized (Schemes 2-5). Determination of the enzyme activity by 13C-NMR spectroscopy in the presence of the new ligands showed inhibitory activities for some of the prepared cytosine and pyridine-2,5-diamine derivatives in the upper micromolar range (IC50 values; Table). The data suggest that it is possible to inhibit IspF protein without binding to the polar diphosphate binding site and the side chain of Asp56′, which interacts with the ribose moiety of the substrate and substrate analogues. Furthermore, a new spacious sub-pocket was discovered which accommodates aromatic spacers between cytosine derivatives or analogues (binding to 'Pocket III') and rings that occupy the flexible hydrophobic region of 'Pocket II'. The proposed binding mode remains to be further validated by X-ray crystallography.
- Baumgartner, Corinne,Eberle, Christian,Diederich, Francois,Lauw, Susan,Rohdich, Felix,Eisenreich, Wolfgang,Bacher, Adelbert
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p. 1043 - 1068
(2008/03/13)
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- Di-μ-hydroxy-bis(N,N,N′,N′-tetramethylenediamine)-copper(II) chloride [Cu(OH)·TMEDA]2Cl2: An efficient, practical catalyst for benzylation and allylation of amides
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An efficient protocol for the benzylation or allylation of amides using the corresponding benzyl or allyl chlorides as electrophiles under basic conditions with commercially available 5 mol % of [Cu(OH)TMEDA]2Cl2 as catalyst was developed. Under these conditions, unprotected amino acids were benzylated without any racemization.
- Kumaraswamy,Pitchaiah,Ramakrishna,Ramakrishna,Sadaiah
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p. 2013 - 2015
(2007/10/03)
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- Tricyclic indole-2-carboxylic acids: Highly in vivo active and selective antagonists for the glycine binding site of the NMDA receptor
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A series of tricyclic indole-2-carboxylic acid derivatives were synthesized and evaluated by the radioligand binding assay and the anticonvulsant effects in the mouse NMDA-induced seizure model. Among them, derivatives of 3S-(-)-4 such as 3a, 3f, and 3g which had certain zwitterionic anilides showed high affinity to the NMDA-glycine binding site. The absolute configuration of 3S-(-)-4 was confirmed by X-ray crystallographic analysis. In particular, 3g (SM-31900) was found to be a highly active glycine antagonist for both in vitro and in vivo assays (Ki = 1.0 ± 0.1 nM, ED50 = 2.3 mg/kg, iv) and also showed high selectivity for the glycine site. In addition, 3g was soluble enough in aqueous media (> 10 mg/mL at pH 7.4) to use for medications by intravenous injection.
- Katayama, Seiji,Ae, Nobuyuki,Kodo, Toru,Masumoto, Shuji,Hourai, Shinji,Tamamura, Chika,Tanaka, Hiroyasu,Nagata, Ryu
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p. 691 - 701
(2007/10/03)
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- Anti-Helicobacter pylori agents. 4. 2-(Substituted guanidino)-4-phenylthiazoles and some structurally rigid derivatives
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In order to find a new class of anti-Helicobacter pylori (H. pylori) agents, a series of 4-[(3-acetamido)phenyl]-2-(substituted guanidino)thiazoles and some structurally rigid analoges were synthesized and evaluated for antimicrobial activity against H. pylori. Among the compounds obtained, high anti-H. pyrori activities were observed in benzyl derivative 34 (MIC = 0.025 μg/mL) and phenethyl derivatives 35 and 36 (MIC = 0.037 μg/mL and 0.017 μg/mL). Though alkyl derivatives generally showed lower activity, the 2-methoxyethyl derivative 28 preserved significant activity (MIC = 0.32 μg/mL) and also exhibited more potent gastric antisecretory activity than ranitidine. Structural restriction by bridging between the thiazole and the phenyl rings with an alkyl chain did not improve the activity in this series.
- Katsura,Tomishi,Inoue,Sakane,Matsumoto,Morinaga,Ishikawa,Takasugi
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p. 3315 - 3321
(2007/10/03)
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- The first preparation of α-functionalized benzylamine
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We have investigated the α-acetoxylation of benzylamine derivatives 4 from substituted benzylphthalimide 3 using NBS/AcONa/AcOH in chlorobenzene at reflux.
- Cho, Su-Dong,Kim, Hyeung-Jae,Ahn, Chuljin,Falckb,Shin, Dong-Soo
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p. 8215 - 8217
(2007/10/03)
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- Benzylphthalimides and phenethylphthalimides with thalidomide-like activity on the production of tumor necrosis factor α
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Benzylphthalimide analogs (P1P's) and phenethylphthalimide analogs (P2P's) have been found to exhibit thalidomide-like activity on the production of tumor necrosis factor (TNF)-α by the human leukemia cell line, HL-60, stimulated by 12-O-tetradecanoylphorbol-13-acetate (TPA). Structure-activity relationships are discussed on the basis of the TNF-α production-enhancing activity. Benzylphthalimide (P1P-00) exhibited activity which is weaker than that of thalidomide, but introduction of a methyl group at the ortho-position of the benzyl moiety (P1P-10) resulted an increase to a level comparable with that of thalidomide. Phenethylphthalimide (P2P-00) is more potent than thalidomide, and its fluorinated derivative, 2-phenethyl-4,5,6,7-tetrafluoro- 1H-isoindole-1,3-dione (FP2P-00), exhibited potent activity at very low concentrations.
- Sasaki,Shibata,Hashimoto,Iwasaki
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p. 1228 - 1233
(2007/10/03)
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- TROEGER'S BASE ANALOGS. NEW STRUCTURAL UNITS FOR THE PREPARATION OF CHIRAL HOSTS AND METAL LIGANDS.
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Several Troeger's base analogs are prepared and presented as practical, structurally well defined and unique "folded" armatures for the preparation of chelating or macrocyclic host molecules.
- Wilcox, Craig S.
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p. 5749 - 5752
(2007/10/02)
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- Synthetic Approaches to some Aza-analogues of Benzimidazole N-Oxides. Part 1. The Imidazopyridine Series
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The 3-oxide of 2-p-nitrophenylimidazopyridine (8) may be obtained in good yield by base-induced cyclisation of 2-nitro-3-(p-nitrobenzylamino)pyridine (18).It is also obtained in lower yield, along with p-nitrobenzoic acid and other cleavage products, by the corresponding reactions of bases with the N-ethoxycarbonyl, N-methylsulphonyl, and N-p-tolylsulphonyl derivatives of 2-nitro-3-(p-nitrobenzylamino)pyridine .Cleavage is the main reaction when N-(2-nitro-3-pyridyl)-N-phenacylmethanesulphonamide (17) is treated with bases: phenylglyoxal, or its Schiff base with 3-amino-2-nitropyridine, are possible intermediates in the cleavage process. 3-Nitro-2-(p-nitrobenzylamino)pyridine (31) is similarly cyclised in basic media to give the 1-oxide of 2-p-nitrophenylimidazopyridine (32).
- Andrews, Adrian F.,Smith, David M.,Hodson, Harold F.,Thorogood, Peter B.
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p. 2995 - 3006
(2007/10/02)
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- NMR STUDIES ON IMIDINES. I. AN 1H AND 13C NMR STUDY OF 10,12-DIHYDROISOINDOLOQUINAZOLINE-12-ONE
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10,12-Dihydroisoindoloquinazoline-12-one (5) was prepared and fully examined by 1H and 13C NMR spectroscopy in CDCl3 and DMSO-d6 solution.
- Spiessens, Luc I.,Anteunis, Marc J. O.
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p. 1167 - 1176
(2007/10/02)
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