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Molecules, Volume 8, Issue 7 (July 2003) – 8 articles , Pages 520-606

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8 KiB  
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Withdrawn Paper: Molecules 2001, 6, 647-654 [1]
by Derek McPhee
Molecules 2003, 8(7), 520; https://doi.org/10.3390/80700520 - 31 Jul 2003
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170 KiB  
Article
Preparation and Crystal Structure of (1S, 5S, 7S, 8R)-8-Hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-one
by Vratislav Langer, Dalma Gyepesová, Marian Koman, Peter Kapitán, Matej Babjak, Tibor Gracza and Miroslav Koóš
Molecules 2003, 8(7), 599-606; https://doi.org/10.3390/80700599 - 15 Jul 2003
Cited by 2 | Viewed by 8618
Abstract
The absolute configuration at two newly formed stereogenic centres (5S, 7S) during the key steps of the total synthesis of naturally occuring goniothalesdiol was established by single-crystal X-ray diffraction analysis relative to stereocentres (1S, 8R) of the title compound (alternatively named 3,6-anhydro-2-deoxy-6-phenyl-L-ido-1,4-hexonolactone, C [...] Read more.
The absolute configuration at two newly formed stereogenic centres (5S, 7S) during the key steps of the total synthesis of naturally occuring goniothalesdiol was established by single-crystal X-ray diffraction analysis relative to stereocentres (1S, 8R) of the title compound (alternatively named 3,6-anhydro-2-deoxy-6-phenyl-L-ido-1,4-hexonolactone, C12H12O4). The conformation of both 5-membered lactone and furanose fused rings is also discussed. Full article
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29 KiB  
Article
Selective Nitration of Aromatic Compounds with Bismuth Subnitrate and Thionyl Chloride
by Hussni A. Muathen
Molecules 2003, 8(7), 593-598; https://doi.org/10.3390/80700593 - 15 Jul 2003
Cited by 37 | Viewed by 13219
Abstract
Bismuth subnitrate/thionyl chloride have been found to be an efficient combination of reagents for nitration of a wide range of aromatic compounds in dichloromethane. Phenols, in particular, were easily mononitrated and dinitrated with the reagents by controlling the stoichiometry, Full article
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3765 KiB  
Article
Phthalimides: Supramolecular Interactions in Crystals, Hypersensitive Solution 1H-NMR Dynamics and Energy Transfer to Europium(III) and Terbium(III) States
by Robertha C. Howell, Selvin H. Edwards, Alison S. Gajadhar-Plummer, Ishenkumba A. Kahwa, Gary L. McPherson, Joel T. Mague, Andrew J. P. White and David J. Williams
Molecules 2003, 8(7), 565-592; https://doi.org/10.3390/molecules8070565 - 15 Jul 2003
Cited by 13 | Viewed by 12623
Abstract
Detailed crystal structures and 1H-NMR characteristics of some alkylaminephthalimides, including dendritic polyphthalimides, are reported. These investigations were undertaken in order to obtain a better understanding of the relationship between solid-state supramolecular interactions, their persistence in solution and associated dynamics of magnetically hypersensitive [...] Read more.
Detailed crystal structures and 1H-NMR characteristics of some alkylaminephthalimides, including dendritic polyphthalimides, are reported. These investigations were undertaken in order to obtain a better understanding of the relationship between solid-state supramolecular interactions, their persistence in solution and associated dynamics of magnetically hypersensitive phthalimide aromatic AA'BB'-AA'XX' proton NMR resonances. Some alkylamine phthalimides feature folded molecular geometries, which we attribute to n-π interactions among proximal amine-phthalimide sites; those alkylamine-phthalimides that have no possibility for such interactions feature fully extended phthalimide functionalities. Accordingly, alkylamine phthalimide compounds with folded solid-state geometries feature solvent and temperature dependent hypersensitive AA'BB'-AA'XX' 1H-NMR line profiles, which we attribute to the n-π interactions. Luminescence of Eu3+(5D0) and Tb3+(5D4) states show well defined metal ion environments in their complexes with dendritic phthalimides, as well as relatively weak phthalimide-lanthanide(III) interactions. Full article
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52 KiB  
Article
Synthesis of Plasmepsin II Inhibitors – Potential Antimalarial Agents
by Reto Mueller, Marianne Huerzeler and Christoph Boss
Molecules 2003, 8(7), 556-564; https://doi.org/10.3390/80700556 - 15 Jul 2003
Cited by 12 | Viewed by 9297
Abstract
A new series of plasmepsin II (PM II) inhibitors has been prepared based on 4-aminopiperidine-tert-butyl-carbamate (1). These compounds might be useful as antimalarial drugs acting via a new mechanism, and therefore be less susceptible to parasite resistance now often observed with [...] Read more.
A new series of plasmepsin II (PM II) inhibitors has been prepared based on 4-aminopiperidine-tert-butyl-carbamate (1). These compounds might be useful as antimalarial drugs acting via a new mechanism, and therefore be less susceptible to parasite resistance now often observed with current antimalarial therapies. Some of the final compounds prepared exhibited encouraging inhibitory activity towards PM II. Full article
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133 KiB  
Article
Microwave Assisted Synthesis, Part 1: Rapid Solventless Synthesis of 3-Substituted Coumarins and Benzocoumarins by Microwave Irradiation of the Corresponding Enaminones
by Khadijah M. Al-Zaydi
Molecules 2003, 8(7), 541-555; https://doi.org/10.3390/80700541 - 15 Jul 2003
Cited by 50 | Viewed by 10448
Abstract
The reactivity of enaminones toward a variety of reagents under microwave irradiation is reported. The results are compared with traditional solution methods. Full article
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109 KiB  
Article
Synthesis and Reactivity of New 1-Pentafluorophenyl-1Hpyrrole Derivatives
by Katarína Hrnčariková and Daniel Végh
Molecules 2003, 8(7), 536-540; https://doi.org/10.3390/80700536 - 15 Jul 2003
Cited by 11 | Viewed by 7920
Abstract
We present 1-pentafluorophenyl-1H-pyrrole and some of its electrophilic substitution reactions: formylation and acetylations. The 2-substituted products formed in these reactions are selectively and in high yield converted into 3-substituted products by treatment with trifluoromethanesulfonic acid. A general synthesis of 3-acylpyrroles was developed by [...] Read more.
We present 1-pentafluorophenyl-1H-pyrrole and some of its electrophilic substitution reactions: formylation and acetylations. The 2-substituted products formed in these reactions are selectively and in high yield converted into 3-substituted products by treatment with trifluoromethanesulfonic acid. A general synthesis of 3-acylpyrroles was developed by the trifluoromethanesulfonic acid-mediated rearrangement of the corresponding 2-acylpyrroles. Full article
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131 KiB  
Article
Synthesis and Characterization of Acyclic and Cyclic Azabridged Ligands Incorporating 2,2'-Bipyridine Subunits and Their Complexes With Copper(II), Cobalt(II), and Nickel(II)
by Antonino Mamo and Andrea Pappalardo
Molecules 2003, 8(7), 521-535; https://doi.org/10.3390/80700521 - 15 Jul 2003
Cited by 2 | Viewed by 10067
Abstract
The synthesis of a series of N,N'-disubstituted acyclic (AL) and cyclic (CL) aza-bridged ligands incorporating 2,2-pipryidine subunits is described. 1H-NMR and IR spectral data support the proposed ligand structures. Dynamic 1H-NMR studies on diurea and diamide derivatives point to the presence [...] Read more.
The synthesis of a series of N,N'-disubstituted acyclic (AL) and cyclic (CL) aza-bridged ligands incorporating 2,2-pipryidine subunits is described. 1H-NMR and IR spectral data support the proposed ligand structures. Dynamic 1H-NMR studies on diurea and diamide derivatives point to the presence of slowly interconverting conformers on the 1H-NMR time-scale, owing to N−H···N hydrogen bonding and/or a restricted rotation around the amide bonds. The ligands synthesized form 1:1 complexes with divalent transition metal ions. Upon complexation, bis-ester derivatives AL5 and CL5 undergo a metal-induced hydrolysis of the ester groups to carboxyl functions, which act as additional binding sites for the metal ion, as well as hydrogen-bonding donor-acceptor binding site to produce dimeric complexes. Full article
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