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Molecules, Volume 11, Issue 6 (June 2006), Pages 383-495

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Research

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Open AccessArticle Synthesis and Antifungal Bioactivities of 3-Alkylquinazolin- 4-one Derivatives
Molecules 2006, 11(6), 383-392; doi:10.3390/11060383
Received: 26 April 2006 / Accepted: 12 June 2006 / Published: 12 June 2006
Cited by 38 | PDF Full-text (70 KB) | HTML Full-text | XML Full-text
Abstract
A simple, efficient, and general method has been developed for the synthesis ofvarious 3-alkylquinazolin-4-one derivatives from quinazolin-4-one treated with alkylbromides under phase transfer catalysis condition. The structures of the compounds werecharacterized by elemental analysis, IR, 1H-NMR and 13C-NMR spectra. Title [...] Read more.
A simple, efficient, and general method has been developed for the synthesis ofvarious 3-alkylquinazolin-4-one derivatives from quinazolin-4-one treated with alkylbromides under phase transfer catalysis condition. The structures of the compounds werecharacterized by elemental analysis, IR, 1H-NMR and 13C-NMR spectra. Title compound6-bromo-3-propylquinazolin-4-one (3h) was found to possess good antifungal activity. Full article
Open AccessArticle Synthesis and Analgesic Activity Evaluation of Some Agmatine Derivatives
Molecules 2006, 11(6), 393-402; doi:10.3390/11060393
Received: 10 May 2006 / Accepted: 9 June 2006 / Published: 12 June 2006
Cited by 4 | PDF Full-text (127 KB) | HTML Full-text | XML Full-text
Abstract
A series of N,N’-disubstituted-2-nitroethene-1,1-diamine and N,N’-disubstituted- N’’-cyanoguanidine derivatives were prepared and evaluated for in vivo analgesic activity. The blood brain barrier (BBB) VolSurf model was used to predict the BBB permeation profiles of our synthesized compounds. Some compounds show both remarkable analgesic [...] Read more.
A series of N,N’-disubstituted-2-nitroethene-1,1-diamine and N,N’-disubstituted- N’’-cyanoguanidine derivatives were prepared and evaluated for in vivo analgesic activity. The blood brain barrier (BBB) VolSurf model was used to predict the BBB permeation profiles of our synthesized compounds. Some compounds show both remarkable analgesic activity and good BBB permeation profiles, and these compounds might be developed for treatment of opioid tolerance and dependence. Full article
Open AccessArticle Synthesis of New trans-2-Benzyl-3-(furan-2-yl)-4-substituted-1,2,3,4-tetrahydroisoquinolinones
Molecules 2006, 11(6), 403-414; doi:10.3390/11060403
Received: 10 May 2006 / Accepted: 8 June 2006 / Published: 12 June 2006
Cited by 17 | PDF Full-text (87 KB) | HTML Full-text | XML Full-text
Abstract
The reaction of homophthalic anhydride and N-(furan-2-yl-methylidene)- benzylamine in different solvents and varying temperatures was studied in detail. Mixtures of the expected trans- and cis-1,2,3,4-tetrahydroisoquinoline-4-carboxylic acids trans-5 and cis-5, alongwith by-products 6 and 7 were obtained in dichloroethane or benzene. In pyridine, [...] Read more.
The reaction of homophthalic anhydride and N-(furan-2-yl-methylidene)- benzylamine in different solvents and varying temperatures was studied in detail. Mixtures of the expected trans- and cis-1,2,3,4-tetrahydroisoquinoline-4-carboxylic acids trans-5 and cis-5, alongwith by-products 6 and 7 were obtained in dichloroethane or benzene. In pyridine, used for the first time, the reaction became completely diastereoselective, giving only the trans isomer. The carboxylic acid group of trans-5 was transformed in four steps into cyclic aminomethyl groups which yielded various new tetrahydroisoquinolinones trans- 11a-g, incorporating both a known fragment of pharmacological interest and various pharmacophoric substituents. Full article
Open AccessCommunication Theoretical Studies on the Tautomerism of 1,5,6,7-Tetrahydro-4H-indazol-4-ones
Molecules 2006, 11(6), 415-420; doi:10.3390/11050415
Received: 7 June 2006 / Accepted: 9 June 2006 / Published: 12 June 2006
Cited by 4 | PDF Full-text (59 KB) | HTML Full-text | XML Full-text
Abstract
Computational studies on three tautomeric forms of four 1,5,6,7-tetrahydro- 4H-indazol-4-one derivatives: 1,5,6,7-tetrahydro-4H-indazol-4-one (1), 6,6-dimethyl- 1,5,6,7-tetrahydro-4H-indazol-4-one (2), 3-methyl-1,5,6,7-tetrahydro-4H-indazol-4-one (3) and 3,6,6-trimethyl-1,5,6,7-tetrahydro-4H-indazol-4-one (4), have been performed at different levels, ranging from semiempirical AM1, ab initio Hartree-Fock HF/6-31G* and HF/6-31G** to B3LYP/6-31G** density functional calculations. [...] Read more.
Computational studies on three tautomeric forms of four 1,5,6,7-tetrahydro- 4H-indazol-4-one derivatives: 1,5,6,7-tetrahydro-4H-indazol-4-one (1), 6,6-dimethyl- 1,5,6,7-tetrahydro-4H-indazol-4-one (2), 3-methyl-1,5,6,7-tetrahydro-4H-indazol-4-one (3) and 3,6,6-trimethyl-1,5,6,7-tetrahydro-4H-indazol-4-one (4), have been performed at different levels, ranging from semiempirical AM1, ab initio Hartree-Fock HF/6-31G* and HF/6-31G** to B3LYP/6-31G** density functional calculations. These calculations have been used to establish the most stable tautomer, which in all cases was in agreement with the experimental data. Full article
Open AccessArticle A Convenient Asymmetric Synthesis of a β-amino Ester with Additional Functionalization as a Precursor for Peptide Nucleic Acid (PNA) Monomers
Molecules 2006, 11(6), 435-443; doi:10.3390/11060435
Received: 8 June 2006 / Revised: 13 June 2006 / Accepted: 15 June 2006 / Published: 21 June 2006
Cited by 4 | PDF Full-text (93 KB) | HTML Full-text | XML Full-text
Abstract
We report the asymmetric synthesis of di-3-pentyl (3S,αS,7E)-3-N-benzyl-N- α-methylbenzylamino-dec-7-enedioate (9), which contains the correct functionalization to produce δ-amino acid derivatives to be used as monomers for Peptide Nucleic Acid (PNA) formation With this aim, thymine-pentanoic acid 15 and some of its ester [...] Read more.
We report the asymmetric synthesis of di-3-pentyl (3S,αS,7E)-3-N-benzyl-N- α-methylbenzylamino-dec-7-enedioate (9), which contains the correct functionalization to produce δ-amino acid derivatives to be used as monomers for Peptide Nucleic Acid (PNA) formation With this aim, thymine-pentanoic acid 15 and some of its ester derivatives were obtained, their reactivity was studied and the noteworthy ethyl ester 12 was quantitatively produced by transesterification of methyl ester 11, thus paving the way for the synthesis of the thymine-containing amino ester IV, which has been designed as a building block for a Nucleic-Acid analog with a chiral, flexible peptide backbone Full article
Open AccessArticle Synthesis, Molecular Structure and Characterization of Allylic Derivatives of 6-Amino-3-methyl-1,2,4-triazolo[3,4-f][1,2,4]-triazin-8(7H)-one
Molecules 2006, 11(6), 444-452; doi:10.3390/11060444
Received: 31 May 2006 / Revised: 17 June 2006 / Accepted: 19 June 2006 / Published: 22 June 2006
PDF Full-text (259 KB) | HTML Full-text | XML Full-text
Abstract
1-Allyl- (2) and 7-allyl-6-amino-3-methyl-1,2,4-triazolo[3,4-f][1,2,4]triazin-8(7H)-one (3) were obtained via the 18-crown-6-ether catalyzed room temperature reactionof 6-amino-3-methyl-1,2,4-triazolo[3,4-f][1,2,4]triazin-8(7H)-one (1) with potassiumcarbonate and allyl bromide in dry acetone. The structures of these two derivatives wereverified by 2D-NMR measurements, including gHSQC and gHMBC measurements. Theminor compound 2 [...] Read more.
1-Allyl- (2) and 7-allyl-6-amino-3-methyl-1,2,4-triazolo[3,4-f][1,2,4]triazin-8(7H)-one (3) were obtained via the 18-crown-6-ether catalyzed room temperature reactionof 6-amino-3-methyl-1,2,4-triazolo[3,4-f][1,2,4]triazin-8(7H)-one (1) with potassiumcarbonate and allyl bromide in dry acetone. The structures of these two derivatives wereverified by 2D-NMR measurements, including gHSQC and gHMBC measurements. Theminor compound 2 may possess aromatic character. A single crystal X-ray diffractionexperiment indicated that the major compound 3 crystallizes from dimethyl sulfoxide in themonoclinic space group P21/n and its molecular structure includes an attached dimethylsulfoxide molecule, resulting in the molecular formula C10H16N6O2S. Molecular structuresof 3 are linked by extensive intermolecular N-H···N hydrogen bonding [graph set C 1 (7)]. 1Each molecule is attached to the dimethyl sulfoxide oxygen via N-H···O intermolecularhydrogen bonding. The structure is further stabilized by π-π stacking interactions. Full article
Open AccessArticle Syntheses and Structural Studies of Schiff Bases Involving Hydrogen Bonds
Molecules 2006, 11(6), 453-463; doi:10.3390/11060453
Received: 7 June 2006 / Revised: 20 June 2006 / Accepted: 20 June 2006 / Published: 21 June 2006
Cited by 7 | PDF Full-text (239 KB) | HTML Full-text | XML Full-text
Abstract
New Schiff bases have been prepared by reacting 3-hydroxy-4-pyridine- carboxaldehyde with various amines. NMR spectroscopic methods provided clear evidence that the Schiff bases exist in the solid state and in solution as hydroxyimino tautomers with the E-configuration. A study of the stabilities [...] Read more.
New Schiff bases have been prepared by reacting 3-hydroxy-4-pyridine- carboxaldehyde with various amines. NMR spectroscopic methods provided clear evidence that the Schiff bases exist in the solid state and in solution as hydroxyimino tautomers with the E-configuration. A study of the stabilities of the tautomeric forms and the different conformers has been carried out using density functional calculations at the B3LYP/6-31G** level. Full article
Open AccessArticle Ionic Liquid-promoted Ring-closure Reactions between 1,4-Dihydroxyanthraquinone and Diamines
Molecules 2006, 11(6), 464-468; doi:10.3390/11060464
Received: 10 May 2006 / Revised: 15 June 2006 / Accepted: 19 June 2006 / Published: 21 June 2006
Cited by 1 | PDF Full-text (57 KB) | HTML Full-text | XML Full-text
Abstract The reaction of 1,4-Dihydroxyanthraquinone with diamines was carried out in thepresence of CuCl2, CuCl in the ionic liquid [Bmim]PF6, [Bmim]BF4 or [Bmim]Cl·CuCl. Full article
Open AccessArticle Synthesis of New Bis-1,2,4-Triazole Derivatives
Molecules 2006, 11(6), 469-477; doi:10.3390/11060469
Received: 10 May 2006 / Revised: 20 June 2006 / Accepted: 21 June 2006 / Published: 21 June 2006
Cited by 46 | PDF Full-text (77 KB) | HTML Full-text | XML Full-text
Abstract
A series of new 1,2/1,3-bis[o-(N-methylidenamino-3-aryl-5-phenyl-4H-1,2,4-triazole-4-yl)phenoxy]ethane/propane derivatives 4 were prepared in good yields bytreatment of 4-amino-3-aryl-5-phenyl-4H-1,2,4-triazoles 2 with certain bis-aldehydes 1.Compounds 4 were reduced with NaBH4 to afford the corresponding 1,2/1,3-bis[o-(N-methylamino-3-aryl-5-phenyl-4H-1,2,4-triazole-4-yl)phenoxy]ethane/propane derivatives5. All new compounds were characterized by IR, 1H-NMR, 13 [...] Read more.
A series of new 1,2/1,3-bis[o-(N-methylidenamino-3-aryl-5-phenyl-4H-1,2,4-triazole-4-yl)phenoxy]ethane/propane derivatives 4 were prepared in good yields bytreatment of 4-amino-3-aryl-5-phenyl-4H-1,2,4-triazoles 2 with certain bis-aldehydes 1.Compounds 4 were reduced with NaBH4 to afford the corresponding 1,2/1,3-bis[o-(N-methylamino-3-aryl-5-phenyl-4H-1,2,4-triazole-4-yl)phenoxy]ethane/propane derivatives5. All new compounds were characterized by IR, 1H-NMR, 13C-NMR and mass spectraldata. Full article
Open AccessArticle Host-Guest Chemistry of Tolbutamide
Molecules 2006, 11(6), 478-485; doi:10.3390/11060478
Received: 29 April 2006 / Revised: 13 June 2006 / Accepted: 15 June 2006 / Published: 23 June 2006
Cited by 7 | PDF Full-text (225 KB) | HTML Full-text | XML Full-text
Abstract
The molecular recognition features of tolbutamide with four synthetic hosts have been studied by means of NMR titrations, NOESY experiments and Monte Carlo (MC) conformational search. The interaction strength and the most probable structure reveal new insights on the recognition phenomena of [...] Read more.
The molecular recognition features of tolbutamide with four synthetic hosts have been studied by means of NMR titrations, NOESY experiments and Monte Carlo (MC) conformational search. The interaction strength and the most probable structure reveal new insights on the recognition phenomena of this urea derivative in comparison with close related compounds. Full article
Open AccessArticle Solid Phase Synthesis of a Metronidazole Oligonucleotide Conjugate
Molecules 2006, 11(6), 486-495; doi:10.3390/11060486
Received: 26 April 2006 / Revised: 23 May 2006 / Accepted: 29 May 2006 / Published: 23 June 2006
PDF Full-text (76 KB) | HTML Full-text | XML Full-text
Abstract
Direct, solid phase synthesis of an oligonucleotide conjugate of the antibioticdrug metronidazole was accomplished by the phosphoramidite method. Removal ofprotecting groups and cleavage from the controlled pore glass (CPG) solid support wassuccessful using mild conditions (20% Et3N in pyridine, then [...] Read more.
Direct, solid phase synthesis of an oligonucleotide conjugate of the antibioticdrug metronidazole was accomplished by the phosphoramidite method. Removal ofprotecting groups and cleavage from the controlled pore glass (CPG) solid support wassuccessful using mild conditions (20% Et3N in pyridine, then conc. NH3 (aq) at rt for 30min) whereas standard conditions (conc. NH3 (aq) at 55 °C for 16 h) cleaved the drug. Full article

Review

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Open AccessReview Hypervalent Iodine–Mediated Ring Contraction Reactions
Molecules 2006, 11(6), 421-434; doi:10.3390/11060421
Received: 27 November 2005 / Accepted: 2 May 2006 / Published: 20 June 2006
Cited by 47 | PDF Full-text (104 KB) | HTML Full-text | XML Full-text
Abstract
Hypervalent iodine reagents constitute a powerful tool in modern synthetic organic chemistry, promoting several important reactions. One such reaction is the ring contraction of cycloalkenes and cycloalkanones promoted by iodine(III) compounds, such as iodobenzene diacetate, iodosylbenzene, iodotoluene difluoride, and [hydroxy(tosyloxy)- iodo]benzene (Koser [...] Read more.
Hypervalent iodine reagents constitute a powerful tool in modern synthetic organic chemistry, promoting several important reactions. One such reaction is the ring contraction of cycloalkenes and cycloalkanones promoted by iodine(III) compounds, such as iodobenzene diacetate, iodosylbenzene, iodotoluene difluoride, and [hydroxy(tosyloxy)- iodo]benzene (Koser ́s reagent). This review covers all the literature related to the ring contraction of cyclic ketones and olefins promoted by iodine(III) species. Full article

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