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Molecules, Volume 11, Issue 4 (April 2006), Pages 212-308

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Open AccessArticle 2,6-Dichloro-9-thiabicyclo[3.3.1]nonane: Multigram Display of Azide and Cyanide Components on a Versatile Scaffold
Molecules 2006, 11(4), 212-218; doi:10.3390/11040212
Received: 16 March 2006 / Accepted: 27 March 2006 / Published: 27 March 2006
Cited by 10 | PDF Full-text (215 KB) | HTML Full-text | XML Full-text
Abstract
2,6-Dichloro-9-thiabicyclo[3.3.1]nonane, easily available by an improved condensation of sulfur dichloride, sulfuryl chloride, and 1,5-cyclooctadiene, is a well- behaved scaffold for the nucleophilic substitution of azides and cyanides via neighboring- group participation by the sulfur atom. The products are isolated in high yields with
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2,6-Dichloro-9-thiabicyclo[3.3.1]nonane, easily available by an improved condensation of sulfur dichloride, sulfuryl chloride, and 1,5-cyclooctadiene, is a well- behaved scaffold for the nucleophilic substitution of azides and cyanides via neighboring- group participation by the sulfur atom. The products are isolated in high yields with purity >95% by simple extraction and washing protocols. Full article
Open AccessArticle A Java Chemical Structure Editor Supporting the Modular Chemical Descriptor Language (MCDL)
Molecules 2006, 11(4), 219-231; doi:10.3390/11040219
Received: 7 December 2005 / Revised: 24 March 2006 / Accepted: 24 March 2006 / Published: 29 March 2006
Cited by 6 | PDF Full-text (85 KB) | HTML Full-text | XML Full-text
Abstract
A compact Modular Chemical Descriptor Language (MCDL) chemical structure editor (Java applet) is described. The small size (approximately 200 KB) of the applet allows its use to display and edit chemical structures in various Internet applications. The editor supports the MCDL format, in
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A compact Modular Chemical Descriptor Language (MCDL) chemical structure editor (Java applet) is described. The small size (approximately 200 KB) of the applet allows its use to display and edit chemical structures in various Internet applications. The editor supports the MCDL format, in which structures are presented in compact canonical form and is capable of restoring bond orders as well as of managing atom and bond drawing overlap. A small database of cage and large cyclic fragment is used for optimal representation of difficult-to-draw molecules. The improved algorithm of the structure diagram generation can be used for other chemical notations that lack atomic coordinates (SMILES, InChI). Full article
Open AccessArticle Substituted Pyrazinecarboxamides: Synthesis and Biological Evaluation
Molecules 2006, 11(4), 242-256; doi:10.3390/11040242
Received: 20 July 2005 / Revised: 19 March 2006 / Accepted: 20 March 2006 / Published: 29 March 2006
Cited by 39 | PDF Full-text (103 KB) | HTML Full-text | XML Full-text
Abstract
Condensation of the corresponding chlorides of some substituted pyrazine-2-carboxylic acids (pyrazine-2-carboxylic acid, 6-chloropyrazine-2-carboxylic acid, 5-tert-butylpyrazine-2-carboxylic acid or 5-tert-butyl-6-chloropyrazine-2-carboxylic acid) withvarious ring-substituted aminothiazoles or anilines yielded a series of amides. Thesyntheses, analytical and spectroscopic data of thirty newly prepared compounds arepresented. Structure-activity relationships between
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Condensation of the corresponding chlorides of some substituted pyrazine-2-carboxylic acids (pyrazine-2-carboxylic acid, 6-chloropyrazine-2-carboxylic acid, 5-tert-butylpyrazine-2-carboxylic acid or 5-tert-butyl-6-chloropyrazine-2-carboxylic acid) withvarious ring-substituted aminothiazoles or anilines yielded a series of amides. Thesyntheses, analytical and spectroscopic data of thirty newly prepared compounds arepresented. Structure-activity relationships between the chemical structures and the anti-mycobacterial, antifungal and photosynthesis-inhibiting activity of the evaluatedcompounds are discussed. 3,5-Bromo-4-hydroxyphenyl derivatives of substitutedpyrazinecarboxylic acid, 16-18, have shown the highest activity against Mycobacteriumtuberculosis H37Rv (54-72% inhibition). The highest antifungal effect againstTrichophyton mentagrophytes, the most susceptible fungal strain tested, was found for5-tert-butyl-6-chloro-N-(4-methyl-1,3-thiazol-2-yl)pyrazine-2-carboxamide (8, MIC =31.25 μmol·mL-1). The most active inhibitors of oxygen evolution rate in spinachMolecules 2006, 11 243 chloroplasts were the compounds 5-tert-butyl-6-chloro-N-(5-bromo-2-hydroxyphenyl)- pyrazine-2-carboxamide (27, IC50 = 41.9 μmol·L-1) and 5-tert-butyl-6-chloro-N-(1,3- thiazol-2-yl)-pyrazine-2-carboxamide (4, IC50 = 49.5 μmol·L-1). Full article
Open AccessCommunication Isolation and Biological Activity of New and Known Diterpenoids From Sideritis stricta Boiss. & Heldr.
Molecules 2006, 11(4), 257-262; doi:10.3390/11040257
Received: 28 October 2005 / Revised: 20 February 2006 / Accepted: 21 February 2006 / Published: 29 March 2006
Cited by 18 | PDF Full-text (55 KB) | HTML Full-text | XML Full-text
Abstract
Nine known and one new ent-kaurene diterpenoid were isolated from the acetone extract of Sideritis stricta Boiss & Heldr. The new compound, identified as ent-1β-hydroxy-7α-acetyl-15β,16β-epoxykaurane (1) by IR, 1D and 2D NMR techniques and mass spectra, was isolated along with sideroxol (2), 7-acetyl
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Nine known and one new ent-kaurene diterpenoid were isolated from the acetone extract of Sideritis stricta Boiss & Heldr. The new compound, identified as ent-1β-hydroxy-7α-acetyl-15β,16β-epoxykaurane (1) by IR, 1D and 2D NMR techniques and mass spectra, was isolated along with sideroxol (2), 7-acetyl sideroxol (3), 7-epicandicandiol (4), linearol (5), ent-7α,15β,18-trihydroxy-kaur-16-ene (6), ent-7α-acetyl,15,18-dihydroxy-kaur-16-ene (7), foliol (8), sideridiol (9) and siderol (10). The antibacterial and antifungal activities of these compounds and the whole crude acetone extract were evaluated against E. coli, S. aureus, K. pneumeonia and C. albicans. Full article
Open AccessArticle ZrOCl2·8H2O: An Efficient, Cheap and Reusable Catalyst for the Esterification of Acrylic Acid and Other Carboxylic Acids with Equimolar Amounts of Alcohols
Molecules 2006, 11(4), 263-271; doi:10.3390/11040263
Received: 20 January 2006 / Accepted: 9 April 2006 / Published: 10 April 2006
Cited by 17 | PDF Full-text (52 KB) | HTML Full-text | XML Full-text
Abstract
Esterifications of carboxylic acids with equimolar amount of alcohols could beefficiently catalyzed by ZrOCl2·8H2O. Acrylate esters were obtained in good yields undersolvent-free conditions at ambient temperature. The esterification of other carboxylicacids with alcohols also proceeded at ambient temperature or
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Esterifications of carboxylic acids with equimolar amount of alcohols could beefficiently catalyzed by ZrOCl2·8H2O. Acrylate esters were obtained in good yields undersolvent-free conditions at ambient temperature. The esterification of other carboxylicacids with alcohols also proceeded at ambient temperature or at 50 oC to afford esters inhigh yields. If the esterification was performed in toluene under azeotropic refluxconditions to remove water, both the catalytic activity of ZrOCl2·8H2O and the rate ofesterification could be increased greatly. Furthermore, in the present catalytic system, theesters could be easily separated from the reaction mixtures and the catalyst could beeasily recovered and reused. Full article
Open AccessArticle Microwave Assisted Synthesis of N-Arylheterocyclic Substituted-4-aminoquinazoline Derivatives
Molecules 2006, 11(4), 272-278; doi:10.3390/11040272
Received: 16 January 2006 / Revised: 25 March 2006 / Accepted: 7 April 2006 / Published: 10 April 2006
Cited by 15 | PDF Full-text (47 KB) | HTML Full-text | XML Full-text
Abstract
A simple, efficient, and general method has been developed for the synthesis of various N-aryl heterocylic substituted-4-aminoquinazoline compounds from 4-chloro- quinazoline and aryl heterocyclic amines under microwave irradiation using 2-propanol as solvent. The advantages of the use of microwave irradiation in relation to
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A simple, efficient, and general method has been developed for the synthesis of various N-aryl heterocylic substituted-4-aminoquinazoline compounds from 4-chloro- quinazoline and aryl heterocyclic amines under microwave irradiation using 2-propanol as solvent. The advantages of the use of microwave irradiation in relation to the classical method were demonstrated. Full article
Open AccessArticle Reactions of (Benzamidomethyl)triethylammonium Chloride with Some Inorganic Nucleophiles in Aqueous Media
Molecules 2006, 11(4), 279-285; doi:10.3390/11040279
Received: 3 March 2006 / Accepted: 9 April 2006 / Published: 10 April 2006
Cited by 4 | PDF Full-text (58 KB) | HTML Full-text | XML Full-text
Abstract
A variety of benzamidomethyl derivatives were prepared in water under alkaline conditions (pH>9) via reaction of (benzamidomethyl)triethylammonium chloride (1) with different inorganic nucleophiles. Reaction of 1 with hydroxylamine did not give the expected mono(benzamidomethyl)-hydroxylamine (3) but rather gave N,N- di(benzamidomethyl)hydroxylamine (2). Reactions of
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A variety of benzamidomethyl derivatives were prepared in water under alkaline conditions (pH>9) via reaction of (benzamidomethyl)triethylammonium chloride (1) with different inorganic nucleophiles. Reaction of 1 with hydroxylamine did not give the expected mono(benzamidomethyl)-hydroxylamine (3) but rather gave N,N- di(benzamidomethyl)hydroxylamine (2). Reactions of 1 with sodium azide and potassium cyanide gave benzamidomethyl azide (4a) and benzamidomethyl cyanide (4b) respectively. Potassium thiocyanate and sodium iodide reacted with 1, and the anion- exchanged products (benzamidomethyl)triethylammonium isothiocyanate (5a) and (benzamidomethyl)triethylammonium iodide (5b) were thus obtained. Cyanamide and potassium cyanate reacted readily with 1 and both gave the same mixture of di(benzamidomethyl)amine (7) and tri(benzamidomethyl)amine (8). All the reactions occurred smoothly, under mild conditions, to give the products in moderate to high yields. Full article
Open AccessArticle Improved Synthesis of Substituted 6,7-Dihydroxy-4-quinazolineamines: Tandutinib, Erlotinib and Gefitinib
Molecules 2006, 11(4), 286-297; doi:10.3390/11040286
Received: 9 March 2006 / Accepted: 10 April 2006 / Published: 10 April 2006
Cited by 52 | PDF Full-text (66 KB) | HTML Full-text | XML Full-text
Abstract The synthesis of three substituted 6,7-dihydroxy-4-quinazolineamines: tandutinib (1), erlotinib (2) and gefitinib (3) in improved yields is reported. The intermediates were characterized by NMR and the purities determined by HPLC. Full article
Open AccessArticle Catalytic Properties of the Dioxomolybdenum Siloxide MoO2(OSiPh3)2 and its 2,2'-Bipyridine Adduct MoO2(OSiPh3)2(bpy)
Molecules 2006, 11(4), 298-308; doi:10.3390/11040298
Received: 31 March 2006 / Revised: 10 April 2006 / Accepted: 10 April 2006 / Published: 12 April 2006
Cited by 15 | PDF Full-text (115 KB) | HTML Full-text | XML Full-text
Abstract
The tetrahedral triphenylsiloxy complex MoO2(OSiPh3)2 (1) and its Lewis baseadduct with 2,2'-bipyridine, MoO2(OSiPh3)2(bpy) (2), were prepared and characterised byIR/Raman spectroscopy, and thermogravimetric analysis. Both compounds catalyse theepoxidation of cis-cyclooctene at 55 o
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The tetrahedral triphenylsiloxy complex MoO2(OSiPh3)2 (1) and its Lewis baseadduct with 2,2'-bipyridine, MoO2(OSiPh3)2(bpy) (2), were prepared and characterised byIR/Raman spectroscopy, and thermogravimetric analysis. Both compounds catalyse theepoxidation of cis-cyclooctene at 55 oC using tert-butylhydroperoxide (t-BuOOH) isdecane as the oxidant, giving 1,2-epoxycyclooctane as the only product. The best resultswere obtained in the absence of a co-solvent (other than the decane) or in the presence of1,2-dichloroethane, while much lower activities were obtained when hexane oracetonitrile were added. With no co-solvent, catalyst 1 (initial activity 272 mol·molMo-1·h-1for a catalyst:substrate: oxidant molar ratio of 1:100:150) is much more active than 2(initial activity 12 mol·molMo–1·h–1). The initial reaction rates showed first orderdependence with respect to the initial concentration of olefin. With respect to the initialamount of oxidant, the rate order dependence for 1 (1.9) was higher than that for 2 (1.6).The dependence of the initial reaction rate on reaction temperature and initial amount ofcatalyst was also studied for both catalysts. The lower apparent activation energy of 1 (11kcal·mol–1) as compared with 2 (20 kcal·mol–1) is in accordance with the higher activity ofthe former. Full article

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Open AccessCorrection Publisher's Note added on 29 June 2006
Molecules 2006, 11(4), 232-241; doi:10.3390/11040232
Published: 29 June 2006
PDF Full-text (84 KB)
Abstract
There is a pagination error in this paper. The page number for the first page (Sergei V. Trepalin et al. Molecules 2006, 11, 219) is assigned correctly. However, the following pages were not correctly paginated and the final page number should be
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There is a pagination error in this paper. The page number for the first page (Sergei V. Trepalin et al. Molecules 2006, 11, 219) is assigned correctly. However, the following pages were not correctly paginated and the final page number should be 231 instead of 241. The original file is still provided. Pages 232-241 are thus taken as blank pages. We apologize for this error and for any inconvenience Full article

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