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Molecules, Volume 2, Issue 1 (January 1997), Pages 1-30

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Editorial

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Open AccessEditorial Preserving and Exploiting Molecular Diversity: Deposit and Exchange of Chemical Information and Chemical Samples
Molecules 1997, 2(1), 1-2; doi:10.3390/jan97p1
Received: 27 December 1996 / Accepted: 7 January 1997 / Published: 17 January 1997
Cited by 1 | PDF Full-text (6 KB)

Research

Jump to: Editorial

Open AccessArticle Synthesis of the Demospongic Compounds, (6Z, 11Z)-Octadecadienoic Acid and (6Z, 11Z)-Eicosadienoic Acid
Molecules 1997, 2(1), 3-6; doi:10.3390/jan97p2
Received: 20 December 1996 / Accepted: 10 January 1997 / Published: 29 January 1997
Cited by 2 | PDF Full-text (25 KB)
Abstract
A stereoselective synthesis of (6Z, 11Z)-octadecadienoic acid (1) and (6Z, 11Z)-eicosadienoic acid (2) from easily accessible pentane-1,5-diol (3) is described. Thus, compound 3 on pyranylation and oxidation gave the aldehyde 5 which was converted to the acid 7 by Wittig reaction with [...] Read more.
A stereoselective synthesis of (6Z, 11Z)-octadecadienoic acid (1) and (6Z, 11Z)-eicosadienoic acid (2) from easily accessible pentane-1,5-diol (3) is described. Thus, compound 3 on pyranylation and oxidation gave the aldehyde 5 which was converted to the acid 7 by Wittig reaction with a suitable phosphorane. Its depyranylation and oxidation furnished the key aldehyde 9 which upon Wittig reaction with n-heptylidene and n-nonylidene phosphoranes, respectively followed by alkaline hydrolysis afforded the title acids. Full article
Open AccessArticle Synthesis of New 2-(1,3-Dithianyl)phenols and Hexakis-[p-(1,3-dithian-2-yl)phenoxy]cyclotriphosphazene
Molecules 1997, 2(1), 7-10; doi:10.3390/jan97p3
Received: 14 October 1996 / Accepted: 27 November 1996 / Published: 29 January 1997
Cited by 3 | PDF Full-text (21 KB)
Abstract 2-Chloro-1,3-dithiane was obtained by the chlorination of 1,3-dithiane with N-chlorosuccinimide. Reactions of 2-chloro-1,3-dithiane with various substituted phenols lead to 2-(1,3-dithianyl)phenols (3). Hexakis-[p-(1,3-dithian-2-yl)phenoxy]cyclotriphosphazene (6) was obtained by reaction with hexachlorotriazacyclotriphosphazene (5). Full article
Open AccessArticle Photoinduced Electron-transfer Reaction of Pentafluoroiodobenzene with Alkenes
Molecules 1997, 2(1), 11-16; doi:10.3390/jan97p4
Received: 5 December 1996 / Accepted: 15 January 1997 / Published: 29 January 1997
Cited by 1 | PDF Full-text (51 KB)
Abstract Irradiation of pentafluoroiodobenzene and alkenes gave the corresponding adducts. The presence of single electron-transfer scavengers, (p-dinitrobenzene and t-Bu2NO) and the free radical inhibitor (hydroquinone) suppressed the reaction. A photoinduced electron-transfer mechanism is proposed. Full article
Open AccessArticle Combinatorial Libraries on Rigid Scaffolds: Solid Phase Synthesis of Variably Substituted Pyrazoles and Isoxazoles
Molecules 1997, 2(1), 17-30; doi:10.3390/jan97p5
Received: 22 September 1996 / Accepted: 17 January 1997 / Published: 29 January 1997
Cited by 12 | PDF Full-text (95 KB)
Abstract
The synthesis of combinatorial compound libraries has become a powerful lead finding tool in modern drug discovery. The ability to synthesize rapidly, in high yield, new chemical entities with low molecular weight on a solid support has a recognized strategic relevance (“small [...] Read more.
The synthesis of combinatorial compound libraries has become a powerful lead finding tool in modern drug discovery. The ability to synthesize rapidly, in high yield, new chemical entities with low molecular weight on a solid support has a recognized strategic relevance (“small molecule libraries”). We designed and validated a novel solid phase synthesis scheme, suitable to generate diversity on small heterocycles of the pyrazole and isoxazole type. Appropriate conditions were worked out for each reaction, and a variety of more or less reactive agents (building blocks) was utilized for discrete conversions, in order to exploit the system’s breadth of applicability. Four sequential reaction steps were validated, including the loading of the support with an acetyl bearing moiety, a Claisen condensation, an a-alkylation and a cyclization of a b-diketone with monosubstituted hydrazines. In a second stage, the reaction sequence was applied in a split and mix approach, in order to prepare a combinatorial library built-up from 4 acetyl carboxylic acids (R1), 35 carboxylic esters (R2) and 41 hydrazines (R4) (and 1 hydroxylamine) to yield a total of 11,760 compounds divided into 41 pyrazole sublibraries with 140 pairs of regioisomers and 1 isoxazole sublibrary of equal size. Full article

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