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Molecules, Volume 6, Issue 8 (August 2001), Pages 647-715

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Research

Open AccessArticle Synthesis, Structure and Antitumor Activity of Dibutyltin Oxide Complexes with 5-Fluorouracil Derivatives. Crystal Structure of [(5-Fluorouracil)-1-CH2CH2COOSn(n-Bu) 2]4O2
Molecules 2001, 6(8), 647-654; doi:10.3390/60800647
Received: 19 March 2001 / Revised: 20 March 2001 / Accepted: 2 May 2001 / Published: 31 July 2001
Cited by 3 | PDF Full-text (101 KB) | HTML Full-text | XML Full-textRetraction
Abstract
Dibutyltin (IV) oxide complex reacts with the fluorouracil compounds 5-fluorouracil-1-propanonic or 5-fluorouracil-1-acetic acid (Fu) to give the complexes [(5-Fu)-1-(CH2)nCOOSn(n-Bu)2]4O2 (I, n=2; II, n=1) which were characterized by IR and 1H-NMR. [...] Read more.
Dibutyltin (IV) oxide complex reacts with the fluorouracil compounds 5-fluorouracil-1-propanonic or 5-fluorouracil-1-acetic acid (Fu) to give the complexes [(5-Fu)-1-(CH2)nCOOSn(n-Bu)2]4O2 (I, n=2; II, n=1) which were characterized by IR and 1H-NMR. The crystal structure of complex I shows that the molecular is a dimer, in which two [(5-Fu)-1-CH2CH2COOSn(n-Bu)2]2O units are linked by a bridging oxygen atom, and the tin atoms adopt distorted trigonal bipyramids via two carbons from a dibutyl moiety and three oxygen atoms from 5-Fu and bridging oxygen. These complexes have potential anti-tumour activity: in vitro tests showed that complexes I and II exhibit high cytotoxicity against OVCAR-3 and PC-14. Full article
Open AccessArticle Use of Cyclic Allylic Bromides in the Zinc–Mediated Aqueous Barbier–Grignard Reaction
Molecules 2001, 6(8), 655-662; doi:10.3390/60800655
Received: 27 February 2001 / Accepted: 12 June 2001 / Published: 31 July 2001
Cited by 13 | PDF Full-text (35 KB) | HTML Full-text | XML Full-text
Abstract
The zinc–mediated aqueous Barbier–Grignard reaction of cyclic allylic bromide substrates with various aldehydes and ketones to afford homoallylic alcohols was investigated. Aromatic aldehydes and ketones afforded adducts in good yields (66–90%) and with good diastereoselectivities. Non–aromatic aldehydes also reacted well under these [...] Read more.
The zinc–mediated aqueous Barbier–Grignard reaction of cyclic allylic bromide substrates with various aldehydes and ketones to afford homoallylic alcohols was investigated. Aromatic aldehydes and ketones afforded adducts in good yields (66–90%) and with good diastereoselectivities. Non–aromatic aldehydes also reacted well under these conditions, but only poor yields were obtained with non–aromatic ketones. Regioselectivity was high when some substituted cyclic allylic bromides were investigated. Full article
Open AccessArticle Stilbenes and a New Acetophenone Derivative from Scirpus holoschoenus
Molecules 2001, 6(8), 663-667; doi:10.3390/60800663
Received: 7 February 2001 / Revised: 11 June 2001 / Accepted: 10 July 2001 / Published: 31 July 2001
Cited by 4 | PDF Full-text (27 KB) | HTML Full-text | XML Full-text
Abstract
Separation of the extract of the tubers of Scirpus holoschoenus L. (family Cyperaceae), a species easily confused with Juncus plants, afforded 2-prenyl-3,5,4'-trimethoxystilbene, 2-prenyl-3-hydroxy-5,4'-dimethoxystilbene, 2-prenyl-3,4'-dihydroxy-5-methoxy-stilbene and 3,5,4'-trimethoxystilbene, in addition to a new acetophenone derivative. The isolated compounds were identified on the basis of [...] Read more.
Separation of the extract of the tubers of Scirpus holoschoenus L. (family Cyperaceae), a species easily confused with Juncus plants, afforded 2-prenyl-3,5,4'-trimethoxystilbene, 2-prenyl-3-hydroxy-5,4'-dimethoxystilbene, 2-prenyl-3,4'-dihydroxy-5-methoxy-stilbene and 3,5,4'-trimethoxystilbene, in addition to a new acetophenone derivative. The isolated compounds were identified on the basis of spectral measurements. Full article
Open AccessArticle Modified Methods for the Synthesis of Carbazole from Phenothiazine
Molecules 2001, 6(8), 668-672; doi:10.3390/60800668
Received: 14 January 2001 / Revised: 14 June 2001 / Accepted: 15 June 2001 / Published: 31 July 2001
Cited by 3 | PDF Full-text (23 KB) | HTML Full-text | XML Full-text
Abstract Lithium, used in conjunction with triphenylphosphine or sodium metal, produces a high yield of carbazole when reacted with phenothiazine. Full article
Open AccessArticle Synthesis of new Bis- and Tetra-Acridines
Molecules 2001, 6(8), 673-682; doi:10.3390/60800673
Received: 10 April 2001 / Revised: 11 July 2001 / Accepted: 11 July 2001 / Published: 31 July 2001
Cited by 15 | PDF Full-text (51 KB) | HTML Full-text | XML Full-text
Abstract A new series of bis- and tetra-acridines has been prepared from 4-(bromomethyl) acridine; some of them exhibited encouraging in vitro cytotoxic activities against murine cell lines. Full article
Open AccessArticle Rearrangement of o-Nitrobenzaldehyde in the Hantzsch Reaction
Molecules 2001, 6(8), 683-693; doi:10.3390/60800683
Received: 13 December 2000 / Revised: 6 June 2001 / Accepted: 16 July 2001 / Published: 21 July 2001
Cited by 6 | PDF Full-text (68 KB) | HTML Full-text | XML Full-text
Abstract
The reaction of 5-hydroxy-2-nitrobenzaldehyde with ethyl acetoacetate in ammonia gave the two expected isomeric 1,4- and 1,2-dihydropyridines resulting from the normal Hantzsch reaction. However, the combination of 2-nitrobenzaldehyde with ethyl acetoacetate under the same conditions yielded four products: the two normal isomeric [...] Read more.
The reaction of 5-hydroxy-2-nitrobenzaldehyde with ethyl acetoacetate in ammonia gave the two expected isomeric 1,4- and 1,2-dihydropyridines resulting from the normal Hantzsch reaction. However, the combination of 2-nitrobenzaldehyde with ethyl acetoacetate under the same conditions yielded four products: the two normal isomeric dihydropyridines and two tricyclic compounds. When we attempted to independently synthesize the two tricyclic compounds by reductive cyclization of 4-(2-nitrophenyl)-2,6-dimethyl-3,5-dicarbetoxy-1,4-dihydropyridine and 2-(2-nitrophenyl)-4,6-dimethyl-3,5-dicarbetoxy-1,2-dihydropyridine with tin (II) chloride in hydrochloric acid media, we obtained instead an indole and a quinoline derivative, respectively. Full article
Open AccessArticle An Efficient and Chemoselective Method for Oximination of β-Diketones Under Mild and Heterogeneous Conditions
Molecules 2001, 6(8), 694-698; doi:10.3390/60800694
Received: 26 August 2000 / Revised: 10 June 2001 / Accepted: 10 July 2001 / Published: 31 July 2001
Cited by 6 | PDF Full-text (26 KB) | HTML Full-text | XML Full-text
Abstract A combination of oxalic acid dihydrate and sodium nitrite in the presence of wet SiO2 was used as an effective nitrosating agent for the nitrosation of β-diketones to their corresponding α-oximinoketones in moderate to excellent yields under mild and heterogenous conditions. Full article
Open AccessArticle Solvent and Substituent Effects on the Kinetics of Thermolysis of cis-Fused 1,2,4-Trioxanes
Molecules 2001, 6(8), 699-709; doi:10.3390/60800699
Received: 12 December 2000 / Revised: 21 June 2001 / Accepted: 9 July 2001 / Published: 31 July 2001
Cited by 3 | PDF Full-text (62 KB) | HTML Full-text | XML Full-text
Abstract
The kinetics of the thermal decomposition reaction of cis-6-phenyl-5,6-(2-phenylpropyliden)-3,3-pentamethylene-1,2,4-trioxacyclohexane (Ia) were investigated in benzene and methanol solutions in the temperature and concentration ranges of 353.3 – 413.2 K and (1.1 – 13.1)x10-3 M, respectively. First-order rate constant values were obtained for [...] Read more.
The kinetics of the thermal decomposition reaction of cis-6-phenyl-5,6-(2-phenylpropyliden)-3,3-pentamethylene-1,2,4-trioxacyclohexane (Ia) were investigated in benzene and methanol solutions in the temperature and concentration ranges of 353.3 – 413.2 K and (1.1 – 13.1)x10-3 M, respectively. First-order rate constant values were obtained for up to at least ca. 20% conversions of that cyclic peroxide. The activation parameter values for the initial unimolecular homolysis of that molecule, results supported by the effect of the addition of di-tert-butyl-p-cresol as a free radical scavenger, indicate a stepwise reaction mechanism which is in keeping with the reaction products analysis. The corresponding activation parameters for the reaction of Ia in methanol (ΔH# = 20.2 ± 0.6 kcal mol-1; ΔS# = 0.1 ± 1.6 cal mol-1 K-1; ΔG# = 20.2 ± 0.6 kcal mol-1) and in benzene (ΔH# = 15.4 ± 0.2 kcal mol-1; ΔS# = -13.2 ± 0.5 cal mol-1 K-1; ΔG# = 20.5 ± 0.2 kcal mol-1) solutions are compared with values obtained for cis-6-phenyl-5,6-(2-phenylpropyliden)-3,3-tetramethylene-1,2,4-trioxacyclohexane (Ib) thermolysis in the same solvents. The thermolysis kinetics of Ia are less sensitive to solvent changes compared to the behaviour already reported for the analogous reactions of Ib. Because both molecules in solution are flexible structures due to their configurations, the relatively small solvent effect found on the former trioxane reaction is attributed to the extent of the chain of methylene groups attached on C-3 of the corresponding molecular rings. Furthermore, the pertinent substituent effect on the peroxidic bond strength of those molecules in solution was evaluated. Full article
Open AccessArticle Synthesis of 1-Benzyl-6-(4-chlorophenyl)-2-(4-R-phenyl)-4-(4-Rstyryl)-2,3-dihydropyrazolo[3,4-b][1,4]diazepines
Molecules 2001, 6(8), 710-715; doi:10.3390/60800710
Received: 14 December 2000 / Revised: 20 July 2001 / Accepted: 26 July 2001 / Published: 31 July 2001
Cited by 5 | PDF Full-text (77 KB) | HTML Full-text | XML Full-text
Abstract
The reaction of 4-amino-5-benzylamino-3-(4-chlorophenyl)-1H-pyrazole (1) with substituted diarylidenketones (2) constitutes a convenient synthetic route to the hitherto unknown 1-benzyl-6-(4-chlorophenyl)-2-(4-R-phenyl)-4-(4-R-styryl)-2,3-dihydropyrazolo-[3,4-b][1,4]diazepines (3). Structures of all products were consistent with their IR, 1H-NMR, 13C-NMR and MS spectral data. X-ray crystallography data confirm the [...] Read more.
The reaction of 4-amino-5-benzylamino-3-(4-chlorophenyl)-1H-pyrazole (1) with substituted diarylidenketones (2) constitutes a convenient synthetic route to the hitherto unknown 1-benzyl-6-(4-chlorophenyl)-2-(4-R-phenyl)-4-(4-R-styryl)-2,3-dihydropyrazolo-[3,4-b][1,4]diazepines (3). Structures of all products were consistent with their IR, 1H-NMR, 13C-NMR and MS spectral data. X-ray crystallography data confirm the assigned structures. Full article

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