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Molecules, Volume 6, Issue 3 (March 2001) , Pages 142-286, Articles M193-M210

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Open AccessArticle
Intramolecular Acylation of Aryl- and Aroyl-Aliphatic Acids by the Action of Pyrophosphoryl Chloride and Phosphorus Oxychloride
Molecules 2001, 6(3), 279-286; https://doi.org/10.3390/60300279 - 31 Mar 2001
Cited by 19 | Viewed by 7070
Abstract
Both pyrophosphoryl chloride and phosphorus oxychloride react with aryl aliphatic acids to form mixed anhydrides which undergo intramolecular acylation to afford cyclic ketones without the addition of a Friedel-Crafts catalyst. Aryl and aroylbenzoic acids could be cyclized to the corresponding anthrones and anthraquinones [...] Read more.
Both pyrophosphoryl chloride and phosphorus oxychloride react with aryl aliphatic acids to form mixed anhydrides which undergo intramolecular acylation to afford cyclic ketones without the addition of a Friedel-Crafts catalyst. Aryl and aroylbenzoic acids could be cyclized to the corresponding anthrones and anthraquinones respectively. Full article
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Open AccessShort Note
(2,2'-Bipyridine-N,N')dibutyldiisothiocyanotin
Molecules 2001, 6(3), M210; https://doi.org/10.3390/M210 - 25 Mar 2001
Viewed by 2331
Abstract
Diorganotin dihalide complexes with bidentate nitrogen ligands exhibit some pharmaceutical activities such as antitumour activity, antiviral activity and anti-microbiological activity[1-3], we have synthesized some diorganotin dihalide and dipseudohalide complexes with bidentate nitrogen ligands, one of which is (2,2'-bipyridine-N,N')dibutyldiisothiocyanotin.[...] Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Open AccessShort Note
Dibutyldichloro(1,10-phenanthroline-N1,N10)tin
Molecules 2001, 6(3), M209; https://doi.org/10.3390/M209 - 25 Mar 2001
Viewed by 2410
Abstract
Diorganotin dihalide complexes with bidentate nitrogen ligands exhibit some pharmaceutical activities such as antitumour activity, antiviral activity and anti-microbiological activity[1-3], we have synthesized some diorganotin dihalide complexes with bidentate nitrogen ligands, one of which is dibutyldichloro(1,10-phenanthroline-N1,N10)tin.[...] Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Open AccessShort Note
2-Methyl-5-chloromethyl-8-hydroxyquinoline
Molecules 2001, 6(3), M208; https://doi.org/10.3390/M208 - 25 Mar 2001
Cited by 1 | Viewed by 3165
Abstract
Quinoline and its derivatives have been widely used as metal ion chelating agents, metal extracting agents, corrosive inhibitors and they often show biological activity.[...] Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Open AccessShort Note
1-(Pyridin-3-yl)-4-(triethylsilyloxy)-2-butyn-1-ol
Molecules 2001, 6(3), M207; https://doi.org/10.3390/M207 - 25 Mar 2001
Viewed by 2627
Abstract
The general part of the experimental section [1] has been presented elsewhere.[...] Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Open AccessShort Note
1-(Pyridin-3-yl)but-2-yn-1,4-diol
Molecules 2001, 6(3), M206; https://doi.org/10.3390/M206 - 25 Mar 2001
Viewed by 2671
Abstract
The general part of the experimental section [1] has been presented elsewhere.[...] Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Open AccessShort Note
4-Hydroxy-methylen-4'-methyl-2,2'-bipyridine
Molecules 2001, 6(3), M205; https://doi.org/10.3390/M205 - 25 Mar 2001
Viewed by 2213
Abstract
A key intermediate in the synthesis of extended bipyridine ligands [1] is 4-hydroxymethylene-4-methyl-2,2-bipyridine (3), because the hydroxy group is readily converted into a variety of other chemical moieties, such as leaving or carbonyl groups.[...] Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Open AccessShort Note
4,5-Dimethoxy-2-(4-methylbenzoyl)-1-(4-methylphenylsulfonylamido)benzene
Molecules 2001, 6(3), M204; https://doi.org/10.3390/M204 - 25 Mar 2001
Viewed by 2434
Abstract
For this synthesis, we propose a modification of the reaction procedure described in [1].[...] Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Open AccessShort Note
Methyl 3-Hydroxythieno[2,3-b]pyridine-2-carboxylate
Molecules 2001, 6(3), M203; https://doi.org/10.3390/M203 - 25 Mar 2001
Cited by 17 | Viewed by 2030
Abstract
As part of a research programme targeting novel molecules as potential anti-inflammatory agents we synthesised methyl 3-hydroxythieno[2,3-b]pyridine-2-carboxylate based on the reported anti-inflammatory activity of the structurally related molecule 3-isopropoxy-5-methoxy-N-(1H-1,2,3,4-tetraazol-5-yl)-1-benzothiophene-2-carboxamide [1,2].[...] Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Open AccessShort Note
Pyridine-3-carboxaldehyde O-methyloxime
Molecules 2001, 6(3), M202; https://doi.org/10.3390/M202 - 25 Mar 2001
Viewed by 2765
Abstract
The general part of the experimental section [1] has been presented elsewhere.[...] Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Open AccessShort Note
1-(2-Vinyl-pyridin-3-yl)propanal O-methyloxime and 1-(6-Vinyl-pyridin-3-yl)propanal O-methyloxime
Molecules 2001, 6(3), M201; https://doi.org/10.3390/M201 - 25 Mar 2001
Viewed by 3017
Abstract
The general part of the experimental section [1] has been presented elsewhere. Boron trifluoride diethyl etherate (313 mg, 2.21 mmol) was added dropwise to a solution of oxime 1 (100 mg, 0.735 mmol) in toluene (8 mL) at -78oC under nitrogen [...] Read more.
The general part of the experimental section [1] has been presented elsewhere. Boron trifluoride diethyl etherate (313 mg, 2.21 mmol) was added dropwise to a solution of oxime 1 (100 mg, 0.735 mmol) in toluene (8 mL) at -78oC under nitrogen and the mixture stirred for 5 min.[...] Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Open AccessShort Note
tert-Butyl methoxy(2-propynyl)carbamate
Molecules 2001, 6(3), M200; https://doi.org/10.3390/M200 - 25 Mar 2001
Viewed by 2497
Abstract
The general part of the experimental section [1] has been presented elsewhere.[...] Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Open AccessShort Note
N-Benzyl-3-(2-morpholine)ethoxy-5-methoxy benzofuran-2-carboxamide
Molecules 2001, 6(3), M199; https://doi.org/10.3390/M199 - 25 Mar 2001
Viewed by 2049
Abstract
As part of a research programme targeting novel indole-like molecules as potential cannabinoid agonists [1-4] we synthesised methyl 3-(2-(N-morpholino)ethyl-5-methoxybenzofuran-2-carboxylate.[...] Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Open AccessShort Note
N-(2-Ethylmorpholino)-3-bis-ketothiene
Molecules 2001, 6(3), M198; https://doi.org/10.3390/M198 - 25 Mar 2001
Viewed by 1940
Abstract
As part of a research programme targeting novel indole-like molecules as potential cannabinoid agonists [1-4] we synthesised N-(2-ethylmorpholino)-3-bis-ketothiene.[...] Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Open AccessShort Note
1-(2-Ethylmorpholino)-5-benzyloxy-3-(1-napthoyl)pyrrolopyridine
Molecules 2001, 6(3), M197; https://doi.org/10.3390/M197 - 25 Mar 2001
Viewed by 2012
Abstract
As part of a research programme targeting novel indole-like molecules as potential cannabinoid agonists [1-4] we synthesised N-(2-ethylmorpholino)-3-bis keto(1-naphthyl) oxindole.[...] Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Open AccessShort Note
N-(2-Ethylmorpholino)-3-bis-keto(1-naphthyl)oxindole
Molecules 2001, 6(3), M196; https://doi.org/10.3390/M196 - 25 Mar 2001
Viewed by 2007
Abstract
As part of a research programme targeting novel indole-like molecules as potential cannabinoid agonists [1-4] we synthesised N-(2-ethylmorpholino)-3-bis-keto(1-naphthyl)oxindole.[...] Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Open AccessShort Note
5-Isopropyl-N-(1H-1,2,3,4-tetrazol-5-yl)thiobenzo-2-oxazole Acetamide
Molecules 2001, 6(3), M195; https://doi.org/10.3390/M195 - 25 Mar 2001
Viewed by 1977
Abstract
As part of a research programme targeting novel molecules as potential anti-inflammatory agents we synthesised 3-Chloro-5-methoxy-1-benzo[b]thiophene-2-sulphonylamide base on the reported anti-inflammatory activity of the structurally related molecule 3-isopropoxy-5-methoxy-N-(1H-1,2,3,4-tetraazol-5-yl)-1-benzothiophene-2-carboxamide [1,2]. Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Open AccessShort Note
[5-Hydroxy-1-(2-morpholinoethyl)-1H-indol-3-yl](4-methoxyphenyl)methanone
Molecules 2001, 6(3), M194; https://doi.org/10.3390/M194 - 25 Mar 2001
Viewed by 2019
Abstract
As part of a research programme targeting novel indole-based molecules as potential cannabinoid agonists we synthesised [5-hydroxy-1-(2-morpholinoethyl)-1H-indol-3-yl](4-methoxyphenyl)methanone [1-4].[...] Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Open AccessShort Note
Bis(p-allylhimachalene)dichlorodipalladium
Molecules 2001, 6(3), M193; https://doi.org/10.3390/M193 - 25 Mar 2001
Viewed by 2476
Abstract
The title organometallic compound, potentially important synthetic intermediate, was prepared regio- and stereospecifically from b-himachalene ((4aR)-3,5,5,9-Tetramethyl-2,4a,5,6,7,8-hexahydro-1H-benzocycloheptene), essentiel component of cedrus atlantica oil [1].[...] Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Open AccessArticle
Aminoacids in the Synthesis of Heterocyclic Systems: The Synthesis of Triazinoquinazolinones, Triazepinoquinazolinones and Triazocinoquinazolinones of Potential Biological Interest
Molecules 2001, 6(3), 267-278; https://doi.org/10.3390/60300267 - 28 Feb 2001
Cited by 39 | Viewed by 7469
Abstract
A number of novel triazinoquinazolinones (5b,c and 8), triazepinoquinazolinones(5a, 6b, 7 and 9) and triazocinoquinazolinones (6a and 10) were obtained via nucleophilic interaction of 3-aminoquinazolinone derivatives 3 with different reagents. Full article
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Open AccessArticle
Enantioselective Intramolecular CH-Insertions upon Cu-Catalyzed Decomposition of Phenyliodonium Ylides
Molecules 2001, 6(3), 258-266; https://doi.org/10.3390/60300258 - 28 Feb 2001
Cited by 26 | Viewed by 5482
Abstract
The Cu-catalyzed intramolecular CH insertion of phenyliodonium ylide 5b has been investigated at 0° C in the presence of several chiral ligands. Enantioselectivities vary in the range of 38–72 %, and are higher than those resulting from reaction of the diazo compound 5c [...] Read more.
The Cu-catalyzed intramolecular CH insertion of phenyliodonium ylide 5b has been investigated at 0° C in the presence of several chiral ligands. Enantioselectivities vary in the range of 38–72 %, and are higher than those resulting from reaction of the diazo compound 5c at 65° C. The results are consistent with a carbenoid mechanism for Cu-catalyzed decomposition of phenyliodonium ylides. Full article
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Open AccessArticle
Preparation of Arylthiocyanates Using N,N′-Dibromo-N,N′-bis(2,5-dimethylbenzenesulphonyl) ethylenediamine and N,NDibromo-2,5-dimethylbenzenesulphonamide in the Presence of KSCN as a Novel Thiocyanating Reagent
Molecules 2001, 6(3), 253-257; https://doi.org/10.3390/60300253 - 28 Feb 2001
Cited by 18 | Viewed by 4782
Abstract
N-Bromosulphonamides, synthesized via direct bromination of sulphonamides, react with several types of arene substrates in the presence of KSCN to afford aryl thiocyanates. The method appears to be generally applicable to benzenoid substrates with a wide range of substituents, such as N [...] Read more.
N-Bromosulphonamides, synthesized via direct bromination of sulphonamides, react with several types of arene substrates in the presence of KSCN to afford aryl thiocyanates. The method appears to be generally applicable to benzenoid substrates with a wide range of substituents, such as N,N-dimethylaniline, p-xylene, anisole, mesitylene and cumene. Full article
Open AccessArticle
Synthesis of (±)-trans-2,5-Diisopropylborolane
Molecules 2001, 6(3), 244-252; https://doi.org/10.3390/60300244 - 28 Feb 2001
Cited by 1 | Viewed by 4437
Abstract
The cyclic hydroboration of 2,7-dimethyl-2,6-octadiene (6) was studied. It was found that the stereochemical outcome of the reaction was dependent upon the solvent, temperature, time and the nature of the borane reagent. Pure racemic trans-2,5-diisopropylborolane (14) was isolated following selective complexation of [...] Read more.
The cyclic hydroboration of 2,7-dimethyl-2,6-octadiene (6) was studied. It was found that the stereochemical outcome of the reaction was dependent upon the solvent, temperature, time and the nature of the borane reagent. Pure racemic trans-2,5-diisopropylborolane (14) was isolated following selective complexation of the cis-2,5-diisopropylborolane (15) with 1-(2-hydroxyethyl)-pyrrolidine. Full article
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Open AccessArticle
Synthesis of Acridine-based DNA Bis-intercalating Agents
Molecules 2001, 6(3), 230-243; https://doi.org/10.3390/60300230 - 28 Feb 2001
Cited by 27 | Viewed by 8851
Abstract
Methods for the synthesis of N1, N8-bis(9-acridinyl)-N4-(4-hydroxybenzyl)-spermidine and N1, N7-(hydroxybenzyl)-bis-(3-aminopropyl)amine were investigated. Thus monocyanoethylation of 4-methoxybenzylamine followed by treatment with 4-chlorobutyronitrile gave the dinitrile N-(2-cyanoethyl)-N-(3-cyanopropyl)-4-methoxybenzylamine. Subsequent in situ reduction with lithium aluminium hydride [...] Read more.
Methods for the synthesis of N1, N8-bis(9-acridinyl)-N4-(4-hydroxybenzyl)-spermidine and N1, N7-(hydroxybenzyl)-bis-(3-aminopropyl)amine were investigated. Thus monocyanoethylation of 4-methoxybenzylamine followed by treatment with 4-chlorobutyronitrile gave the dinitrile N-(2-cyanoethyl)-N-(3-cyanopropyl)-4-methoxybenzylamine. Subsequent in situ reduction with lithium aluminium hydride gave the corresponding diamine. Biscyanoethylation of 4-methoxybenzylamine with 2 mole of acrylonitrile followed by reduction yielded the diamine N, N-bis-(3-aminopropyl)-4-methoxybenzylamine. Both diamines reacted smoothly with 9-methoxyacridine to give the bis-(9-acridinyl) compounds 11 and 15 but with 4,5-dimethyl-9-methoxyacridine, the bis compound 16 was produced in only low yields. Demethylation of the dinitriles by a variety of approaches all failed to give the corresponding hydroxybenzyl derivatives. These studies yielded useful methylated tyrosine derivatives which could also be iodinated. This study has been useful for elucidating chemical methods needed for the synthesis of the desired tyrosine-based bis acridine compound and for alerting us to the need to synthesise a more labile protected tyrosine intermediate which will be easily deprotected to afford the desired tyrosine-based bis acridine compound. Full article
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Open AccessArticle
Comparison of Association Constants of Cyclodextrins and Their tert-Butyl Derivatives With Halogenbenzoic Acids and Acridine Derivatives
Molecules 2001, 6(3), 221-229; https://doi.org/10.3390/60300221 - 28 Feb 2001
Cited by 10 | Viewed by 6177
Abstract
Association constants of complexes of a new class of cyclodextrin alkyl derivatives - randomly susbstituted tert-butyl derivatives (TB-CDs) with complete set of mono-halobenzoic acids and acridine derivatives were measured using capillary electrophoresis and compared with association constants of natural cyclodextrins. In most cases [...] Read more.
Association constants of complexes of a new class of cyclodextrin alkyl derivatives - randomly susbstituted tert-butyl derivatives (TB-CDs) with complete set of mono-halobenzoic acids and acridine derivatives were measured using capillary electrophoresis and compared with association constants of natural cyclodextrins. In most cases the association constants of natural cyclodextrin and its corresponding tert-butyl derivative were comparable. Strong dependence of association constants on actual cyclodextrin concentration was observed for complexes of tert-butyl-α-cyclodextrin with acridine derivatives. Significant increase of the association constant occurred below the critical micelle concentration of the cyclodextrin derivative, while an increase above this value was less significant. Full article
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Open AccessArticle
Crystal and Molecular Structures of N-benzyl-C-(2-pyridyl) nitrone and its ZnBr2 Complex. A Study of Their Reactivity
Molecules 2001, 6(3), 208-220; https://doi.org/10.3390/60300208 - 28 Feb 2001
Cited by 17 | Viewed by 7563
Abstract
The ZnBr2 complex of the title compound has been studied by both structural and theoretical methods. Similar reactivities have been observed for the nitrone alone and the complex in 1,3-dipolar cycloadditions and nucleophilic additions. Full article
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Open AccessArticle
Synthesis of 1-(2'-O-Methyl-ß-D-ribofuranosyl)-1H-imidazo[4,5-d]pyridazine-4,7(5H,6H)-dione: An Attractive Building Block for Antisense and Triple-helical Applications
Molecules 2001, 6(3), 203-207; https://doi.org/10.3390/60300203 - 28 Feb 2001
Cited by 4 | Viewed by 5593
Abstract
Synthesis of the title compound,1-(2'-O-methyl-ß-D-ribofuranosyl)-1H-imidazo-[4,5-d]pyridazine-4,7(5H,6H)-dione (1), is reported. It was synthesized in four steps, starting from methyl 1-(ß-D-ribofuranosyl)imidazo-4,5-dicarboxylate (2). The 3',5'-hydroxyl groups of 2 was protected with a bis-silylating agent to form 3, which was then methylated to form the corresponding 2'-O-methyl derivative [...] Read more.
Synthesis of the title compound,1-(2'-O-methyl-ß-D-ribofuranosyl)-1H-imidazo-[4,5-d]pyridazine-4,7(5H,6H)-dione (1), is reported. It was synthesized in four steps, starting from methyl 1-(ß-D-ribofuranosyl)imidazo-4,5-dicarboxylate (2). The 3',5'-hydroxyl groups of 2 was protected with a bis-silylating agent to form 3, which was then methylated to form the corresponding 2'-O-methyl derivative 5. The silyl deprotection of the latter (to form 6), followed by treatment with hydrazine afforded the target nucleoside 1. The reported nucleoside has potentially beneficial applications in biomedicine based on antisense and triple-helical nucleic acid technologies. Full article
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Open AccessArticle
7-(1-Acetoxymethylidene)Benzonorbornadiene: A Versatile Reagent for the Synthesis of 7-Formyl and 7-Hydroxymethyl Benzonorbornadienes
Molecules 2001, 6(3), 194-202; https://doi.org/10.3390/60300194 - 28 Feb 2001
Cited by 4 | Viewed by 4677
Abstract
7-(1-Acetoxymethylidene)benzonorbornadiene 3, prepared in one step by the addition of benzyne to 6-acetoxyfulvene 2, is hydrolysed in acid solution to form a 3:2-epimeric mixture of syn- and anti- 7-formylbenzonorbornadienes 4 and 5, respectively; the corresponding 7-hydroxymethylbenzonorbornadienes 6 and 9 were produced by reduction [...] Read more.
7-(1-Acetoxymethylidene)benzonorbornadiene 3, prepared in one step by the addition of benzyne to 6-acetoxyfulvene 2, is hydrolysed in acid solution to form a 3:2-epimeric mixture of syn- and anti- 7-formylbenzonorbornadienes 4 and 5, respectively; the corresponding 7-hydroxymethylbenzonorbornadienes 6 and 9 were produced by reduction of the formyl isomers with sodium borohydride. Full article
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Open AccessReview
Muscarinic Receptor Agonists and Antagonists
Molecules 2001, 6(3), 142-193; https://doi.org/10.3390/60300142 - 28 Feb 2001
Cited by 49 | Viewed by 9781
Abstract
A comprehensive review of pharmacological and medical aspects of the muscarinic class of acetylcholine agonists and antagonists is presented. The therapeutic benefits of achieving receptor subtype selectivity are outlined and applications in the treatment of Alzheimer’s disease are discussed. A selection of chemical [...] Read more.
A comprehensive review of pharmacological and medical aspects of the muscarinic class of acetylcholine agonists and antagonists is presented. The therapeutic benefits of achieving receptor subtype selectivity are outlined and applications in the treatment of Alzheimer’s disease are discussed. A selection of chemical routes are described, which illustrate contemporary methodology for the synthesis of chiral medicinal compounds (asymmetric synthesis, chiral pool, enzymes). Routes to bicyclic intrannular amines and intramolecular Diels-Alder reactions are highlighted. Full article
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