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Molecules, Volume 6, Issue 3 (March 2001) – 29 articles , Pages 142-286, Articles M193-M210

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31 KiB  
Article
Intramolecular Acylation of Aryl- and Aroyl-Aliphatic Acids by the Action of Pyrophosphoryl Chloride and Phosphorus Oxychloride
by Sami El-Sayrafi and Saleh Rayyan
Molecules 2001, 6(3), 279-286; https://doi.org/10.3390/60300279 - 31 Mar 2001
Cited by 21 | Viewed by 11887
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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89 KiB  
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(2,2'-Bipyridine-N,N')dibutyldiisothiocyanotin
by Chun Hu, Rihong Tan, Jianping Wang, Yu Ji and Shengfu Wang
Molecules 2001, 6(3), M210; https://doi.org/10.3390/M210 - 25 Mar 2001
Viewed by 3444
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)
89 KiB  
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Dibutyldichloro(1,10-phenanthroline-N1,N10)tin
by Chun Hu, Rihong Tan, Jianping Wang, Yu Ji and Shengfu Wang
Molecules 2001, 6(3), M209; https://doi.org/10.3390/M209 - 25 Mar 2001
Viewed by 3840
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)
86 KiB  
Short Note
2-Methyl-5-chloromethyl-8-hydroxyquinoline
by Ke-Qing Zhao, Ping Hu, Yu-Quan Zhou and Hong-Bo Xu
Molecules 2001, 6(3), M208; https://doi.org/10.3390/M208 - 25 Mar 2001
Cited by 1 | Viewed by 4457
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)
87 KiB  
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1-(Pyridin-3-yl)-4-(triethylsilyloxy)-2-butyn-1-ol
by Vittorio E. Caprio, Michael W. Jones and Margaret A. Brimble
Molecules 2001, 6(3), M207; https://doi.org/10.3390/M207 - 25 Mar 2001
Viewed by 3630
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)
86 KiB  
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1-(Pyridin-3-yl)but-2-yn-1,4-diol
by Vittorio E. Caprio, Michael W. Jones and Margaret A. Brimble
Molecules 2001, 6(3), M206; https://doi.org/10.3390/M206 - 25 Mar 2001
Viewed by 3693
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)
15 KiB  
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4-Hydroxy-methylen-4'-methyl-2,2'-bipyridine
by Michael Kercher and Burkhard König
Molecules 2001, 6(3), M205; https://doi.org/10.3390/M205 - 25 Mar 2001
Viewed by 3210
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)
89 KiB  
Short Note
4,5-Dimethoxy-2-(4-methylbenzoyl)-1-(4-methylphenylsulfonylamido)benzene
by Sergey K. Smirnov, Artem S. Dmitriyev and Irina V. Lodina
Molecules 2001, 6(3), M204; https://doi.org/10.3390/M204 - 25 Mar 2001
Viewed by 3505
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)
77 KiB  
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Methyl 3-Hydroxythieno[2,3-b]pyridine-2-carboxylate
by Gerard P. Moloney
Molecules 2001, 6(3), M203; https://doi.org/10.3390/M203 - 25 Mar 2001
Cited by 26 | Viewed by 3570
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)
89 KiB  
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Pyridine-3-carboxaldehyde O-methyloxime
by Vittorio E. Caprio, Michael W. Jones and Margaret A. Brimble
Molecules 2001, 6(3), M202; https://doi.org/10.3390/M202 - 25 Mar 2001
Cited by 1 | Viewed by 3839
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)
97 KiB  
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1-(2-Vinyl-pyridin-3-yl)propanal O-methyloxime and 1-(6-Vinyl-pyridin-3-yl)propanal O-methyloxime
by Vittorio E. Caprio, Michael W. Jones and Margaret A. Brimble
Molecules 2001, 6(3), M201; https://doi.org/10.3390/M201 - 25 Mar 2001
Viewed by 4558
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)
88 KiB  
Short Note
tert-Butyl methoxy(2-propynyl)carbamate
by Vittorio E. Caprio, Michael W. Jones and Margaret A. Brimble
Molecules 2001, 6(3), M200; https://doi.org/10.3390/M200 - 25 Mar 2001
Cited by 1 | Viewed by 3578
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)
94 KiB  
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N-Benzyl-3-(2-morpholine)ethoxy-5-methoxy benzofuran-2-carboxamide
by Gerard P. Moloney
Molecules 2001, 6(3), M199; https://doi.org/10.3390/M199 - 25 Mar 2001
Cited by 1 | Viewed by 3389
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)
90 KiB  
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N-(2-Ethylmorpholino)-3-bis-ketothiene
by Gerard P. Moloney
Molecules 2001, 6(3), M198; https://doi.org/10.3390/M198 - 25 Mar 2001
Viewed by 2886
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)
91 KiB  
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1-(2-Ethylmorpholino)-5-benzyloxy-3-(1-napthoyl)pyrrolopyridine
by Gerard P. Moloney
Molecules 2001, 6(3), M197; https://doi.org/10.3390/M197 - 25 Mar 2001
Viewed by 3008
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)
92 KiB  
Short Note
N-(2-Ethylmorpholino)-3-bis-keto(1-naphthyl)oxindole
by Gerard P. Moloney
Molecules 2001, 6(3), M196; https://doi.org/10.3390/M196 - 25 Mar 2001
Viewed by 3320
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)
92 KiB  
Short Note
5-Isopropyl-N-(1H-1,2,3,4-tetrazol-5-yl)thiobenzo-2-oxazole Acetamide
by Gerard P. Moloney
Molecules 2001, 6(3), M195; https://doi.org/10.3390/M195 - 25 Mar 2001
Viewed by 3321
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)
92 KiB  
Short Note
[5-Hydroxy-1-(2-morpholinoethyl)-1H-indol-3-yl](4-methoxyphenyl)methanone
by Gerard P. Moloney
Molecules 2001, 6(3), M194; https://doi.org/10.3390/M194 - 25 Mar 2001
Viewed by 3450
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)
85 KiB  
Short Note
Bis(p-allylhimachalene)dichlorodipalladium
by Larbi El Firdoussi and Abdellah Karim
Molecules 2001, 6(3), M193; https://doi.org/10.3390/M193 - 25 Mar 2001
Viewed by 3586
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)
67 KiB  
Article
Aminoacids in the Synthesis of Heterocyclic Systems: The Synthesis of Triazinoquinazolinones, Triazepinoquinazolinones and Triazocinoquinazolinones of Potential Biological Interest
by A. M.Sh. El-Sharief, Y. A. Ammar, M. A. Zahran, A. H. Ali and M. S.A. El-Gaby
Molecules 2001, 6(3), 267-278; https://doi.org/10.3390/60300267 - 28 Feb 2001
Cited by 46 | Viewed by 10389
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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48 KiB  
Article
Enantioselective Intramolecular CH-Insertions upon Cu-Catalyzed Decomposition of Phenyliodonium Ylides
by Paul Müller and Christelle Boléa
Molecules 2001, 6(3), 258-266; https://doi.org/10.3390/60300258 - 28 Feb 2001
Cited by 33 | Viewed by 8113
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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66 KiB  
Article
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
by Ardeshir Khazaei, Abdolhamid Alizadeh and Ramin Ghorbani Vaghei
Molecules 2001, 6(3), 253-257; https://doi.org/10.3390/60300253 - 28 Feb 2001
Cited by 23 | Viewed by 7155
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
44 KiB  
Article
Synthesis of (±)-trans-2,5-Diisopropylborolane
by Gerhard Laschober, Massimo Zorzi and Kevin J. Hodgetts
Molecules 2001, 6(3), 244-252; https://doi.org/10.3390/60300244 - 28 Feb 2001
Cited by 2 | Viewed by 7018
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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142 KiB  
Article
Synthesis of Acridine-based DNA Bis-intercalating Agents
by Gerard P. Moloney, David P. Kelly and P. Mack
Molecules 2001, 6(3), 230-243; https://doi.org/10.3390/60300230 - 28 Feb 2001
Cited by 38 | Viewed by 14124
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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127 KiB  
Article
Comparison of Association Constants of Cyclodextrins and Their tert-Butyl Derivatives With Halogenbenzoic Acids and Acridine Derivatives
by Martin Pumera, Radka Matalová, Ivan Jelínek, Jindřich Jindřich and Josef Jůza
Molecules 2001, 6(3), 221-229; https://doi.org/10.3390/60300221 - 28 Feb 2001
Cited by 11 | Viewed by 8393
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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121 KiB  
Article
Crystal and Molecular Structures of N-benzyl-C-(2-pyridyl) nitrone and its ZnBr2 Complex. A Study of Their Reactivity
by Pedro Merino, Sonia Anoro, Elena Cerrada, Mariano Laguna, Ana Moreno and Tomas Tejero
Molecules 2001, 6(3), 208-220; https://doi.org/10.3390/60300208 - 28 Feb 2001
Cited by 17 | Viewed by 10626
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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29 KiB  
Article
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
by Huan-Ming Chen and Ramachandra S. Hosmane
Molecules 2001, 6(3), 203-207; https://doi.org/10.3390/60300203 - 28 Feb 2001
Cited by 4 | Viewed by 7734
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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55 KiB  
Article
7-(1-Acetoxymethylidene)Benzonorbornadiene: A Versatile Reagent for the Synthesis of 7-Formyl and 7-Hydroxymethyl Benzonorbornadienes
by Ronald N. Warrener, Geoffrey J. Collin and Patrick J. Foley
Molecules 2001, 6(3), 194-202; https://doi.org/10.3390/60300194 - 28 Feb 2001
Cited by 4 | Viewed by 6691
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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320 KiB  
Review
Muscarinic Receptor Agonists and Antagonists
by Kenneth J. Broadley and David R. Kelly
Molecules 2001, 6(3), 142-193; https://doi.org/10.3390/60300142 - 28 Feb 2001
Cited by 80 | Viewed by 25103
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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