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Special Issue "Selected Papers from the “2nd International Conference on Natural Products and Physiologically Active Substances” (ICNPAS-2004) and the 3rd EuroAsian Heterocyclic Meeting “Heterocycles in Organic and Combinatorial Chemistry”"

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A special issue of Molecules (ISSN 1420-3049).

Deadline for manuscript submissions: closed (17 September 2004)

Special Issue Editors

Guest Editor
Prof. Dr. Eugene Babaev (Website)

Chemistry Department, Moscow State University, GSP-3, Moscow 119991, Russia
Interests: heterocyclic chemistry; periodic table
Guest Editor
Prof. Dr. Alexey V. Tkachev (Website)

Terpenoids Laboratory, Novosibirsk Institute of Organic Chemistry, 9 Acad. Lavrentjev Ave., Novosibirsk 630090, Russia
Interests: study of chemical communication of taiga tick Ixodes persulcatus and siberian moth Dendrolimus superans; chemistry of nitrogen-containing terpenoids; study of oxidative transformation of lower terpenoids; development of new methods of utilization of the terpenoids-containing plant raw materials; syntheses based on available natural terpenoids; synthesis and study of chiral terpenoids-based transition metal ions; study of chemical structure and conformational behavior of natural terpenoids and synthetic derivatives; NMR spectroscopy of natural products; computational methods in organic chemistry and education

Keywords

Selected Papers from the 2nd International Conference on Natural Products and Physiologically Active Substances” (ICNPAS-2004) and the 3rd EuroAsian Heterocyclic Meeting “Heterocycles in Organic and Combinatorial Chemistry

Published Papers (13 papers)

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Editorial

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Open AccessEditorial Special Issue: Selected Papers from the 2nd International Conference on Natural Products and Physiologically Active Substances (ICNPAS-2004) and the 3rd EuroAsian Heterocyclic Meeting “Heterocycles in Organic and Combinatorial Chemistry” (EAHM-2004)
Molecules 2005, 10(9), 1021-1022; doi:10.3390/10091021
Received: 23 April 2005 / Published: 30 September 2005
PDF Full-text (101 KB) | HTML Full-text | XML Full-text

Research

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Open AccessArticle The Preparation of New Phosphorus-Centered Functional Groups for Modified Oligonucleotides and Other Natural Phosphates
Molecules 2005, 10(9), 1048-1073; doi:10.3390/10091048
Received: 23 April 2005 / Accepted: 30 September 2005 / Published: 30 September 2005
Cited by 3 | PDF Full-text (440 KB) | HTML Full-text | XML Full-text
Abstract
Efforts to develop synthetic methodologies allowing the preparation of α,α– difluorophosphonothioates, α,α–difluorophosphonodithioates, α,α–difluorophosphono- trithioates, and α,α–difluorophosphinates are reviewed in the light of applications in the field of modified oligonucleotides and cyclitol phosphates. Two successful approaches have been developed, based either on the [...] Read more.
Efforts to develop synthetic methodologies allowing the preparation of α,α– difluorophosphonothioates, α,α–difluorophosphonodithioates, α,α–difluorophosphono- trithioates, and α,α–difluorophosphinates are reviewed in the light of applications in the field of modified oligonucleotides and cyclitol phosphates. Two successful approaches have been developed, based either on the addition of phosphorus-centered radicals onto gem–difluoroalkenes or on a process involving the addition of lithiodifluorophosphono- thioates 91 onto a ketone and the subsequent deoxygenation reaction of the adduct. The radical route successfully developed a practical route to α,α–difluoro–H–phosphinates which proved to be useful intermediates to a variety of phosphate isosters. The ionic route led to the first preparation of phosphonodifluoromethyl analogues of nucleoside– 3’–phosphates. Full article
Open AccessArticle An Improved Synthesis of Some 5-Substituted Indolizines Using Regiospecific Lithiation
Molecules 2005, 10(9), 1074-1083; doi:10.3390/10091074
Received: 23 April 2005 / Accepted: 30 September 2005 / Published: 30 September 2005
Cited by 13 | PDF Full-text (175 KB) | HTML Full-text | XML Full-text
Abstract
Various 2-substituted indolizines can be directly and selectively lithiated in the 5 position and subsequent reactions with different electrophiles lead to some novel classes of indolizines. In particular, previously unknown 5-formyl- and 5-iodoindolizine have been prepared by this way and the molecular [...] Read more.
Various 2-substituted indolizines can be directly and selectively lithiated in the 5 position and subsequent reactions with different electrophiles lead to some novel classes of indolizines. In particular, previously unknown 5-formyl- and 5-iodoindolizine have been prepared by this way and the molecular structure of 5-formyl-2- phenylindolizine was confirmed by X-Ray analysis. The reactivity of the 5-CHO- and 5- COPh groups toward some nucleophiles has been examined, and some additional classes of derivatives (oximes and alcohols) have been obtained. The possibility of Suzuki cross- coupling of 5-iodoindolizines and boronic acids was proven. Full article
Open AccessArticle Studies Towards the Total Synthesis of Di- and Sesterterpenes with Dicyclopenta[a,d]cyclooctane Skeletons. Three-component Approach to the A/B Rings Building Block
Molecules 2005, 10(9), 1084-1100; doi:10.3390/10091084
Received: 23 April 2005 / Accepted: 30 September 2005 / Published: 30 September 2005
Cited by 15 | PDF Full-text (265 KB) | HTML Full-text | XML Full-text
Abstract
Sesqui- and sesterterpenes of ophiobolin and fusicoccin families are important synthetic targets because of complexity of structure and potentially useful physiological activities, including anti-tumor activity. A synthesis of versatile building blocks for these terpenoids is described. Cyclopenta[8]annulene rings system with properly dislocated [...] Read more.
Sesqui- and sesterterpenes of ophiobolin and fusicoccin families are important synthetic targets because of complexity of structure and potentially useful physiological activities, including anti-tumor activity. A synthesis of versatile building blocks for these terpenoids is described. Cyclopenta[8]annulene rings system with properly dislocated substituents was constructed using as key steps ring closing metathesis reaction and Wagner - Meerwein rearrangement. Ring closing metathesis reaction leading to cyclopenta[8]annulene was studied in detail. Full article
Open AccessArticle The tert-Amino Effect in Heterocyclic Chemistry. Synthesis of Spiro Heterocycles
Molecules 2005, 10(9), 1101-1108; doi:10.3390/10091101
Received: 23 April 2005 / Accepted: 30 September 2005 / Published: 30 September 2005
Cited by 13 | PDF Full-text (225 KB) | HTML Full-text | XML Full-text
Abstract
The tert-amino reaction effect was examined. A new method to synthesize spiro heterocycles is presented. It was shown that the “tert-amino effect” could be applied to the formation of spiro-fused heterocycles. The formation of spiro compounds proceeds in most cases in good [...] Read more.
The tert-amino reaction effect was examined. A new method to synthesize spiro heterocycles is presented. It was shown that the “tert-amino effect” could be applied to the formation of spiro-fused heterocycles. The formation of spiro compounds proceeds in most cases in good yields in a one-pot reaction. Full article
Open AccessArticle A Facile Synthesis of Novel Herbicidal 1-Phenyl-piperazine-2,6-diones
Molecules 2005, 10(9), 1119-1125; doi:10.3390/10091119
Received: 23 April 2005 / Accepted: 30 September 2005 / Published: 30 September 2005
Cited by 1 | PDF Full-text (132 KB) | HTML Full-text | XML Full-text
Abstract Novel 1-phenyl-piperazine-2,6-diones were prepared by a new facile synthetic routeusing methyl N-substituted iminomonoacetate as starting material. The structures of thesecompounds were established by 1H-NMR, 13C-NMR and GC/MS. 2-(4-Chloro-5-cyclo-pentyl-oxy-2-fluorophenyl)-tetrahydro-2H-pyrido-[1,2-a]-pyrazine-1,3-(4H,6H)-dione displayed thegreatest herbicidal activity. Full article
Open AccessArticle New Multi-1,2,3-Selenadiazole Aromatic Derivatives
Molecules 2005, 10(9), 1126-1134; doi:10.3390/10091126
Received: 23 April 2005 / Accepted: 30 September 2005 / Published: 30 September 2005
Cited by 9 | PDF Full-text (160 KB) | Retraction
Abstract
The aromatic polyketones 3a-d are versatile compounds for the synthesis of the multi-1,2,3-selenadiazole aromatic derivatives 1a-d. The preparation starts with the reaction between the multi-bromomethylene benzene derivatives 2a-d and 4-hydroxy- acetophenone to give compounds 3a-d which are transformed through the reaction with [...] Read more.
The aromatic polyketones 3a-d are versatile compounds for the synthesis of the multi-1,2,3-selenadiazole aromatic derivatives 1a-d. The preparation starts with the reaction between the multi-bromomethylene benzene derivatives 2a-d and 4-hydroxy- acetophenone to give compounds 3a-d which are transformed through the reaction with semicarbazide hydrochloride or ethyl hydrazine carboxylate into the corresponding semicarbazones derivatives 4a-d or hydrazones 5a-d. The reaction with selenium dioxide leads to regiospecific ring closure of semicarbazones or hydrazones to give the multi- 1,2,3-selenadiazole aromatic derivatives in high yield. Full article
Open AccessArticle Poly[3-(3,4-dihydroxyphenyl)glyceric Acid], A New Biologically Active Polymer from Symphytum Asperum Lepech. and S.Caucasicum Bieb. (Boraginaceae)
Molecules 2005, 10(9), 1135-1144; doi:10.3390/10091135
Received: 23 April 2005 / Accepted: 30 September 2005 / Published: 30 September 2005
Cited by 11 | PDF Full-text (256 KB) | HTML Full-text | XML Full-text
Abstract
Two high-molecular water-soluble preparations with high anticomplementary, antioxidant, antilipoperoxidant and antiinflammatory activities were isolated from the roots of Symphytum asperum and S. caucasicum. Their main chemical constituent was found to be poly[oxy-1-carboxy-2-(3,4-dihydroxyphenyl)ethylene], according to IR and NMR spectroscopy. The Symphytum high-molecular preparations [...] Read more.
Two high-molecular water-soluble preparations with high anticomplementary, antioxidant, antilipoperoxidant and antiinflammatory activities were isolated from the roots of Symphytum asperum and S. caucasicum. Their main chemical constituent was found to be poly[oxy-1-carboxy-2-(3,4-dihydroxyphenyl)ethylene], according to IR and NMR spectroscopy. The Symphytum high-molecular preparations can modulate in vitro B- chronic lymphocytic leukaemia (B-CLL) cells apoptosis and cell cycle progression. Full article
Open AccessArticle Oxidative Stress, Lipid Profile and Liver Functions in Average Egyptian Long Term Depo Medroxy Progesterone Acetate (DMPA) Users
Molecules 2005, 10(9), 1145-1152; doi:10.3390/10091145
Received: 23 April 2005 / Accepted: 30 September 2005 / Published: 30 September 2005
Cited by 10 | PDF Full-text (75 KB) | HTML Full-text | XML Full-text
Abstract
Depo-medroxy progesterone acetate (DMPA, Depo-Provera®) is used in morethan 80 countries as a long-acting contraceptive administered as a single intramuscular(i.m) injection of 150 mg/3 months. The present study was set up to investigate theeffects of DMPA on 80 average Egyptian [...] Read more.
Depo-medroxy progesterone acetate (DMPA, Depo-Provera®) is used in morethan 80 countries as a long-acting contraceptive administered as a single intramuscular(i.m) injection of 150 mg/3 months. The present study was set up to investigate theeffects of DMPA on 80 average Egyptian women classified into four groups comprisingthose using the drug for one, two, three and four years, respectively, compared to acontrol group (N = 20) of married non-hormonally – treated women of similar ages. Thedrug showed a transient significant elevation of alanine aminotransferase activity (ALT)without an apparent effect on other liver indices, namely total bilirubin (T.Bil) level,aspartate aminotransferase (AST) and alkaline phosphatase (ALP) activities. Only thelow density/high density lipoproteins cholesterol ratio (LDLC/HDLC) was gradually andnon-significantly (ns) increased in comparison to control group, however, neither totalcholesterol (TC) nor triglycerides (TG) were affected by the drug. The lipid peroxideproduct malondialdehyde (MDA) was significantly elevated in an gradual manner with acorresponding decrease in reduced glutathione (GSH), without any change in blood nitricoxide (NO) levels. It can be concluded that DMPA may be considered as a safecontraceptive medication for the studied group of women, but that special care should beexercised for cardiovascular, hepatic and other patients more sensitive to the harmfuleffects of free radicals. Alternatively, supportive medications are advisable for eachexposed case to secure against the possible irreversible adverse effects of the drug by continuous use. In addition, annual re-evaluation is much more advisable despite the proven safety of the drug. Full article
Open AccessArticle Synthesis of Thiadiazoles and 1,2,4-Triazoles Derived from Cyclopropane Dicarboxylic Acid
Molecules 2005, 10(9), 1153-1160; doi:10.3390/10091153
Received: 29 June 2005 / Revised: 29 August 2005 / Accepted: 30 August 2005 / Published: 30 September 2005
Cited by 10 | PDF Full-text (198 KB) | HTML Full-text | XML Full-text
Abstract
New heterocyclic derivatives of cyclopropane dicarboxylic acid comprising thiadiazole and 1,2,4-triazole moieties are reported. Reaction of 1,1-cyclopropane dicarboxylic acid (1) with thiosemicarbazide and phosphorous oxychloride resulted in 1,1-bis (2-amino-1,3,4-thiadiazol-5- yl)cyclopropane (2). Cyclopropane dicarboxylic acid thiosemicarbazide (6) was converted into 1,1-bis(3-thio-4H-1,2,4-triazol-5-yl) cyclo- propane [...] Read more.
New heterocyclic derivatives of cyclopropane dicarboxylic acid comprising thiadiazole and 1,2,4-triazole moieties are reported. Reaction of 1,1-cyclopropane dicarboxylic acid (1) with thiosemicarbazide and phosphorous oxychloride resulted in 1,1-bis (2-amino-1,3,4-thiadiazol-5- yl)cyclopropane (2). Cyclopropane dicarboxylic acid thiosemicarbazide (6) was converted into 1,1-bis(3-thio-4H-1,2,4-triazol-5-yl) cyclo- propane (7) by ring closure in an alkaline medium. The thiadiazole 2 and the triazole 7 were converted into a variety of derivatives. Full article
Open AccessArticle Synthesis of Oxadiazoles, Thiadiazoles and Triazoles Derived from Benzo[b]thiophene
Molecules 2005, 10(9), 1161-1168; doi:10.3390/10091161
Received: 29 June 2005 / Revised: 29 August 2005 / Accepted: 30 August 2005 / Published: 30 September 2005
Cited by 13 | PDF Full-text (137 KB) | HTML Full-text | XML Full-text
Abstract
In this work 3-chloro-2-chlorocarbonylbenzo[b]thiophene (1) was prepared from cinnamic acid and then converted into the acid hydrazide 2. The azomethines 3a-e were prepared from the corresponding aryl aldehydes and the acid hydrazide 2. Treatment of compound 2 with formic acid gave the [...] Read more.
In this work 3-chloro-2-chlorocarbonylbenzo[b]thiophene (1) was prepared from cinnamic acid and then converted into the acid hydrazide 2. The azomethines 3a-e were prepared from the corresponding aryl aldehydes and the acid hydrazide 2. Treatment of compound 2 with formic acid gave the N-formyl acid hydrazide 4, which upon refluxing with phosphorous pentoxide or phosphorous pentasulphide in xylene yielded the corresponding 2- (3-chloro-1-benzothien-2-yl)-1,3,4-oxadiazole (5) and 2-(3-chloro-1-benzo-thien-2-yl)-1,3,4- thiadiazole (6). Reaction of 1-thiosemicarbazide 7 with NaOH leads to ring closure giving 5- (3-chloro-1-benzothien-2- yl)-4H–triazole-3-thiol (8) which is converted into a number of derivatives 9-12 Reaction of 2 with phenyl isothiocyanate and NaOH afforded 5-(3-chloro- 1-benzothien-2-yl)-4-(phenyl)-4H-1,2,4-triazole-3-thiol (14). Full article
Open AccessArticle Dakin-West Trick in the Design of Novel 2-Alkyl(aralkyl) Derivatives of Oxazolo[3,2-a]pyridines
Molecules 2005, 10(9), 1109-1118; doi:10.3390/10091109
Received: 23 April 2005 / Accepted: 1 September 2005 / Published: 1 September 2005
Cited by 5 | PDF Full-text (251 KB) | HTML Full-text | XML Full-text
Abstract
A series of previously unavailable derivatives of 2-alkyl- and 2-benzylderivatives of oxazolo[3,2-a]pyridines III were obtained via tandem ring opening and ring closure from stable mesoionic 3-acyloxazolo[3,2-a]pyridinium-2-olates I. The key intermediates of this tandem transformation are N-(b-oxoethyl)pyridones-2 II obtained by Dakin-West acylation of [...] Read more.
A series of previously unavailable derivatives of 2-alkyl- and 2-benzylderivatives of oxazolo[3,2-a]pyridines III were obtained via tandem ring opening and ring closure from stable mesoionic 3-acyloxazolo[3,2-a]pyridinium-2-olates I. The key intermediates of this tandem transformation are N-(b-oxoethyl)pyridones-2 II obtained by Dakin-West acylation of (pyridone-2-yl-1)acetic acid. An example of further utilization of this strategy is illustrated by preparation of unknown 2-benzylimidazo[1,2-a]pyridine from the salt I and ammonia. Full article

Other

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Open AccessOther Organic Synthesis in Pheromone Science
Molecules 2005, 10(9), 1023-1047; doi:10.3390/10091023
Received: 23 April 2005 / Published: 30 September 2005
Cited by 5 | PDF Full-text (460 KB) | HTML Full-text | XML Full-text
Abstract
Examples are given to illustrate the use of chemical and/or enzymatic asymmetric reactions in the synthesis of the new pheromones of the broad-horned flour beetle, flea beetle, currant stem girdler and Colorado potato beetle. The relationships between stereochemistry and bioactivity among pheromones [...] Read more.
Examples are given to illustrate the use of chemical and/or enzymatic asymmetric reactions in the synthesis of the new pheromones of the broad-horned flour beetle, flea beetle, currant stem girdler and Colorado potato beetle. The relationships between stereochemistry and bioactivity among pheromones are summarized to emphasize biodiversity as revealed in pheromone perception. Full article

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