Organic Communications Articles
Issue: 2 April-June
Year: 2017 Volume: 10 Issue:2 April-June
1) Fused thiophenes: an overview of the computational investigations
Computational investigations of fused thiophenes including not only thienothiophene, ditihienothiophene and thienoacene but also other thiophene-fused (hetero)-aromatic rings have been surveyed. The effect of the methods and basis sets applied on promising optoelectronic materials were elaborated. This brief review suggests the best method for the fused thiophenes to be B3LYP functional. ©2016 ACG Publications. All rights reserved.DOI http://doi.org/10.25135/acg.oc.9.17.04.014 Keywords Computation DFT fused thiophenes optoelectronic DETAILS PDF OF ARTICLE © 2017 ACG Publications. All rights reserved.
2) Formation of bioactive benzofuran via oxidative coupling, using coconut water (Cocos nucifera L.) as biocatalyst
The capacity of simple coconut water, which contains natural peroxidases, to act as a biocatalyst for the oxidative coupling-cyclization of p-(OH)-phenylpropanoids, was evaluated in this work. As a result, dimeric forms of isoeugenol (licarin A) and methyl p-coumarate (methyl dehydrodicoumarate) were obtained. The products of the reactions were characterized by optical rotatory dispersion, and 1H-NMR and 13C-NMR spectroscopy. The oxidative coupling-cyclization mechanism for coniferyl alcohol is proposed.DOI http://doi.org/10.25135/acg.oc.10.16.11.449 Keywords Bioprocess biotransformation neolignans peroxidase Cocos nucifera DETAILS PDF OF ARTICLE © 2017 ACG Publications. All rights reserved.
3) Asymmetric cyclopropanation of olefins catalyzed by a chiral cobalt(II) porphyrin
The cobalt(II) complex of the Halterman porphyrin, 5,10,15,20-tetrakis[(1S,4R,5R,8S)-1,2,3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracene-9-yl]porphyrinato cobalt(II) [Co(por*)], was synthesized and its structure was identified by X-ray analysis. Up to 80:20 trans:cis diastereomeric ratio and 82% ee were achieved in the cyclopropanation of styrene with ethyl diazoacetate by using this cobalt(II) porphyrin complex as catalyst.DOI http://doi.org/10.25135/acg.oc.11.17.04.019 Keywords Asymmetric catalysis cyclopropanation cobalt porphyrin ethyl diazoacetate DETAILS PDF OF ARTICLE © 2017 ACG Publications. All rights reserved.
4) Synthesis and anti-bacterial activity of novel 1,3-phenylene-bis-N-acetyl- and N-phenylenepyrazole derivatives
The 1,1'-(5,5'-(1,3-phenylene)bis(3-aryl-4,5-dihydro-1H-pyrazole-5,1-diyl))di-ethanone (5a-e) and 1,3-bis(1-phenyl-3-(aryl)-4,5-dihydro-1H-pyrazol-5-yl)benzene (6a-e) were synthesized by addition of hydrazine hydrate and/or phenylhydrazine to 1,3-phenylene-bis-chalcone derivatives (3a-e), respectively. The structures of obtained compounds (5a-e and 6a-e) were characterized using the spectroscopic methods (NMR, IR) and elemental analysis. Addition, the in vitroantibacterial activities of compounds (5a-e) was tested against the five human pathogenic bacteria. Gentamycin and Fluconazole were used as positive control. The results were given as inhibition zone (mm) and the compounds 5d and 5e showed the same activity with standard (Fluconazole) against C. albinas.DOI http://doi.org/10.25135/acg.oc.126.96.36.1993 Keywords 1 3-Phenylene-b is-N-acetylpyrazoles 1 3-phenylene-bis-N-phenylpyrazoles antibacterial activity DETAILS PDF OF ARTICLE © 2017 ACG Publications. All rights reserved.
5) Short asymmetric synthesis of a model monomeric unit for a/g peptide foldamers based on b -amino linked D-leucine – cis- g -butyrolactone g -acetic acid conjugate
This synthetic work reports a concise, asymmetric synthesis of b -amino- g -butyrolactone acetic acid – D-leucine hybrid 1 which will serve as model starting template sub-unit for preparing a/g foldameric oligopeptides containing unnatural g -amino acid residues. The synthesis of cis-substituted 1 was successfully achieved in six linear steps with very good stereoinduction.DOI http://doi.org/10.25135/acg.oc.188.8.131.524 Keywords cis- g -butyrolactone foldamer oligopeptide asymmetric epoxide opening g -amino acid DETAILS PDF OF ARTICLE © 2017 ACG Publications. All rights reserved.
6) A green protocol for the synthesis of bis(indolyl)methanes catalyzed by succinic acid under microwave irradiation
An eco-friendly simple and efficient synthesis of 3,3’-bis(indolyl)methanes was carried out by electrophilic substitution reaction of indole with structurally divergent aldehydes by using succinic acid as green catalyst and water as green solvent under microwave irradiation. The advantages of this protocol are excellent yields, higher availability, inexpensive catalyst, lack of toxicity, shorter reaction time and more environmentally friendly catalyst. The reaction is chemoselective applicable only to aldehydes.DOI http://doi.org/10.25135/acg.oc.184.108.40.2060 Keywords Indole aldehydes succinic acid water bis(indolyl)methanes microwave irradiation DETAILS PDF OF ARTICLE © 2017 ACG Publications. All rights reserved.
7) An optimized and very detailed, grams scale synthesis of CTEP, through a complete characterization of all the isolated and purified intermediates
Glutamate is the major excitatory neurotransmitter in the brain. 2-Chloro-4-[2,5-dimethyl-1-(4-trifluoromethoxyphenyl)-1H-imidazol-4-ylethynyl]pyridine (5) (CTEP) is the first reported negative allosteric modulator of the metabotropic glutamate receptor 5 (mGlu5NAM) with a biological half-life of 48 hours in rodents and therefore considered an ideal tool for chronic studies in rats and mice. In this work an optimized protocol for the synthesis and purification of CTEP is reported. Through the developed new work up scrupulously described in detail, CTEP was obtained in 63 % yield, with a significant improvement in comparison with the methods reported in literature (27%) and in a tripled overall yield (27% versus 9%). Furthermore, all the intermediates between which the unreported multifunctional and appealing compound 8 as well as the final compound 5 were isolated, purified and fully characterized by IR, NMR ( 1H NMR and 13C NMR), melting point, except for the oily 7, and Elemental analysis.DOI http://doi.org/10.25135/acg.oc.220.127.116.114 Keywords Acetylene-type mGlu5 NAMs optimization isolation purification NMR characterization DETAILS PDF OF ARTICLE © 2017 ACG Publications. All rights reserved.
8) Preparation and biological evaluation of novel acylhydrazide derivatives of 2,3-dichloronaphthoquinone
Naphthoquinones have been reported to possess a variety of pharmacological properties including antibacterial, antifungal, antiviral, anti-inflammatory, anti-artherosclerotic and anticancer effects. We have successfully synthesized a series of novel naphthoquinone acylhydrazides. The straightforward synthesis of these molecules involves a coupling reaction between 2,3-dichloro-1,4-naphthoquinone and several alkyl and aromatic hydrazides and the hydrazides of the pyrimidine nucleobases, uracil and thymine. The product hydrazides were isolated in good yields and completely characterized by spectroscopic analysis. Biological evaluation against human colon cancer HCT116 cells and human breast cancer MCF-7 cells indicated that the novel hydrazides possessed significant anticancer activity.DOI http://doi.org/10.25135/acg.oc.16.17.00.012 Keywords 2 3-dichloro-1 4-naphthoquinone acylhydrazide 1 4-napththoquinone-2-acyl hydrazides pyrimidine nucleobase DETAILS PDF OF ARTICLE © 2017 ACG Publications. All rights reserved.
9) First consecutive linear synthesis of hostmaniene, 5-formyl-2-(isopropyl- 1 ’- ol)benzofuran and anadendroic acid using prenylated phenol
The paper describes a new pathway for the syntheses of three natural bioactive benzofuran type compounds, namely, hostmaniene, 5-formyl-2-(isopropyl-1’-ol)benzofuran and anadendroic acid. The key synthetic strategy involved prenylation of the carboxy-phenol 7 and followed by the [5-exo-tet]cyclization reaction to furnish the benzofuran ring synthon. Subsequently, performing sequences of reactions of epoxide ring opening, ester reduction and re-oxidation of the alcohol from the benzofuran ring synthon gave all the title compounds in reasonable yield. Their structures were confirmed by both spectroscopic data and chemical transformations.DOI http://doi.org/10.25135/acg.oc.17.17.03.011 Keywords Hostmaniene anadendroic acid prenylated pheno benzofuran DETAILS PDF OF ARTICLE © 2017 ACG Publications. All rights reserved.