فهرست مطالب

Organic Chemistry Research - Volume:7 Issue: 1, Winter 2021
  • Volume:7 Issue: 1, Winter 2021
  • تاریخ انتشار: 1400/11/01
  • تعداد عناوین: 10
  • Neda Attaran *, Hossein Eshghi Pages 1-11

    Meso-Tetraarylporphyrins are synthesized from pyrrole and aryl aldehydes cleanly and efficiently using an equimolar amount of Cr(HSO4)3 in the presence of chloranil as oxidant. Also, for the first time, meso-tetraphenylporphyrinogen is oxidized by HAuCl4 to obtain meso-tetraphenylporphyrin and valuable gold nanoparticles as byproduct, in good yield. Transmission electron microscopy (TEM) analysis indicated that spherical gold nanoparticles in the 25 diameter were obtained in the presence of meso-tetraphenylporphyrinogen at room temperature without using any capping agents. The Fourier transform infrared spectroscopy (FT-IR) supports the presence of tetraphenylporphyrin dye molecules on the surface of gold nanoparticles. These obtained gold nanoparticles could be used for various unknown and known applications, especially for designing efficient dye sensitized solar cells, selective catalysts and photodynamic therapy agents.

    Keywords: Meso-tetraarylporphyrins, Gold Nanoparticles, Transmission electron microscopy, Dye molecules
  • Zohreh Khanjari, Bita Mohtat *, Reza Ghiasi, Hoorieh Djahaniani, Farahnaz Kargar Behbahani Pages 12-22

    The effects of substituent and temperature on the 1- (benzothiazolylamino) methyl - 2- naphthol molecules were studied at CAM-B3LYP/6-311G (d,p) level of theory. Selected substitutions were NH2, OH, Me, F, Cl, CHO, COOH, CN and NO2. Substituent effect on the frontier orbitals energies, HOMO-LUMO gap, chemical potential, and electrophilicity were explored. Dependencies of energy changes, reactivity properties and thermodynamics parameters (G, H and S) on the Hammett's constants (p) were provided. Thermodynamics parameters values of the formation reaction were studied reaction at 100-1000 K range. Computational investigation of the substituents and temperature influences on the formation reaction of the 1-(benzothiazolylamino) methyl-2-naphthol showed the negative E values in the studied reactions. Calculated dipole moment values reveal the presence of the EWGs induced a larger dipole moment compared with the EDGs. Higher negative values were found in the presence of EWGs compared to EDGs. Frontier orbitals were stabilized in the presence of EWGs. However, frontier orbitals were destabilized in the presence of EDGs. Thermodynamic analysis revealed that these reactions were non-spontaneous and exothermic. The G and negative H values were increased with increasing the temperature. Optimization and vibrational analysis were done with Gaussian 09 software package. The standard 6-311G(d,p) basis set was considered for the elements, respectively. CAM-B3LYP functional was used for the optimization of the geometries of the compound . This functional is Handy and coworkers’ long range corrected version of B3LYP using the Coulomb-attenuating method The identities of the optimized structures as an energy minimum were confirmed by vibrational analysis

    Keywords: 1-(Benzothiazolylamino)methyl-2-naphthol, Substituent effect, Temperature effect, Thermodynamics parameters
  • Sara Azad, Bi Bi Fatemeh Mirjalili *, Abdolhamid Bamoniri Pages 23-31

    Nano-Fe3O4/TiCl2/cellulose as a green and recyclable nanocatalyst was synthesized and characterized by FT-IR, FESEM, TEM, XRF, BET, VSM, EDX and XRD. The prepared magnetic nanocatalyst was applied for the synthesis of 2,3-dihydro-2-substituted-1H-naphtho[1,2-e][1,3]oxazine under room temperature grinding condition. Short reaction time, high yield, green media, easy work-up, simple magnetic recovery and reusability of the catalyst are the important features of the present protocol.

    Keywords: 3-Oxazines, Solvent-free reaction, Magnetic nanocatalyst, Grinding
  • MohammadReza Dayer * Pages 32-41

    The COVID-19 outbreak caused by the SARS-CoV-2 virus in late 2019 and early 2020 comprises a serious pandemic threat worldwide. Given the severity of the disease and the fact that there is no approved cure for this infectious disease, it seems reasonable to search for better candidates' drugs among approved antiviral or even antibacterial drugs for their anti-COVID-19 capability in contrast to the currently approved drugs. The enzyme main protease of SARS-CoV-2 that plays an important role in the virus life cycle seems to be a good target for inhibition by drugs. Accordingly, in the present work by using the molecular docking method we used the newly released coordinate structure of the protease as a target and 40 approved drugs from anti-viral, anti-parasite anti-malaria groups as ligands for docking experiments. Blind and active site-directed docking experiments were carried out on the optimized and equilibrated structure of protease at pH 7, 37 degrees centigrade of temperature, and 1 atmosphere of pressure. Our results indicate that based on binding energy, percent of binding site occupation, membrane transportability, and the maximum allowed dosage, erythromycin, clarithromycin, Amprenavir, Darunavir, Cefixime, and Tetracycline are among the enrolled drugs merit best parameters for clinical evaluation and their therapeutic potential in COVID-19 outbreak.

    Keywords: Coronavirus, COVID-19 Outbreak, Docking, Antibiotics, Anti-HIV Drugs, Macrolides
  • Javad Safaei Ghomi *, Seyed Hadi Nazemzadeh, Mohammed Alnasrawi, Hossein Shahbazi Alavi Pages 42-53

    An effective way for the synthesis of bis-thiazolidinones was applied by one-pot pseudo-five-component reaction of benzaldehydes, ethylenediamine, 2-mercaptoacetic acid with nano-Fe3O4-tethered polyhedral oligomeric silsesquioxanes with eight branches as catalyst under ultrasonic conditions. The catalyst has been characterized by FT-IR (Fourier-transform infrared spectroscopy), SEM (scanning electron microscope), XRD (X-ray diffraction), EDS (Energy-dispersive X-ray spectroscopy), BET (Brunauer-Emmett-Teller), TGA (Thermogravimetric analysis) and VSM (vibrating-sample magnetometer). The remarkable advantages of this methodology are easy work-up, short reaction times, high to excellent product yields, low catalyst loading and reusability of the catalyst.

    Keywords: Ultrasonic irradiation, Heterogeneous catalysts, Fe3O4, nanocatalyst, Bis-thiazolidinones
  • Sedighe Mozafari Vanani, MohammadAli Amrollahi * Pages 54-60

    This report provides a description of a novel and efficient procedure for the synthesis of substituted 4H-1,3,4-oxadiazines via reaction of various vinyl cyanides and acetohydrazide in H2O under catalyst-free conditions. The remarkable advantages are the simplicity of the experimental procedures, high yields, and avoidance of organic solvents. Products were characterized by melting point, IR, 1H- and 13C-NMR spectra, and elemental analysis. The desired products were obtained in >85% yields.

    Keywords: Acetohydrazide, Catalyst-free, Cyclization, Oxadiazines, Vinyl cyanides, Aqueous
  • Robabeh Sayyadi Kord Abadi, Omid Alizadeh, Ghasem Ghasemi Pages 61-76

    The activity of the 25 different Carfilzomib derivatives was estimated using multiple linear regression (MLR), artificial neural network (ANN), and genetic algorithm(GA) and simulated annealing algorithm (SA) and Imperialist Competitive Algorithm (ICA) as optimization methods. The obtained results from MLR-MLR, MLR-GA, SA-ANN and GA-ANN techniques were compared and for combinations of modelling-optimization methods observed root mean sum square errors (RMSE) of 0.290, 0.0482, 0.0294, 0.0098 in gas phase, respectively (N=25). A high predictive ability was observed for the MLR-ICA model with the best number of empires/ imperialists (nEmp=50 ) and nEmp=100 with root-mean-sum-squared error (RMSE) of 0.00996 in gas phase. From the MLR-ICA method, it was revealed that RDF 075m, MATS1m, F04[N-O], O-059, F09[C-O] and Mor21p are the most important descriptors. From Monte Carlo simulations, it was found that the presence of double, absence of halogens, oxygen connected to double bond, sp2 carbon connected to double bond, double bond with ring, branching, nitrogen are the most important molecular features affecting the biological activity of the drug. It was concluded that simultaneous utilization of MLR-ICA, GA-ANN and Monte Carlo method can lead to a more comprehensive understanding of the relation between physico-chemical, structural or theoretical molecular descriptors of drugs to their biological activities and facilitate designing of new drugs.

    Keywords: Carfilzomib, Antitumor drugs, QSAR, Genetic Algorithm, Monte Carlo method
  • Marzieh Daryanavard, Behzad Mohammadi, Shirin Nadri, Mohammad Joshaghani Pages 77-85

    The Mizoroki-Heck coupling reaction has been carried out using Pd(OAc)2 and bisimidazolium (1,1′-methylene-3,3′-bis[(N-(isopropyl)imidazol-2-ylidene]dibromide) for aryl bromides as well as less reactive chlorobenzene with mono- and di-substituted olefins. Only 0.025 mol% of Pd(II) shows a high activity toward the coupling reaction with turnover number (TON) ≈ 600-3960. Further, this catalyst system, Pd(OAc)2/Bisimidazolium, exhibits the excellent selectivity for the trans-isomer coupling products and the terminal arylation coupling products for mono- and di-substituted olefins, respectively. The nature of olefins (n-butyl acrylate, styrene, and 1,1-disubstituted olefins) has a significant contribution on the yield of the coupling products.

    Keywords: Bisimidazolium, Heck reaction, Homogeneous, Mono-, di-substituted olefins, Selectivity
  • Zahra Damanzan, Mohammad Anary-Abbasinejad, Mozhgan Masoudi Pages 86-91

    An efficient one-pot three-component reaction of pyrrole with arylglyoxal derivatives and Meldrum’s acid (MA) in water at room temperature afforded 2,2-dimethyl-5- (2-oxo-2-aryl-1- (1H-pyrrol-2-yl) ethyl) -1,3-dioxane-4,6-dione derivatives under catalyst-free conditions in high yields. Products were isolated and purified by simple filtration and washing with diethyl ether and their structures were established from their IR and NMR spectroscopic data.

    Keywords: Pyrrole, Arylglyoxals, Meldrum's acid, green synthesis, Three-component reaction
  • Hossein Eshghi, Aida Mansoori Pages 92-108

    The development of diastereoselective, catalytic methodologies for synthesis of Mannich products presents specific promise for synthetic applications. Only highly reactive aldehydes such as formaldehyde and acetaldehyde, secondary amine, have been ruled out of the classical Mannich reaction. Highly stereoselective Mannich reactions have been extensively studied and reported. The most powerful enantioselective and diastereoselective C-C bond forming reactions include the asymmetric Mannich reaction such as oxidative and reductive Mannich-reaction. In oxidative type, an oxidizing agent such as oxygen, air, etc. is used. Whereas in reductive Mannich reaction, a reducing agent produces enolate for the generation of a reactive iminium ion. Cross-dehydrogenative coupling reactions (CDC) are a method for generating more complex amines from simpler materials by oxidatively functionalizing amine -CH bonds. Besides, the redox-Mannich reaction uses the same raw materials but includes an isomerization step that makes it simple to create ring-substituted -amino ketones. In this review article, we have tried to study the research that has been done in recent years for oxidative and reductive Mannich reactions.

    Keywords: Oxidative, Reductive, Mannich reaction, CDC reactions