Publications by authors named "Parviz Rashidi Ranjbar"

11 Publications

  • Page 1 of 1

Biscoumarin-1,2,3-triazole hybrids as novel anti-diabetic agents: Design, synthesis, in vitro α-glucosidase inhibition, kinetic, and docking studies.

Bioorg Chem 2019 11 16;92:103206. Epub 2019 Aug 16.

Nano Alvand Company, Avicenna Tech Park, Tehran University of Medical Sciences, Tehran 1439955991, Iran. Electronic address:

A novel series of biscoumarin-1,2,3-triazole hybrids 6a-n was prepared and evaluated for α-glucosidase inhibitory potential. All fourteen derivatives exhibited excellent α-glucosidase inhibitory activity with IC values ranging between 13.0 ± 1.5 and 75.5 ± 7.0 µM when compared with the acarbose as standard inhibitor (IC = 750.0 ± 12.0 µM). Among the synthesized compounds, compounds 6c (IC = 13.0 ± 1.5 µM) and 6g (IC = 16.4 ± 1.7 µM) exhibited the highest inhibitory activity against α-glucosidase and were non-cytotoxic towards normal fibroblast cells. Kinetic study revealed that compound 6c inhibits the α-glucosidase in a competitive mode. Furthermore, molecular docking investigation was performed to find interaction modes of the biscoumarin-1,2,3-triazole derivatives.
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http://dx.doi.org/10.1016/j.bioorg.2019.103206DOI Listing
November 2019

Novel fused 1,2,3-triazolo-benzodiazepine derivatives as potent anticonvulsant agents: design, synthesis, in vivo, and in silico evaluations.

Mol Divers 2020 Feb 20;24(1):179-189. Epub 2019 Mar 20.

Experimental Medicine Research Center, Tehran University of Medical Sciences, Tehran, Iran.

A novel series of 1,2,3-triazolo-benzodiazepine derivatives 6a-o has been synthesized and evaluated in vivo for their anticonvulsant activities using by pentylenetetrazole (PTZ)- and maximal electroshock (MES)-induced seizures in mice. The synthetic approach started with diazotizing 2-aminobenzoic acids 1 to produce 2-azidobenzoic acids 2. Next, reaction of the latter compounds with propargylamine 3, benzaldehyde 4, and isocyanides 5 led to the formation of the title compounds 6a-o, in good yields. All the synthesized compounds exhibited high anticonvulsant activity in the PTZ test, comparable to or better than the standard drug diazepam. Among the tested compounds, N-(tert-butyl)-2-(9-chloro-6-oxo-4H-[1,2,3]triazolo[1,5-a][1,4]benzodiazepin-5(6H)-yl)-2-(3-bromophenyl)acetamide 6h was the most potent compound in this assay. Moreover, compounds 6i and 6k showed excellent activity in MES test. Loss of the anticonvulsant effect of compound 6h in the presence of flumazenil in the PTZ test and appropriate interaction of this compound in the active site of benzodiazepine (BZD)-binding site of GABA receptor confirm involvement of BZD receptors in the anticonvulsant activity of compound 6h. A novel series of 1,2,3-triazolo-benzodiazepine derivatives 6a-o have been synthesized and evaluated in vivo for their anticonvulsant activities using by pentylenetetrazole (PTZ)- and maximal electroshock (MES)-induced seizures in mice. All the synthesized compounds exhibited high anticonvulsant activity, comparable to or better than the standard drug diazepam in the PTZ test and compounds 6i and 6k showed excellent activity in MES test. Flumazenil test and in silico docking study confirm involvement of benzodiazepine receptors in the anticonvulsant activity of these compounds.
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http://dx.doi.org/10.1007/s11030-019-09940-9DOI Listing
February 2020

A Convenient Method for the Synthesis of Chromeno[4,3-b]pyridines Via Three-component Reaction.

Comb Chem High Throughput Screen 2018 ;21(5):344-348

The Institute of Pharmaceutical Sciences (TIPS) and Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran.

Aim And Objective: The importance of Chromeno[4,3-b]pyridines in bioactive compounds, highlighted the ongoing research on developing novel methods for the construction of this heterocyclic scaffold. Regarding the advantageous features of multi-component reactions in organic synthesis, we will try to synthesize pyridocoumarins through this method.

Materials And Methods: Chromeno[4,3-b]pyridines were conveniently prepared from a threecomponent condensation reaction between 4-hydroxy coumarin, ammonia and ethyl 2,4-dioxo-4- arylbutanoates in refluxing n-propanol. The synthesized compounds were characterized by NMR, IR and Mass spectroscopy.

Results: The reaction proceeded through an in situ formed 4-amino coumarin, affording eight new target compounds in good yields.

Conclusion: This method introduce a novel approach to ethyl 4-aryl-5-oxo-5H-chromeno[4,3- b]pyridine-2-carboxylate derivatives and allow organic chemists to prepare 4-aminocoumarin in reaction medium.
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http://dx.doi.org/10.2174/1386207321666180524110635DOI Listing
December 2019

Novel quinazolin-4(3H)-one linked to 1,2,3-triazoles: Synthesis and anticancer activity.

Chem Biol Drug Des 2018 07 18;92(1):1373-1381. Epub 2018 May 18.

Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Research Institute, Tehran University of Medical Sciences, Tehran, Iran.

In this work, a wide range of novel quinazolin-4(3H)-one linked to 1,2,3-triazoles was designed, synthesized, and evaluated against a panel of three human breast (MDA-MB-231, MCF-7, T-47D), lung (A549), and prostate (PC3) cancer cell lines. Our results revealed that the anticancer activity of the synthesized compounds was selectively affected by the presence of methoxy group on the linker between quinazolinone and 1,2,3-triazole moieties. According to the calculated IC values, compounds 6q, 6w, and 6x showed good cytotoxicity against breast cancer cell lines even more effective than the reference drug, etoposide. Compounds 6q and 6u were found to be potent compounds against A549, non-small-cell lung cancer (NSCLC), comparing with erlotinib. Also, the morphological analysis by acridine orange/ethidium bromide double staining test and flow cytometry analysis indicated that potent compounds induced apoptosis in human cancer cell lines. Molecular docking studies were performed to clarify the inhibition mode of compounds 6g, 6u, 6w, and 6x over the EGFR active site. The most promising compounds, 6q and 6u, possessing 3-methoxy group were well oriented to the gatekeeper hydrophobic pocket of EGFR active site and interact well with Ala719, Val702, and Leu820 through hydrophobic interaction.
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http://dx.doi.org/10.1111/cbdd.13203DOI Listing
July 2018

Design, synthesis and in vitro α-glucosidase inhibition of novel dihydropyrano[3,2-c]quinoline derivatives as potential anti-diabetic agents.

Bioorg Chem 2018 04 3;77:280-286. Epub 2018 Feb 3.

Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran. Electronic address:

A novel series of dihydropyrano[3,2-c]quinoline derivatives 6a-q were synthesized and evaluated for their in vitro α-glucosidase inhibitory activities. All newly synthesized compounds displayed potent α-glucosidase inhibitory activity in the range of 10.3 ± 0.3 µM-172.5 ± 0.8 µM against the yeast α-glucosidase enzyme when compared to the standard drug acarbose (IC = 750.0 ± 1.5 µM). Among these compounds, compounds 6e and 6d displayed the most potent α-glucosidase inhibitory activity (IC = 10.3 ± 0.3 and 15.7 ± 0.5 µM, respectively). The kinetic analysis of the most potent compounds 6e and 6d revealed that compound 6e inhibited α-glucosidase in an uncompetitive manner (K = 11 µM) while compound 6d was a non-competitive inhibitor (K = 28 µM) of the enzyme. Then, the cytotoxicity of the most potent compounds (i.e., compounds 6a, 6d, 6e, 6 g, 6j, and 6l) were evaluated for toxicity using the breast cancer cell lines MDA-MB231, MCF-7, and T-47D by using a MTT assay, and no toxicity was observed.
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http://dx.doi.org/10.1016/j.bioorg.2018.01.025DOI Listing
April 2018

All-Metal Aromaticity: Revisiting the Ring Current Model among Transition Metal Clusters.

J Chem Theory Comput 2013 Nov 30;9(11):4789-96. Epub 2013 Oct 30.

Centre for Theoretical and Computational Chemistry, Department of Chemistry, University of Tromsø-The Arctic University of Norway , N-9037 Tromsø, Norway.

We present new insight into the nature of aromaticity in metal clusters. We give computational arguments in favor of using the ring-current model over local indices, such as nucleus independent chemical shifts, for the determination of the magnetic aromaticity. Two approaches for estimating magnetically induced ring currents are employed for this purpose, one based on the quantum theory of atoms in molecules (QTAIM) and the other where magnetically induced current densities (MICD) are explicitly calculated. We show that the two-zone aromaticity/antiaromaticity of a number of 3d metallic clusters (Sc3(-), Cu3(+), and Cu4(2-)) can be explained using the QTAIM-based magnetizabilities. The reliability of the calculated atomic and bond magnetizabilities of the metallic clusters are verified by comparison with MICD computed at the multiconfiguration self-consistent field (MCSCF) and density functional levels of theory. Integrated MCSCF current strength susceptibilities as well as a visual analysis of the calculated current densities confirm the interpretations based on the QTAIM magnetizabilities. In view of the new findings, we suggest a simple explanation based on classical electromagnetic theory to explain the anomalous magnetic shielding in different transition metal clusters. Our results suggest that the nature of magnetic aromaticity/antiaromaticity in transition-metal clusters should be assessed more carefully based on global indices.
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http://dx.doi.org/10.1021/ct4007184DOI Listing
November 2013

Method/basis set dependence of NICS values among metallic nano-clusters and hydrocarbons.

Phys Chem Chem Phys 2012 Mar 3;14(10):3471-81. Epub 2012 Feb 3.

School of Chemistry, College of Science, University of Tehran, Tehran, Iran.

The influence of various all-electron basis sets and effective core potentials employed along with several DFT functionals (B3LYP, B3PW91, BLYP, BP86 and M06) on the magnitude of nucleus independent chemical shift (NICS) values in different metallic nano-clusters and hydrocarbons is studied. In general, it is demonstrated that the NICS values are very sensitive to the applied method/basis set; however, the method/basis set dependence is more prominent for computed NICS values in transition metal clusters. In hydrocarbons, medium-size basis sets perform roughly similar to large basis sets in most cases. It is also found that NICS(0) values are more sensitive to the method/basis set variation compared to the NICS values computed at 1 or 2 Å above the ring plane. However, in many cases, no broad-spectrum regulation is found for the effect of basis set/method on the magnitude of NICS values. A detailed study showed that bond length alternation in a molecule has an insignificant effect on the magnitude of NICS values so the influence of method/basis sets on the magnitude of NICS values mostly arises from the different predicted ring current intensities at various computational levels.
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http://dx.doi.org/10.1039/c2cp23205gDOI Listing
March 2012

The Laplacian of electron density versus NICSzz scan: measuring magnetic aromaticity among molecules with different atom types.

J Phys Chem A 2011 Nov 1;115(45):12708-14. Epub 2011 Jul 1.

School of Chemistry, College of Science, University of Tehran, Tehran, Iran.

The electron density versus NICS(zz) (the out-of-plane component of nucleus-independent chemical shifts (NICS)) scan for assessing magnetic aromaticity among similar molecules with different ring sizes is improved by scanning the Laplacian of electron density versus NICS(zz) to include molecules containing different types of atoms. It is demonstrated that the new approach not only reproduces the results of the previous method but also surpasses that in the case of species with different atom types. The relative positions of curves in the plots of the Laplacian of electron density versus NICS(zz) correlate well with the ring current intensities of these molecules both near and far from the ring planes of the considered molecules. Accordingly, relative magnetic aromaticity of a number of planar hydrocarbons and a group of double aromatic metallic/semimetallic species are studied and discussed.
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http://dx.doi.org/10.1021/jp203681xDOI Listing
November 2011

A dissected ring current model for assessing magnetic aromaticity: a general approach for both organic and inorganic rings.

J Comput Chem 2011 Aug 19;32(11):2422-31. Epub 2011 May 19.

School of Chemistry, College of Science, University of Tehran, Tehran, Iran.

A model based on classical electrodynamics is used to measure the strength of ring currents of different molecular orbitals, i.e., σ- and π-orbitals, and characteristics of ring current loops, i.e., ring current radii and height of current loops above/below the ring planes, among a number of organic as well as inorganic molecules. For the π-current, the present model represents an improvement of previous approaches to determine ring current intensity. It is proven that the present model is more precise than previous models as they could not explain presence of the minimum in the plot of NICS(πzz) versus distance close to the ring plane. Variations in the charge of molecules and the types of constituent atoms of each species affect the ring current radii of both σ- and π-current loops as well as the height of π-current loops above/below the ring plane. It is suggested that variation in the distribution of the one-electron density in different systems is the main source of differences of the ring current characteristics.
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http://dx.doi.org/10.1002/jcc.21824DOI Listing
August 2011

The critical re-evaluation of the aromatic/antiaromatic nature of Ti3(CO)3: a missed opportunity?

Phys Chem Chem Phys 2011 Mar 31;13(10):4576-82. Epub 2011 Jan 31.

School of Chemistry, College of Science, University of Tehran, Tehran, Iran.

The nature of bonding and aromaticity of Ti(3)(CO)(3), a mill-shaped metal-carbonyl complex, is studied carefully. A unique bonding mechanism between metal and carbonyl groups is found in this species. Ti(3)(CO)(3) is an example of a metal-carbonyl complex with prominent metal to carbonyl donation. Moreover, it is proven that not only is Ti(3)(CO)(3) not an antiaromatic complex but also it is the first synthesized example of d-block, σ+π aromatic species. A quick survey among the first row of transition metals in the periodic table shows that other local minima with similar structures and aromaticity are present and Ti(3)(CO)(3) is the first synthesized species of an unknown family.
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http://dx.doi.org/10.1039/c0cp01519aDOI Listing
March 2011

The electron density vs. NICS scan: a new approach to assess aromaticity in molecules with different ring sizes.

Phys Chem Chem Phys 2010 Oct 23;12(39):12630-7. Epub 2010 Aug 23.

School of Chemistry, College of Science, University of Tehran, Tehran, Iran.

The influence of electron density on the magnitude of non-nuclear magnetic shielding, NICS, is studied in detail by scanning the electron density vs. NICS(zz) (the out-of-plane component of NICS). This study sheds new light on the role of electron density on the magnitude of NICS. Scanning the electron density vs. NICS(zz) not only helps to discriminate the electronic ring currents operative in aromatic, nonaromatic and antiaromatic species, but also yields a measure to compare the strength of diatropic/paratropic currents in molecules with different ring sizes or different number of π electrons without relying on the methods of σ-π separation.
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http://dx.doi.org/10.1039/c004254dDOI Listing
October 2010