Mehran Ghasemi

University of Nizwa

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Farnaz Jafarpour

University of Tehran

Maryam Dehghan

University of Tehran

Azizollah Habibi

Kharazmi University

Banafshe Rahimi

University of Tehran

Ahmed Al‐Harrasi

University of Nizwa

Mohammad Mahdavi

Tehran University of Medical Sciences

Mohammad Hossein Bernoosha

University of Tehran

Aida Iraji

Shiraz University of Medical Sciences

Mohammad Ali Faramarzi

Biotechnology Research Center

Alireza Abbasi

University of Tehran

Cooperative Institutions

University of Tehran

Tehran University of Medical Sciences

Shiraz University of Medical Sciences

Iran University of Medical Sciences

Shiraz University

Alzahra University

Biotechnology Research Center

Endocrinology and Metabolism Clinical Sciences Institute

Kharazmi University

Tarbiat Modares University

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CCDC 2248038: Experimental Crystal Structure Determination

The Cambridge Structural Database (2023)

Mehran Ghasemi Banafshe Rahimi Maryam Dehghan Mohammad Hossein Bernoosha Farnaz Jafarpour

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccdc.csd.cc2fg8ck

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Substituted piperazine conjugated to quinoline-thiosemicarbazide as potent α-glucosidase inhibitors to target hyperglycemia

Scientific Reports (2025)

Mehran Ghasemi Mohammad Mahdavi Maryam Dehghan Mohammadreza Eftekharian Somayeh Mojtabavi

Diabetes mellitus, particularly type 2 diabetes, is a growing global health challenge characterized by chronic hyperglycemia due to insulin resistance. One therapeutic approach to managing this condition is the inhibition of α-glucosidase, an enzyme involved in carbohydrate digestion, to reduce postprandial blood glucose levels. In this study, a series of thiosemicarbazide-linked quinoline-piperazine derivatives were synthesized and evaluated for their α-glucosidase inhibitory activity, to identify new agents for type 2 diabetes management. Structure-activity relationship (SAR) analysis revealed that the nature and position of substituents on the aryl ring significantly impacted the inhibitory potency. Among the synthesized derivatives, the 2,5-dimethoxy phenyl substitution (7j) exhibited the most potent activity with an IC50 value of 50.0 µM, demonstrating a 15-fold improvement compared to the standard drug acarbose. Kinetic studies identified compound 7j as a competitive inhibitor, with a Ki value of 32 µM. Molecular docking simulations demonstrated key interactions between compound 7j and the active site of α-glucosidase, while molecular dynamics simulations confirmed the stability of the enzyme-ligand complex, reflected in low RMSD and RMSF values.

Acarbose

Piperazine

Quinoline

IC50

Docking (animal)

Lead compound

10.1038/s41598-024-83917-z

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Assembly of Indole Cores through a Palladium-Catalyzed Metathesis of Ar–X σ-Bonds

Organic Letters (2020)

Farnaz Jafarpour Mehran Ghasemi Hamed Navid Niloofar Safaie Saideh Rajai‐Daryasarei

We describe the development of a new method for construction of highly substituted indole scaffolds through the strategic utilizing of the metathesis of Ar-X σ-bonds based on the dynamic nature of palladium-based oxidative addition/reductive elimination. A suitable and simple catalytic system has provided an appropriate platform for a productive ligand exchange and consecutive carbopalladation/C–H activation/amination of phosphine ligands with alkynes and aromatic/aliphatic amines for construction of structurally diverse indoles.

Salt metathesis reaction

Reductive elimination

Oxidative addition

10.1021/acs.orglett.0c03611

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Syn-versus anti-carbopalladation of alkynes with organoborons: access to indoles symmetrically and unsymmetrically substituted on their 2,3-positions

Chemical Communications (2023)

Mehran Ghasemi Banafshe Rahimi Maryam Dehghan Mohammad Hossein Bernoosha Farnaz Jafarpour

A palladium (II)-catalyzed borono-ortho-CH activation/amination cascade for the construction of two C-N bonds and one C-C bond in a single synthetic sequence is reported. This method proceeds through a formal syn-carbopalladation of alkynes with organoboron compounds, forming alkenyl palladium species, which are trapped by simple amines to provide highly substituted indoles. Remarkably, with an electron-rich arylboronic acid, the reaction proceeds through an unexpected anti-carbopalladation terminated by ortho-CH activation of diarylalkyne/amination reaction to provide an unsymmetrically substituted 2,3-diaryl indole instead. In the follow-up chemistry, we demonstrate that urea participates in this cascade to offer a variety of free NH-indoles.

Cascade reaction

Sequence (biology)

10.1039/d3cc01753b

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Transition Metal‐Catalyzed Dual C−H Activation/Annulation Reactions Involving Internal Alkynes

The Chemical Record (2024)

Fatemeh Doraghi Mohammad Sadegh Karimtabar Mehran Ghasemi Bagher Larijani Mohammad Mahdavi

Recently, transition metal-catalyzed ortho-C-H bond activation/annulations involving two internal alkyne molecules have been extensively used to synthesize highly substituted polycyclic aromatic scaffolds. Such reactions have emerged as a powerful atom and step-economical strategy for the assembly of multifunctional bioactive molecules. In this context, we focused on the recent achievements of dual C-H bond activation/annulations, as well as functionalization reactions involving diaryl/alkyl alkynes.

Annulation

Alkyne

Dual role

10.1002/tcr.202400069

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Combining Trifunctionalization of Alkynoic Acids, Arene ortho C–H Functionalization and Amination: An Approach to Unsymmetrical 2,3-Diaryl Substituted Indoles

Organic Letters (2024)

Narges Mohammadi Farid Mohaghegh Mehran Ghasemi Farnaz Jafarpour

Here we report a simultaneous construction of two C-C and two C-N bonds in a unified procedure that incorporates alkynoic acid trifunctionalization, ortho C-H functionalization, and amination cascade. In an ordered process, the regioselective alkyne insertion reaction is favored over the decarboxylation process. The presence of the carboxyl group in alkynoic acid ensures the high regioselectivity in the carbopalladation process, paving the way for a novel method to synthesize unsymmetrically 2,3-diaryl substituted indole scaffolds with excellent regioselectivity. The protocol is demonstrated to be suitable for gram-scale synthesis.

Surface Modification

10.1021/acs.orglett.4c03446

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Base/Solvent Controlled Divergent Synthesis of Norbornane-Fused Dihydrophenanthrenes and Triphenylenes via Palladium Catalyst

Organic Letters (2023)

Maryam Dehghan Mehran Ghasemi Farnaz Jafarpour Alireza Abbasi

A base/solvent controlled divergent synthesis for the construction of polycyclic hydrocarbons has been developed. In this process, norbornene through a reagent role leads to the synthesis of norbornane-fused dihydrophenanthrenes, which are essential due to their biological activities. Amazingly, by switching solvent and base, the role of norbornene becomes limited to a mediator/catalyst; therefore, it is removed from the final scaffold, and triphenylenes are regioselectively synthesized. Additionally, by removing norbornene from the reaction conditions, a different path leading to synthesis of unsymmetrically substituted triphenylenes with exceptional regioselectivity is established. This reaction includes a rare domino decarboxylation/C-H activation/annulation in a chemo- and regioselective manner.

Norbornane

Base (topology)

10.1021/acs.orglett.3c02577

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CCDC 2241510: Experimental Crystal Structure Determination

The Cambridge Structural Database (2023)

Mehran Ghasemi Banafshe Rahimi Maryam Dehghan Mohammad Hossein Bernoosha Farnaz Jafarpour

10.5517/ccdc.csd.cc2f7gsy

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CCDC 2214873: Experimental Crystal Structure Determination