4.5 Article

One-pot synthesis of 1,2,3-triazole linked dihydropyrimidinones via Huisgen 1,3-dipolar/Biginelli cycloaddition

Journal

MOLECULAR DIVERSITY
Volume 15, Issue 4, Pages 833-837

Publisher

SPRINGER
DOI: 10.1007/s11030-011-9313-6

Keywords

Click chemistry; 1,2,3-Triazole; Multicomponent reaction; One-pot reaction; Dihydropyrimidinone; Biginelli

Funding

  1. Research Council of Shahid Beheshti University

Ask authors/readers for more resources

The combination of the Biginelli reaction with click chemistry has been used for the one-pot synthesis of 1,2,3-triazole linked dihydropyrimidinones from azides, aromatic aldehydes containing a propargyl ether group, urea, and 1,3-dicarbonyl compounds using Cu(OAc)(2)/sodium ascorbate as catalyst in acetic acid under mild reaction conditions.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.5
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

Article Biochemistry & Molecular Biology

Molecular networking based dereplication of AChE inhibitory compounds from the medicinal plantVincetoxicum funebre(Boiss. & Kotschy)

Mahdi Abbas-Mohammadi, Mahdi Moridi Farimani, Peyman Salehi, Samad Nejad Ebrahimi, Ali Sonboli, Celine Kelso, Danielle Skropeta

Summary: In this study, a molecular networking approach was used to analyze the chemical profile of a medicinal plant extract with AChE activity. A total of 44 compounds were identified, with glycosylated flavonoid querciturone showing the highest affinity and several compounds showing stronger activity against AChE than the clinically used drug donepezil.

JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS (2022)

Article Chemistry, Applied

Chemical composition and bioactivities of essential oils from different plant parts of Ferula pseudalliacea Rech.f. as an endemic plant from Iran

Dara Dastan, Baram Ahmed Hamah-Ameen, Peyman Salehi, Hiva Ghaderi, Mansour Miran

Summary: The essential oils from leaves, flowers, immature and mature fruits of Ferula pseudalliacea, a wild plant in Iran, demonstrated antibacterial and antioxidant activities. They showed inhibition against several bacteria and had potential applications in the food and medicine industry.

NATURAL PRODUCT RESEARCH (2022)

Article Chemistry, Physical

Antimicrobial multi-component lipid-based nanoemulsion of Eucalyptus globulus and Mentha piperita as natural preservative

Faezeh Fathi, Samad N. Ebrahimi, Peyman Salehi, Atefeh Safari, Zeinab Shahsavari, Javad Hadian, Luis Carlos Matos, Rita C. Alves, Maria Beatriz Prior Pinto Oliveira

Summary: This study formulated a multi-component nanoemulsion with significant antibacterial activity, which could potentially be used as a natural preservative in the food, agriculture, and cosmetic industries.

JOURNAL OF DISPERSION SCIENCE AND TECHNOLOGY (2023)

Article Chemistry, Multidisciplinary

Tungstate supported on magnetic ionic liquid-modified graphene oxide as an efficient and recyclable catalyst for the selective oxidation of sulfides

Minoo Dabiri, Hassan Esmaielie Tavil, Noushin Farajinia Lehi, Siyavash Kazemi Movahed, Aram Mnachekanian Salmasi, Sepideh Souri

Summary: An effective and recyclable catalyst based on tungstate ion immobilization on magnetic ionic liquid modified graphene oxide (WO4@Fe3O4/GO-IL) was synthesized, characterized, and demonstrated to have catalytic activity in the selective oxidation of sulfides. The catalyst was easily recovered and successfully reused using an external magnet for multiple reaction cycles without significant reduction in activity or selectivity.

JOURNAL OF PHYSICS AND CHEMISTRY OF SOLIDS (2022)

Article Chemistry, Multidisciplinary

New organocatalysts derived from tetrahydropapaverine for asymmetric aldol reaction

Sedigheh Sadat Naeimi, Peyman Salehi, Morteza Bararjanian

Summary: The synthesis of prolinamide derivatives of (R)-tetrahydropapaverine and their application as organocatalysts in asymmetric Aldol reaction were reported. Catalyst 2 showed the best catalytic activity in the reaction between cyclohexanone and 4-nitrobenzaldehyde, achieving up to 90% enantiomeric excess. Unlike the anti-stereoselectivity observed in the presence of L-proline alone, the hybridization with (R)-tetrahydropapaverine resulted in the formation of syn products as the major compounds.

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY (2022)

Article Chemistry, Medicinal

Novel norsufentanil analogues containing triazole ring; synthesis, radioligand binding assay, and pharmacological evaluation

Majid Nami, Peyman Salehi, Morteza Bararjanian, Nazanin Seighal Delshad, Bahareh Heidari, Mona Khoramjouy, Soraya Shahhosseini, Mehrdad Faizi

Summary: A series of novel triazole compounds containing derivatives of norsufentanil were synthesized and evaluated for their affinity and anti-nociceptive activity. Compound 3h exhibited the highest affinity and potency among all the selected compounds.

MEDICINAL CHEMISTRY RESEARCH (2022)

Article Chemistry, Physical

Directed aromatic C-H functionalization of N-arylcarbamates and quinazolinones catalyzed by palladium nanoparticles supported on nitrogen-doped graphene

Neda Salarinejad, Minoo Dabiri, Siyavash Kazemi Movahed

Summary: Pd/N-RGO nanohybrid was used as a catalyst for efficient C-H acyloxylation and halogenation reactions. The introduction of nitrogen into the graphene lattice enhanced the catalytic activities of palladium, and the catalyst showed no significant palladium leaching, allowing for its successful recovery and reuse without any noticeable decrease in catalytic activity.

COLLOID AND INTERFACE SCIENCE COMMUNICATIONS (2022)

Article Chemistry, Medicinal

A new chiral stationary phase based on noscapine: Synthesis, enantioseparation, and docking study

Zohreh Mousavimanesh, Mostafa Shahnani, Amirmohammad Faraji-Shovey, Morteza Bararjanian, Ahmad Shahir Sadr, Alireza Ghassempour, Peyman Salehi

Summary: Noscapine, a compound derived from opium poppy, shows potential for enantioselective separation of various compounds due to its distinctive chiral structure and chemistry. Researchers have synthesized a new noscapine derivative chiral stationary phase (ND-CSP) with better enantioresolution performance, stability, reproducibility, and loading capacity. This stationary phase provides a considerable surface coverage and has been successfully used for the enantioseparation of different compounds.

CHIRALITY (2022)

Article Chemistry, Physical

Synthesis, characterization, and micelle formation of novel PEGylated derivatives of noscapine with anti-cancer activity

Niloofar Savadkouhi, Peyman Salehi, Houri Sepehri, Ladan Delphi, Hasan Rafati

Summary: In this study, PEGylated derivatives of noscapine with enhanced solubility were synthesized and their anticancer activities were evaluated. The results showed that increasing the PEG chain length improved the water solubility and cytotoxicity of the derivatives. These new PEGylated compounds may have the potential to be developed as novel anticancer drugs.

JOURNAL OF MOLECULAR LIQUIDS (2022)

Article Chemistry, Medicinal

Semi-synthesis of novel thebaine derivatives with low cytotoxicity and their antibacterial and antihemolytic properties

Zahra Hasanpour, Peyman Salehi, Atousa Aliahmadi, Mahdieh Hoseinpour, Hossein Behboodi, Dan Staerk, Morteza Bararjanian

Summary: In this study, new 1,2,3-triazole-tethered analogs of N-northebaine were synthesized and their anti-bacterial properties were evaluated. Compounds 5b, 5j, and 5m showed strong activities against Staphylococcus aureus, surpassing the parent compound. These compounds and thebaine were also found to have potential as wound healing agents based on their cytotoxicity, proliferation, and anti-hemolytic activities. Compound 5j showed no inhibition of cell line growth and exhibited no hemolysis activity at different doses.

MEDICINAL CHEMISTRY RESEARCH (2023)

Article Plant Sciences

Semi-synthesis of novel 1,4-disubstituted-1,2,3-triazole derivatives of penicillin G and their antibacterial activity

Kaveh Rasoolijokari, Peyman Salehi, Atousa Aliahmadi, Bahareh Heidari, Morteza Bararjanian

Summary: A series of 12 novel 1,2,3-triazole penicillin G derivatives were synthesized and evaluated for their antimicrobial activity. Compounds 5a and 5b showed the highest potency in inhibiting the growth of Staphylococcus aureus.

PHYTOCHEMISTRY LETTERS (2023)

Review Pharmacology & Pharmacy

Synthesis and Modification of Morphine and Codeine, Leading to Diverse Libraries with Improved Pain Relief Properties

Mona Kamelan Zargar Zarin, Wim Dehaen, Peyman Salehi, Amir Ata Bahmani Asl

Summary: Morphine and codeine, commonly used opioids, have significant side effects, necessitating the development of derivatives. Biological studies on semi-synthetic derivatives of both morphine and codeine have shown their significance in the development of potent opioids.

PHARMACEUTICS (2023)

Article Chemistry, Multidisciplinary

Synthesis of novel menthol derivatives containing 1,2,3-triazole group and their in vitro antibacterial activities

Mohadeseh Karbasi, Peyman Salehi, Atousa Aliahmadi, Morteza Bararjanian, Farzaneh Zandi

Summary: New N-substituted alpha-aminonitrile derivatives were synthesized from menthol via consecutive succinic ester formation, propargylation, 1,3-dipolar Huisgen cycloaddition, and Strecker reaction. The structures of the synthesized compounds were confirmed using spectroscopic techniques. These novel compounds showed strong inhibitory effects against Staphylococcus aureus and Escherichia coli, with the best inhibitory effects exhibited by derivatives 6a2, 6b1, 6b4, and 6b5.

JOURNAL OF THE SERBIAN CHEMICAL SOCIETY (2023)

Article Chemistry, Multidisciplinary

Synthesis of novel menthol derivatives containing 1,2,3-triazole group and their in vitro antibacterial activities

Mohadeseh Karbasi, Peyman Salehi, Atousa Aliahmadi, Morteza Bararjanian, Farzaneh Zandi

Summary: New N-substituted alpha-aminonitrile derivatives from menthol were synthesized using consecutive chemical reactions, and their structures were confirmed by spectroscopic techniques. The synthesized compounds showed strong inhibitory effects against Staphylococcus aureus.

JOURNAL OF THE SERBIAN CHEMICAL SOCIETY (2023)

Article Chemistry, Multidisciplinary

Design, Synthesis, and Functional Studies on Noscapine and Cotarnine Amino Acid Derivatives as Antitumor Agents

Zahra Davarzani, Peyman Salehi, S. Mohsen Asghari, Morteza Bararjanian, Ali Hamrahi Mohsen, Helia Dehghan Harati

Summary: In this study, 20 amino acid conjugated derivatives of noscapine and cotarnine were synthesized and evaluated for their anticancer activity. The results showed that noscapine-tryptophan exhibited higher antitumor activity and inhibited tumor growth more effectively in a mouse model of mammary carcinoma, without adverse effects.

ACS OMEGA (2023)

No Data Available