Parviz Rashidi Ranjbar

Reaction of Isatoic Anhydride, Amine, and N,N′-Dialkyl Carbodiimides Under Solvent-Free Conditions: New and Efficient Synthesis of 3-Alkyl-2-(alkylamino)quinazolin-4(3H)-ones

Abstract Heating a mixture of isatoic anhydride, amines, and N,N′-dialkyl carbodiimides under solvent-free conditions provided novel 3-alkyl-2-(alkylamino)quinazolin-4(3H)-one derivatives for the first time. The products were obtained in moderate to good yields without formation of any by-products. Supplemental materials are available for this article. Go to the publishers online edition of Synthetic Communications® to view the free supplemental file. GRAPHICAL ABSTRACT

Copper supported β-cyclodextrin grafted magnetic nanoparticles as an efficient recyclable catalyst for one-pot synthesis of 1-benzyl-1H-1,2,3-triazoldibenzodiazepinone derivatives via click reaction

An efficient and recoverable copper catalyst was prepared by the immobilization of Cu into β-cyclodextrin covalently attached to magnetic nanoparticles (denoted as [Cu@β-CD@SPIONs]). A novel and one-pot synthetic approach was introduced for the synthesis of novel 1-benzyl-1H-1,2,3-triazoldibenzodiazepinone derivatives through a click reaction using [Cu@β-CD@SPIONs] as a green catalyst. The magnetic recoverable catalyst was characterized using TEM, VSM, TGA, and FT-IR techniques. This nanocatalyst appeared efficient and robust in a multicomponent reaction for the preparation of benzodiazepinones followed by a click reaction for the synthesis of 1,2,3-triazoles in an ethanol/water mixture as solvent at room temperature under mild reaction conditions and with a facile work-up process. Interesting features including water-tolerance, robustness, efficiency, mild reaction conditions, utilization of green solvents, and simple catalyst recovery make [Cu@β-CD@SPIONs] favourable from economic and environmental points of view.

Experimental and computational evidence for KOt-Bu-promoted synthesis of oxopyrazino[1,2-a]indoles

A novel series of oxopyrazino[1,2-a]indole derivatives were prepared via a two-step synthetic procedure including a Ugi-four-component reaction followed by the transition metal-free intramolecular hydroamination of Ugi adducts in the presence of KOt-Bu in DMF at room temperature. Density functional theory (DFT) calculations were also performed to elucidate the mechanistic aspects of the reaction.

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

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 (IC50 = 750.0 ± 1.5 µM). Among these compounds, compounds 6e and 6d displayed the most potent α-glucosidase inhibitory activity (IC50 = 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 (Ki = 11 µM) while compound 6d was a non-competitive inhibitor (Ki = 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.

An efficient four-component reaction for the synthesis of chromeno[4,3- b ]quinolone derivatives

Chromenoquinolines have been prepared via an efficient one-pot, multi-component reaction of 4-hydroxy coumarin, aqueous ammonia, dimedone and different aldehydes.

1‐[(2‐Hydroxy‐1‐naphthyl)(phenyl)methyl]‐2‐naphthol ethanol solvate

In the title compound, C27H20O2 center dot C2H6O, intra- and intermolecular O-H center dot center dot center dot O hydrogen bonds link the molecules and seem to be effective in the stabilization of the crystal structure. All the H atoms in the hydroxyl groups are disordered.

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

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 IC50 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.

Pyrano[3,2-c]quinoline derivatives as new class of α-glucosidase inhibitors to treat type 2 diabetes: synthesis, in vitro biological evaluation and kinetic study

BACKGROUND Pyrano[3,2-c]quinoline derivatives 6a-n were synthesized via simple two-step reactions and evaluated for their in vitro α-glucosidase inhibitory activity. METHODS Pyrano[3,2-c]quinoline derivatives 6a-n derivatives were prepared from a two-step reaction: cycloaddition reaction between 1-naphthyl amine 1 and malonic acid 2 to obtain benzo[h]quinoline-2(1H)-one 3 and reaction of 3 with aryl aldehydes 4 and Meldrums acid 5. The anti- α-glucosidase activity and kinetic study of the synthesized compounds were evaluated using α-glucosidase from Saccharomyces cerevisiae and p-nitrophenyl-a-D-glucopyranoside as substrate. The α-glucosidase inhibitory activity of acarbose was evaluated as positive control. RESULTS All of the synthesized compounds, except compounds 6i and 6n, showed more inhibitory activity than the standard drug acarbose and were also found to be non-cytotoxic. Among the synthesized compounds, 1-(2-bromophenyl)-1H-benzo[h]pyrano[3,2-c]quinoline-3,12(2H,11H)-dione 6e displayed the highest α-glucosidase inhibitory activity (IC50 = 63.7 ± 0.5 µM). Kinetic study of enzyme inhibition indicated that the most potent compound, 6e, is a non-competitive inhibitor of α-glucosidase with a Ki value of 72 µM. Additionally, based on the Lipinski rule of 5, the synthesized compounds were found to be potential orally active drugs. CONCLUSION Our results suggest that the synthesized compounds are promising candidates for treating type 2 diabetes.

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

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.

An efficient approach to the synthesis of coumarin-fused dihydropyridinones

Abstract 3,4-Dihydro-2H-chromeno[4,3-b]pyridine-2,5(1H)-dione derivatives were efficiently prepared by the reaction of 4-hydroxycoumarin, ammonia, aromatic aldehyde and Meldrum’s acid in refluxing 1-propanol.