Microwave-Assisted Synthesis of 2,5-Piperazinediones under Solvent-Free Conditions

López-Cobeñas, Alberto; Cledera, Pilar; Sánchez, Juan Domingo; López‐Alvarado, Pilar; Ramos, M. Teresa; Avendaño, Carmen; Menéndez, J. Carlos

doi:10.1055/s-2005-918473

Cited by 5 publications

(1 citation statement)

References 18 publications

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“…To investigate structure-activity relationship of 1 on protective activity against ER stress-dependent cell death, analogues (3-9) of 1 were synthesized as described previously except for a new compound (7). [16][17][18][19][20][21] Compounds 4 and 6-8 did not show any activity. Compounds 3, 5 and 9 having a formamide group in each molecule exhibited the tendency of protective activity in a dose-dependent manner as 1, although the data showed no significant differences (data not shown).…”

Section: Resultsmentioning

confidence: 99%

Leccinine A, an endoplasmic reticulum stress-suppressive compound from the edible mushroom Leccinum extremiorientale

Choi¹,

Ozawa²,

Yamakawa³

et al. 2011

Tetrahedron

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Section: Resultsmentioning

confidence: 99%

Leccinine A, an endoplasmic reticulum stress-suppressive compound from the edible mushroom Leccinum extremiorientale

Choi¹,

Ozawa²,

Yamakawa³

et al. 2011

Tetrahedron

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Mechanochemical Synthesis of Primary Amides

et al. 2021

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Ball milling of aromatic, heteroaromatic, vinylic, and aliphatic esters with ethanol and calcium nitride afforded the corresponding primary amides in a transformation that was compatible with a variety of functional groups and maintained the integrity of a stereocenter α to carbonyl. This methodology was applied to α-amino esters and N -BOC dipeptide esters and also to the synthesis of rufinamide, an antiepileptic drug.

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Catch and Release Photosensitizers: Combining Dual-Action Ruthenium Complexes with Protease Inactivation for Targeting Invasive Cancers

et al. 2018

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Dual action agents containing a cysteine protease inhibitor and Rubased photosensitizer for photodynamic therapy (PDT) were designed, synthesized, and validated in 2D culture and 3D functional imaging assays of triple-negative human breast cancer (TNBC). These combination agents deliver and release Rubased PDT agents to tumor cells and cause cancer cell death upon irradiation with visible light, while at the same time inactivating cathespin B (CTSB), a cysteine protease strongly associated with invasive and metastatic behavior. In total five Rubased complexes were synthesized with the formula [Ru(bpy)2(l)](O2CCF3)2 (3), where bpy = 2,2′-bipyridine and 1 = a bipyridine-based epoxysuccinyl inhibitor; [Ru(tpy)(NN)(2)](PF6)2, where tpy = terpiridine, 2 = a pyridine-based epoxysuccinyl inhibitor and NN = 2,2′-bipyridine (4); 6,6′-dimethyl-2,2′-bipyridine (5); benzo[i]dipyrido[3,2-a:2′,3′-c]phenazine (6); and 3,6-dimethylbenzo[i]-dipyrido[3,2-a:2′,3′ -c]phenazine (7). Compound 3 contains a [Ru(bpy)3]2+ fluorophore and was designed to track the subcellular localization of the conjugates, whereas compounds 4–7 were designed to undergo either photoactivated ligand dissociation and/or singlet oxygen generation. Photochemical studies confirmed that complexes 5 and 7 undergo photoactivated ligand dissociation, whereas 6 and 7 generate singlet oxygen. Inhibitors 1–7 all potently and irreversibly inhibit CTSB. Compounds 4–7 were evaluated against MDA-MB-231 TNBC and MCF-10A breast epithelial cells in 2D and 3D culture for effects on proteolysis and cell viability under dark and light conditions. Collectively, these data reveal that 4–7 potently inhibit dye-quenched (DQ) collagen degradation, whereas only compound 7 causes efficient cell death under light conditions, consistent with its ability to release a Ru(II)-based photosensitizer and to also generate 1O2.

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Microwave-Assisted Synthesis of 2,5-Piperazinediones under Solvent-Free Conditions

Abstract: A general, efficient and environmentally friendly procedure for the synthesis of 2,5-piperazinediones is described, involving the microwave irradiation of N-Boc dipeptide esters.

Cited by 5 publications

References 18 publications

Leccinine A, an endoplasmic reticulum stress-suppressive compound from the edible mushroom Leccinum extremiorientale

Leccinine A, an endoplasmic reticulum stress-suppressive compound from the edible mushroom Leccinum extremiorientale

Mechanochemical Synthesis of Primary Amides

Catch and Release Photosensitizers: Combining Dual-Action Ruthenium Complexes with Protease Inactivation for Targeting Invasive Cancers

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