Highly Efficient Synthesis of Fatty Acid Dopamides

“…Benzotriazol-1-yloxytris(dimethylamino) phosphonium hexafluorophosphate (BOP) 13) showed the same efficacy as EDCI (entry 4). However, propylphosphoric anhydride (propylphosphoric acid cyclic anhydride, PPACA) 4) gave 2 exclusively (entry 3); therefore, this condensation agent was tested for further investigation using procedures 1 and 3 (entries 10-17).…”

mentioning

confidence: 85%

“…The best condition for the selective N-oleoyldopamine (2) synthesis is shown in entry 13, i.e., dopamine·HCl 1 eq, PPACA 1 eq, Et 3 N 3 eq, in CH 2 Cl 2 solvent with procedure 3 (Table 1). Although several N-acyldopamine syntheses were previously reported, for example, the mixed anhydride method, 1,10,14,15) EDCI method, 12) BOP method, 13) and O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU) method, 7) PPACA was used by Walker's group in 2003 for the synthesis of N-acyldopamine.…”

mentioning

confidence: 99%

Efficient <i>N</i>-Acyldopamine Synthesis

Matsumoto

Ito

Uesugi

et al. 2016

CHEMICAL & PHARMACEUTICAL BULLETIN

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In addition, some N-acyldopamines including NADA and N-oleoyldopamine (ODA) act as agonists for the transient receptor potential vanilloid type V1 channel (TRPV1), while N-palmitoyldopamine (PALDA) and N-stearoyldopamine (STEARDA) are nearly inactive as TRPV1 ligands 3-5) (Chart 1). In addition to their ligand activities, recent studies suggest that N-acyldopamines possess diverse biological and pharmacological properties including anti-inflammatory and immunomodulatory activities, 6,7) hypoximimetic activities, 8) antioxidant and neuroprotective activities, 9) and anti-proliferation activity against cancer cells. 10)

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“…(Warsaw, Poland Figure 1, was prepared from dopamine hydrochloride and cis-9-octadecenoic acid in the presence of BOP reagent according to the method described previously [Czarnocki et al, 1998]. Briefly, DA was mixed with equimolar amounts of oleic acid and BOP reagent in dry tetrahydrofuran.…”

Section: Methodsmentioning

confidence: 99%

“…The natural existence of dopamides in mammalian tissues and their potential biological activity have been envisioned on theoretical grounds [Pokorski and Matysiak, 1997], but the research story of dopamides has not attracted sufficient interest until the elaboration of methods of their synthesis [Czarnocki et al, 1998;Bezuglov et al, 2001]. Among the dopamides, N-arachidonoyl-dopamine (NADA) seems the most extensively studied one, as it was the first dopamide identified in cultured mammalian neural cells and found later in multiple brain regions [Huang et al, 2002].…”

Section: Introductionmentioning

confidence: 99%

Brain uptake of radiolabeled N‐oleoyl‐dopamine in the rat

Pokorski

Matysiak

Marczak

et al. 2003

Drug Development Research

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N-acyl-dopamines are a novel class of biologically active lipids that have recently been identified in the brain and have the potential to interact with neural signaling pathways. This study seeks to determine the ability of N-oleoyl-dopamine, a synthetic amide of oleic acid and dopamine, to cross the blood brain barrier. We determined the tissue content of radioactivity in selected brain regions, in a shortrun study design, following injections of [ 3 H]N-oleoyl-dopamine (0.4 mCi) into the internal carotid artery in the rat. These results were compared with intracarotid injections of [ 3 H]dopamine and with intravenous injections of both radiolabeled compounds. The level of radioactivity was determined using liquid scintillation and was expressed as the percentage of its total dose injected per gram of tissue. We found that the 15-min brain uptake of radioactivity, with no distinct regional variations, amounted to about 6% following the intracarotid [ 3 H]N-oleoyl-dopamine, which was a significant 3-4-fold increase over that following similar administration of [ H]dopamine. Intravenous injections of [3 H]N-oleoyl-dopamine gave a much smaller yield of radioactivity in brain tissue samples which was still severalfold greater than that for intravenous [ 3 H]dopamine. Qualitative thin-layered chromatography screening showed the presence of unchanged N-oleoyl-dopamine in the brain following injections. We conclude that N-oleoyl-dopamine has an appreciable ability to cross the blood-brain barrier, which contrasts the limited transfer of dopamine alone. N-oleoyl-dopamine might exert physiological effects due to its known affinity for the central vanilloid receptors or to better satisfying the brain tissue demand for dopamine. The study suggests a potential pharmacological role for N-oleoyl-dopamine delivered exogenously in helping regulate the brain function. Drug Dev. Res. 60:217-224, 2003.

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Highly Efficient Synthesis of Fatty Acid Dopamides

Cited by 16 publications

References 4 publications

Synthesis of a novel class of fatty acids-derived isoquinolines

Synthesis of a novel class of fatty acids-derived isoquinolines

Efficient <i>N</i>-Acyldopamine Synthesis

Brain uptake of radiolabeled N‐oleoyl‐dopamine in the rat

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