Synthesis of 1-Oxo-1-(3-pyridazinyl) Derivatives - Potent Inhibitors of Fatty Acid Amide Hydrolase (FAAH): An Improved and Optimized Procedure

Rosini, Goffredo; Andreotti, Daniele G.; D'Ambrosio, Primiano; Marotta, Emanuela; Tinarelli, Alessandro; Righi, Paolo

doi:10.1055/s-2007-990774

Cited by 4 publications

(2 citation statements)

References 1 publication

(1 reference statement)

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“…1 H NMR (300 MHz, acetone-d 6 ): δ 3.70 (s, 3H), 3.10 (s, 3H), 2.39 (t, J = 7.4 Hz, 2H), 1.57 (quint, J = 7.4 Hz, 2H), 1.29 (m, 28 H), 0.88 (t, J = 7.4 Hz, 3H) ppm. 1 H NMR spectrum of 3 matched the previously reported data [36].…”

Section: Synthesis Of Laurdan Analogssupporting

confidence: 88%

Investigation of the Membrane Fluidity Regulation of Fatty Acid Intracellular Distribution by Fluorescence Lifetime Imaging of Novel Polarity Sensitive Fluorescent Derivatives

Bianchetti¹,

Azoulay-Ginsburg²,

Keshet-Levy³

et al. 2021

IJMS

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Free fatty acids are essential structural components of the cell, and their intracellular distribution and effects on membrane organelles have crucial roles in regulating the metabolism, development, and cell cycle of most cell types. Here we engineered novel fluorescent, polarity-sensitive fatty acid derivatives, with the fatty acid aliphatic chain of increasing length (from 12 to 18 carbons). As in the laurdan probe, the lipophilic acyl tail is connected to the environmentally sensitive dimethylaminonaphthalene moiety. The fluorescence lifetime imaging analysis allowed us to monitor the intracellular distribution of the free fatty acids within the cell, and to simultaneously examine how the fluidity and the microviscosity of the membrane environment influence their localization. Each of these probes can thus be used to investigate the membrane fluidity regulation of the correspondent fatty acid intracellular distribution. We observed that, in PC-12 cells, fluorescent sensitive fatty acid derivatives with increased chain length compartmentalize more preferentially in the fluid regions, characterized by a low microviscosity. Moreover, fatty acid derivatives with the longest chain compartmentalize in lipid droplets and lysosomes with characteristic lifetimes, thus making these probes a promising tool for monitoring lipophagy and related events.

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Section: Synthesis Of Laurdan Analogssupporting

confidence: 88%

Investigation of the Membrane Fluidity Regulation of Fatty Acid Intracellular Distribution by Fluorescence Lifetime Imaging of Novel Polarity Sensitive Fluorescent Derivatives

Bianchetti¹,

Azoulay-Ginsburg²,

Keshet-Levy³

et al. 2021

IJMS

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show abstract

“…Using the classic Weinreb ketone synthesis, we obtained 3 in poor yield (<5%) due to the low reactivity of the pyridazine nucleophile 1 (Scheme 2). 7 We envisioned a halo-selecting cross-coupling strategy using pyridazine dibromide 4a en route to intermediate enol ether 6a (Table 1), which would provide ketone 3 upon acid-catalyzed hydrolysis. As such, we began testing different cross-coupling approaches using bromide 4a.…”

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confidence: 99%

Direct Enol Ether Metalation–Negishi Coupling Strategy To Prepare α-Heteroaryl Enol Ethers

Peng,

Liu,

Zhang

et al. 2023

Org. Lett.

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Pyridazine

Genovino

Encyclopedia of Reagents for Organic Synthesis

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Synthesis of 1-Oxo-1-(3-pyridazinyl) Derivatives - Potent Inhibitors of Fatty Acid Amide Hydrolase (FAAH): An Improved and Optimized Procedure

Cited by 4 publications

References 1 publication

Investigation of the Membrane Fluidity Regulation of Fatty Acid Intracellular Distribution by Fluorescence Lifetime Imaging of Novel Polarity Sensitive Fluorescent Derivatives

Investigation of the Membrane Fluidity Regulation of Fatty Acid Intracellular Distribution by Fluorescence Lifetime Imaging of Novel Polarity Sensitive Fluorescent Derivatives

Direct Enol Ether Metalation–Negishi Coupling Strategy To Prepare α-Heteroaryl Enol Ethers

Pyridazine

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