Synthesis of compounds related to the anti-migraine drug eletriptan hydrobromide

Madasu, Suri Babu; Vekariya, Nagaji Ambabhai; Kiran, M N V D Hari; Gupta, Badarinadh; Islam, Aminul; Douglas, Paul S; Babu, K. Raghu

doi:10.3762/bjoc.8.162

Cited by 38 publications

(17 citation statements)

References 8 publications

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“…Nucleophilic attack onto vinyl sulfones by cysteine or serine residues can block the catalytic sites in enzymes . Furthermore, the vinyl sulfone can be converted to an alkyl sulfone after reduction, as exemplified in the preparation of the antimigraine drug eletriptan …”

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confidence: 99%

Visible-Light-Mediated Photoredox-Catalyzed Regio- and Stereoselective Chlorosulfonylation of Alkynes

et al. 2018

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Herein, a one-step chlorosulfonylation of alkynes via a photocatalytic redox process is described. A variety of commercially available sulfonyl chlorides can be applied for the generation of sulfonyl radical species under visible-light irradiation. Regio-and stereoselective addition of the sulfonyl radical and chloride leads to the efficient formation of (E)-selective β-chlorovinyl sulfones from a broad range of terminal and internal alkynes. The reported method represents an operationally simple and mild way to furnish vinyl sulfones.

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confidence: 99%

Visible-Light-Mediated Photoredox-Catalyzed Regio- and Stereoselective Chlorosulfonylation of Alkynes

et al. 2018

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“…Eletriptan Hydrobromide (EH), a second generation triptan, is a well-tolerated drug in migraine treatment [9]. It acts through the reduction of blood vessel swelling, associated with the head pain of a migraine attack, surrounding the brain.…”

Section: Introductionmentioning

confidence: 99%

Assessment of Nasal-Brain-Targeting Efficiency of New Developed Mucoadhesive Emulsomes Encapsulating an Anti-Migraine Drug for Effective Treatment of One of the Major Psychiatric Disorders Symptoms

et al. 2022

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Migraine is one of the major symptoms of many psychiatric and mental disorders like depression and anxiety. Eletriptan Hydrobromide (EH) is a well-tolerated drug in migraine treatment, but suffers from low oral bioavailability and low brain targeting after oral delivery. New nasal mucoadhesive EH-emulsomes development could be a new means to direct the drug from the nose-to-brain to achieve rapid onset of action and high drug concentration in the brain for acute migraine treatment. Eletriptan mucoadhesive emulsomes formulations were prepared using thin-film hydration method and 23 full factorial design was adopted to study different formulation factors’ effect on the emulsomes characters. The emulsomes were characterized for entrapment efficiency (EE%), zeta potential (ZP), particle size (PS), morphology, and ex-vivo permeation through the nasal mucosa. The selected formula was evaluated in mice for its in-vivo bio-distribution in comparison with EH intranasal and intravenous solutions. Drug targeting efficacy (DTE%) and nose-to-brain direct transport percentage (DTP%) were calculated. The optimization formulation showed a nanoparticle size of 177.01 nm, EE 79.44%, and ZP = 32.12 ± 3.28 mV. In addition, in-vitro permeability studies revealed enhanced drug permeability with suitable mean residence time up to 120 ± 13 min. EH-emulsomes were stable under different storage conditions for three months. In vivo examination and pharmacokinetic drug targeting parameters revealed EH transport to the CNS after EH nanoparticle nasal administration. Histopathology study showed no ciliotoxic effect on the nasal mucosa. From the results, it can be confirmed that the emulsomes formulation of EH proved safe direct nose-to-brain transport of EH after nasal administration of EH emulsomes.

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“…Transition metal-catalyzed cross-coupling reactions have emerged as one of the most powerful tools for the creative construction of both carbon–carbon and carbon–heteroatom bonds, especially in the multistep synthesis of biologically active compounds. − From the series of typically applied d 10 metals, Pd-catalyzed transformations have received great interest, due to their excellent chemoselectivity, functional group tolerance, and mild operation conditions, which are of great importance in the synthesis of pharmaceuticals and agrochemicals. − Among these reactions, the Heck cross-coupling between an aryl halide and an sp 2 carbon atom represents a facile protocol to access fine chemicals including complex structures of active pharmaceutical ingredients, for example, montelukast (Merck, antiasthma agent), rilpivirine (Johnson & Johnson, anti-AIDS), eletriptan (Pfizer, antimigraine), and naproxen (Albemarle, anti-inflammatory) (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Homogeneous Pd-Catalyzed Heck Coupling in γ-Valerolactone as a Green Reaction Medium: A Catalytic, Kinetic, and Computational Study

Fodor

Kégl

Tukacs

et al. 2020

ACS Sustainable Chem. Eng.

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γ-Valerolactone (GVL) was proposed as an environmentally benign reaction medium for phosphine-free Pd-catalyzed homogeneous Heck coupling reaction of iodobenzene and styrene derivatives. Detailed catalytic, kinetic, and computational studies were performed for this industrially important transformation in GVL, which shows remarkable tolerance for the moisture content of the reaction mixture and gives good efficiency for Pd(II) catalyst precursors such as PdCl 2 and Pd(OAc) 2 . Excellent functional group tolerance for both iodoaromatic substances and styrene derivatives was shown, and the reaction efficiency was correlated by the Hammet-constant of corresponding substrates. A simplified kinetic model was subsequently found to model the transformation, which can be represented by an excellent fitting of the calculated concentration of corresponding species to the experimentally determined ones. ΔH app ⧧ = +103.0 kJ•mol −1 for the apparent overall activation enthalpy of the reaction in GVL, and ΔH app ⧧ = +103.7 kJ•mol −1 in the case of DMF have been obtained. ΔS app ⧧ = +139.7 J• mol −1 •K −1 was calculated for the apparent overall activation entropy of the reaction in the presence of GVL, and ΔS app ⧧ = +138.1 J• mol −1 •K −1 in the presence of DMF, very similar values suggesting that no medium effect on the mechanism can be proposed. The computational study confirmed the experimentally observed trends regarding the effect of electron-donating and -withdrawing substituents of iodobenzene and styrene as follows: the electron-donating substituents accelerate the reaction rate for iodobenzene but decrease the reactivity for styrene derivatives.

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Synthesis of compounds related to the anti-migraine drug eletriptan hydrobromide

Cited by 38 publications

References 8 publications

Visible-Light-Mediated Photoredox-Catalyzed Regio- and Stereoselective Chlorosulfonylation of Alkynes

Visible-Light-Mediated Photoredox-Catalyzed Regio- and Stereoselective Chlorosulfonylation of Alkynes

Assessment of Nasal-Brain-Targeting Efficiency of New Developed Mucoadhesive Emulsomes Encapsulating an Anti-Migraine Drug for Effective Treatment of One of the Major Psychiatric Disorders Symptoms

Homogeneous Pd-Catalyzed Heck Coupling in γ-Valerolactone as a Green Reaction Medium: A Catalytic, Kinetic, and Computational Study

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