Synthesis and biological evaluation of (phenylpiperazinyl-propyl)arylsulfonamides as selective 5-HT2A receptor antagonists

Yoo, Euna; Yoon, Juhee; Pae, Ae Nim; Rhim, Hyewhon; Park, Woo‐Kyu; Kong, Jae Yang; Choo, Hea-Young Park

doi:10.1016/j.bmc.2009.12.067

Cited by 9 publications

(5 citation statements)

References 17 publications

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“…To confirm the involvement of 5‐HTR2A, the effects of 5‐HTR2A antagonists and gene silencing on 5‐HT‐induced melanin pigmentation were examined. 5‐HTR2A antagonists, ketanserin and a new 5‐HTR2A antagonist (E‐HT16a), 9 dose‐dependently suppressed the 5‐HT‐induced melanin pigmentation in SK‐MEL‐2 cells (Fig. 2a,b).…”

Section: Resultsmentioning

confidence: 95%

Serotonin induces melanogenesis via serotonin receptor 2A

Lee

Park

Kim

et al. 2011

British Journal of Dermatology

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Section: Resultsmentioning

confidence: 95%

Serotonin induces melanogenesis via serotonin receptor 2A

Lee

Park

Kim

et al. 2011

British Journal of Dermatology

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“…2-[4-(3-Trifluoromethylphenyl)piperazin-1-yl]propan-1-amine and 3-[4-(3,4-dichlorophenyl)piperazin-1-yl]propan-1-amine were obtained by using a procedure described elsewhere [ 20 ]. Additionally, 3-[4-(4-fluorophenyl)piperazin-1-yl]propan-1-amine [ 43 ], 3-[4-(3-chlorophenyl)piperazin-1-yl]propan-1-amine [ 44 ], 3-[4-(2-chlorophenyl)piperazin-1-yl]propan-1-amine [ 44 ], and 3-[4-(4-chlorophenyl)piperazin-1-yl]propan-1-amine [ 44 ], as well as 3-[4-(2,3-dichlorophenyl)piperazin-1-yl]propan-1-amine [ 45 ]. Additionally, 2-morpholinoethan-1-amine and 3-morpholinopropan-1-amine were purchased from Sigma–Aldrich (Steinheim, Germany).…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Anticonvulsant and Antinociceptive Activity of New Hybrid Compounds: Derivatives of 3-(3-Methylthiophen-2-yl)-pyrrolidine-2,5-dione

Góra

Czopek

Rapacz

et al. 2020

IJMS

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The present study aimed to design and synthesize a new series of hybrid compounds with pyrrolidine-2,5-dione and thiophene rings in the structure as potential anticonvulsant and antinociceptive agents. For this purpose, we obtained a series of new compounds and evaluated their anticonvulsant activity in animal models of epilepsy (maximal electroshock (MES), psychomotor (6 Hz), and subcutaneous pentylenetetrazole (scPTZ) seizure tests). To determine the mechanism of action of the most active anticonvulsant compounds (3, 4, 6, 9), their influence on the voltage-gated sodium and calcium channels as well as GABA transporter (GAT) was assessed. The most promising compound 3-(3-methylthiophen-2-yl)-1-(3-morpholinopropyl)pyrrolidine-2,5-dione hydrochloride (4) showed higher ED50 value than those of the reference drugs: valproic acid (VPA) and ethosuximide (ETX) (62.14 mg/kg vs. 252.7 mg/kg (VPA) in the MES test, and 75.59 mg/kg vs. 130.6 mg/kg (VPA) and 221.7 mg/kg (ETX) in the 6 Hz test, respectively). Moreover, in vitro studies of compound 4 showed moderate but balanced inhibition of the neuronal voltage-sensitive sodium (site 2) and L-type calcium channels. Additionally, the antinociceptive activity of the most active compounds (3, 4, 6, 9) was also evaluated in the hot plate test and writhing tests, and their hepatotoxic properties in HepG2 cells were also investigated. To determine the possible mechanism of the analgesic effect of compounds 3, 6, and 9, the affinity for the TRPV1 receptor was investigated.

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“…The importance of phenylpiperazine derivatives has prompted many workers to synthesize these compounds by various chemical methods [15][16][17][18][19]. But, literature survey reveals that, in contrast to these vast number reports on chemical synthesis, no paper has reported on the electrochemical synthesis of phenylpiperazine derivatives.…”

Section: Introductionmentioning

confidence: 99%