Benzimidazolone-based serotonin 5-HT1A or 5-HT7R ligands: Synthesis and biological evaluation
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2020, NeuropharmacologyCitation Excerpt :3) Does [18F]2FP3 bind to an off-target that is more abundant in cats than in pigs and more abundant in pigs than in NHPs? In 2014, an attempt to optimize the binding characteristics of [18F]2FP3 was carried out and the linker between the pyrrolidine and the piperidine rings was elongated (Badarau et al., 2009). The compound 2FP3, showed higher affinity for the 5-HT7R, increased selectivity over 5-HT1AR and a lipophilicity of clogD7.4 = 1.58 (Table 3) (Colomb et al., 2014).
Benzyne-Induced Ring Opening Reactions of DABCO: Synthesis of 1,4-Disubstituted Piperazines and Piperidines
2020, Advanced Synthesis and CatalysisTowards new 5-HT<inf>7</inf> antagonists among arylsulfonamide derivatives of (aryloxy)ethyl-alkyl amines: Multiobjective based design, synthesis, and antidepressant and anxiolytic properties
2016, European Journal of Medicinal ChemistryCitation Excerpt :Initially, the quest for selective 5-HT7R ligands led to arylsulfonamide derivatives of alkylamines (e.g., SB-269970 and SB-656104) [10,11]. Soon after long-chain arylpiperazines/piperidines functionalized with different terminal fragments (e.g., tetrahydrobenzindoles, oxindoles, benzothiophenes, biphenyl, benzoimidazolones) [12–21] and their bioisosteres (i.e., tetrahydroisoquinoline) [22] have emerged as an important class of 5-HT7R agents. Further efforts resulted in the identification of JNJ-18038683 with efficacy confirmed in preclinical models, which has been recently evaluated in a clinical trial (phase II) for the treatment of major depression [23].
Synthesis and binding properties of new long-chain 4-substituted piperazine derivatives as 5-HT<inf>1A</inf> and 5-HT<inf>7</inf> receptor ligands
2015, Bioorganic and Medicinal Chemistry LettersStructure-activity relationships and molecular modeling studies of novel arylpiperazinylalkyl 2-benzoxazolones and 2-benzothiazolones as 5-HT<inf>7</inf> and 5-HT<inf>1A</inf> receptor ligands
2014, European Journal of Medicinal ChemistryCitation Excerpt :Among the first identified 5-HT7 ligands, SB-269970 (1, Fig. 1) is representative of the sulfonamide class and DR-4004 (2, Fig. 1) is representative of the tetrahydrobenzindole family [21,22]. Some other selective 5-HT7 ligands are compounds 3–6 [23–25]. Among them, 3–5 represent examples of Long-Chain Arylpiperazines (LCPAs).