52600-99-4Relevant academic research and scientific papers
Assembling the prenylneoflavone system through a Pechmann condensation/Mitsunobu reaction/Claisen rearrangement/olefin cross-metathesis sequence
Bennetau-Pelissero, C.,Bistodeau, J.,Khilya, Vladimir P.,Lozinski, Oleg A.,Shinkaruk, S.
, p. 605 - 610 (2020)
Abstract: The multistep synthesis of a prenylneoflavone through a sequence of the Mitsunobu reaction/Claisen rearrangement/olefin cross-metathesis reaction has been accomplished in 5% yield over six steps starting from commercially available 3-methoxyacet
KV1.3 INHIBITORS AND THEIR MEDICAL APPLICATION
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Page/Page column 34; 48-49, (2016/10/04)
The present invention relates to a compound of the general formula (III) or a salt, solvate or prodrug thereof, as well as medical uses involving them, wherein (III) A1 is selected from the group consisting of N and C-R8; A2 is selected from the group consisting of N and C-R3; A3 is selected from the group consisting of N and C-R9; A4 and A5 and A6 are independently selected from the group consisting of N and C-R1; R1 is selected from the group consisting of hydrogen, (C1-C3)alkyl, halogen, (C1-C3)alkoxy and (C1-C3)haloalkyl; R2 is selected from the group consisting of hydrogen, halogen and (C1-C3)alkyl; R3 is selected from the group consisting of hydrogen, (C1-C3)alkyl, NR4R5, (C1-C3)alkyl- NR4R5 and cyano; wherein R4 and R5 are independently selected from the group consisting of hydrogen, (C3- C5)cycloalkyl, (C3-C5)heterocycloalkyl, (C1-C3)alkyl, or R4 and R5 together with the nitrogen atom to which they are attached form a 5- to 7-membered heterocyclic ring optionally comprising in addition to the aforementioned nitrogen atom a further heteroatom group selected from the group consisting of O and NR6, wherein R6 is selected from the group consisting of hydrogen, methyl, acetyl and formyl; Y is selected from the group consisting of O and S; R7 is selected from the group consisting of hydrogen, and (C1-C3)alkyl; R8 is selected from the group consisting of (C1-C4)alkyl, (C3-C5)cycloalkyl, and (C3- C5)heterocycloalkyl; R9 is selected from the group consisting of hydrogen, (C1-C3)alkyl, (C1-C3)alkoxy, and methods for producing such compounds.
Synthesis and biological investigation of coumarin piperazine (piperidine) derivatives as potential multireceptor atypical antipsychotics
Chen, Yin,Wang, Songlin,Xu, Xiangqing,Liu, Xin,Yu, Minquan,Zhao, Song,Liu, Shicheng,Qiu, Yinli,Zhang, Tan,Liu, Bi-Feng,Zhang, Guisen
, p. 4671 - 4690 (2013/07/19)
The discovery and synthesis of potential and novel antipsychotic coumarin derivatives, associated with potent dopamine D2, D3, and serotonin 5-HT1A and 5-HT2A receptor properties, are the focus of the present article. The most-promising derivative was 7-(4-(4-(6-fluorobenzo[d]isoxazol-3-yl)-piperidin-1-yl)butoxy) -4-methyl-8-chloro-2H-chromen-2-one (17m). This derivative possesses unique pharmacological features, including high affinity for dopamine D2 and D3 and serotonin 5-HT1A and 5-HT2A receptors. Moreover, it possesses low affinity for 5-HT2C and H1 receptors (to reduce the risk of obesity associated with chronic treatment) and hERG channels (to reduce the incidence of torsade des pointes). In animal models, compound 17m inhibited apomorphine-induced climbing behavior, MK-801-induced hyperactivity, and the conditioned avoidance response without observable catalepsy at the highest dose tested. Further, fewer preclinical adverse events were noted with 17m compared with risperidone in assays that measured prolactin secretion and weight gain. Acceptable pharmacokinetic properties were also noted with 17m. Taken together, 17m may constitute a novel class of drugs for the treatment of schizophrenia.
