114144-17-1Relevant articles and documents
Synthesis and structure-affinity relationships of novel small molecule natural product derivatives capable of discriminating between serotonin 5-HT1A, 5-HT2A, 5-HT2C receptor subtypes
Cummings, David F.,Canseco, Diana C.,Sheth, Pratikkumar,Johnson, James E.,Schetz, John A.
, p. 4783 - 4792 (2010)
Efforts to develop ligands that distinguish between clinically relevant 5-HT2A and 5-HT2C serotonin receptor subtypes have been challenging, because their sequences have high homology. Previous studies reported that a novel aplysinopsin belonging to a chemical class of natural products isolated from a marine sponge was selective for the 5-HT2C over the 5-HT2A receptor subtype. Our goal was to explore the 5-HT2A/2C receptor structure-affinity relationships of derivatives based on the aplysinopsin natural product pharmacophore. Twenty aplysinopsin derivatives were synthesized, purified and tested for their affinities for cloned human serotonin 5-HT1A, 5-HT2A, and 5-HT2C receptor subtypes. Four compounds in this series had >30-fold selectivity for 5-HT2A or 5-HT2C receptors. The compound (E)-5-((5,6-dichloro-1H-indol-3-yl)methylene)- 2-imino-1,3-dimethylimidazolidin-4-one (UNT-TWU-22, 16) had approximately 2100-fold selectivity for the serotonin 5-HT2C receptor subtype: an affinity for 5-HT2C equal to 46 nM and no detectable affinity for the 5-HT1A or 5-HT2A receptor subtypes. The two most important factors controlling 5-HT2A or 5-HT2C receptor subtype selectivity were the combined R1,R3-alkylation of the imidazolidinone ring and the type and number of halogens on the indole ring of the aplysinopsin pharmacophore.
Triphenylphosphine/1,2-Diiodoethane-Promoted Formylation of Indoles with N, N -Dimethylformamide
Zhu, Yu-Rong,Lin, Jin-Hong,Xiao, Ji-Chang
supporting information, p. 259 - 263 (2021/11/22)
Despite intensive studies on the synthesis of 3-formylindoles, it is still highly desirable to develop efficient methods for the formylation of indoles, due to the shortcomings of the reported methods, such as inconvenient operations and/or harsh reaction conditions. Here, we describe a Ph3P/ICH2CH2I-promoted formylation of indoles with DMF under mild conditions. A Vilsmeier-type intermediate is readily formed from DMF promoted by the Ph3P/ICH2CH2I system. A onestep formylation process can be applied to various electron-rich indoles, but a hydrolysis needs to be carried out as a second step in the case of electron-deficient indoles. Convenient operations make this protocol attractive.
Synthesis method of 5-iodoindole compound
-
Paragraph 0014-0015, (2021/03/13)
The invention discloses a synthesis method of a 5-iodo indole compound, and the method comprises the following steps: by using an indole compound as a starting raw material and Niodo succinimide or iodine as an iodine source, carrying out free radical reaction in a halogenated organic solvent at normal temperature and normal pressure in the presence of Lewis acid to synthesize the 5-iodo indole compound. The synthesis method is mild in condition, wide in substrate application range, good in functional group tolerance and free of metal participation, and has the advantages of being easy to operate, environmentally friendly, high in specific regioselectivity and the like.
