50720-05-3Relevant articles and documents
Synthesis of phidianidines A and B
Lin, Hong-Yu,Snider, Barry B.
, p. 4832 - 4836 (2012)
Reaction of a substituted indole-3-acetyl chloride with N-5-azidopentyl-N′-hydroxyguanidine generated a substituted 3-(5-azidopentylamino)-5-((indol-3-yl)methyl)-1,2,4-oxadiazole. Reduction of the azide with zinc and ammonium formate afforded the amine, which was elaborated to the guanidine, completing short and efficient syntheses of the cytotoxic natural products phidianidines A and B in 19% overall yield by a convergent route that will make analogues readily available for biological evaluation. Initial screening in the NCI 60 cell line at 10-5 M indicated that the bromine on the indole is necessary for activity and that the amine precursor to phidianidine A is more potent than phidianidine A.
Concise total synthesis of phidianidine A and B
Buchanan, Jacob C.,Petersen, Brandon P.,Chamberland, Stephen
, p. 6002 - 6004 (2013)
The shortest total synthesis of cytotoxic indole alkaloids phidianidine A and B is described. Rapid assembly of the 1,2,4-oxadiazole core from a novel N-hydroxyguanidine and the corresponding indole-3-acetic acid chloride led to formal syntheses of phidianidine A and B in only three steps from known compounds. Deprotection under standard conditions provided the trifluoroacetate salts of phidianidine A and B in quantitative yield.
Observations arising from a Beckmann rearrangement-Mannich cyclization approach to the azepinobisindole alkaloid iheyamine A
Lindsay, Ashley C.,Sperry, Jonathan
, p. 4355 - 4362 (2017)
An overview of an iterative Beckmann rearrangement-Mannich cyclization approach to the azepinobisindole alkaloid iheyamine A is described. In a preliminary model study, the (E)-oxime 10 underwent Beckmann rearrangement to give the bisindolylacetamide 4 followed by an intramolecular Mannich cyclization affording 2-(indolin-2-yl)indole 5 containing the heterocyclic framework of the iheyamine alkaloids. However, the 2-(indolin-2-yl)indole 5 could not be converted into the azepinobisindole core of iheyamine A. When the same Beckmann-Mannich approach was applied toward the natural product itself, a result was obtained that contrasted the model study. The (E)-oxime 3 did not undergo Beckmann rearrangement, but instead an intramolecular Mannich cyclization whereby the electron rich C4 site attacked the intermediate iminum ion, generating the 4-(indolin-2-yl)indole 25 bearing the heterocyclic framework of the slime mould pigment arcyriacyanin A. Although this route did not result in the synthesis of iheyamine A being accomplished, some interesting observations related to the venerable Beckmann rearrangement and Mannich cyclization reactions are described.
Development of [18F]Maleimide-Based Glycogen Synthase Kinase-3β Ligands for Positron Emission Tomography Imaging
Hu, Kongzhen,Patnaik, Debasis,Collier, Thomas Lee,Lee, Katarzyna N.,Gao, Han,Swoyer, Matthew R.,Rotstein, Benjamin H.,Krishnan, Hema S.,Liang, Steven H.,Wang, Jin,Yan, Zhiqiang,Hooker, Jacob M.,Vasdev, Neil,Haggarty, Stephen J.,Ngai, Ming-Yu
supporting information, p. 287 - 292 (2017/03/17)
Dysregulation of glycogen synthase kinase-3β (GSK-3β) is implicated in the pathogenesis of neurodegenerative and psychiatric disorders. Thus, development of GSK-3β radiotracers for positron emission tomography (PET) imaging is of paramount importance, because such a noninvasive imaging technique would allow better understanding of the link between the activity of GSK-3β and central nervous system disorders in living organisms, and it would enable early detection of the enzyme’s aberrant activity. Herein, we report the synthesis and biological evaluation of a series of fluorine-substituted maleimide derivatives that are high-affinity GSK-3β inhibitors. Radiosynthesis of a potential GSK-3β tracer [18F]10a is achieved. Preliminary in vivo PET imaging studies in rodents show moderate brain uptake, although no saturable binding was observed in the brain. Further refinement of the lead scaffold to develop potent [18F]-labeled GSK-3 radiotracers for PET imaging of the central nervous system is warranted.
Indole compound with antivirus activity in radix isatidis and derivative of indole compound
-
Paragraph 0516, (2017/09/29)
The invention discloses an indole compound extracted from radix isatidis shown in a general formula (I) and a derivative of the indole compound, as well as a salt acceptable on pharmacy, a preparation method of the compound, and a medicinal composite. The compound has apparent HIV-resisting activity and influenza virus-resisting activity, and can be used for preparing drugs or healthcare products for resisting HIV or influenza viruses. (The formula is shown in the description.).
