741265-04-3Relevant academic research and scientific papers
A revised synthetic scheme of 6,6′-dibromoindirubin
Tanoue, Yasuhiro,Hara, Akari,Kai, Norihisa,Sakata, Kazunori,Hashimoto, Mamoru,Nagai, Takeshi
, p. 1135 - 1137 (2007)
(Chemical Equation Presented) The synthetic scheme of 6,6′- dibromoindirubin (2) was investigated in detail. The reaction of 6-fluoro-3-acetoxyindole (7) with isatin (8) in methanol with Na 2CO3 produced 6′-fluoroindirubin in moderate yields. Its structure determination was mainly undertaken using 1H NMR spectroscopy. On the basis of this result, the synthetic scheme of 2 reported by Cooksey was revised.
Synthesis and evaluation of 6-[18F]fluoro-3-(pyridin-3-yl)-1H-indole as potential PET tracer for targeting tryptophan 2, 3-dioxygenase (TDO)
Bhalla, Rajiv,Mardon, Karine,Migotto, Mary-anne,Qiao, Zheng,Reutens, David C.,Stimson, Damion H. R.
, p. 1 - 10 (2020/01/11)
Introduction: The increase in expression of tryptophan 2, 3-dioxygenases (TDO) and indoleamine 2,3-dioxygenase (IDO) have been reported as potential tumor biomarkers. TDO and IDO are enzymes that catalyze the first and rate-limiting step of the kynurenine pathway. Positron emitting tomography (PET) tracers investigating the kynurenine pathway may allow for the detection of different disease pathologies in vivo including cancer. However, current PET tracers being developed for TDO and IDO have suffered from either multi-step low yielding syntheses or de-fluorination of the tracer in vivo. Results: TDO inhibitors based on 6-fluoroindole with C3 substituents are a class of small molecules that have been shown to bind to TDO effectively, restore tryptophan concentration and decrease the production of immunosuppressive metabolites. The compound 6-fluoro-3-(pyridine-3-yl)-1H-indole has been reported to have high in vitro affinity for TDO. Herein we report the fully automated radiosynthesis of 6-[18F]fluoro-3-(pyridine-3-yl)-1H-indole [18F]4 using a copper-mediated nucleophilic 18F-fluorination resulting in a non-corrected yield of 5 to 6% of the tracer with a radiochemical purity of >99% after 4 h. Small animal dynamic PET/CT imaging of [18F]4 intravenously injected into normal C57BL/6 mice revealed rapid accumulation in heart and brain, reaching maximum occupancy in heart (10.9% ID/g) and brain (8.1% ID/g) at 1.75 min and 2.25 min, respectively. Furthermore, these in vivo studies revealed no de-fluorination of the tracer, as evidence by the absence of [18F]fluoride accumulation in bone. Conclusion: In vitro studies demonstrate that 4 has good affinity for hTDO and the radiolabeled analogue [18F]4 can be synthesized with suitable radiochemical yields. [18F]4 demonstrates good uptake in the brain and the radiolabeled compound shows no de-fluorination in vivo in C57BL/6 mice.
A Versatile C–H Halogenation Strategy for Indole Derivatives under Electrochemical Catalyst- and Oxidant-Free Conditions
Sun, Linhao,Zhang, Xing,Li, Zilong,Ma, Jimei,Zeng, Zhen,Jiang, Hong
supporting information, p. 4949 - 4952 (2018/05/15)
Halogenated indoles are essential structural motifs in bioactive natural products. Reported herein is an economical and scalable electrochemical protocol for regioselective 3C–H halogenation of indole derivatives. This strategy provides access to a host of 3-iodo-, 3-bromo-, 3-chloro-, and 3-thiocyanoindole derivatives under mild conditions using inexpensive (pseudo)halide salts as the sole reagent. The optimized conditions do not require any supplementary electrolyte salts.
BICYCLIC INDOLE-PYRIMIDINE PI3K INHIBITOR COMPOUNDS SELECTIVE FOR P110 DELTA, AND METHODS OF USE
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Page/Page column 102, (2010/12/26)
Formula I (Ia and Ib) compounds wherein (i) X1 is N and X2 is S, (ii) X1 is CR7 and X2 is S, (iii) X1 is N and X2 is NR2, (iv) X1 is CR7 and X2 is O, or (v) X1 is CR7 and X2 is NR2, including stereoisomers, tautomers, metabolites and pharmaceutically acceptable salts thereof, are useful for inhibiting the delta isoform of PBK, and for treating disorders mediated by lipid kinases such as inflammation, immunological, and cancer. Methods of using compounds of Formula I for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.
Synthesis of 2-(3-indolyl)-1,4-naphthoquinones using 3-iodoindoles
Tanoue, Yasuhiro,Hamada, Moritsugu,Kai, Norihisa,Sakata, Kazunori,Hashimoto, Mamoru,Nagai, Takeshi
, p. 1195 - 1199 (2007/10/03)
The usefulness of 3-iodoindoles available for introduction of an indole unit is presented. The reaction of various halo-3-iodoindoles with 1,4-naphthoquinone gave the corresponding 2-(3-indolyl)-1,4-naphthoquinones in moderate yields. The 3-iodoindole was used for synthesis of a compound containing both naphthazarin and indole skeletons.
