65618-07-7Relevant articles and documents
Microwave-assisted, catalyst and solvent free synthesis of tryptanthrin derivatives and their in-vitro cytotoxic activity on prostate DU145 cancer cell lines
Kaishap, Partha Pratim,Duarah, Gauri,Pal, Mintu
supporting information, p. 3740 - 3747 (2021/10/21)
A straightforward and efficient synthesis of tryptanthrin derivatives has been accomplished by the addition reaction of isatoic anhydrides and isatins under microwave irradiation. This decarboxylative and dehydrative addition reaction proceeded under solvent free conditions. In vitro cell based bioassay results revealed that 3ab and 3bb had unique cytotoxicity and selectivity with IC50 values of 5.90 ± 3.65 μM and 1.96 ± 0.83 μM, respectively in DU145 cells and they were found to be nontoxic to normal prostate epithelial RWPE-1 cells up to 25 μM.
A biomimetic, one-step transformation of simple indolic compounds to malassezia-related alkaloids with high ahr potency and efficacy
Mexia, Nikitia,Koutrakis, Stamatis,He, Guochun,Skaltsounis, Alexios-Leandros,Denison, Michael S.,Magiatis, Prokopios
, p. 2238 - 2249 (2019/11/19)
Malassezia furfur isolates from diseased skin preferentially biosynthesize compounds which are among the most active known aryl-hydrocarbon receptor (AhR) inducers, such as indirubin, tryptanthrin, indolo[3,2-b]carbazole, and 6-formylindolo[3,2-b]carbazole. In our effort to study their production from Malassezia spp., we investigated the role of indole-3-carbaldehyde (I3A), the most abundant metabolite of Malassezia when grown on tryptophan agar, as a possible starting material for the biosynthesis of the alkaloids. Treatment of I3A with H2O2 and use of catalysts like diphenyldiselenide resulted in the simultaneous one-step transformation of I3A to indirubin and tryptanthrin in good yields. The same reaction was first applied on simple indole and then on substituted indoles and indole-3-carbaldehydes, leading to a series of mono- A nd bisubstituted indirubins and tryptanthrins bearing halogens, alkyl, or carbomethoxy groups. Afterward, they were evaluated for their AhR agonist activity in recombinant human and mouse hepatoma cell lines containing a stably transfected AhR-response luciferase reporter gene. Among them, 3,9-dibromotryptanthrin was found to be equipotent to 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) as an AhR agonist, and 3-bromotryptanthrin was 10-times more potent than TCDD in the human HG2L7.5c1 cell line. In contrast, 3,9-dibromotryptanthrin and 3-bromotryptanthrin were 4000 and >10,000 times less potent than TCDD in the mouse H1L7.5c3 cell line, respectively, demonstrating that they are species-specific AhR agonists. Involvement of the AhR in the action of 3-bromotryptanthrin was confirmed by the ability of the AhR antagonists CH223191 and SR1 to inhibit 3-bromotryptanthrin-dependent reporter gene induction in human HG2L7.5c1 cells. In conclusion, I3A can be the starting material used by Malassezia for the production of both indirubin and tryptanthrin through an oxidation mechanism, and modification of these compounds can produce some highly potent, efficacious and species-selective AhR agonists.
With anti-tumor activity of tryptamine alkone bromo derivative and its synthesis method
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Paragraph 0022; 0052; 0053; 0056; 0059; 0062, (2018/04/02)
The invention discloses a tryptanthrin bromo derivative with antineoplastic activity and a preparation method therefor. The tryptanthrin bromo derivation is 2,8-dibromo-tryptanthrin. The preparation method comprises the following steps: using tryptanthrin as a raw material, adding trifluoroacetic acid as a solvent, adding concentrated sulfuric acid as a catalyst after the tryptanthrin is dissolved, adding N-bromo-succinimide for reaction, reacting for 40-50 hours while controlling temperature to be 35-45 DEG C, cooling, standing, removing the trifluoroacetic acid, pouring reaction liquid into ice water to separate out light yellow solid, neutralizing, carrying out suction filtration, washing the light yellow solid with water, carrying out acetone washing, and drying, to obtain the 2,8-dibromo-tryptanthrin. The product has excellent antineoplastic activity, and can be applied to anti-lung cancer and anti-stomach cancer drugs.