65618-07-7

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General Description

2,8-dibromoindolo[2,1-b]quinazoline-6,12-dione is a chemical compound with a molecular formula C16H8Br2N2O2. It is a heterocyclic organic compound that is formed by the fusion of an indole and a quinazoline ring system. 2,8-dibroMoindolo[2,1-b]quinazoline-6,12-dione has two bromine atoms attached to the indole ring, and it forms a quinazoline-6,12-dione structure. 2,8-dibromoindolo[2,1 -b]quinazoline-6,12-dione has potential applications in the field of medicinal chemistry and drug development, as it may exhibit biological activity due to its unique structure and properties. Further research and investigation are needed to determine the specific characteristics and potential uses of this chemical compound.

Upstream product

• 877-03-2 5-bromo-1H-indole-3-carboxaldehyde 
• 10075-50-0 5-bromo-1H-indole 
• 13220-57-0 tryptanthrine 
• 5794-88-7 5-Bromo-2-aminobenzoic acid 
• 4692-98-2 5-bromoisatoic anhydride 
• 87-48-9 5-Bromo-1H-indole-2,3-dione 
• 608-05-9 5-methyl-indole-2,3-dione 
• 91-56-5 indole-2,3-dione 
• 110-86-1 pyridine 

Relevant academic research and scientific papers

Microwave-assisted, catalyst and solvent free synthesis of tryptanthrin derivatives and their in-vitro cytotoxic activity on prostate DU145 cancer cell lines

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.

Divergent Synthesis of Methylisatoid and Tryptanthrin Derivatives by Ph3P-I2-Mediated Reaction of Isatins with and without Alcohols

A novel phosphonium-mediated reaction of isatins is described. In the presence of alcohol, the reaction proceeds to furnish C-12 modified tryptanthrin derivatives. Without alcohol, self-dimerization of isatins gives rise to tryptanthrin and its analogs. T

Conversion of Isatins to Tryptanthrins, Heterocycles Endowed with a Myriad of Bioactivities

The numerous bioactivities exhibited by tryptanthrins led chemists to develop synthetic approaches towards this important scaffold. In particular, conversion of isatins into tryptanthrins has been the subject of several studies. In this context, by using iodine and potassium hydroxide at room temperature, we have discovered a simple way to convert isatin and seven of its 5-substituted derivatives (Bu, F, Cl, Br, I, OMe and OCF3) into the corresponding tryptanthrins. Furthermore, a mechanism was proposed to explain this original reactivity. Finally, we evaluated the antibacterial, antifungal, antioxidant and cytotoxic properties of the synthesized tryptanthrins. The unprecedented inhibition of human 20S constitutive proteasome was finally evaluated.

A biomimetic, one-step transformation of simple indolic compounds to malassezia-related alkaloids with high ahr potency and efficacy

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

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.

Synthesis of Tryptanthrins by Organocatalytic and Substrate Co-catalyzed Photochemical Condensation of Indoles and Anthranilic Acids with Visible Light and O2

A metal-free catalytic approach to tryptanthrins has been achieved for the first time. The unique process is realized by an organocatalytic and indole and anthranilic acid substrate co-catalyzed photochemical oxidative condensation with visible light and O2. The truly environmentally friendly reaction conditions enable various reactants to participate in the process to deliver structurally diverse tryptanthrins.

Cobalt(III)-porphyrin complex (CoTCPP) as an efficient and recyclable homogeneous catalyst for the synthesis of tryptanthrin in aqueous media

The water soluble cobalt(III) porphyrin complex (CoTCPP) was employed as an efficient catalyst for the synthesis of the biologically active natural product tryptanthrin. The reaction proceeded under mild conditions in aqueous media at room temperature from various isatoic anhydride and isatin derivatives. The advantages of these reactions were excellent yields, short reaction times and a recoverable catalyst.

One-pot synthesis of tryptanthrin by the Dakin oxidation of indole-3-carbaldehyde

A one-pot approach to indolo[2,1-b]quinazolines from indole-3-carbaldehydes through the Dakin oxidation was developed. It was shown that the reaction proceeded through the condensation of indole-3-carbaldehydes with isatoic anhydrides, derived in situ from indole-3-carbaldehydes by the Dakin oxidation, and further oxidation/cyclization steps.

Formation of tryptanthrin compounds upon Oxone-induced dimerization of indole-3-carbaldehydes

Tryptanthrin is a natural product with numerous important pharmacological properties. Tryptanthrin and its analogs are commonly prepared by condensation of isatoic anhydride and isatin. In this Letter we investigate the formation of tryptanthrin derivatives upon Oxone-induced oxidative dimerization of indole-3-carbaldehydes.

Synthesis of substituted tryptanthrins via oxidation of isatin and its derivatives

Oxidation of isatin and its 5-substituted analogs with potassium permanganate in anhydrous acetonitrile gave indolo[2,1-b]quinazoline-6,12-dione (tryptanthrin) and its 2,8-dimethyl-, 2,8-dibromo-, and 2,8-diiodo derivatives. Oxidative coupling of 5,7-dichloroisatin with isatin under analogous conditions afforded 2,4-dichloroindolo[2,1-b]quinazoline-6,12-dione, while 1,4-dichloroindolo[2,1-b]quinazoline-6,12-dione and 1,4-dichloro-8- methylindolo[2,1-b]quinazoline-6,12-dione were obtained by oxidative coupling of 4,7-dichloroisatin with isatin and 5-methylisatin, respectively.