77603-42-0

Basic information

• Product Name: 8-Nitrotryptanthrin
• Synonyms: 8-Nitrotryptanthrin
• CAS NO: 77603-42-0
• Molecular Formula: C₁₅H₇N₃O₄
• Molecular Weight: 266.33124
• Mol File: 77603-42-0.mol

Chemical Properties

• Melting Point: >250 °C
• Boiling Point: 551.2±52.0 °C(Predicted)
• Appearance: /
• Density: 1.67±0.1 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• PKA: -7.55±0.20(Predicted)
• CAS DataBase Reference: 8-Nitrotryptanthrin(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Nitrotryptanthrin(77603-42-0)
• EPA Substance Registry System: 8-Nitrotryptanthrin(77603-42-0)

Safety Data

• Hazardous Substances Data: 77603-42-0(Hazardous Substances Data)

Usage

Uses

Used in Photodynamic Therapy:
8-Nitrotryptanthrin is used as a photosensitizer for photodynamic therapy, where it is activated by light to kill cancer cells. This method is particularly effective in targeting and destroying cancerous tissues while minimizing damage to surrounding healthy cells.
Used in Anticancer Applications:
8-Nitrotryptanthrin is used as an anticancer agent due to its potential to inhibit tumor growth and proliferation. Its antitumor properties make it a candidate for further research and development in cancer treatment.
Used in Antibacterial Applications:
8-Nitrotryptanthrin is used as an antibacterial agent, exhibiting activity against various bacterial strains. This property can be harnessed for the development of new antibiotics to combat drug-resistant infections.
Used in Inflammatory Disease Treatment:
8-Nitrotryptanthrin is used as an anti-inflammatory agent, as it has been shown to inhibit the production of inflammatory mediators. This makes it a potential candidate for the treatment of inflammatory diseases, where reducing inflammation is crucial for managing the condition.

Upstream product

• 118-48-9 isatoic anhydride 
• 611-09-6 5-nitroisatin 
• 42366-35-8 hydroxyimino-N-phenylacetamide 
• 62-53-3 aniline 
• 91-56-5 indole-2,3-dione 
• 13220-57-0 tryptanthrine 

Relevant articles and documents

Design, synthesis and biological evaluation of 8-substituted-6-hydrazonoindolo[2,1-b]quinazolin-12(6H)-one scaffolds as potential cytotoxic agents: IDO-1 targeting molecular docking studies

Herein, we have reported the synthesis of 18 novel 8-substituted tryptanthrin analogues based on our earlier work. All these tryptanthrin analogues were well characterized by 1H & 13C NMR, FT-IR, Mass Spectrometry and Elemental Analy

Tryptanthrin derivative and preparation thereof and application of tryptanthrin derivative in prevention and treatment of plant viruses and pathogenic bacteria

The invention relates to tryptanthrin derivatives I-1 to I-7, and a preparation method thereof and application of the tryptanthrin derivatives I-1 to I-7 in prevention and treatment of plant viruses and pathogenic bacteria. The tryptanthrin derivatives I-

Discovery of Tryptanthrins as Novel Antiviral and Anti-Phytopathogenic-Fungus Agents

Plant diseases seriously affect the yield and quality of crops and are difficult to control. Tryptanthrin and its derivatives (tryptanthrins) were synthesized and evaluated for their antiviral activities and fungicidal activities. We found that tryptanthrins have good antiviral activities against tobacco mosaic virus (TMV) for the first time. Most of the tryptanthrins showed higher anti-TMV activities than that of ribavirin (inhibitory rates of 40, 37, and 38% at 500 μg/mL for inactivation, curative, and protection activities in vivo, respectively). Compound 3n (inhibitory rates of 52, 49, and 54% at 500 μg/mL for inactivation, curative, and protection activities in vivo, respectively) and compound 14 (inhibitory rates of 51, 48, and 53% at 500 μg/mL for inactivation, curative, and protection activities in vivo, respectively) emerged as new antiviral lead compounds with excellent antiviral activities. Compound 16 was selected for further antiviral mechanism research, which revealed that compound 16 could inhibit virus assembly by decomposing 20S coat protein (CP) disk. Molecular docking results showed that compounds 3n and 14, which have higher antiviral activities in vivo than that of compound 16, do show stronger interaction with TMV CP. Further fungicidal activity tests showed that tryptanthrins displayed broad-spectrum fungicidal activities, especially for compound 16. These compounds showed good selectivity to Physalospora piricola. In the current study, a small molecular library of tryptanthrin was constructed and the bioactivity spectrum of these compounds was broadened, which lays a foundation for their application in plant protection.

1-Butyl-2-methylpipyridinium iodide ([BMPPY]I): novel ionic liquid for the synthesis of 6-hydroxy-6-(1H-indol-3-yl)indolo[2,1-b]quinazolin-12(6H)-ones under green solvent-free conditions

Abstract: In this article we reported preparation of 1-butyl-2-methylpipyridinium iodide ([BMPPY]I), as a novel ionic liquid (IL) through simple procedure. This newly prepared IL has been characterized by FT-IR, FESEM, EDX, TGA/DTG, 1H NMR, 13C NMR, and Gc-mass techniques. The FESEM images revealed nano scale for the IL with the average diameter of 150–185?nm. Its efficacy examined for the synthesis of 6-hydroxy-6-(1H-indol-3-yl)indolo[2,1-b]quinazolin-12(6H)-ones via domino three-component reaction of isatin derivatives, isatoic anhydride, and indoles under solvent-free conditions at 100?°C. The results affirmed that ([BMPPY]I) possessed a dual catalytic/solvent role to promote this condensation. Non-flammability, thermal stability, non-toxicity and low cost of the IL that led to obtain pharmaceutically-active heterocycles though easy work-up procedure and short reaction times, are some highlighted features of this green protocol. Graphical abstract: [Figure not available: see fulltext.].

Zinc oxide-NP catalyzed direct indolation of: In situ generated bioactive tryptanthrin

A ZnO-NP catalyzed direct indolation of in situ generated tryptanthrin via C-H functionalization and C-C bond formation has been developed. This novel and greener approach has been effectively utilized to accomplish the synthesis of 6-hydroxy-6-(1H-indol-3-yl)indolo[2,1-b]quinazolin-12(6H)-one derivatives in good to excellent yields with high product selectivity. Besides the in situ approach, a direct indolation of tryptanthrin has also been developed.

Discovery of tryptanthrin derivatives as potent inhibitors of indoleamine 2,3-dioxygenase with therapeutic activity in lewis lung cancer (LLC) tumor-bearing mice

Indoleamine 2,3-dioxygenase (IDO-1) is emerging as an important new therapeutic target for the treatment of cancer, neurological disorders, and other diseases that are characterized by pathological tryptophan metabolism. However, only a few structural classes are known to be IDO-1 inhibitors. In this study, a natural compound tryptanthrin was discovered to be a novel potent IDO-1 inhibitor by screening of indole-based structures. Three series of 13 tryptanthrin derivatives were synthesized, and the structure-activity analysis was undertaken. The optimization led to the identification of 5c, which exhibited the inhibitory activity at a nanomolar level. In vitro 5c dramatically augmented the proliferation of T cells. When administered to Lewis lung cancer (LLC) tumor-bearing mice, 5c significantly inhibited IDO-1 activity and suppressed tumor growth. In addition, 5c reduced the numbers of Foxp3 + regulatory T cells (Tregs), which are known to prevent the development of efficient antitumor immune responses.

Design, synthesis, and structure-activity relationship studies of tryptanthrins as antitubercular agents

The natural product tryptanthrin (1a) represents a potential lead for new tuberculosis (TB) drugs since tryptanthrin and its synthetic analogues possess potent in vitro activity against Mycobacterium tuberculosis (Mtb). However, in spite of their in vitro activity, none of these agents have been shown to be efficacious in vivo against animal models of TB. Described herein are syntheses of new tryptanthrin analogues together with a systematic investigation of their in vitro antitubercular activity and ADME properties followed by pharmacokinetic characterization in rodents for the most promising compounds. Those with the best potency and oral bioavailability were progressed to evaluations of efficacy against acute murine TB. The work aimed to prove the concept that this compound class can limit growth of Mtb during infection as well as to establish the SAR for in vitro activity against Mtb and the range of in vitro ADME parameters for this class of natural products. Novel C-11-deoxy (5b) and A-ring-saturated (6) tryptanthrin analogues were discovered that maintained activity against Mtb and showed improved solubility compared to tryptanthrin as well as evidence of oral bioavailability in rodents. However, neither 5b nor 6 demonstrated efficacy against acute murine TB following administration at doses up to 400 mg/kg daily for 4 weeks. Although 5b and 6 failed to inhibit replication or kill Mtb in vivo, they illuminate a path to new structural variations of the tryptanthrin scaffold that may maximize the potential of this class of compounds against TB.

β-Cyclodextrin catalysed synthesis of tryptanthrin in water

An efficient and green method has been developed for the synthesis of tryptanthrin employing β-cyclodextrin as a catalyst in aqueous media at room temperature from isatoic anhydride and isatin. The reactions were performed under mild conditions to afford biologically active natural product tryptanthrin in excellent yields.

Antimicrobial activity of tryptanthrins in escherichia coli

Tryptanthrins have potential therapeutic activity against a wide variety of pathogenic organisms, although little is known about their mechanism. Activity against Escherichia coli, however, has not been examined. The effects of tryptanthrin (indolo[2,1-b]quinazolin-6,12-dione) and nine derivatives on growth, survival, and mutagenesis in E. coli were examined. Analogues with a nitrogen atom at the 4-position of tryptanthrin stopped log phase growth of E. coli cultures at concentrations as low as 5 μM. Tryptanthrins decreased viability during incubation with cells in buffer by factors of 10-2 to -6 at 0.2-40 μM. Derivatives with an oxime group at the 6-position exhibited the greatest bactericidal activity. Most tryptanthrins were not mutagenic in several independent assays, although the 4-aza and 4 aza-8-fluoro derivatives increased frameshift mutations about 22- and 4-fold, respectively. Given the structure of trypanthrins, binding to DNA may occur by intercalation. From analysis using a sensitive linking number assay, several tryptanthrins, especially the 4-aza and 6-oximo derivatives, intercalate into DNA.

Novel indolo[2,1-b]quinazoline analogues as cytostatic agents: synthesis, biological evaluation and structure-activity relationship.

In our endeavor to design and synthesize novel anticancer agents, a new series of indoloquinazoline compounds were prepared and tested initially for anticancer activity in vitro against a panel of human cancer cell lines. Most of these compounds exhibited cytotoxic activity in in vitro screens. Compounds were selected and further evaluated using a modified Hollow Fiber Assay for their preliminary in vivo activity against 12 cell lines implanted in the subcutaneous and intraperitoneal compartments in mice. The results indicate that these compounds may constitute a new class of anticancer agents.