6054-10-0

Usage

Uses

Used in Dye and Pigment Production:
2H, 8H-Benzo[1,2-b:3,4-b']dipyran-2 is used as a key intermediate in the synthesis of dyes and pigments due to its aromatic structure and color-producing capabilities. Its incorporation enhances the color intensity and stability of these products, making them suitable for various applications such as textiles, plastics, and printing inks.
Used in Antioxidant Formulation:
As an antioxidant, 2H, 8H-Benzo[1,2-b:3,4-b']dipyran-2 is used to protect materials from oxidative degradation, thereby extending their shelf life and maintaining their quality. It is particularly useful in the food, cosmetic, and pharmaceutical industries, where it helps prevent the spoilage of products and the formation of harmful compounds.
Used in Fluorescence Microscopy and Labeling:
Leveraging its fluorescent properties, 2H, 8H-Benzo[1,2-b:3,4-b']dipyran-2 is employed as a fluorescent probe in microscopy and labeling applications. It allows for the visualization and tracking of specific molecules, cells, or tissues, providing valuable insights in biological research and diagnostics.
Used in Photodynamic Therapy for Cancer Treatment:
2H, 8H-Benzo[1,2-b:3,4-b']dipyran-2 has been studied for its potential as a photodynamic therapy agent. Upon light activation, it generates reactive oxygen species that can induce cell death in tumors, offering a targeted and non-invasive approach to cancer treatment.
Used as a Chemical Intermediate in Pharmaceutical Synthesis:
Due to its unique structure and functional properties, 2H, 8H-Benzo[1,2-b:3,4-b']dipyran-2 serves as a valuable chemical intermediate in the synthesis of various pharmaceuticals and organic compounds. Its versatility enables the development of new drugs and advanced materials with improved therapeutic and functional properties.

Upstream product

• 34191-74-7 7-(1,1-dimethyl-prop-2-ynyloxy)-6-methoxy-chromen-2-one 
• 92-61-5 7-hydroxy-6-methoxy-2H-1-benzopyran-2-one 
• 1740-74-5 1,1-diethoxy-3-methyl-2-butene 
• 1111-97-3 3-chloro-3-methylbut-1-yne 
• 51061-83-7 2,4-dihydroxy-5-methoxybenzaldehyde 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 

Relevant academic research and scientific papers

Synthesis and evaluation of substituted 8,8-dimethyl-8H-pyrano[2,3-f]chromen-2-one derivatives as vasorelaxing agents

A series of substituted 8,8-dimethyl-8H-pyrano[2,3-f]chromen-2-ones (chromeno-coumarin hybrids) was synthesized from scopoletin (11) as vasorelaxing agents. The synthesized compounds 21a-f, 22, 23a-e and scopoletin (11) were evaluated for vasorelaxation in endothelium intact rat main mesenteric artery (MMA). Compounds 11, 21a, 21c-f and 22 showed significant vasorelaxation in precontracted MMA within the range of EC50 value 1.58–5.02 μM. These derivatives presented 29.40–70.89 fold increased sensitivity for experimental tissue compared to scopoletin (11), the parent molecule. Among others, 22 was found to be the most active compound which had EC50 1.58 μM with 70.89 fold increased sensitivity. The mechanistic evaluation of 22 showed that it exerted vasorelaxation through Ca2+-activated K+ (BKca) channel and the effect was endothelium-independent.

A One-Pot Synthesis of Pyranocoumarins Through Microwave-Promoted Propargyl Claisen Rearrangement/Wittig Olefination

The reaction between propargyl ethers of hydroxybenzaldehydes and the ylide ethyl (triphenylphosphoranylidene)acetate was carried out under microwave irradiation to regioselectively afford angular pyranocoumarins. The chromene and coumarin heterocyclic scaffolds were simultaneously formed in the same synthetic step without changing the reaction conditions. The natural products seselin, braylin, and dipetalolactone were among the products synthesized by this method.

Anti-AIDS agents. 37. Synthesis and structure-activity relationships of (3'R,4'R)-(+)-cis-khellactone derivatives as novel potent anti-HIV agents

To explore the structural requirements of (+)-cis-khellactone derivatives as novel anti-HIV agents, 24 monosubstituted 3',4'-di-O-(S)- camphanoyl-(+)-cis-khellactone (DCK) derivatives were synthesized asymmetrically. These compounds included 4 isomeric monomethoxy analogues (3- 6), 4 isomeric monomethyl analogues (7-10), 4 4-alkyl/aryl-substituted analogues (11-14), and 12 4-methyl-(+)-cis-khellactone derivatives (15-26) with varying 3',4'-substituents. These (+)-cis-khellactone derivatives were screened against HIV-1 replication in acutely infected H9 lymphocytes. The results demonstrated that the (3'R,4'R)-(+)-cis-khellactone skeleton, two (S)-(-)-camphanoyl groups at the 3'- and 4'-positions, and a methyl group on the coumarin ring, except at the 6-position, were optimal structural moieties for anti-HIV activity. 3-Methyl- (7), 4-methyl- (8), and 5-methyl- (9) 3',4'- di-O-(S)-camphanoyl-(3'R,4'R)-(+)-cis-khellactone showed EC50 and therapeutic index values of -5 μM and >2.15 x 106, respectively, in H9 lymphocytes, which are much better than those of DCK and AZT in the same assay. Furthermore, 8 and 9 also showed potent inhibitory activity against HIV-1 replication in the CEM-SS cell line, and most monosubstituted DCK analogues were less toxic than DCK in both assays.

Anti-AIDS agents - XXVIII. Synthesis and anti-HIV activity of methoxy substitute 3',4'-di-O-(-)-Camphanoyl-(+)-cis-Khellactone (DCK) analogues

Four isomeric methoxy substituted DCK analogues (3-6) were asymmetrically synthesized from different starting materials. 5-Methoxy-3',4'-di-O-(-)-camphanoyl-(+)-cis-khellactone (5) exhibited extremely potent anti-HIV activity against HIV-1 replication in H9 lymphocyte cells with EC50 and therapeutic index values of 0.00038 μM and >402,632, respectively, which are better than those of DCK and AZT in this assay.