62174-08-7

Usage

Uses

Used in Pharmaceutical Industry:
(E)-3-(4-chlorobenzylidene)-2,3-dihydrochromen-4-one is used as a pharmaceutical compound for its potential therapeutic applications in treating various diseases and conditions. Its antioxidant, anti-inflammatory, and antitumor properties make it a promising candidate for drug development and treatment of related health issues.
Used in Antioxidant Applications:
In the field of antioxidant research, (E)-3-(4-chlorobenzylidene)-2,3-dihydrochromen-4-one is utilized for its ability to combat oxidative stress and protect cells from damage. Its antioxidant properties can be beneficial in the development of treatments for conditions associated with oxidative stress, such as neurodegenerative diseases and cardiovascular disorders.
Used in Anti-inflammatory Applications:
(E)-3-(4-chlorobenzylidene)-2,3-dihydrochromen-4-one is employed as an anti-inflammatory agent, potentially aiding in the treatment of inflammation-related diseases such as arthritis, asthma, and inflammatory bowel disease. Its anti-inflammatory properties can help alleviate symptoms and improve the quality of life for patients suffering from these conditions.
Used in Antitumor Applications:
In the realm of oncology, (E)-3-(4-chlorobenzylidene)-2,3-dihydrochromen-4-one is used for its antitumor properties, showing potential in the treatment of various types of cancer. Its ability to target and inhibit cancer cell growth and proliferation makes it a valuable compound in the development of novel cancer therapies.
Used in Drug Delivery Systems:
To enhance the bioavailability and therapeutic outcomes of (E)-3-(4-chlorobenzylidene)-2,3-dihydrochromen-4-one, researchers are exploring the use of various drug delivery systems, such as organic and metallic nanoparticles. These carriers can improve the compound's delivery to target sites, increasing its efficacy and reducing potential side effects.

InChI:InChI=1/C16H11ClO2/c17-13-7-5-11(6-8-13)9-12-10-19-15-4-2-1-3-14(15)16(12)18/h1-9H,10H2/b12-9+

Upstream product

• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 104-88-1 4-chlorobenzaldehyde 
• 7170-38-9 3-phenoxypropanoic acid 
• 108-95-2 phenol 
• 533-58-4 2-Iodophenol 
• 103979-29-9 para-chlorocinnamyl chloride 
• 1126-20-1 2-allyloxyphenol 
• 108-73-6 3,5-dihydroxyphenol 
• 3055-86-5 3-phenoxypropionitrile 

Downstream Products

• 76285-74-0 3-(4-chlorobenzyl)-chroman-4-one 
• 114283-20-4 2-Amino-4-(4-chloro-phenyl)-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile 
• 91126-26-0 C₁₆H₁₁ClO₃ 

Relevant academic research and scientific papers

I2/TBHP mediated diastereoselective synthesis of spiroaziridines

Eventhough spiroheterocycles are considered as emerging drug candidates, synthesis of spiroaziridines has not been well explored so far. Herein, we disclose an efficient I2/TBHP mediated diastereoselective synthesis of N-alkyl spiroaziridines from primary amines and easily accessible α,β-unsaturated ketones. The reaction is also compatible for the synthesis of 2-aroylaziridines.

A Convenient Palladium-Catalyzed Carbonylative Synthesis of (E)-3-Benzylidenechroman-4-ones

A convenient palladium-catalyzed carbonylation reaction for the efficient synthesis of (E)-3-benzylidenechroman-4-ones has been developed. Using TFBen as a solid CO source, a range of substituted (E)-3-benzylidenechroman-4-ones were prepared in moderate to good yields with 2-iodophenols and allyl chlorides as the substrates. Additionally, substituted quinolin-4(1H)-ones can also be obtained with 2-iodoaniline as the starting material.

Synthesis and biological evaluation of 3-benzylidene-4-chromanone derivatives as free radical scavengers and α-glucosidase inhibitors

A series of 3-benzylidene-4-chromanone derivatives (3-20) were synthesized and the structure-activity relationships for antioxidant and α-glucosidase inhibitory activities were evaluated. Among synthesized compounds, compounds 5, 13, 18, which contain catechol moiety, showed the potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity (5: EC50 13 μM; 13: EC50 14 μM; 18: EC50 13 μM). The compounds 12, 14, 18 showed higher α-glucosidase inhibitory activity (12: IC50 15 μM; 14: IC50 25 μM; 18: IC50 28 μM). The compound 18 showed both of potent DPPH radical scavenging and α-glucosidase inhibitory activities. These data suggest that 3-benzylidene-4-chromanone derivatives, such as compound 18, may serve as the lead compound for the development of novel α-glucosidase inhibitors with antioxidant activity.

Structural studies of seven homoisoflavonoids, six thiohomoisoflavonoids, and four structurally related compounds

1H and 13C NMR chemical shifts have been determined and assigned based on PFG 1H, 13C HM...C, and HMBC experiments for 3-(4'-X-benzyl)-4-chromenones (Ia, X = CN and Ib, X = NO 2), 3-(4'-X-benzyl)-4-th

Facile condensation of aromatic aldehydes with chroman-4-ones and 1-thiochroman-4-ones catalysed by amberlyst-15 under microwave irradiation condition

Different aromatic aldehydes and cinnamaldehyde undergo crossaldol condensation with chroman-4-ones and 1-thiochroman-4-ones in the presence of amberlyst-15 under microwave irradiation in solvent free condition to afford rapidly the corresponding E-3-arylidene and E-3-cinnamylidene derivatives, respectively, in high yield. This process is simple, efficient and environmentally benign.

Topochemical photodimerization of (E)-3-benzylidene-4-chromanone derivatives from β-type structures directed by halogen groups

Halogen substituent plays an important role in the crystalline packing of aromatic compounds. The [2+2] photocycloaddition of (E)-3-benzylidene-4- chromanones in the crystalline state was investigated, and halogen substitution has been adopted to organize molecules with proper arrangement for photodimerization. Not halogen bonds, but the electron-withdrawing property of halogen atoms can enhance the face-to-face π-π interactions. Therefore, F, Cl or Br substitution at the para position of phenyl gave rise to almost the same β-structures with face-to-face π-stacking. Only resulted β-structures can undergo photodimerization, which gave the syn-HH (syn-head-to-head) products with high regio-/stereoselectivity.

Synthesis and antirhinovirus activity of new 3-benzyl chromene and chroman derivatives

A series of 3-benzyl chromenes and chromans were synthesized and tested in vitro against human rhinovirus (HRV) 1B and 14, two representative serotypes for rhinovirus group B and A, respectively. All the new compounds, with the exception of 3-benzyl-2H-chromene (3a), showed a potent activity against HRV serotype 1B within micro or submicromolar range (IC50s from 0.11 to 6.62 μM). The low cytotoxicity of all the derivatives resulted in compounds with high therapeutic index (TI). On the contrary, HRV 14 infection was only weakly inhibited by the majority of these compounds. The 3-benzylidenechromans 2b and 2c showed the highest anti-HRV 1B activity (IC50 0.12 and 0.11 μM, respectively) coupled with remarkable TI (625.00 and 340.91, respectively). Mechanism of action studies on (Z)-3-(4-chlorobenzylidene)chroman (2b) suggest that the new compounds behave as capsid binders and interfere with very early stages of HRV 1B replication, similarly to related flavanoids.

Design, synthesis and antiproliferative activity of some 3-benzylidene-2,3-dihydro-1-benzopyran-4-ones which display selective toxicity for malignant cells

A series of 3-benzylidene-4-chromanones 1a-l were prepared and their cytotoxicity towards human Molt 4/C8 and CEM T-lymphocytes as well as murine L1210 lymphoid leukemia cells were compared to the previously generated biodata in these three assays for the

One-pot synthesis of trans-7-aryl-6H-6a,7-dihydro[1]benzopyrano[3,4-c][1,5]benzothiazepines

Green chemical approaches for the condensation reaction of benzenethiols and 3-arylidenenchroman-4-ones as synthons for the synthesis of a series of newtrans-7-aryl-6H-6a,7-dihydro[1]benzo pyrano[3,4-c][1,5]benzothiazepines which may possess potential biological activity are described.{A figure is presented}.

Novel synthesis of N-methyl spiropyrrolidines by 1,3-dipolar cycloaddition reaction of azomethine ylides

A series of novel N-methyl spiropyrrolidines have been synthesized in good yield by the cycloaddition reaction of azomethine ylides generated by a decarboxylative route from sarcosine and paraformaldehyde with conformationally locked s-trans enone functionality present in the (E)-3-arylidene-4-chromanone as dipolarophiles. The structure of the title compound was established by spectroscopic techniques. Copyright Taylor & Francis, Inc.