484-51-5

Usage

InChI:InChI=1/C12H12O5/c1-6(13)8-9(14)12(16-3)11-7(4-5-17-11)10(8)15-2/h4-5,14H,1-3H3

Upstream product

• 668-10-0 Ammiol 
• 88897-93-2 1-(2,3-dihydro-6,7-dihydroxy-5-benzofuranyl)-ethanone 
• 52249-80-6 2,4-dihydroxy-3,6-dimethoxybenzaldehyde 
• 52249-81-7 4-benzyloxy-2-hydroxy-3,6-dimethoxybenzaldehyde 
• 42528-81-4 2,6-bis-benzyloxy-benzene-1,4-diol 
• 20032-42-2 2,5-dimethoxyresorcinol 
• 6274-74-4 2,6-dibenzyloxy-1,4-dimethoxybenzene 
• 88897-95-4 1-(6-hydroxy-7-methoxy-5-benzofuranyl)-ethanone 
• 40512-23-0 1-(4,6,7-trimethoxybenzofuran-5-yl)ethan-1-one 
• 100884-66-0 1-(6-acetoxy-4,7-dimethoxy-2,3-dihydro-benzofuran-5-yl)-ethanone 
• 854898-32-1 6-benzyloxy-4,7-dimethoxy-benzofuran-2-carboxylic acid ethyl ester 
• 99059-07-1 4,7-dimethoxy-benzofuran-6-ol 
• 37833-19-5 6-hydroxy-4,7-dimethoxy-5-acetoacetylbenzofuran 
• 88897-94-3 1-(2,3-dihydro-6-hydroxy-7-methoxy-5-benzofuranyl)-ethanone 

Downstream Products

• 124112-96-5 (4,8-dimethoxy-3-methyl-benzo[1,2-b;5,4-b']difuran-2-yl)-(5-isopropyl-4-methoxy-2-methyl-phenyl)-ketone 
• 2549-21-5 1-(4,7-Dimethoxy-6-hydroxy-5-benzofuryl)-3-phenyl-propan-1,3-dion 
• 111824-69-2 (4-bromo-phenyl)-(4,8-dimethoxy-3-methyl-benzo[1,2-b;5,4-b']difuran-2-yl)-ketone 
• 41225-90-5 1-[6-(2-dimethylamino-ethoxy)-4,7-dimethoxy-benzofuran-5-yl]-ethanone 
• 49572-76-1 1-(6-hydroxy-4,7-dimethoxy-benzofuran-5-yl)-3t-phenyl-propenone 
• 49572-77-2 1-(6-hydroxy-4,7-dimethoxy-benzofuran-5-yl)-3t-(4-methoxy-phenyl)-propenone 
• 85517-95-9 (5-Acetyl-4,7-dimethoxy-6-benzofuranyl)-benzoat 
• 85518-00-9 (5-Acetyl-4,7-dimethoxy-6-benzofuranyl)-4-methoxybenzoat 
• 55008-26-9 1-(6-hydroxy-4,7-dimethoxy-benzofuran-5-yl)-3t-(4-hydroxy-3-methoxy-phenyl)-propenone 
• 37694-51-2 3t-(3,4-dimethoxy-phenyl)-1-(6-hydroxy-4,7-dimethoxy-benzofuran-5-yl)-propenone 
• 877169-32-9 (5-acetyl-4,7-dimethoxy-benzofuran-6-yloxy)-acetic acid anilide 
• 122802-29-3 biphenyl-4-yl-(4,8-dimethoxy-3-methyl-benzo[1,2-b;5,4-b']difuran-2-yl)-ketone 
• 73909-43-0 3t-(4-dimethylamino-phenyl)-1-(6-hydroxy-4,7-dimethoxy-benzofuran-5-yl)-propenone 
• 115003-30-0 (4,8-dimethoxy-3-methyl-benzo[1,2-b;5,4-b']difuran-2-yl)-(4-methoxy-phenyl)-ketone 

Relevant academic research and scientific papers

Total Synthesis of the Lipid-Altering and Antiatherosclerotic Furochromone Khellin. The Furoic Acid Route to Highly Functionalized Benzofurans

3-Furoic acid is converted to enaminone diester 8, which undergoes Dieckmann cyclization to yield the highly functionalized benzofuran 9.Methylation, Baeyer-Villager oxidation (CHO -> OH) and conversion of the resulting hydroxy ester 10 to khellinone constitutes a formal synthesis of khellin.

Non-ulcerogenic pyrazolyl 2-hydroxychalcones and pyrazolylpyrazolines derived from naturally existing furochromone (khellin): semi-synthesis, docking study and anti-inflammatory activity

Novel pyrazolyl 2-hydroxychalcone derivatives 3a–e and pyrazolylpyrazoline derivatives 4a–e and 5a–j derived from the naturally existing furochromone (Khellin) were synthesized and evaluated for their in?vivo anti-inflammatory activity. Most of the synthesized compounds showed better or comparable activity to that of Diclofenac as reference drug. Twelve compounds were evaluated for their ulcerogenic potential and exhibited no ulcerogenic effect. In addition compounds 3c, 5c and 5h as examples showed PGE2 inhibition % 88.86, 65.87 and 44.06, respectively and TNFα inhibition % 48.62, 31.11 and 16.02, respectively in rat serum samples. Compounds 3c, 5c, 5h and Celecoxib were subjected to in?vitro COX-1 and COX-2 inhibition assay, showed selectivity index 45.04, 102.04, 131.58 and 185.18, respectively. The computational finding supported those of in?vitro, where the pyrazolylpyrazolines interacted with the COX-2 enzyme in a similar orientation to that of Celecoxib, while chlacones were found to exhibit similar orientation to that of Diclofenac.

Synthesis and antimicrobial activity of novel 1, 2, 4-triazolopyrimido-furo-quinazolinones from natural furochromones (Visnagenone and khellinone)

Background: Previous and recent scientific research has shown that triazolopyrimidine and furochromones have a wide range of pharmacological activities for the treatment of numerous diseases, including anticancer, antiviral, anti-depressant, anti-microbial, anti-inflammatory, and analgesic activities. Objective: Preparation of new drugs derived from a natural furochromones as (1-hydrazinyl or methylthio),-furopyrimidoquinazolinone, 1, 2, 4-triazolopyrimidofuroquinazolin-5-one, and quina-zoline-pyrimidofuro-quinazoline-8, 10-dione and the study of their biological activity as antimi-crobial agents. Method: A series of novel N’-furopyrimidoquinazoline-hydrazide; 1, 2, 4-triazolopyrimidofuro-quinazolin-5-one; furopyrimidoquinazolin-3-one and quinazoline-pyrimidofuroquinazoline-8, 10-dione derivatives were synthesized from substituted (methylthio)-furopyrimidoquinazolinone (3a-b) and 1-hydrazinyl-furopyrimido-quinazolinone (4a-b) as the starting material. Results: All compounds were synthesized in good yields (71-95%) in a gradually efficient system under mild condition and some of the procedures were used such as microwave oven. The new compounds have been confirmed by means of different spectroscopic methods such as IR, 1D and 2D-NMR techniques and mass spectrum. The in vitro antimicrobial activities were evaluated for the prepared compounds using many types of bacteria (Gram-positive and Gram-negative) and fungi. Conclusion: 1, 2, 4-triazolopyrimidofuroquinazolin-5-one derivatives (10a-f, 8a-b, 7a-b and 6a-d) showed the most efficient antimicrobial activities compared with the cefotaxime sodium and nys-tatin as standard drugs.

Natural chalcone derivative as well as preparation method and application thereof

The invention provides a natural chalcone derivative as well as a preparation method and application thereof, and belongs to the technical field of chemical medicines. The natural chalcone derivative is a compound represented by formula (I), or a salt thereof, or a stereoisomer thereof, or a hydrate thereof. The derivative has remarkable inhibitory activity on IL-1beta and can effectively inhibit release of IL-1beta, and the inhibitory effect of the derivative is even superior to that of compounds with a similar structure in the prior art, wherein the compound 19, the compound 27, the compound 30, the compound 32 and the compound 40 have the optimal inhibition effect on IL-1beta. The derivative can be used as an IL-1beta inhibitor, is used for preparing medicines for treating inflammation and inflammation-related diseases, such as medicines for treating neurological inflammation, Alzheimer's disease, systemic lupus erythematosus, atherosclerosis, allergic asthma, arthritis, colitis and other diseases, and has a good application prospect.

Synthesis of Hydroxybenzofuranyl-Pyrazolyl and Hydroxyphenyl-pyrazolyl Chalcones and Their Corresponding Pyrazoline Derivatives as COX Inhibitors, Anti-inflammatory and Gastroprotective Agents

Five new series of hydroxybenzofuranyl-pyrazolyl chalcones 3a,b, hydroxyphenyl-pyrazolyl chalcones 6a–c and their corresponding pyrazolylpyrazolines 4a, d, 7a–c and 8a–f have been synthesized and evaluated for their in vitro cyclooxygenase (COX)-1 and COX-2 inhibitory activity. All the synthesized compounds exhibited dual COX-1 and COX-2 inhibitory activity with obvious selectivity against COX-2. The pyrazolylpyrazolines 4a–d and 8a–f bearing two vicinal aryl moieties in the pyrazoline nucleus showed more selectivity towards COX-2. Within these two series, derivatives 4c, d and 8d–f bearing the benzenesulfonamide group were the most selective. Compounds 4a–d and 8a–f were further subjected to in vivo anti-inflammatory screening, ulcerogenic liability and showed good anti-inflammatory activity with no ulcerogenic effect. In addition compounds 4c and 8d as examples showed prostaglandin (PG)E2 inhibition % 44.23 and 51.4 respectively, tumor necrosis factor α (TNFα) inhibition % 33.48 and 41.41 respectively and gastroprotective effect in ethanol induced rodent gastric ulcer model. In addition, to explore the binding mode and selectivity of our compounds, 8d and celecoxib were docked into the active site of COX-1 and COX-2. It was found that compound 8d exhibited a binding pattern and interactions similar to that of celecoxib with COX-2 active site, while bitter manner of interaction than celecoxib to COX-1 active site.

FURANOCHALCONES AS INHIBITORS OF CYP1A1, CYP1A2 AND CYP1B1 FOR CANCER CHEMOPREVENTION

The present invention relates to the furanochalcone class of compounds of general formula A. The present invention particularly relates to the synthesis of furanochalcones and their CYP1A1, CYP1A2 and CYP1B1 inhibitory activity. In addition, the invention relates to the prevention or treatment of cancer caused by polyaromatic hydrocarbons (PAHs), 4-nitroquinoline-1-oxide, and N-nitroso-N- methylurea, heterocyclic amines, estrogen and 17β-estradiol, resulting from the inhibition of CYP1A1, CYP1A2 and CYP1B1 enzymes.

Synthesis of new furothiazolo pyrimido quinazolinones from visnagenone or khellinone and antimicrobial activity

Substituted-6-methyl-1-thioxo-1,2-dihydro-3H-furo[3,2-g]pyrimido[1,6-a]quinazolin-3-ones (5a,b) were synthesized from condensation of visnagenone (2a) or khellinone (2b) with 6-amino-thiouracil (3) in dimethylformamide or refluxing of (4a) or (4b) in dimethylformamide. Hence, compounds (5a,b) were used as the starting materials for preparing many new heterocyclic compounds such as; furo[3,2-g]pyrimido[1,6-a]quinazoline (6a,b), furo[3,2-g]thiazolo[20,30:2,3] pyrimido[1,6-a]quinazolinone (7a,b), substituted-benzylidene-furo[3,2-g]thiazolo[20,30:2,3]pyrimido [1,6-a]quinazoline-3,5-dione (8a-f), 3-oxo-furo[3,2-g]pyrimido[1,6-a]quinazoline-pentane-2,4-dione (9a,b), 1-(pyrazole)-furo[3,2-g]pyrimido[1,6-a]quinazolinone (10a,b), 2-(oxo or thioxo)-pyrimidinefuro[ 3,2-g]pyrimido[1,6-a]quinazolinone (11a-d), 1-(methylthio)-furo[3,2-g]pyrimido[1,6-a] quinazolinone (12a,b), 1-(methyl-sulfonyl)-furo[3,2-g]pyrimido[1,6-a]quinazolinone (13a,b) and 6-methyl-1-((piperazine) or morpholino)-3H-furo[3,2-g]pyrimido[1,6-a]quinazolin-3-one (14a-d). The structures of the prepared compounds were elucidated on the basis of spectral data (IR, 1H-NMR, 13C-NMR, MS) and elemental analysis. Antimicrobial activity was evaluated for the synthesized compounds against Gram-positive, Gram-negative bacteria and fungi. The new compounds, furothiazolo pyrimido quinazolines 8a-f and 11a-d displayed results excellent for growth inhibition of bacteria and fungi.

Metal-Free Activation of C(sp3)–H Bond, and a Practical and Rapid Synthesis of Privileged 1-Substituted 1,2,3,4-Tetrahydroisoquinolines

The reaction of cotarnine and acyl/aryl ketones in “green” solvents provides an efficient approach to an array of privileged 1,2,3,4-tetrahydroisoquinolines in excellent yields by metal-free activation of C(sp3)–H bonds. This one-pot procedure takes place under base-free conditions at room temperature, and tolerates a wide range of functionalities. The reaction is highly chemoselective, can be performed on a multi-gram scale, and pure products are isolated by simple filtration without workup. Interestingly, the complementary two-step procedure from cotarnine halide salts gives the Mannich products in good yields. The scope was elaborated to 9-bromocotarnine salts to access a range of 9-bromonoscapine-derived analogues. The methodology has been developed considering the structural similarity of cotarnine derivatives to noscapinoids, which represent an emerging class of microtubule-modulating anticancer agents.

Synthesis of new quinoxaline, pyrimidine, and pyrazole furochromone derivatives as cytotoxic agents

Abstract: A series of novel quinoxaline, pyrimidine, and pyrazole furochromone derivatives were synthesized for the first time. These derivatives were prepared under mild conditions using a stepwise efficient methodology. The developed protocol led to the synthesis of furochromone derivatives in moderate to good yields (60–75%). The structures of the prepared derivatives were identified using several spectroscopic techniques including IR, NMR, and mass spectrometry. The cytotoxic activity of the synthesized derivatives was evaluated using in vitro Ehrlich ascites assay. Pyrazolobenzofurans exhibited the most potent effect suggesting the importance of pyrazole nucleus for the cytotoxic activity. Graphical abstract: [Figure not available: see fulltext.].

Design, synthesis and anticancer activity of furochromone and benzofuran derivatives targeting VEGFR-2 tyrosine kinase

In continuation of our work concerning the relation between the anticancer and anti-vascular endothelial growth factor receptor (anti-VEGFR-2) activity of some synthesized compounds, we hereby designed and prepared three new series of furochromone and benzofuran derivatives (carbonitriles, sulfonyl hydrazides and imides). The prepared compounds were evaluated for their in vitro VEGFR-2 inhibitory activity, their cytotoxicity on fifteen human cancer cell lines and their in vivo antiprostate cancer activity. The highest anti-VEGFR-2 activity was demonstrated by 6-acetyl-4-methoxy-7-methyl-5H-furo[3,2-g]chromen-5-one (3), which exhibited the same IC50 value as the reference drug sorafenib (2.00 × 10-3 μM). On the other hand, most of the synthesized compounds showed potent cytotoxicity against most of the tested cell lines, in particular, the carbonitrile series (4a,b and 5a,d) which exhibited the best activity with IC50 values ranging from 3.56 × 10-13 to 4.89 × 10-7 μM. Moreover, the imide series (15-17) showed the most significant in vivo antiprostate cancer activity. An in silico GOLD molecular docking study has been done to explore the binding mode of interaction of the furochromone and benzofuran derivatives to VEGFR-2 kinase, and to reveal the correlation between IC50 (μM) of the enzymatic inhibition of VEGFR-2 kinase and the GoldScore fitness for further therapeutic application. This journal is