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InChI:InChI=1/C16H16O5/c1-21-12-5-2-10(3-6-12)4-7-13(18)16-14(19)8-11(17)9-15(16)20/h2-3,5-6,8-9,17,19-20H,4,7H2,1H3

Upstream product

• 137225-57-1 (E)-3-(4-methoxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one 
• 480-43-3 5,7-dihydroxy-2-(4-methoxyphenyl)chroman-4-one 
• 108-73-6 3,5-dihydroxyphenol 
• 1929-29-9 3-(4-methoxyphenyl)propanoic acid 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 123-11-5 4-methoxy-benzaldehyde 
• 128837-25-2 1-[2,4-bis(ethoxymethoxy)-6-hydroxyphenyl]ethan-1-one 
• 18065-05-9 1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone 
• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 

Relevant academic research and scientific papers

An Efficient Regioselective Synthesis of 8-Formylhomoisoflavonoids with Neuroprotective Activity by Enhancing Autophagy

6-Formylisoophiopogonone B (7a) and 8-formylophiopogonone B (7b), two natural products isolated fromOphiopogonjaponicus, represent a subgroup of rare 6/8-formyl/methyl-homoisoflavonoid skeletons. Herein we report an efficient method for the synthesis of these formyl/methyl-homoisoflavonoids. The synthesized compounds were evaluated for their neuroprotective effects on the MPP+-induced SH-SY5Y cell injury model and showed marked activity. Exploration of the neuroprotective mechanisms of compound7bled to an increased expression of autophagy marker LC3-II and down-regulation of autophagy substrate p62/SQSTM1. Molecular docking studies showed that7bmay prevent the inhibition of the classic PI3K-AKT-mTOR signaling pathway by interfering with the human HSP90AA1.

Quinoid dihydrochalcone dicarbonyl glycoside compound with glucose on A ring, preparation method and neuroprotective activity thereof

The invention discloses a class of quinoid dihydrochalcone C-glycoside compounds with glucose on a ring A, a preparation method and anti-cerebral ischemia injury activity thereof, wherein the compoundhas a structure represented by a general formula (I). The preparation method of the compound comprises the following steps: (1) synthesizing a 2,4,6-trihydroxy dihydrochalcone compound; (2) synthesizing a 2,4,6-trihydroxy-3,5-diglucosyl dihydrochalcone C-glycoside compound; and (6) synthesizing a class of quinoid dihydrochalcone C-glycoside compound with glucose in the A ring. The compound disclosed by the invention is simple in preparation method and has a remarkable effect of resisting cerebral ischemia injury.

Base-catalyzed oxidative dearomatization of multisubstituted phloroglucinols: An easy access to C-glucosyl 3,5,6-trihydroxycyclohexa-2,4-dienone derivatives

An efficient and simple method for the protecting group-free synthesis of C-glucosyl 3,5,6-trihydroxycyclohexa-2,4-dienone has been firstly established. This method is compatible with various functional groups, such as benzyl and phenethyl groups, affording a range of C-glucosyl 3,5,6-trihydroxycyclohexa-2,4-dienone derivatives.

New homoisoflavonoid analogues protect cells by regulating autophagy

As a special group of naturally occurring flavonoids, homoisoflavonoids have been discovered as active components of several traditional Chinese medicines for nourishing heart and mind. In this study, twenty homoisoflavonoid analogues, including different substitution groups on rings A and B, as well as heteroaromatic B ring, were synthesized and evaluated for their cardioprotective and neuroprotective activities. In a H2O2-induced H9c2 cardiomyocytes injury assay, nine homoisoflavonoid analogues showed promising activities in the same level as the positive control, diazoxide. Six cardioprotective compounds with representative structure diversities were then evaluated for their neuroprotective effects on MPP+ induced SH-SY5Y cell injury model. Furthermore, autophagy inducing monodansylcadaverine (MDC) fluorescence staining methods and molecular docking studies indicated the action mechanism of these compounds may involve autophagy regulating via class I PI3K signaling pathway.

Targeting type 2 diabetes with c-glucosyl dihydrochalcones as selective sodium glucose co-transporter 2 (sglt2) inhibitors: Synthesis and biological evaluation

Inhibiting glucose reabsorption by sodium glucose co-transporter proteins (SGLTs) in the kidneys is a relatively new strategy for treating type 2 diabetes. Selective inhibition of SGLT2 over SGLT1 is critical for minimizing adverse side effects associated with SGLT1 inhibition. A library of C-glucosyl dihydrochalcones and their dihydrochalcone and chalcone precursors was synthesized and tested as SGLT1/SGLT2 inhibitors using a cell-based fluorescence assay of glucose uptake. The most potent inhibitors of SGLT2 (IC50 = 9.23 nM) were considerably weaker inhibitors of SGLT1 (IC50 = 10.19 μM). They showed no effect on the sodium independent GLUT family of glucose transporters, and the most potent ones were not acutely toxic to cultured cells. The interaction of a C-glucosyl dihydrochalcone with a POPC membrane was modeled computationally, providing evidence that it is not a pan-assay interference compound. These results point toward the discovery of structures that are potent and highly selective inhibitors of SGLT2.

Dihydrochalcones: Evaluation as novel radical scavenging antioxidants

Dihydrochalcones are a family of bicyclic flavonoids, defined by the presence of two benzene rings joined by a saturated three carbon bridge. In the present study, we systematically examined the antioxidant activities of dihydrochalcones against the stable free radical (1,1-diphenyl-2-picrylhydrazyl) and lipid peroxidation in the erythrocyte membrane. All dihydrochalcones exhibited higher antioxidant activities than the corresponding flavanones. The 1H NMR analysis indicated that the active dihydrochalcone has a time-averaged conformation in which the aromatic A ring is orthogonal to the carbonyl group, while the inactive dihydrochalcone such as 2′-O-methyl-phloretin has a strongly hydrogen-bonded phenolic hydroxyl group, suggestive of a coplanar conformation. A hydroxyl group at the 2′-position of the dihydrochalcone A ring, newly formed by reduction of the flavanone C ring, is an essential pharmacophore for its radical scavenging potential.

Synthesis of 2′ 4′-dihydroxy-6′-methoxy-3, 4-methylenedioxydihydro chalcone and 2′, 4,′6′-trihydroxy-4-methoxydihydrochalcone

The world of nature abounds in organic compounds of every conceivable structural classes. Every year Organic Chemists isolate and characterize a lot of compound from medicinal plants all over the World. The isolation and characterization of 2′, 4′-dihydroxy-6′-methoxy-3, 4-methylenedioxy dihydrochalcone reported in 1990 from the bark of Iryanthera sagotiana (Benth.) Warb. In 1997 the isolation and characterization of 2′, 4′, 6′-trihydroxy-4-methoxydihydrochalcone from the woody part and the ripe fruit of Iryanthera Laevis reported. The syntheses of these two dihydrochalcones have not been reported yet. In this paper we wish to report the syntheses of the above two dihydrochalcones by Claisen - Schmidt reaction and other subsequent steps.

PHENOLIC CONSTITUENTS FROM SEEDS OF COPTIS JAPONICA VAR. DISSECTA

In addition to coumarinolignans (cleomiscosin A and aquillochin) and 7,4'-dihydroxy-5-methoxyflavanone, a new dihydrochalcone, 2',4,4'-trihydroxy-6'-methoxydihydrochalcone, was isolated from the seeds of Coptis japonica var. dissecta.The structure of the dihydrochalcone was confirmed by comparison with relevant synthetic samples. - Key Word Index: Coptis japonica var. dissecta; Ranunculaceae; cleomiscosin A; aquillochin; 2',4,4'-trihydroxy-6'-methoxydihydrochalcone; 7,4'-dihydroxy-5-methoxyflavanone.

Process for treating inflammation

A process for treating inflammation locally or topically by administering a compound of the formula: STR1 wherein M and M' are hydrogen, hydroxy, halogen, lower alkyl of from 1 to 3 carbon atoms, lower alkoxy of from 1 to 3 carbon atoms; NH2, RNH, R'2 N where R is lower alkyl of from 1 to 3 carbon atoms or lower acyl of from 1 to 3 carbon atoms and R' is lower alkyl of from 1 to 3 carbon atoms; X, Y and Z are hydrogen, hydroxy, halogen, lower alkoxy of from 1 to 3 carbon atoms or lower acyloxy of from 1 to 6 carbon atoms, in association with appropriate pharmaceutical carriers.