62014-87-3

Basic information

• Product Name: helichrysetin
• Synonyms: helichrysetin;1-(2,4-Dihydroxy-6-methoxy-phenyl)-3-(4-hydroxy-phenyl)-propenone
• CAS NO: 62014-87-3
• Molecular Formula: C₁₆H₁₄O₅
• Molecular Weight: 286.282
• Mol File: 62014-87-3.mol

Chemical Properties

• Melting Point: 220 °C (decomp)
• Boiling Point: 532°C at 760 mmHg
• Flash Point: 201°C
• Appearance: /
• Density: 1.369g/cm³
• Vapor Pressure: 6.2E-12mmHg at 25°C
• Refractive Index: 1.684
• PKA: 7.08±0.40(Predicted)
• CAS DataBase Reference: helichrysetin(CAS DataBase Reference)
• NIST Chemistry Reference: helichrysetin(62014-87-3)
• EPA Substance Registry System: helichrysetin(62014-87-3)

Safety Data

• Hazardous Substances Data: 62014-87-3(Hazardous Substances Data)

Usage

Uses

Used in Cancer Treatment:
Helichrysetin is used as an anti-cancer agent for its ability to inhibit the growth of cancer cells and promote apoptosis in cancerous cells. This makes it a potential therapeutic option for various types of cancer.
Used in Neurodegenerative Disease Prevention:
Helichrysetin is used as a protective agent against neurodegenerative diseases due to its potential to shield the nervous system from degeneration, thereby helping to maintain cognitive function and prevent the progression of such diseases.
Used in Skin Health Applications:
Helichrysetin is used as an anti-inflammatory and wound healing agent in the treatment of skin conditions. Its properties can help reduce inflammation, promote skin repair, and improve overall skin health.

InChI:InChI=1/C16H14O5/c1-21-15-9-12(18)8-14(20)16(15)13(19)7-4-10-2-5-11(17)6-3-10/h2-9,17-18,20H,1H3/b7-4+

Upstream product

• 1034276-39-5 C₂₂H₂₆O₈ 
• 119136-14-0 2,4-bis(benzyloxy)-6-methoxyacetophenone 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 3602-54-8 4,6-dihydroxy-2-methoxyacetophenone 
• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 404597-94-0 1-(2-methoxy-4,6-bis(methoxymethoxy)phenyl)ethan-1-one 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 108-73-6 3,5-dihydroxyphenol 
• 1070781-94-0 (2E)-1-[2-methoxy-4,6-bis(2-propenyloxy)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one 
• 123-08-0 4-hydroxy-benzaldehyde 

Downstream Products

• 94103-36-3 (2E)-1-(2,4,6-trimethoxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one 
• 3420-72-2 2'-hydroxy-4,4',6'-trimethoxychalcone 
• 37308-75-1 flavokawain C 

Relevant articles and documents

Design, synthesis and biological evaluation of dimethyl cardamonin (DMC) derivatives as P-glycoprotein-mediated multidrug resistance reversal agents

Background: P-glycoprotein (P-gp) has been regarded as an important factor in the multidrug resistance (MDR) of tumor cells within the last decade, which can be solved by inhibiting P-gp to reverse MDR. Thus, it is an effective strategy to develop inhibitor of P-gp. Objective: In this study, the synthesis of a series of derivatives had been carried out by bioisosterism design on the basis of Dimethyl Cardamonin (DMC). Subsequently, we evaluated their reversal activities as potential P-glycoprotein (P-gp)-mediated Multidrug Resistance (MDR) agents. Methods: Dimethyl cardamonin derivatives were synthesized from acetophenones and the corresponding benzaldehydes in the presence of 40% KOH by Claisen-Schmidt reaction. Their cytotoxicity and reversal activities in vitro were assessed with MTT. Moreover, the compound B4 was evaluated by Doxorubicin (DOX) accumulation, Western blot and wound-healing assays deeply. Results and Discussion: The results showed that compounds B2, B4 and B6 had the potency of MDR reversers with little intrinsic cytotoxicity. Meanwhile, these compounds also demonstrated the capability to inhibit MCF-7 and MCF-7/DOX cells migration. Besides, the most compound B4 was selected for further study, which promoted the accumulation of DOX in MCF-7/DOX cells and inhibited the expressionof P-gp at protein levels. Conclusion: The above findings may provide new insights for the research and development of P-gp-mediated MDR reversal agents.

Synthesis of xanthohumol analogues and discovery of potent thioredoxin reductase inhibitor as potential anticancer agent

The selenoprotein thioredoxin reductases (TrxRs) are attractive targets for anticancer drugs development. Xanthohumol (Xn), a naturally occurring polyphenol chalcone from hops, has received increasing attention because of its multiple pharmacological activities. We synthesized Xn and its 43 analogues and discovered that compound 13n displayed the highest cytotoxicity toward HeLa cells (IC50 = 1.4 μM). Structure-activity relationship study indicates that the prenyl group is not necessary for cytotoxicity, and introducing electron-withdrawing group, especially on the meta-position, is favored. In addition, methylation of the phenoxyl groups generally improves the potency. Mechanistic study revealed that 13n selectively inhibits TrxR and induces reactive oxygen species and apoptosis in HeLa cells. Cells overexpressing TrxR are resistant to 13n insult, while knockdown of TrxR sensitizes cells to 13n treatment, highlighting the physiological significance of targeting TrxR by 13n. The clarification of the structural determinants for the potency would guide the design of novel potent molecules for future development.

In vitro and in vivo anti-Leishmania activity of polysubstituted synthetic chalcones

The in vitro screening of 43 polysubstituted chalcones against Leishmania amazonensis axenic amastigotes, led to the evaluation of 9 of them in a macrophage-infected model with the two other most infectious Leishmania species prevalent in Peru (L. braziliensis and L. peruviana). The five most active and selective chalcones were studied in vivo, resulting on the identification of two chalcones with high reduction parasite burden percentages.

COMPOUNDS, THEIR SYNTHESES, AND THEIR USES

Embodiments of the present invention provide compounds (such as Formula (I) compounds, Formula (II) compounds, and various embodiments thereof). Compositions comprising those compounds are also provided. Methods for their preparation are included. Also, uses of the compounds are included, such as administering and treating diseases (e.g., cancer and infections).

Natural and non-natural prenylated chalcones: Synthesis, cytotoxicity and anti-oxidative activity

A general strategy for the synthesis of 3′-prenylated chalcones was established and a series of prenylated hydroxychalcones, including the hop (Humulus lupulus L.) secondary metabolites xanthohumol (1), desmethylxanthohumol (2), xanthogalenol (3), and 4-methylxanthohumol (4) were synthesized. The influence of the A-ring hydroxylation pattern on the cytotoxic activity of the prenylated chalcones was investigated in a HeLa cell line and revealed that non-natural prenylated chalcones, like 2′,3,4′,5-tetrahydroxy-6′-methoxy-3′-prenylchalcone (9, IC50 3.2 ± 0.4 μM) as well as the phase 1 metabolite of xanthohumol (1), 3-hydroxyxanthohumol (8, IC50 2.5 ± 0.5 μM), were more active in comparison to 1 (IC50 9.4 ± 1.4 μM). A comparison of the cytotoxic activity of xanthohumol (1) and 3-hydroxyxanthohumol (8) with the non-prenylated analogs helichrysetin (12, IC50 5.2 ± 0.8) and 3-hydroxyhelichrysetin (13, IC50 14.8 ± 2.1) showed that the prenyl side chain at C-3′ has an influence on the cytotoxicity against HeLa cells only for the dihydroxylated derivative. This offers interesting synthetic possibilities for the development of more potent compounds. The ORAC activity of the synthesized compounds was also investigated and revealed the highest activity for compounds 12, 4′-methylxanthohumol (4), and desmethylxanthohumol (2), with 4.4 ± 0.6, 3.8 ± 0.4, and 3.8 ± 0.5 Trolox equivalents, respectively.

Synthesis and structural reassignment of (+)-epicalyxin F

We have established the structure of (+)-epicalyxin F through chemical synthesis. An acid-promoted rearrangement of synthetic benzopyran 6 led to the identification of the natural product as (3S,5S,7R)-epicalyxin F (22). Comparison with NMR spectra and op

Novel flavanone and chalcone glycosides from Clerondendron phlomidis (Verbenaceae)

Oven dried ground roots and flowers of Clerodendron phlomidis yield two flavonoidglycosides, ∞-L-Rhamnopyranosyl-(1→2)-∞-D-glucopyranosyl-7-O- naringin-4'-O-∞-D-glucopyranoside-5-methyl ether 1 and 4, 2', 4'-trihydroxy- 6'-methoxychalcone-4, 4'-∞-D-diglucoside 5.

Novel flavone and chalcone glycosides from clerodendron phlomidis (verbenaceae)

Photochemical investigation of oven dried ground roots and flowers of Clerodendron phlomidis lead to the isolation of two flavonoidglycosides, α-L-Rhamnopyranosyl-(1→2)-α-.D-Glucopyranosyl-7-0-naringin-4-0- α-D-glucopyranoside-5-methylether 1 and 4, 2′, 4′-trihydroxy-6′-methoxy chalcone-4,4′-α-D-diglucoside 5.Their structures have been established by spectroscopic studies . . .