6184-16-3

Usage

Uses

1. Used in Pharmaceutical Industry:
(2S,4aR,6aS,6aS,6bR,8aS,12aS,14bS)-2,4a,6a,6b,9,9,12a-heptamethyl-10,13-dioxo-1,3,4,5,6,6a,7,8,8a,11,12,14b-dodecahydropicene-2-carboxylic acid can be used as a pharmaceutical compound for the development of new drugs. Its unique structure may allow it to interact with specific biological targets, potentially leading to the creation of novel therapeutic agents.
2. Used in Chemical Research:
This complex molecule can be utilized in chemical research to study its properties, reactivity, and potential applications in various chemical reactions. Its unique structure may provide insights into new reaction mechanisms or catalysis processes.
3. Used in Material Science:
The unique structure of (2S,4aR,6aS,6aS,6bR,8aS,12aS,14bS)-2,4a,6a,6b,9,9,12a-heptamethyl-10,13-dioxo-1,3,4,5,6,6a,7,8,8a,11,12,14b-dodecahydropicene-2-carboxylic acid may offer potential applications in the development of new materials with specific properties, such as improved strength, flexibility, or chemical resistance.
4. Used in Environmental Applications:
(2S,4aR,6aS,6aS,6bR,8aS,12aS,14bS)-2,4a,6a,6b,9,9,12a-heptamethyl-10,1 3-dioxo-1,3,4,5,6,6a,7,8,8a,11,12,14b-dodecahydropicene-2-carboxylic a cid may also find use in environmental applications, such as the development of new methods for pollution control or the creation of environmentally friendly materials.
5. Used in Cosmetics Industry:
Due to its unique chemical properties, (2S,4aR,6aS,6aS,6bR,8aS,12aS,14bS)-2,4a,6a,6b,9,9,12a-heptamethyl-10,13-dioxo-1,3,4,5,6,6a,7,8,8a,11,12,14b-dodecahydropicene-2-carboxylic acid could potentially be used in the development of new cosmetic products with specific benefits, such as improved skin hydration or anti-aging properties.

InChI:InChI=1/C30H44O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21,23H,8-15,17H2,1-7H3,(H,33,34)/t19-,21+,23-,26-,27+,28+,29-,30-/m1/s1

Upstream product

• 1405-86-3 glycyrrhizin 
• 1449-05-4 3β-hydroxy-18β-GA 
• 471-53-4 3β-hydroxy-18α-GA 
• 410097-37-9 18β-glycyrrhetinic acid 
• 471-53-4 enoxolone 

Downstream Products

• 1449-05-4 3β-hydroxy-18β-GA 
• 471-53-4 3α-hydroxy-18β-GA 
• 471-53-4 3α-hydroxy-18α-GA 
• 471-53-4 3β-hydroxy-18α-GA 
• 1477-44-7 methyl 3α-hydroxy-18α-glycyrrhetate 
• 1477-44-7 methyl 3α-hydroxy-18β-glycyrrhetate 

Relevant academic research and scientific papers

Synthesis and biological evaluation of pentacyclic triterpenoid derivatives as potential novel antibacterial agents

A series of ursolic acid (UA), oleanolic acid (OA) and 18β-glycyrrhetinic acid (GA) derivatives were synthesized by introducing a range of substituted aromatic side-chains at the C-2 position after the hydroxyl group at C-3 position was oxidized. Their antibacterial activities were evaluated in vitro against a panel of four Staphylococcus spp. The results revealed that the introduction of aromatic side-chains at the C-2 position of GA led to the discovery of potent triterpenoid derivatives for inhibition of both drug sensitive and resistant S. aureus, while the other two series derivatives of UA and OA showed no significant antibacterial activity even at high concentrations. In particular, GA derivative 33 showed good potency against all four Staphylococcus spp. (MIC = 1.25–5 μmol/L) with acceptable pharmacokinetics properties and low cytotoxicity in vitro. Molecular docking was also performed using S. aureus DNA gyrase to rationalize the observed antibacterial activity. This series of GA derivatives has strong potential for the development of a new type of triterpenoid antibacterial agent.

Indole-and pyrazole-glycyrrhetinic acid derivatives as ptp1b inhibitors: Synthesis, in vitro and in silico studies

Regulating insulin and leptin levels using a protein tyrosine phosphatase 1B (PTP1B) inhibitor is an attractive strategy to treat diabetes and obesity. Glycyrrhetinic acid (GA), a triter-penoid, may weakly inhibit this enzyme. Nonetheless, semisynthetic derivatives of GA have not been developed as PTP1B inhibitors to date. Herein we describe the synthesis and evaluation of two series of indole-and N-phenylpyrazole-GA derivatives (4a–f and 5a–f). We measured their inhibitory activity and enzyme kinetics against PTP1B using p-nitrophenylphosphate (pNPP) assay. GA derivatives bearing substituted indoles or N-phenylpyrazoles fused to their A-ring showed a 50% inhibitory concentration for PTP1B in a range from 2.5 to 10.1 μM. The trifluo-romethyl derivative of indole-GA (4f) exhibited non-competitive inhibition of PTP1B as well as higher potency (IC50 = 2.5 μM) than that of positive controls ursolic acid (IC50 = 5.6 μM), claramine (IC50 = 13.7 μM) and suramin (IC50 = 4.1 μM). Finally, docking and molecular dynamics simulations provided the theoretical basis for the favorable activity of the designed compounds.

Glycyrrhetinic acid derivative Z-type isomer and preparation method thereof

The invention discloses a glycyrrhetinic acid derivative Z-type isomer and a preparation method thereof. The method comprises the following steps: dissolving a glycyrrhetinic acid derivative E-type isomer in a mixed solvent of an organic solvent and water, and stirring under 254-380nm light to obtain the glycyrrhetinic acid derivative Z-type isomer. According to the method, through a green and healthy mode, no catalyst is used, and isomerization from the glycyrrhetinic acid derivative E-type isomer to the glycyrrhetinic acid derivative Z-type isomer is caused only in the mixed solution of the organic solvent and water by utilizing distortion and relaxation of a central double bond of the isomer under induction of a clean light energy source. The glycyrrhetinic acid derivative E-type isomer provided by the invention has relatively good stability and antibacterial property.

Structurally modified glycyrrhetinic acid derivatives as anti-inflammatory agents

With the aim of finding new anti-inflammatory drugs, a series of new Glycyrrhetinic acid derivatives (1–34) have been designed and synthesized by structural modification, and their anti-inflammatory activities in vitro have been evaluated. The anti-inflammatory activities assay demonstrated that compound 5b suppressed the expression of pro-inflammatory cytokines including IL-6, TNF-α and NO, it also suppressed the expression of iNOS and COX-2 in LPS-induced RAW264.7 cells in a dose-dependent manner. Additionally, western blot results indicated that the suppressing effect of compound 5b on pro-inflammatory cytokines were correlated with the suppression of NF-κB and MAPK signaling pathways. The results attained in this study indicated that compound 5b had the potential to be developed into an anti-inflammation agent and it may be applied to the prevention and treatment of inflammatory diseases.

A versatile tailoring tool for pentacyclic triterpenes of Penicillium griseofulvum CICC 40293

In the biosynthetic pathway of pentacyclic triterpenes (PTs), tailoring reactions can produce a wide range of end products from a small number of common scaffolds and the microbial transformation has also been established as an alternative technique for this purpose. In this study, we explored the tailoring reactions involved in the microbial transformation of pentacyclic triterpenes by Penicillium griseofulvum CICC 40293. Preparative biotransformation of eight different PTs from three scaffolds resulted in the isolation of thirteen metabolites. The structures of metabolites were elucidated by HR-ESI-MS, 1D, and 2D NMR spectroscopy. We discovered the highly efficient regio- and stereo-selective hydroxylation of inactivated sp3 CH2 and CH3 on the position of 2α, 7β, 15α, 21β, 23(angular methyl), and 30?COOH glycosylation, this versatile tailoring system for PTs would provide an effective method for expanding their structural diversities. In addition, all compounds were subjected to the bioassay on the model of lipopolysaccharide (LPS)-stimulated RAW 264.7 cells to evaluate their anti-inflammatory activity through nitric oxide (NO) inhibition activity. Compounds 2a and 5a exhibited excellent NO inhibitory activity with IC50 values of 8.35 ± 2.81 μM and 19.60 ± 4.25 μM, respectively.

Synthesis and antitumor effects of novel 18β-glycyrrhetinic acid derivatives featuring an exocyclic α,β-unsaturated carbonyl moiety in ring A

A series of novel 18β-glycyrrhetinic acid (GA) derivatives featuring an exocyclic α,β-unsaturated carbonyl moiety in ring A were synthesized and evaluated for their antitumor activities. Compounds 5c and 5l showed stronger cytotoxicity than other compounds and reported GA analogue CDODA-Me (methyl 2-cyano-3,11-dioxo-18β-olean-1,12-dien-30-oate). 5c and 5l induced apoptosis in cancer cells accompanying with c-Flip reduction and Noxa induction, associated with decreased HDAC3 expression and increased acetylation of H3. 5l displayed better stability properties than 5c and CDODA-Me in microsomes and plasma, 5l also showed favorable pharmacokinetic profiles and inhibited tumor growth in mice. Compound 5l represents a new type of GA derivatives with improved antitumor activity.

Pentacyclic triterpenoid glycyrrhetinic acid derivative as well as preparation method and application thereof

The invention discloses a pentacyclic triterpenoid glycyrrhetinic acid derivative which has a structure as shown in a general formula 1 or a formula 7 in the specification, wherein each substituent isdefined in detail in the specification. The invention also discloses application of the pentacyclic triterpenoid glycyrrhetinic acid derivative in preparation of anti-HCV drugs. Huh7 cytotoxic activity results show that the pentacyclic triterpenoid glycyrrhetinic acid derivative is low in cytotoxicity and has research value. In-vitro anti-HCVcc result shows that glycyrrhetinic acid has relativelyweak anti-HCVcc activity, but the pentacyclic triterpenoid glycyrrhetinic acid derivative has relatively good anti-HCV activity.

Nitrogenous heterocyclic glycyrrhetinic acid derivatives, and preparation method and anti-influenza A virus application thereof

The invention discloses nitrogenous heterocyclic glycyrrhetinic acid derivatives, and a preparation method and an anti-influenza A virus application thereof. The glycyrrhetinic acid derivatives comprise a nitrogen heterocyclic ring. A series of the glycyrrhetinic acid derivatives with anti-IAV activity are synthesized. The glycyrrhetinic acid derivatives have strong inhibitory activity on the influenza A virus (IAV), and have obviously stronger inhibitory activity on the influenza A virus than a common positive drug ribavirin, so that the glycyrrhetinic acid derivatives can be used for preparing anti-IAV drugs, and have no side effects.

Drug design method based on natural product, pentacyclic triterpenoid compound, preparation method and application of pentacyclic triterpenoid compound

The invention discloses a drug design method based on a natural product, a pentacyclic triterpenoid compound, and a preparation method and application of the pentacyclic triterpenoid compound. The design method comprises the following steps: (1) acquiring template molecules; (2) selecting a natural product which is similar to the template structure in a threshold range and has the specific biological activity as an alternative reference molecule set; (3) selecting one or more reference molecules from the reference molecule set, and comparing with the template molecule to obtain different active functional groups; and constructing the active functional groups with difference on a molecular skeleton which is commonly possessed by the template molecule and the reference molecule. According tothe invention, a cheap lead compound which is easy to obtain in quantity is successfully designed to replace triterpene molecules by taking the biological content of a plant triterpene natural product in a host plant and a numerical value similar to the structures of tripterine and a crosolic acid compound as screening conditions; experiments prove that the traditional Chinese medicine composition has obvious physiological activity of resisting inflammation and metabolic syndrome caused by chronic inflammation.

Nucleophilic (Radio)Fluorination of Redox-Active Esters via Radical-Polar Crossover Enabled by Photoredox Catalysis

We report a redox-neutral method for nucleophilic fluorination of N-hydroxyphthalimide esters using an Ir photocatalyst under visible light irradiation. The method provides access to a broad range of aliphatic fluorides, including primary, secondary, and tertiary benzylic fluorides as well as unactivated tertiary fluorides, that are typically inaccessible by nucleophilic fluorination due to competing elimination. In addition, we show that the decarboxylative fluorination conditions are readily adapted to radiofluorination with [18F]KF. We propose that the reactions proceed by two electron transfers between the Ir catalyst and redox-active ester substrate to afford a carbocation intermediate that undergoes subsequent trapping by fluoride. Examples of trapping with O- and C-centered nucleophiles and deoxyfluorination via N-hydroxyphthalimidoyl oxalates are also presented, suggesting that this approach may offer a general blueprint for affecting redox-neutral SN1 substitutions under mild conditions.