10379-74-5

Upstream product

• 471-53-4 enoxolone 
• 152832-24-1 C₄₂H₆₆O₁₃ 
• 67-56-1 methanol 
• 83896-44-0 glycyrrizhin 
• 186581-53-3 diazomethane 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 10527-59-0 methyl 3β-hydroxy-18β-olean-12-en-30-oate 
• 10379-73-4 acetoxolone 
• 74-88-4 methyl iodide 
• 10301-74-3 3β-acetoxy-11-oxo-olean-12-en-30-oic acid methyl ester 
• 471-53-4 3α-hydroxy-18β-GA 
• 1449-05-4 3β-hydroxy-18β-GA 
• 471-53-4 3α-hydroxy-18α-GA 
• 471-53-4 18β-glycyrrhetinic acid 

Downstream Products

• 10301-75-4 18ξ-Oleanadien-(2.12)-on-(11)-30-saeure-methylester 
• 5092-06-8 apo-allo-18β-glycyrrhetinic-30-methyl ester 
• 6471-55-2 3-Isopropyliden-11-oxo-4.23.24-trisnor-18αH-Δ¹²-oleanen-30-saeure-methylester 
• 125897-95-2 C₆₀H₇₈O₁₀ 
• 125897-95-2 C₆₀H₇₈O₁₀ 
• 138268-03-8 C₆₀H₇₆O₁₁ 
• 138268-03-8 C₆₀H₇₆O₁₁ 
• 34096-83-8 1-(18β-glycyrrhet-3-yl)-β-D-glucopyranuronic acid 
• 182423-85-4 C₅₀H₇₀O₁₂ 
• 182423-83-2 C₅₀H₇₀O₁₂ 
• 187218-59-3 C₅₃H₇₁FO₉ 
• 187218-57-1 C₅₃H₇₁FO₉ 
• 10301-74-3 3β-acetoxy-11-oxo-olean-12-en-30-oic acid methyl ester 
• 52189-19-2 trans-cyclohexane-1,2-dicarboxylic acid mono-((3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-methoxycarbonyl-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picen-3yl) ester 

Relevant academic research and scientific papers

Photoinduced Deoxygenative Borylations of Aliphatic Alcohols

A photochemical method for converting aliphatic alcohols into boronic esters is described. Preactivation of the alcohol as a 2-iodophenyl-thionocarbonate enables a novel Barton–McCombie-type radical deoxygenation that proceeds efficiently with visible light irradiation and without the requirement for a photocatalyst, a radical initiator, or tin or silicon hydrides. The resultant alkyl radical is intercepted by bis(catecholato)diboron, furnishing boronic esters from a diverse range of structurally complex alcohols.

Synthesis and antiproliferative activity of novel A-ring cleaved glycyrrhetinic acid derivatives

A series of new glycyrrhetinic acid derivatives was synthesized via the opening of its ring A along with the coupling of an amino acid. The antiproliferative activity of the derivatives was evaluated against a panel of nine human cancer cell lines. Compound 17 was the most active compound, with an IC50 of 6.1 μM on Jurkat cells, which is 17-fold more potent than that of glycyrrhetinic acid, and was up to 10 times more selective toward that cancer cell line. Further biological investigation in Jurkat cells showed that the antiproliferative activity of compound 17 was due to cell cycle arrest at the S phase and induction of apoptosis.

Modification, Antitumor Activity, and Targeted PPARγStudy of 18β-Glycyrrhetinic Acid, an Important Active Ingredient of Licorice

Licorice is a traditional Chinese medicine, which is often used as sweetener and cosmetic ingredients in food and pharmaceutical industries. Among them, glycyrrhetic acid is one of the most important agents. Studies have shown that glycyrrhetic acid exhibited antitumor activities as PPARγagonist. However, the limited number of PPARγglycyrrhetinic agonists and their high toxicity greatly limit the design based on the structure. Therefore, clarifying the binding mode between PPARγand small molecules, we focused on the introduction of a natural active piperazine skeleton in the position of glycyrrhetinic acid C-3. According to the Combination Principle and the Structure-Based Drug Design, 19 glycyrrhetic acid derivatives were designed and synthesized as potential PPARγagonists. Compounds 4c and 4q were screened as high-efficiency and low-toxicity lead compounds.

Synthesis and Hypoglycemic Activity of 11-Deoxoglycyrrhetic Acid Derivatives

New 2-hydroxy-1-en-3-ones were prepared by oxidation of 11-deoxoglycyrrhetic acid 3-oxo-derivatives and its 30-methyl ester by atmospheric oxygen in the presence of t-BuOK. 2-Hydroxy-3-oxo-18βH-olean-1,12-dien-30-oic acid at a dose of 50 mg/kg reduced the blood glucose concentration in the alloxan-induced rat diabetes mellitus model by 34% compared with the control after 120 min.

Synthesis of 2-Cyanoethoxy and 2-(1H-Tetrazol-5-yl)ethoxy Derivatives of Glycyrrhetic Acid Methyl Ester

Cyanoethylation of natural glycyrrhetic acid methyl ester gave the corresponding 3β-O-(2-cyanoethyl) derivative which was treated with sodium azide to obtain a novel tetrazolyl derivative of biologically active triterpenoid, methyl 3β-[2-(1H-tetrazol-5-yl)ethoxy]-11-oxoolean-12-en-30-oate.

First Occurrence of a Furano-glycyrrhetinoate and Its Cytotoxicity

(18α)-Glycyrrhetinic acid (4) was prepared from (18β)-glycyrrhetinic acid (1), and the cytotoxicity of some derivatives was investigated by photometric SRB assays employing several human tumor cell lines. In summary, (18β)-1 is slightly more cytotoxic than its (18α) epimer 4, but its cytotoxicity is negligible. Higher cytotoxicity was observed for the esters 2 and 5 and for the 3-O-acetylated esters 3 and 6. Cytotoxicity was improved dramatically when the hydroxyl group at position C-3 was replaced by an amino moiety. SeO2 oxidations gave access to a novel furano-glycyrrhetinoate 15. Interestingly, its seleno analog 16 is approximately five to six times less cytotoxic for the tumor cell lines tested, and tumor/non-tumor selectivity is lost upon replacement of the oxygen by a selenium substituent.

A Simple Method for Preparation of 18α-Glycyrrhetinic Acid and Its Derivatives

Treatment of 18β-glycyrrhizic acid with a methanolic solution of HCl resulted in 1:1 mixture of methyl esters of 18α- and 18β- glycyrrhetinic acids. Benzoylation of the mixture led to methyl esters of 3-benzoyl-18α-glycyrrhetinic acid and 3-benzoyl-18β-glycyrrhetinic acid, which were separated by chromatography on silica gel. 18α- Glycyrrhetinic acid was prepared by alkaline hydrolysis of methyl 3-benzoyl-18α-glycyrrhetinate and was further used for the syntheses of 3-keto-18α-glycyrrhetinic acid and methyl esters of 18α- glycyrrhetinic acid and 3-keto-18α-glycyrrhetinic acid.

Synthesis of fan-shaped C3 molecule with three glycyrrhetinic acid units and self-assembly properties

A novel fan-shaped C3 molecule with three glycyrrhetinic acid units was synthesized via "click chemistry" in high yield and the self-assembly characteristics were studied in different mixed solvents.

Sulfamates of methyl triterpenoates are effective and competitive inhibitors of carbonic anhydrase II

Carbonic anhydrase II, belonging to one of the most important enzyme groups of the human body, is a well-studied isozyme from the family of the carbonic anhydrases. Since it is involved in several physiological processes, it has been a pharmaceutical target for many years. In this study we synthesized a number of sulfamates derived from pentacyclic methyl triterpenoates, and we demonstrate their potential as carbonic anhydrase II inhibitors using the well-established photometric 4-nitrophenyl acetate assay. Inhibition constants, as an indicator of their inhibition strength, were in the micromolar range; one compound (10, methyl (3β) 3-(aminosulfonyloxy)-oleanoate) showed a Ki value as low as 0.3 μM. This Ki value is comparable to that of acetazolamide which is a potent carbonic anhydrase inhibitor and a drug for the treatment of glaucoma.

Development of glycyrrhetinic acid-modified stealth cationic liposomes for gene delivery

The glycyrrhetinic acid-modified stealth cationic liposomes (GA-PEG-CLs) loaded with pDNA (GA-PEG-CLPs) were developed and found to transfect human hepatocellular carcinoma cell line HepG2 with high efficiency. GA-PEG-CLs were comprised of DOTAP, cholesterol (Chol) and glycyrrhetinic acid-polyethyleneglycol-cholesterol conjugate (GA-PEG-Chol). Agarose gel electrophoresis revealed that 5% GA-PEG-CLs constituted by DOTAP/Chol/GA-PEG-Chol at molar ratio of 50:45:5 could completely entrap pDNA at a lower liposomes/pDNA weight ratios of 4:1 (N/P ratio: 1.14). Compared to ordinary cationic liposomes (CLs), steric cationic liposomes (PEG-CLs) and 1% GA-PEG-CLs made from DOTAP/Chol/MPEG2000-Chol/GA-PEG-Chol at molar ratio of 50:45:4:1, 5% GA-PEG-CLs were found to possess the highest transfection efficiency as gene vectors in serum-free or serum-containing medium in PKCα over-expressed HepG2 cells but no significance difference in human embryonic kidney cell line HEK 293. Additionally, 5% GA-PEG-CLs have the lowest cytotoxicity on human normal hepatocyte cell line L02. The competitive inhibition experiments mediated by GA were carried out in HepG2 cells, which demonstrated that GA-PEG-CLs could deliver selectively pDNA to hepatoma cells by the targeting moiety GA. In conclusion, GA-PEG-CLs containing 5% GA-PEG-Chol might be one of the most potential gene vectors as hepatoma targeting therapy.