564-16-9

Usage

Uses

Used in Pharmaceutical Applications:
11-Deoxo-18beta-glycyrrhetic acid is used as a therapeutic agent for various diseases due to its anti-inflammatory, anti-cancer, and anti-viral properties. It has shown promise in the treatment of skin disorders, viral infections, and cancer, making it a potential candidate for pharmaceutical development.
Used in Cosmetic Applications:
In the cosmetic industry, 11-Deoxo-18beta-glycyrrhetic acid is used as an active ingredient for its potential skin health benefits. Its anti-inflammatory properties may contribute to soothing and healing effects on the skin, making it suitable for inclusion in skincare products.
Used in Hepatoprotective Applications:
11-Deoxo-18beta-glycyrrhetic acid is used as a hepatoprotective agent for its potential in treating liver diseases. Its ability to protect the liver from damage and support liver function makes it a promising candidate for liver health supplements and treatments.
Overall, 11-Deoxo-18beta-glycyrrhetic acid's diverse pharmacological properties and potential therapeutic applications have garnered significant interest in various industries, including pharmaceutical, cosmetic, and hepatoprotective fields.

InChI:InChI=1/C30H48O3/c1-25(2)21-10-13-30(7)22(28(21,5)12-11-23(25)31)9-8-19-20-18-27(4,24(32)33)15-14-26(20,3)16-17-29(19,30)6/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21+,22-,23+,26-,27-,28+,29-,30-/m1/s1

Upstream product

• 471-53-4 enoxolone 
• 83896-44-0 glycyrrizhin 
• 77397-93-4 11-hydroxymethyl-4,4,6a,6b,8a,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-eicosahydro-picene-3,14-diol 
• 657401-74-6 Acetic acid (3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bR)-11-(tert-butyl-dimethyl-silanyloxymethyl)-4,4,6a,6b,8a,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picen-3-yl ester 
• 657401-73-5 (3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bR)-11-(tert-Butyl-dimethyl-silanyloxymethyl)-4,4,6a,6b,8a,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picen-3-ol 
• 6813-59-8 11-hydroxymethyl-4,4a,6a,6b,8a,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-eicosahydropicen-3-ol 
• 657401-69-9 acetic acid 11-formyl-4,4a,6a,6b,8a,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-eicosahydropicen-3-yl ester 
• 22477-77-6 acetic acid 11-hydroxymethyl-4,4a,6a,6b,8a,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-eicosahydropicen-3-yl ester 
• 53402-18-9 3β-acetoxy-11-dioxyglycyrrhetic acid 

Downstream Products

• 441759-68-8 diphenylmethyl 11-deoxo-18β-glycyrrhetinate 
• 471-53-4 enoxolone 
• 1084889-58-6 (N-cyclohexyl)-11-deoxyglycyrrhetinic acid amide 
• 1375692-97-9 (4-(trifluoromethyl)benzyl) 3-O-(4-oxo-4H-1-benzopyran-2-carbonyl)-olean-12-en-30-oate 
• 1375693-06-3 (4-bromo-2-fluorobenzyl) 3-O-(4-oxo-4H-1-benzopyran-2-carbonyl)-olean-12-en-30-oate 
• 1375692-79-7 (4-(trifluoromethyl)benzyl) 3β-hydroxy-olean-12-en-30-oate 

Relevant academic research and scientific papers

Synthesis, anti-microbial and anti-inflammatory activities of 18β-glycyrrhetinic acid derivatives

Thirteen 18β-glycyrrhetinic acid (GA) derivatives were obtained by reduction at C-11 position, oxidation at C-3 position and condensation at C-2 position of GA. Anti-microbial activity evaluation indicated that compounds 04, 05, 10, 13 and 14 showed more

Microbial transformation of glycyrrhetinic acid derivatives by Bacillus subtilis ATCC 6633 and Bacillus megaterium CGMCC 1.1741

Glycyrrhetinic acid (GA), the major bioactive pentacyclic triterpene aglycone of licorice root, was known to play a vital role in anti-ulcer, anti-depressant, anti-inflammatory, and anti-allergic. In this study, we semi-synthesized five GA derivatives by a series of chemical reactions. They were selected as substrates for the biotransformation and yielded thirteen metabolites by Bacillus subtilis ATCC 6633 and Bacillus megaterium CGMCC 1.1741. Their structures were identified on the basis of extensive spectroscopic methods and nine of them were found for the first time. Two main types of reactions, regio- and stereo-selective hydroxylation and glycosylation, especially in the unactivated C-H bonds including C-11, C-19 and C-27, were observed in the biotransformation process, which greatly expand the chemical diversities of GA derivatives. All compounds were tested for their inhibitory effects on nitric oxide (NO) generation in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells. Among them, olean-12-ene-3β,7β,15α,19α,30-pentol (16) and olean-12-ene-3β,7β,15α,27,30-pentol (17) showed significant inhibitory effect with IC50 values of 0.64 and 0.07 μM, respectively.

11-deoxyglycyrrhetinic acid derivatives as well as preparation method and application thereof

The invention belongs to the technical field of drug synthesis, and in particular relates to 11-deoxyglycyrrhetinic acid derivatives as well as a preparation method and application thereof. The invention provides the 11-deoxyglycyrrhetinic acid derivative

Glycyrrhetinic acid derivative synthesis and use thereof

The invention designs and synthetizes a lead compound by using a glycyrrhetinic acid derivative as a carrier and being connected with norcantharidin and a derivative thereof through ester bonds, the obtained lead compound expects to have the advantages of having liver targeting action, prolonging action time, reducing toxic and side effects and improving the curative effect of resisting liver cancer, and a model compound is provided for the research of a liver targeting medicine for the liver cancer. Firstly, two positions of C11 and C30 in glycyrrhetinic acid molecules are reduced and synthetized respectively, methyl ester is chemically modified into glycyrrhetinic acid (GA) and 18 alpha-glycyrrhetinic acid as well as a derivative thereof, the glycyrrhetinic acid (GA) and 18 alpha-glycyrrhetinic acid as well as the derivative thereof are used as framework molecules, through a series of reactions, the framework molecules and the norcantharidin (NCTD) as well as a derivative thereof are condensed to form ester as a prodrug, a cell activity screening test is performed on 5 object compounds, 13 object compounds in 3 series are synthetized, and structural characterization is performed on a carbon spectrum, a hydrogen spectrum and a mass spectrum; the influence of different concentrations of 5 object compounds on HepG2 cell proliferation of the liver cancer is inspected by a method, results show that inhibitory action presents time-dose dependence, and the suppression ratio of 14 mu g/mL is the highest.

Conjugates of 18β-glycyrrhetinic acid derivatives with 3-(1H-benzo[d]imidazol-2-yl)propanoic acid as Pin1 inhibitors displaying anti-prostate cancer ability

Twenty-six conjugates of 18β-glycyrrhetinic acid derivatives with 3-(1H-benzo[d]imidazol-2-yl)propanoic acid were designed and synthesized as Pin1 inhibitors. Most of these semi-synthetic compounds showed improved Pin1 inhibitory activity and anti-proliferative effects against prostate cancer cells as compared to 3-(1H-benzo[d]imidazol-2-yl)propanoic acid and GA. Compounds 10a and 12i were the most potent to inhibit growth of prostate cancer PC-3 with GI50 values of 7.80 μM and 3.52 μM, respectively. The enzyme inhibition ratio of nine compounds at 10 μM was over 90%. Structure-activity relationships indicated that both appropriate structure at ring C of GA and suitable length of linker between GA skeleton and benzimidazole moiety had significant impact on improving activity. Western blot assay revealed that 10a decreased the level of cell cycle regulating protein cyclin D1. Thus, these compounds might represent a novel anti-proliferative agent working through Pin1 inhibition.

Pentacyclic triterpenoid and application thereof as human intestine carboxylesterase inhibitor

The invention provides pentacyclic triterpenoid and application thereof as a human intestine carboxylesterase inhibitor and belongs to the technical field of biological medicine. The pentacyclic triterpenoid has the advantages that the pentacyclic triterpenoid having a 11-deoxy-glycyrrhetinic acid framework structure can effectively and selectively inhibit the activity of human intestine carboxylesterase subtype 2 so as to increase the bioavailability of orally-taken prodrugs and reduce the ester uptake of the intestinal tract; in addition, the pentacyclic triterpenoid can alleviate the delayed diarrhea caused by irinotecan; in-vitro activity determination discovers that the pentacyclic triterpenoid's IC50 for inhibiting the human carboxylesterase 2 can reach 0.02 micromole, and the ratio of the IC50 for inhibiting human carboxylesterase 1 to the IC50 for inhibiting the human carboxylesterase 2 can reach 1020; the pentacyclic triterpenoid is good in safety, simple in preparation process, high in yield, promising in application prospect, and the like.

Synthesis and biological evaluation of novel hydrogen sulfide releasing glycyrrhetic acid derivatives

A series of hybrids, which are composed of glycyrrhetic acid (GA) and slowly hydrogen sulfide-releasing donor ADT-OH, were designed and synthesized to develop anticancer and anti-inflammatory agents. Most of the compounds, whose inhibitory rates were comparable to or higher than those of GA and aspirin, respectively, significantly inhibited xylene-induced ear edema in mice. Especially, compound V 4 exhibited the most potent inhibitory rate of 60.7%. Furthermore, preliminary structure–activity relationship studies demonstrated that 3-substituted GA derivatives had stronger anti-inflammatory activities than the corresponding 3-unsubstituted GA derivatives. In addition, anti-proliferative activities of compounds V1?9 were evaluated in three different human cancer cell lines. Compound V4 showed the most high potency against all three tumor cell lines with IC50 values ranging from 10.01 μM in Hep G2 cells to 17.8 μM in MDA-MB-231 cells, which were superior to positive GA.

18β-Glycyrrhetinic Acid Derivatives Possessing a Trihydroxylated A Ring Are Potent Gram-Positive Antibacterial Agents

The oleanane-type triterpene 18β-glycyrrhetinic acid (1) was modified chemically through the introduction of a trihydroxylated A ring and an ester moiety at C-20 to enhance its antibacterial activity. Compounds 22, 23, 25, 28, 29, 31, and 32 showed more potent inhibitory activity against Streptomyces scabies than the positive control, streptomycin. Additionally, the inhibitory activity of the most potent compound, 29, against Bacillus subtilis, Staphylococcus aureus, and methicillin-resistant Staphylococcus aureus was greater than that of the positive controls. The antibacterial mode of action of the active derivatives involved the regulation of the expression of genes associated with peptidoglycans, the respiratory metabolism, and the inherent virulence factors found in bacteria, as determined through a quantitative real-time reverse transcriptase PCR assay.

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 methyl 2-cyano-3,12-dioxo-18β-olean-1,9(11)-dien-30-oate analogues to determine the active groups for inhibiting cell growth and inducing apoptosis in leukemia cells

Fourteen of the methyl 2-cyano-3,12-dioxo-18β-olean-1,9(11)-dien-30- oate (CDODO-Me-12, 10d) analogues with different structures of ring C were synthesized to determine the active groups for inhibiting cell growth and inducing apoptosis in human leukemia HL-60 cells. An unsaturated group in ring C was required to maintain the ability to inhibit cell growth and induce apoptosis. Compound 10e with 9(11),12-dien in ring C displayed comparable apoptosis induction ability to 10d associated with decreased levels of c-FLIP, but not Mcl-1 and XIAP. Compound 10e had decreased ability to deplete GSH compared to compound 10d. Compound 10e represents a new active compound acting through a different mechanism from that of compound 10d. This journal is the Partner Organisations 2014.