51984-75-9

Upstream product

• 471-53-4 enoxolone 
• 6738-17-6 O-benzyl-N,N'-dicyclohexylisourea 
• 100-39-0 benzyl bromide 
• 83896-44-0 glycyrrizhin 
• 100-44-7 benzyl chloride 
• 87918-95-4 6',6'',30-tribenzyl-18β-glycyrrhizin 

Downstream Products

• 127290-98-6 benzyl 3β-acetyloxy-11-oxo-olean-12-en-30-oate 
• 127290-97-5 benzyl 3-O-(methyl (2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate))-18β-glycyrrhetinate 
• 1345513-34-9 benzyl (3β)-3-([N-(3-aminopropyl)glycyl]oxy)-11-oxo-olean-12-en-30-oate 
• 34096-83-8 1-(18β-glycyrrhet-3-yl)-β-D-glucopyranuronic acid 
• 1321990-56-0 3,11-dioxo-18β-oleanane-12-ene-30-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

One-pot synthesis of glycyrrhetic acid polyglycosides based on grafting-from method using cyclic sulfite

Glycyrrhetic acid polyglycosides were synthesized in one-pot via cationic ring-opening condensation polymerization of cyclic sulfite (4) initiated by glycyrrhetic acid as an aglycon. Sulfite 4 worked as a practical monomer for the preparation of (1?→?2)-linked polysaccharide skeletons. The chemical stability of 4 was evaluated by the comparison of thermodynamic parameters with those of conventional epoxide (2). The grafting reaction of 4 from glycyrrhetic acid (5) was performed in the presence of TfOH and MS 3A in CH2Cl2at room temperature. The polymerization degree was moderately controllable by the change of feed ratio of initiator.

Synthesis and structure-activity relationship studies of water-soluble β-cyclodextrin-glycyrrhetinic acid conjugates as potential anti-influenza virus agents

Glycyrrhetinic acid (GA) is a major constituent of the herb Glycyrrhiza glabra, and many of its derivatives demonstrate a broad spectrum of antiviral activities. In the current study, 18 water-soluble β-cyclodextrin (CD)-GA conjugates, in which GA was covalently coupled to the primary face of β-CD using 1,2,3-triazole moiety along with varying lengths of linker, were synthesized via copper-catalyzed azide-alkyl cycloaddition reaction. Benefited from the attached β-CD moiety, all these conjugates showed lower hydrophobicity (AlogP) compared with their parent compound GA. With the exception of per-O-methylated β-CD-GA conjugate (35), all other conjugates showed no significant cytotoxicity to MDCK cells, and these conjugates were then screened against A/WSN/33 (H1N1) virus using the cytopathic effect assay. The preliminary results indicated that six conjugates showed promising antiviral activity, and the C-3 and C-30 of GA could tolerate some modifications. Our findings suggested that GA could be used as a lead compound for the development of potential anti-influenza virus agents.

TERPINOID DERIVATIVES AND USES THEREOF

Described herein are terpinoid derivatives as NRF2 inhibitors and pharmaceutical compositions comprising said compounds. The subject compounds and compositions are useful for the treatment of inflammatory diseases.

Synthesis and biological activity of glycyrrhetinic acid derivatives as antitumor agents

Glycyrrhetinic acid (GA) had been the star anticancer lead compound and appealed to many scientists all over the world; however, its antitumor activity was not potent enough. To improve GA's cytoxicity and explore the effect of bonding mode on antitumor activity, 32 compounds including GA-OH series (GO, esters in C-3 position) and GA-NH2 series (GN, with amide linkages in C-3 position) had been designed and synthesized. All the compounds were screened for in vitro cytotoxicity against A549, HepG2, MCF-7, Hela and MDCK cell lines. As a result, all the de-protected (without Boc group) derivatives showed much stronger cytotoxic activity than GA, and surprisingly enough, all the GN series of the compounds were more potent than GO series against various tumor cells. Among them, the compound 26 (amide linkages in C-3 position) exhibited stronger antitumor activity against A549 cell line (IC50 = 2.109 ± 0.11 μM) than the positive drug cisplatin (IC50 = 9.001 ± 0.37 μM). Further studies indicated that compound 26 could induce A549 apoptosis via nuclei fragmentation. The detection of apoptosis and cell cycle analysis indicated that compound 26 could induce the early apoptosis and prevent A549 cells transition from S to G2 phase. Furthermore, the structure-activity relationships were briefly discussed. Among which, current study displayed amide linkages in C-3 position could effectively enhance GA cytotoxicity, providing a new modification strategy for further study.

Chemical synthesis method of glycyrrtinic acid 3-O-mono-beta-D-glucuronide (GAMG)

The invention discloses a chemical synthesis method of glycyrrtinic acid 3-O-mono-beta-D-glucuronide (GAMG), and belongs to the fields of organic synthesis, medicinal chemistry, and food science. Abundant and cheap glycyrrhetinic acid is taken as the primary raw material, and GAMG is simply and easily synthesized by following five steps: carboxyl to benzyl ester conversion, glycosidation between C3 hydroxyl groups and a fully benzoylated methyl glucuronate glycosyl donor, methyl removal, benzoyl removal, and benzyl removal. The raw materials and reagents are cheap, the reaction conditions aremild, the operation is simple, the yield is good, and the GAMG chemical synthesis method is feasible.

Targeting mitochondria: Esters of rhodamine B with triterpenoids are mitocanic triggers of apoptosis

Triterpenoic acids, ursolic acid (1), oleanolic acid (2), glycyrrhetinic acid (3) and betulinic acid (4) were converted into their corresponding methyl 5–8 and benzyl esters 9–12 or benzyl amides 21–24. These derivatives served as starting materials for the synthesis of pink colored rhodamine B derivatives 25–36 which were screened for cytotoxicity in colorimetric SRB assays. All of the compounds were cytotoxic for a variety of human tumor cell lines. The activity of the benzyl ester derivatives 29–32 was lower than the cytotoxicity of the methyl esters 25–28. The benzyl amides 33–36 were the most cytotoxic compounds of this series. The most potential compound was a glycyrrhetinic acid rhodamine B benzyl amide 35. This compound showed activity against the different cancer cell lines in a two-digit to low three-digit nano-molar range. Staining experiments combined with fluorescence microscopy showed that this compound triggered apoptosis in A2780 ovarian carcinoma cells and acted as a mitocan.

Design and preparation of derivatives of oleanolic and glycyrrhetinic acids with cytotoxic properties

Background: The structural modification of natural products with the aim to improve the anticancer activity is a popular current research direction. The pentacyclic triterpenoid compounds oleanolic acid (OA) and glycyrrhetinic acid (GA) are distributed widely in nature. Methods: In this study, various oleanolic acids and glycyrrhetinic acids were designed and synthesized by using the combination principle. The in vitro anticancer activities of new OA and GA derivatives were tested by the 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide (MTT) method with SGC-7901 (gastric cancer), MCF-7 (breast cancer), Eca-109 (esophageal cancer), HeLa (cervical cancer), Hep-G2 (hepatoma cancer) and HSF (normal human skin fibroblast) cells. Results and conclusion: The screening results showed that the compound 3m presented the highest inhibitory activities against SGC-7901, MCF-7 and Eca-109 cell lines with IC50 values of 7.57±0.64 μM, 5.51±0.41 μM and 5.03±0.56 μM, respectively. In addition, this compound also showed effective inhibition of Hep-G2 cells with an IC50 value of 4.11±0.73 μM. Moreover, compound 5b showed the strongest inhibitory activity against Hep-G2 cells with an IC50 value of 3.74±0.18 μM and compound 3l showed strong selective inhibition of the HeLa cells with the lowest IC50 value of 4.32±0.89 μM. A series of pharmacology experiments indicated that compound 5b could induce Hep-G2 cells autophagy and apoptosis. These compounds will expand the structural diversity of anti-cancer targets and confirm the prospects for further research.

METHOD FOR PRODUCING GLYCYRRHIZINIC ACID AND GALACTURO GLYCYRRHIZINIC ACID, AND INTERMEDIATE USED FOR THE PRODUCTION METHOD

PROBLEM TO BE SOLVED: To provide a synthesis method that makes it possible to produce high-purity glycyrrhizinic acid or galacturo glycyrrhizinic acid, simply and in high yields. SOLUTION: A production method includes performing glycosylation of position-3 hydroxy group of glycyrrhetinic acid, then performing selective galactosylation or glycosylation at position-2', and through deprotection, performing selective oxidation of a primary hydroxy group. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

Triterpenoid derivative TBA-X with antitumor effect as well as preparation method and application thereof

The invention provides a compound with a structural general form 1 or 2, a preparation method thereof, and an application of the compound in preparation of antitumor drugs. The composition provided by the invention has a significant inhibitory action on liver cancer, stomach cancer, colon cancer, cervical cancer cell lines.

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.