42895-58-9

Usage

Uses

Used in Pharmaceutical Applications:
14-Deoxy-11,12-didehydroandrographolide is used as an active pharmaceutical ingredient for its various therapeutic properties, including anti-inflammatory, antiallergenic, immuno-stimulatory, antiviral, antioxidant, hepatoprotective, and cardiovascular activities.
Used in Antihepatotoxic Applications:
In the pharmaceutical industry, 14-deoxy-11,12-didehydroandrographolide is used as an antihepatotoxic agent, showing significant action in P. berghei K173-induced hepatic damage in M. natalensis.
Used in Anti-inflammatory Applications:
14-Deoxy-11,12-didehydroandrographolide is used as an anti-inflammatory agent, inhibiting tumor necrosis factor-α (TNF-α)-induced intercellular adhesion mol.-1 (ICAM-1) expression and adhesion of HL-60 cells onto human umbilical vein endothelial cells (HUVEC), which are associated with inflammatory diseases.
Used in Cardiovascular Protection:
In the field of cardiovascular medicine, 14-deoxy-11,12-didehydroandrographolide is used as a potential cardiovascular-protective agent due to its various beneficial properties.

InChI:InChI=1/C20H28O4/c1-13-4-7-16-19(2,10-8-17(22)20(16,3)12-21)15(13)6-5-14-9-11-24-18(14)23/h5-6,9,15-17,21-22H,1,4,7-8,10-12H2,2-3H3/b6-5+/t15-,16+,17-,19+,20+/m1/s1

Upstream product

• 67-56-1 methanol 
• 142037-79-4 andrographolide 
• 372939-35-0 3,18-O-isopropylideneandrographolide 
• 372939-36-1 (S,E)-5-oxo-4-(2-((4aR,6aS,7R,10aS, 10bR)-3,3,6a,10b-tetramethyl-8-methylenedecahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethylidene)tetrahydrofuran-3-yl acetate 
• 142037-79-4 [1R-[1α(E),4aβ,5α,6α,8aα]]-3-[2-[decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethylidene]dihydro-4-hydroxy-2(3H)-furanone 

Downstream Products

• 1575716-72-1 C₄₃H₄₆O₇ 
• 1575716-76-5 C₄₄H₄₈O₇ 
• 947699-85-6 3-oxo-19-O-trityldehydehydroandrographolide 
• 955428-68-9 3-O-acetyl-19-O-trityldehydehydroandrographolide 
• 1575717-04-2 3-O-acetyl-19-O-(2-piperidinoacetyl)dehydroandrographolide 
• 1575717-10-0 3-O-acetyl-19-O-[2-(4-hydroxypiperidino)acetyl]dehydroandrographolide 
• 910582-16-0 19-O-trityldehydroandrographolide 

Relevant academic research and scientific papers

Synthesis of andrographolide cyclophosphate derivatives and their antitumor activities

A series of cyclophosphate andrographolide derivatives were synthesized from andrographolide, the cytotoxic constituent of the plant Andrographis paniculata. The derivative (PR, P′S)-S and (P S, P′S)-6 were synthesized and the proposed mechanism for their formation was discussed. The structures of all compounds were elucidated by IR, NMR, MS (ESI), and HR-MS. The stereochemistry of 6 was confirmed by X-ray analysis. All the derivatives were tested for antitumor activity in vitro, and some of them showed good results. Copyright Taylor & Francis Group, LLC.

Synthesis and biological evaluation of andrographolide C-glycoside derivatives as &α-glycosidase inhibitors

A series of new andrographolide C-glycoside derivatives were synthesized by a facile route. The new compounds showed higher potency than the parent andrographolide evaluated as α-glycosidase inhibitors in the preliminary study. Copyright

Studies on the novel α-glucosidase inhibitory activity and structure-activity relationships for andrographolide analogues

A series of analogues of andrographolide were synthesized and evaluated as novel α-glucosidase inhibitors. Among them compound 23, 15-p-methoxylbenzylidene 14-deoxy-11,12-didehydroandrographolide, was a potent inhibitor against α-glucosidase whose IC

Oligo-polyethene glycol (PEG)-modified 14-deoxy-11,12-didehydroandrographolide derivatives: Synthesis, solubility and anti-bacterial activity

A class of 14-deoxy-11,12-didehydroandrographolide (DA) derivatives with oligo-polyethylene glycol (PEG) substituents has been synthesized. It is found that small degree of polymerization of PEG favors the synthesis of dual-PEGylated DA derivatives, whereas large degree of polymerization is good for the preparation of mono-PEGylated DA derivatives. As compared to the prototype compound DA, the PEGylated DA derivatives show enhanced water solubility which is beneficial to drug's bioavailability. Preliminary study finds that the PEGylated DA derivatives exhibit better anti-bacterial activity than that of DA.

Synthesis of novel andrographolide beckmann rearrangement derivatives and evaluation of their HK2-related anti-inflammatory activities

Two series of andrographolide derivatives with introduction of amide moiety into ring A by Beckmann rearrangement were synthesized. In series 1, the ring A was converted to caprolactam, and an amide moiety was linked to C-19 of ring A in series 2. Among t

Heat-accelerated degradation of solid-state andrographolide

The stability of andrographolide, the major active diterpene lactone from Andrographis paniculata (Burm. f.) Wall. ex Nees., was determined to show that, while crystalline andrographolide was highly stable even at 70°C (75% relative humidity) over a period of 3 months, its amorphous phase degraded promptly. Heat-accelerated conditions revealed second-order kinetics of the decomposition with the rate constant at 25°C (k25°C) predicted from the Arrhenius plot of 3.8×10-6 d-1. The major decomposed product under elevated temperature (70°C, 75% relative humidity) is 14-deoxy-11,12-didehydroandrographolide.

Preparation and α-glucosidase inhibition of andrographolide derivatives

Series of novel analogs, which were primarily modified on its lactone moiety, was synthesized based on Andrographolide (1), a natural product sesquiterpene inhibitor of α-glucosidase. Among new analogs, 14-deoxy-11,12-didehydro-15-(4-ethoxybenzylidene)andrographolide (3h) was determined to have the greatest potential of α-glucosidase inhibitor through the calculation of IC50 value of 160 ± 5.1 μM, a significant improvement compared to the clinical dose of Acarbose, which showed the IC50 value of 390 ± 8.1 μM. In addition, 14-deoxy-11,12-didehydro-3,19-(2′-hydroxybenzylidene)-15-(2-hydroxybenzylidene) andrographolide (7), a 15-benzylidene derivative of 14-deoxy-11,12-didehydroandrographolide containing a 1,3-dioxane moiety at C(3) and C(19), also displayed good inhibition with IC50 260 ± 13 μM. These results are promising avenues in the subsequent optimization of antidiabetic drugs.

Synthesis and anti-fibrosis activity study of 14-deoxyandrographolide-19-oic acid and 14-deoxydidehydroandrographolide-19-oic acid derivatives

A series of 14-deoxyandrographolide-19-oic acid and 14-deoxy-11,12 (or 14,15)-didehydroandrographolide-19-oic acid derivatives were designed, synthesized and screened in vitro against the mouse fibroblast cell lines NIH-3T3. Thirteen compounds 8a-f, 14a-c, 14e-f, and 18a-b were found to exhibit better anti-fibrotic activities than andrographolide, with compounds 8b and 14e displaying best activity with IC50 values of 12.86 and 13.57 μM against NIH-3T3 respectively. Further anti-fibrotic investigation was performed in terms of PCR and western bolt analysis. Our study demonstrated that compounds 8b and 14e suppressed effectively the expression of α-smooth muscle actin, fibronectin and collagen in NIH-3T3. Preliminary structure-activity analysis revealed that 14-deoxygenation and 19-carboxylation of andrographolide could significantly improve its anti-fibrotic effect, which made 14-deoxyandrographolide-19-oic acid and 14-deoxy-11,12-didehydroandrographolide-19-oic acid promising leads for the development of new anti-fibrotic agents.

Discovery of Potent Orally Active Protease-Activated Receptor 1 (PAR1) Antagonists Based on Andrographolide

Protease-activated receptor-1 (PAR1), a G-protein-coupled receptor, plays a critical role in thrombin-mediated platelet aggregation. It is regarded as a promising antithrombosis target that is unlikely to result in bleeding. Here, we describe the synthesi

Design, synthesis, and biological evaluation of andrographolide derivatives as potent hepatoprotective agents

Poor water solubility limits the clinical use of andrographolide and its derivatives. In an attempt to develop potent hepatoprotective drugs, a strategy was proposed to improve the aqueous solubility of andrographolide. Ten andrographolide derivatives were designed, synthesized, evaluated for aqueous solubility and in vivo hepatoprotective activity against CCl4-induced liver injury in mice. As expected, the aqueous solubility of synthetic derivatives was effectively improved. All compounds demonstrated the effect of different degrees in improving the liver enzyme (ALT and AST) activity, especially the most promising compound 9d significantly improved liver enzyme activity, with high potency to be a new lead.