4176-97-0

Usage

Uses

Used in Pharmaceutical Industry:
3-[2-[(1R,4aβ)-2-Methylene-5α-(hydroxymethyl)-5,8aα-dimethyl-6α-hydroxydecalin-1α-yl]ethyl]-2,5-dihydrofuran-2-one is used as a potential therapeutic agent for various medical conditions. Its unique structure may allow it to interact with specific biological targets, making it a candidate for the development of new drugs.
Used in Chemical Research:
3-[2-[(1R,4aβ)-2-Methylene-5α-(hydroxymethyl)-5,8aα-dimethyl-6α-hydroxydecalin-1α-yl]ethyl]-2,5-dihydrofuran-2-one is also used as a research tool in the field of organic chemistry. Its synthesis and study can provide insights into the reactivity and properties of similar complex molecules, contributing to the advancement of chemical knowledge.
Used in Ayurvedic Medicine:
3-[2-[(1R,4aβ)-2-Methylene-5α-(hydroxymethyl)-5,8aα-dimethyl-6α-hydroxydecalin-1α-yl]ethyl]-2,5-dihydrofuran-2-one is used as an active ingredient in Ayurvedic formulations, where it may be employed to combat respiratory viral infections due to its potential antiviral properties.

InChI:InChI=1/C20H30O4/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/h9,15-17,21-22H,1,4-8,10-12H2,2-3H3/t15-,16+,17-,19+,20+/m1/s1

Upstream product

• 82209-72-1 14-deoxyandrographolide 19-glucoside 
• 142037-79-4 andrographolide 
• 42895-61-4 3,19-diacetyl-14-deoxyandrographolide 
• 79233-05-9 (1R,2R,4aS,5R,8aS)-5-((E)-2-((S)-4-acetoxy-2-oxodihydrofuran-3(2H)-ylidene)ethyl)-1-(acetoxymethyl)-1, 4a-dimethyl-6-methylenedecahydronaphthalen-2-yl acetate 
• 496848-48-7 (4S)-4-hydroxyl-3-(2-((1R,4aS,5R,6R,8aS)-6-hydroxyl-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)ethyl)dihydrofuran-2(3H)-one 

Downstream Products

• 79233-15-1 iso-14-deoxyandrographolide 
• 82209-72-1 14-deoxyandrographolide 19-glucoside 

Relevant academic research and scientific papers

Synthesis of andrographolide analogues and their neuroprotection and neurite outgrowth-promoting activities

Alzheimer's disease (AD) is the most prevalent neurodegenerative disease and remains incurable. Currently, neuronal injury and synapse loss have been considered to be main features in the pathophysiology of AD. Thus, modulation of neuronal survival and neurite outgrowth may represent an efficient strategy for the treatment of AD. Based on the isolates from the traditional medicine Andrographis paniculata, a series of andrographolide analogues were prepared and evaluated for the neuroprotection and neurotrophic activity. Two compounds (3 and 12) could effectively inhibit LPS-induced NO production and iNOS expression as well as proinflammatory cytokines TNF-α and IL-6. Moreover, pretreatment with 3 and 12 could protect neurons against microglia-mediated neurotoxicity. Further, H2O2 ? and 6-OHDA induced neurotoxicity in PC12 cells were also attenuated by the novel 12. Our next study indicated that compounds 1, 4 and 10 promoted NGF-induced neurite outgrowth in PC12 cells, with 10 the most potent. To clarify the underlying mechanisms of active compounds (3, 10 and 12), system pharmacology was employed. The results revealed that muscarinic acetylcholine receptors (mAChRs) may be the main targets of 12 against AD, while thyroid hormone signaling pathway was involved in the mechanisms of 10. These study point to the therapeutic potential of andrographolide analogues against AD.

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.

Synthesis of new andrographolide derivatives and evaluation of their antidyslipidemic, LDL-oxidation and antioxidant activity

Andrographis paniculata, native to Taiwan, Mainland China and India, is a medicinal herb, which possesses various biological activities including anti-atherosclerosis. Andrographolide (1) has been identified as one of the active constituents against atherosclerosis. In continuation of our drug discovery program we synthesized few novel derivatives of 1 to improve their antidyslipidemic, LDL-oxidation and antioxidant activity. The tosylated derivative 7 has been turned out to be more potent than the parent compound and comparable activity with marketed antidyslipidemic drugs.

Cytotoxic biotransformed products from andrographolide by Rhizopus stolonifer ATCC 12939

Biotransformation of andrographolide (1) by Rhizopus stolonifer ATCC 12939 was investigated. Ten bioconversion products were isolated and identified. Their structures were elucidated by high resolution mass spectroscopy (HR-MS), extensive NMR techniques,

Chemical transformation of andrographolide

Tosylation of andrographolide 1, with p-TsCl pyridine furnishes compounds 3 and 4. The reaction of 1 with in situ generated nickel boride yields compounds 6 and 8. Monotosylation of 6 followed by reaction with NaI refluxing in acetone furnishes the iodide 13. But all attempts to generate an oxetane moiety in 13 corresponding to compund 2 failed.

On the Diterpenoids of Andrographis paniculata: X-Ray Crystallographic Analysis of Andrographolide and Structure Determination of New Minor Diterpenoids

The crystal structure of andrographolide (8) was determined and the absolute configuration at C-14, which was previously undecided, was established as R.Reexamination of the constituents of Andrographis paniculata NEES resulted in the isolation of three new diterpenoids of ent-labdane type, andrographanin, andropanoside, and 14-deoxy-12-methoxy-andrographolide, together with three known compounds, 14-deoxyandrographolide (4), neoandrographolide (5) and andrographolide (8).The structures of the new diterpenoids were determined to be 1, 2, and 3 on the basis of spectral and chemical evidence.Keywords - Andrographis paniculata; acanthaceae; andrographolide; X-ray analysis; andrograpanin; andropanoside, 14-deoxy-12-methoxy-andrographolide; ent-labdane diterpenoid; structure elucidation