901-36-0

Usage

Uses

Used in Medicinal Chemistry:
(1S,4aS)-6-Methoxy-1,4a-diMethyl-9-oxo-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid is utilized as a compound of interest in medicinal chemistry for its potential biological activities. Its unique structure, including the phenanthrene ring and functional groups, may contribute to its interactions with biological targets, warranting further research into its therapeutic applications.
Used in Drug Development:
In the field of drug development, (1S,4aS)-6-Methoxy-1,4a-diMethyl-9-oxo-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid is considered a candidate molecule for the design and synthesis of new pharmaceutical agents. Its complex structure and functional groups may offer advantages in targeting specific biological pathways or mechanisms, which could lead to the development of novel treatments for various diseases.
Further research is necessary to fully understand the properties and potential uses of (1S,4aS)-6-Methoxy-1,4a-diMethyl-9-oxo-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid, as its complex molecular structure and the presence of various functional groups suggest a wide range of possible applications in both medicinal chemistry and drug development.

InChI:InChI=1/C19H24O4/c1-18-8-5-9-19(2,17(21)23-4)16(18)11-15(20)13-7-6-12(22-3)10-14(13)18/h6-7,10,16H,5,8-9,11H2,1-4H3/t16-,18-,19+/m1/s1

Upstream product

• 1231-74-9 methyl O-methylpodocarpate 
• 1045-54-1 6α-Brom-7-oxo-O-methylpodocarpsaeure-methylester 
• 78-94-4 methyl vinyl ketone 
• 292638-85-8 acrylic acid methyl ester 
• 107-13-1 acrylonitrile 
• 107-02-8 acrolein 
• 623-43-8 methyl crotonate 
• 501-65-5 diphenyl acetylene 
• 74-85-1 ethene 
• 5947-49-9 podocarpic acid 
• 4614-56-6 methyl podocarpate 
• 1231-74-9 methyl 12-methoxypodocarpa-8,11,13-trien-19-oate 

Downstream Products

• 1045-54-1 6α-Brom-7-oxo-O-methylpodocarpsaeure-methylester 
• 64597-67-7 (1S,2R,3S)-3-(2-Hydroxy-5-methoxy-phenyl)-2-methoxycarbonylmethyl-1,3-dimethyl-cyclohexanecarboxylic acid methyl ester 
• 23526-53-6 methyl 7β-hydroxy-12-methoxypodocarpa-8,11,13-trien-19-oate 
• 23526-52-5 methyl 12-methoxypodocarpa-6,8,11,13-tetraen-19-oate 
• 64597-69-9 (1S,2R,3S)-3-(2,5-Dimethoxy-phenyl)-2-methoxycarbonylmethyl-1,3-dimethyl-cyclohexanecarboxylic acid methyl ester 
• 33169-07-2 (1S,4aS,10aR)-1,4a-Dimethyl-6-oxo-1,2,3,4,4a,6,7,8,10,10a-decahydro-phenanthrene-1-carboxylic acid 
• 1865-97-0 methyl O-methyl-Δ^5,6-7-ketopodocarpate 

Relevant academic research and scientific papers

Phenolic diterpenoid derivatives as anti-influenza a virus agents

A series of diterpenoid derivatives based on podocarpic acid were synthesized and evaluated as anti-influenza A virus agents. Several of the novel podocarpic acid derivatives exhibited nanomolar activities against an H1N1 influenza A virus (A/Puerto Rico/8/34) that was resistant to two anti-influenza drugs, oseltamivir and amantadine. This class of compounds inhibits the influenza virus by targeting the viral hemagglutinin-mediated membrane fusion. These results indicated that podocarpic acid derivatives may serve as potential drug candidates to fight drug-resistant influenza A virus infections.

Oxidations of 12-deoxy-, 12-hydroxy-, a 12-methoxy-, and 12-hydroxy-13-methoxypodocarpa-8,11,13-triene derivatives

Methods for the oxidation of the aryl ring of derivatives of podocarpic acid have been examined. Oxidation of methyl 12-hydroxypodocarpa-8,11,13-trien-19-oate (2) with phenyliodonium diacetate in various solvents gives 8β-substituted dienones. An 8β-chloro dienone is formed during oxidation of the phenol (2) with τ-butyl hypochlorite. Oxidation of (2) with dimethyldioxiran gives mainly the 7-ketone (13) but also affords the novel ε-lactone (26), while treatment with ruthenium tetraoxide also affords products of benzylic oxidation. Oxidation of methyl podocarpa-8,11,13-trien-19-oate (4) with m-chloroperbenzoic acid affords a B-ring lactone (29) and, unexpectedly, a 6αz-chloro 7-ketone (30). The action of cerium(IV) ammonium nitrate on (2) gives nitro derivatives rather than oxidation products. Oxidation of methyl 12-hydroxy-13-methoxypodocarpa-8,ll,13-trien-19-oate (22) with mchloroperbenzoic acid gives a low yield of a 7-oxo derivative (17) while treatment with ozone gives an unusual α,β-unsaturated γ-lactone (31), the hydroxy lactone (33), the unsaturated keto ester (34), and the substituted furan (35). Oxidation of (22) with Fremy's salt gives products of ring B oxidation. The structure of (31) has been confirmed by X-ray crystallography.

Skeletal rearrangements of ring C aromatic diterpenoids

The structure of a naphthalene derivative obtained by rearrangement of 13-methoxytotara-5,8,11,13-tetraen-7α-ol (2) has been revised to 5-(5′-isopropyl-6′-methoxy-2′-methyl-1′-naphthyl)-2- methylpent-2-ene (7). A minor oxidation product of 13-methoxytotar

Reaction with alkenes of η2-7-oxotetracarbonylmanganese complexes derived from diterpenoids

A number of activated 7-oxotetracarbonylmanganese(1) complexes derived from podocarpic acid (1) and from dehydroabietic acid have been coupled with alkenes to give C(14) functionalised derivatives in high yields.Some coupling reactions resulted in cyclization to C(7), forming 4H-acephenanthrylene derivatives in moderate yields.Several modes of activating these manganese complexes towards coupling reactions were investigated; these included oxidative decarbonylation at room temperature, thermal promotion, and palladium-mediation.

Reactions of η2-tetracarbonylmanganese complexes derived from podocarpic acid with electrophiles; functionalization of ring C

Reaction of tetracarbonylmanganese(I) complexes derived from podocarpic acid (1) with electrophilic bromine or iodine in CCl4 leads to 14-halogenated derivatives inaccessible by direct halogenation.Similar reactions in protic solvents lead to the formation of γ-lactones in high yield.The structure of one of these was established unequivocally by X-ray crystallograohy.Attempted oxidation of the C-Mn bond with a number of reagents proved generally to be unsuccessful.

Coupling reactions of diterpenoid η2-tetracarbonylmanganese complexes with alkynes

A number of tetracarbonylmanganese complexes derived from podocarpic acid (1) have heen coupled with acetylene or diphenylacetylene to give steroidal analogues in high yield.Several modes of activating these manganese complexes towards coupling reactions

Investigation of the antitumor activity of podocarpic acid derivatives

As a class, octahydrophenanthrene lactones, podolactones, and related podocarpic acid derivatives have been reported to possess a wide variety of biological activities, including antileukemic activity, inhibition of plant cell growth, and hormonal and anti-inflammatory properties. In the present study, a series of synthetic intermediates derived from podocarpic acid have been prepared and evaluated with the respect to their ability to inhibit human epidermoid carcinoma of the nasopharynx in vitro. The significant cytotoxicity demonstrated by methyl 6α-bromo-7-oxo-O-methylpodocarpate (50% inhibition at 8.85 x 10-9 M) was markedly higher than that of the other derivatives examined. Further evaluation against L210 and P388 lymphoid leukemias in mice failed to demonstrate significant antitumor activity.