55303-99-6

Usage

Uses

Used in Pharmaceutical Industry:
Avarone is used as a cystostatic agent for its ability to inhibit the growth of certain types of cancer cells. It is particularly effective against solid malignancies and has shown potential in modulating various oncological signaling pathways.
Used in Antimicrobial Applications:
Avarone is used as an antimicrobial agent for its antibacterial and antifungal activities. It can be employed in the development of new drugs to combat resistant strains of bacteria and fungi, contributing to the fight against antibiotic resistance.
Used in Synthesis of Antitubercular Agents:
Avarone is used as a starting material in the synthesis of antimycobacterial and antibacterial derivatives. Its unique chemical structure makes it a valuable component in the development of new drugs to treat tuberculosis and other bacterial infections.
Used in Synthesis of Phthalazines and Analogues:
Avarone is used as a key intermediate in the synthesis of phthalazines and their analogues, which are known to have benzodiazepine receptor ligand activity. These compounds have potential applications in the treatment of various neurological and psychiatric disorders.

InChI:InChI=1/C21H28O2/c1-14-6-5-7-19-20(14,3)11-10-15(2)21(19,4)13-16-12-17(22)8-9-18(16)23/h6,8-9,12,15,19H,5,7,10-11,13H2,1-4H3/t15?,19-,20?,21-/m1/s1

Upstream product

• 61187-42-6 avarol dimethyl ether 
• 274900-31-1 (4aS,5S,8aS)-5-(2,5-Dimethoxy-benzyl)-5,8a-dimethyl-6-methylene-octahydro-naphthalen-1-one 
• 184485-47-0 (1S,4aS)-(+)-trans-1α-[(2,5-dimethoxyphenyl)methyl]-1β,4aβ-dimethyl-5-(2-methyl-1,3-dioxolan-2-yl)-2-methyleneoctahydro-5(6H)-naphthalenone 
• 184485-46-9 (1S,4aS)-(+)-trans-1α-[(2,5-dimethoxyphenyl)methyl]-1β,4aβ-dimethyl-5-(2-methyl-1,3-dioxolan-2-yl)-hexahydro-2,5(3H,6H)-naphthalenedione 
• 61950-54-7 (8aS)-1,1-(1,2-ethylenedioxy)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-6-oxonaphthalene 
• 481656-29-5 (1R,2S,4aS,8aR)-2-[(1β,2β,4aβ,5-tetramethyl-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-1-yl)methyl]phenol 
• 184485-48-1 (1S,2S,4aS)-(-)-trans-1α-[(2,5-dimethoxyphenyl)methyl]-5-(2-methyl-1,3-dioxolan-2-yl)-octahydro-1β,2β,4aβ-trimethyl-5(6H)-naphthalenone 
• 41722-49-0 (S)-1,4a-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione 
• 60732-17-4 2,5-dimethoxybenzyl bromide 
• 33524-31-1 2,5-dimethoxybenzyl alcohol 
• 26742-33-6 (4aS)-1,4aβ-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione-5-ethyeneacetal 
• 184485-49-2 (-)-(1R,4aS,8aS)-1β,2β,4aβ-trimethyl-1α-[(2',5'-dimethoyphenyl)methyl]-1,2,3,4,4a,5,6,7,8,8aα-decahydronaphthalen-5-one 
• 184485-50-5 (-)-(1R,4aS,8aS)-1β,2β,4aβ-trimethyl-1α-[(2',5'-dimethoxyphenyl)methyl]-5-exo-methylene-(3H)-1,4,4a,5,6,7,8,8a-octahydronaphthalene 
• 252577-53-0 2-(Pyridin-2-ylsulfanyl)-3-((1R,2S,4aS,8aS)-1,2,4a,5-tetramethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ylmethyl)-[1,4]benzoquinone 

Downstream Products

• 55303-98-5 avarol 
• 1092480-08-4 C₂₈H₃₆O₃S 

Relevant academic research and scientific papers

Synthesis and evaluation of diverse thio avarol derivatives as potential UVB photoprotective candidates

Semisynthesis of 13 new thio avarol derivatives (4-16) and in vitro evaluation on the photodamage response induced by UVB irradiation are described. Their ability to inhibit NF-κB activation and TNF-α generation in HaCaT cells as well as their antioxidant

Synthesis and biological activity of amino acid derivatives of avarone and its model compound

A series of eighteen derivatives of marine sesquiterpene quinone avarone and its model system tert-butylquinone with amino acids has been synthesized by nucleophilic addition of amino acids to the quinones. In vitro cytotoxic activity toward human cancer

Avinosol, a meroterpenoid-nucleoside conjugate with antiinvasion activity isolated from the marine sponge Dysidea sp.

The new meroterpenoids avinosol (1), 3′-aminoavarone (2), and 3′-phenethylaminoavarone (3) have been isolated from the marine sponge Dysidea sp. collected in Papua New Guinea, and their structures were elucidated by analysis of spectroscopic data. Avinoso

NOVEL USE OF SESQUITERPENE DERIVATIVE

The present disclosure relates to a novel use of a sesquiterpene derivative, more particularly to a composition for preventing, improving or treating macular degeneration or macular edema caused by vascular leakage in the eye, the composition containing a

Alkylamino and aralkylamino derivatives of avarone and its mimetic as selective agents against non-small cell lung cancer cells, their antibacterial and antifungal potential

In this paper, the synthesis of fourteen alkylamino and arylamino derivatives of sesquiterpene quinone avarone and its model compound tert-but-ylquinone is described. Branched, cyclic, allylic and benzylic alkylamino/arylamino groups were introduced into the quinone moiety. For all the obtained derivatives, their biological activity and redox properties were studied. The cytotoxic activity of the synthesized derivatives towards multidrug resistant (MDR) human non-small cell lung carcinoma NCI-H460/R cells, their sensitive counterpart NCI-H460 and human normal keratinocytes (HaCaT) was investigated. The antimicrobial activity towards Gram-positive and Gram-negative bacteria, and fungal cultures was determined. Some of the synthesized derivatives showed selectivity for cancer cells, including MDR cells. Regarding their cell death induction potential, the most promising compounds were allylamino derivatives, preferentially triggering apoptosis, with high selectivity for cancer cells, including MDR cells. Several compounds showed promising antimicrobial activity, comparable to those of commercial antibiotic and antimycotic agents.

Synthesis and biological activity of derivatives of the marine quinone avarone

Nine alkyl(aryl)thio derivatives of the marine sesquiterpene quinone avarone were synthesized by nucleophilic addition of thiols or thiophenol to avarone. In most cases only one regioisomer was obtained. Their cytotoxic activities, brine shrimp lethality

Highly efficient total synthesis of the marine natural products (+)-avarone, (+)-avarol, (-)-neoavarone, (-)-neoavarol and (+)-aureol

Biologically important and structurally unique marine natural products avarone (1), avarol (2), neoavarone (3), neoavarol (4) and aureol (5), were efficiently synthesized in a unified manner starting from (+)-5-methyl-Wieland- Miescher ketone 10. The synthesis involved the following crucial steps: i) Sequential BF3·Et2O-in-duced rearrangement/ cyclization reaction of 2 and 4 to produce 5 with complete stereoselectivity in high yield (2 → 5 and 4 → 5); ii) strategic salcomine oxidation of the phenolic compounds 6 and 8 to derive the corresponding quinones 1 and 3 (6 → 1 and 8 →3); and iii) Birch reductive alkylation of 10 with bromide 11 to construct the requisite carbon framework 12 (10 + 11 → 12). An in vitro cytotoxicity assay of compounds 1-5 against human histiocytic lymphoma cells U937 determined the order of cytotoxic potency (3 > 1 > 5 > 2 > 4) and some novel aspects of structure-activity relationships.

Synthesis and biological activities of thio-avarol derivatives

Eleven new thio-avarol derivatives (3-13) were synthesized. Their antimicrobial, brine shrimp lethality, and free-radical scavenging activities and acetylcholinesterase inhibition, together with 12 already reported semisynthetic thio-avarol derivatives (14-25), were evaluated. Structure-activity relationships among these thio derivatives were determined.

Potential antipsoriatic avarol derivatives as antioxidants and inhibitors of PGE2 generation and proliferation in the HaCaT cell line

The synthesis and structure-activity relationships for a series of 14 new avarol derivatives as antioxidants and inhibitors of cell proliferation and PGE2 generation in human keratinocytes are described. Compound 6 (thiosalicylic derivative) was the most potent inhibitor of superoxide generation in human neutrophils and also potently inhibited PGE2 generation in the human keratinocyte HaCaT cell line. Compound 7 (3′-methylaminoavarone) presented the best antiproliferative profile, by the inhibition of 3H-thymidine incorporation in HaCaT cells, with potency similar to the reference compound anthralin. None of the avarol derivatives showed any sign of cytotoxicity measured as LDH release in treated keratinocytes. The potency and pharmacological profile of derivatives are also discussed.

Unified synthesis of quinone sesquiterpenes based on a radical decarboxylation and quinone addition reaction

A unified synthesis of several quinone sesquiterpenes is described herein. Essential to this strategy is a novel radical addition reaction that permits the attachment of a fully substituted bicyclic core 16 to a variably substituted quinone 10. The addition product 15 can be further functionalized, giving access to natural products with a high degree of oxygenation at the quinone unit. The quinone addition reaction is characterized by excellent chemoselectivity, taking place only at conjugated and unsubstituted double bonds, and regioselectivity, being strongly influenced by the resonance effect of heteroatoms located on the quinone ring. These features were successfully applied to the synthesis of avarol (1), avarone (2), methoxyavarones (4, 5), ilimaquinone (6), and smenospongidine (7), thereby demonstating the synthetic value of this new method.