26166-39-2

Usage

Uses

Used in Anticancer Applications:
Ascochlarin is used as an antitumor agent for selectively targeting and killing MX-1 cells, a human breast cancer cell line lacking estrogen receptors. It achieves this through the suppression of AP-1, which in turn inhibits the induction of MMP-9 gene expression. Ascochlarin also demonstrates activity against various types of cancer by increasing the expression of p53 and inhibiting signaling through STAT3.
Used in Antiviral Applications:
Ascochlarin is used as an antiviral agent for its activity against Newcastle disease and herpes simplex viruses, providing potential therapeutic benefits in the treatment of these viral infections.
Used in Drug Delivery Systems:
Ascochlarin is used as a compound to suppress PMA-induced invasion in renal carcinoma cells by inhibiting the expression of matrix metalloproteinase-9. It also binds and inhibits the mitochondrial cytochrome bc1 complex, blocking the reduction of cytochrome b by ubiquinone, which may have implications for the development of novel drug delivery systems to enhance its therapeutic outcomes.

InChI:InChI=1/C23H29ClO4/c1-13(10-11-23(5)14(2)7-9-19(26)16(23)4)6-8-17-21(27)18(12-25)15(3)20(24)22(17)28/h6,10-12,14,16,27-28H,7-9H2,1-5H3/b11-10-,13-6+

Upstream product

• 99529-53-0 3-Chloro-4,6-dihydroxy-2-methyl-5-[(2E,4E)-3-methyl-5-((6R,7R,8R)-6,7,8-trimethyl-1,4-dioxa-spiro[4.5]dec-7-yl)-penta-2,4-dienyl]-benzaldehyde 
• 23887-67-4 Cylindrochlorin 
• 943911-93-1 C₃₁H₄₅ClO₈ 
• 75337-05-2 (+)-(R)-4-methyl-2-cyclohexene-1-one 
• 99477-53-9 (6R,7R,8R)-7-((1E,3E)-5-Chloro-3-methyl-penta-1,3-dienyl)-6,7,8-trimethyl-1,4-dioxa-spiro[4.5]decane 
• 26166-39-2 (+/-) ascochlorin 
• 85785-75-7 (+/-)-(2E,4E)-5-(3',3'-ethylenedioxy-1',2',6'-trimethylcyclohexyl)-3-methyl-2,4-pentadienyl bromide 
• 85785-72-4 (+/-)-(2EZ,4E)-5-(1',2',6'-trimethyl-3'-oxocyclohexyl)-3-methyl-2,4-pentadienyl acetate 
• 85785-73-5 (+/-)-(2EZ,4E)-5-(3',3'-ethylenedioxy-1',2',6'-trimethylcyclohexyl)-3-methyl-2,4-pentadienyl acetate 
• 85912-78-3 (+/-)-(2'E,4'E)-3-<5'-(3,3-ethylenedioxy-1,2,6-trimethylcyclohexyl)-3'-methyl-2',4'-pentadienyl>-2,4-dimethoxy-6-methyl-1,4-cyclohexadiene 
• 91854-86-3 (+/-)-(2'E,4'E)-4-chloro-2-<5'-(3,3-ethylenedioxy-1,2,6-trimethylcyclohexyl)-3'-methyl-2',4'-pentadienyl>orcinol 
• 85785-76-8 (+/-)-(2'E,4'E)-3-<5'-(3,3-ethylenedioxy-1,2,6-trimethylcyclohexyl)-3'-methyl-2',4'-pentadienyl>-1,5-dichloro-6-methyl-2,4-cyclohexanedione 
• 85785-74-6 (+/-)-(2E,4E)-5-(3',3'-ethylenedioxy-1',2',6'-trimethylcyclohexyl)-3-methyl-2,4-pentadien-1-ol 
• 91854-87-4 3-chloro-4,6-dihydroxy-2-methyl-5-decane)-2,4-pentadienyl>benzaldehyde 

Downstream Products

• 462125-47-9 3-acetoxy-4-chloro-6-formyl-5-methyl-2-[(2E,4E)-3-methyl-5-((1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl)-2,4-pentadienyl]phenyl acetate 
• 462125-49-1 2,4-di-O-t-butyldimethylsilylascochlorin 
• 26166-39-2 3-Chloro-4,6-dihydroxy-2-methyl-5-[(2Z,4E)-3-methyl-5-((1S,2S,6S)-1,2,6-trimethyl-3-oxo-cyclohexyl)-penta-2,4-dienyl]-benzaldehyde 

Relevant academic research and scientific papers

A novel testosterone 5α-reductase inhibitor, 8',9'-dehydroascochlorin produced by Verticillium sp. FO-2787

A new testosterone 5α-reductase inhibitor, 8',9'-dehydroascochlorin, was isolated from the cultured mycelium of Verticillium sp. FO-2787. This compound (M.W.: 402, C23H27ClO4) consists of 5-chloroorcylic aldehyde and 2,3,4

Facile synthesis of (-)-ascochlorin using palladium-catalyzed three component coupling reaction

(-)-Ascochlorin was synthesized using palladium-catalyzed three component coupling reaction. Reaction of the aryl iodide 3, isoprene, and sodium p-toluenesulfinate in the presence of Pd2(dba)3CHCl 3 catalyst and NaHCO

Total synthesis of (-)-ascochlorin via a cyclobutenone-based benzannulation strategy.

The application of a convergent benzannulation strategy in an efficient synthesis of (-)-ascochlorin is described.

A CONVENIENT SYNTHESIS OF (+/-) ASCOCHLORIN

A convergent total synthesis of (+/-) ascochlorin is described.

SYNTHESIS OF THE NATURAL ENANTIOMERS OF ASCOCHLORIN, ASCOFURANONE AND ASCOFURANOL

Three fungal metabolites with a common structural feature as prenylated phenols were synthesized in their naturally occuring and optically active forms: ascochlorin benzaldehyde>, ascofuranone and ascofuranol benzaldehyde>. (+)-Ascofuranone and (+)-ascofuranol were also synthesized.By the present synthesis the absolute configuration of the natural (-)-ascofuranol was established as (1''S,4''S).

SYNTHESIS OF (+/-)-ASCOCHLORIN, (+/-)-ASCOFURANONE AND LL-Z1272α

Three antibiotics with a common structural feature as prenylated phenols were synthesized: (+/-)-ascochlorin (5-chloro-2,4-dihydroxy-6-methyl-3-benzaldehyde), (+/-)-ascofurano