98886-32-9

Upstream product

• 2832-10-2 ethyl 4-acetyl-5-oxohexanoate 
• 121-33-5 vanillin 

Downstream Products

• 884506-23-4 7-[3-methoxy-4-(tetrahydropyran-2-yloxy)-phenyl]-4-{3-[3-methoxy-4-(tetrahydropyran-2-yloxy)-phenyl]-acryloyl}-5-oxo-hept-6-enoic acid ethyl ester 
• 885064-62-0 4-fluoro-7-[3-methoxy-4-(tetrahydropyran-2-yloxy)-phenyl]-4-{3-[3-methoxy-4-(tetrahydropyran-2-yloxy)-phenyl]-acryloyl}-5-oxo-hept-6-enoic acid ethyl ester 
• 1118765-39-1 ethyl (E,E)-3-(3,5-bis(4-hydroxy-3-methoxystyryl)-1H-pyrazol-4-yl)propanoate 
• 1118765-47-1 ethyl (E,E)-3-(3,5-bis(4-hydroxy-3-methoxystyryl)isoxazol-4-yl)propanoate 

Relevant academic research and scientific papers

Synthesis and evaluation of electron-rich curcumin analogues

The natural product curcumin has long been recognized for its medicinal properties and is utilized for the treatment of many diseases. However, it remains unknown whether this activity is based on its presumably promiscuous scaffold, or if it results from the Michael acceptor properties of the α,β-unsaturated 1,3-diketone moiety central to its structure. To probe this issue, electron-rich pyrazole and isoxazole analogues were prepared and evaluated against two breast cancer cell lines, which resulted in the identification of several compounds that exhibit low micromolar to mid nanomolar anti-proliferative activity. A conjugate addition study was also performed to compare the relative electrophilicity of the diketone, pyrazole and isoxazole analogues.

Antitumor agents 247. New 4-ethoxycarbonylethyl curcumin analogs as potential antiandrogenic agents

4-Ethoxycarbonylethyl curcumin (ECECur) (3) is a current drug candidate for the treatment of prostate cancer. Due to problems inherent in the tautomerism of ECECur, 4-fluoro-4-ethoxycarbonylethyl curcumin (4) and 4- ethoxycarbonylethylenyl curcumin (5) were designed and synthesized. These two target compounds and their synthetic intermediates (4-9) were evaluated for their inhibitory activity against androgen receptor transcription in LNCaP and PC-3 prostate cancer cell lines. While the enol-keto analogs showed varying anti-androgen potencies, the di-keto analogs showed no activity. Tetrahydropyranylation of the phenoxy groups had a positive impact on the anti-AR activity of 4-ethoxycarbonylethylenyl curcumin, but a negative impact on the activity of ECECur. With potent anti-AR activity, di-tetrapyranylated 4-ethoxycarbonylethylenyl curcumin (9), which exists in only one form, is a good drug lead for further structural modification. Based on the SAR information obtained from the above study, five new compounds were designed and subsequently synthesized. Among them, compound 10 was found to be the most potent anti-AR agent and is considered to be a promising drug candidate for the treatment of prostate cancer.

Synthesis of Naturally Occuring Curcuminoids and Related Compounds

Six known naturally occuring curcuminoids like curcumin, and 31 other analogs (Scheme 1) have been synthesized.Among them, 25 curcuminoids were prepared by condensing different substituted 2,4-pentanediones and benzaldehydes.The boron complex 12 has been used to avoid Knoevenagel condensation at C-3 of 2,4-pentanedione.Some curcuminoids containing hydroxy groups in the aromatic moiety have been acylated.Alkylation of the tetrabutylammonium salt of 5-hydroxy-1,7-diphenyl-1,4,6-heptatrien-3-one (1a) by benzyl bromide gave only C-alkylated 4-benzyl-1,7-diphenyl-1,6-heptadiene-3,5-dione (1d*).The 13C NMR data, the UV absorptions, and the tautomerism of the curcuminoids are discussed.