1380294-08-5

Upstream product

• 3749-36-8 2-hydroxymethyl-3,4-dihydro-2H-pyran 
• 100-73-2 acrolein dimer 
• 877-88-3 3,5-dimethoxybenzyl bromide 
• 24131-30-4 (3,5-dimethoxybenzyl)triphenylphosphonium bromide 
• 1429328-18-6 (E)-2-(3,5-dimethoxystyryl)-3,4-dihydro-2H-pyran 
• 121362-78-5 (E)-3-(3,5-dimethoxyphenyl)acrylaldehyde 
• 42174-79-8 (E)-ethyl 3-(3,5-dimethoxyphenyl)acrylate 
• 147663-61-4 trans-3-(3,5-dimethoxyphenyl)-2-propen-1-ol 
• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 1380294-00-7 (E)-1-(3,5-dimethoxyphenyl)hexa-1,5-dien-3-yl acrylate 
• 1380293-92-4 (E)-1-(3,5-dimethoxyphenyl)hexa-1,5-dien-3-ol 

Relevant academic research and scientific papers

Design, synthesis, in vitro cytotoxicity evaluation and structure-activity relationship of Goniothalamin analogs

A series of six/five member (E/Z)-Goniothalamin analogs were synthesized from commercially available (3,4-dihydro-2H-pyran-2-yl)methanol/5- (hydroxymethyl)dihydrofuran-2(3H)-one in three steps with good to moderate overall yields and their cytotoxicity against lymphoblastic leukemic T cell line (Jurkat E6.1) have been evaluated. Among the synthesized analogs, (Z)-Goniothalamin appeared to be the most active in cytotoxicity (IC 50 = 12 μM). Structure-activity relationship study indicates that introducing substituent in phenyl ring or replacing phenyl ring by pyridine/naphthalene, or decreasing the ring size of lactones (from six to five member) do not increase the cytotoxicity.

Synthesis of methoxylated goniothalamin, aza-goniothalamin and γ-pyrones and their in vitro evaluation against human cancer cells

The present work describes the preparation of three novel series of compounds based on the structure of goniothalamin, a natural styryl lactone which has been found to display cytotoxic and antiproliferative activities against a variety of cancer cell lines. A focused library of 29 novel goniothalamin analogues was prepared and evaluated against seven human cancer cell lines. While the γ-pyrones and the aza-goniothalamin analogues were less potent than the lead compound, 2,4-dimethoxy analogue 88 has shown to be more potent in vitro than goniothalamin against all cancer cell lines evaluated. Furthermore, it was more potent than doxorubicin against NCI-ADR/RES, OVCAR-03 and HT-29 while being less toxic to human keratinocytes (HaCat). The 3,5-dimethoxy analogue 90 and 2,4,5-trimethoxy analogue 92 also displayed promising antiproliferative activity when compared to goniothalamin (1). These results provide new elements for the design and synthesis of novel representatives of this family of natural compounds.