936253-53-1

Upstream product

• 121-33-5 vanillin 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 936253-52-0 6-(3-methoxy-4-benzyloxyphenyl)hexa-3,5-dien-2-one 
• 223801-41-0 3-(4-(benzyloxy)-3-methoxyphenyl)-prop-2-enal 

Downstream Products

• 1330753-47-3 1-(3-bromo-4-methoxyphenyl)-7-(3-methoxy-4-hydroxyphenyl)heptan-3-one 
• 61576-08-7 galeon 
• 936253-55-3 1-(3-bromo-4-benzyloxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)heptan-3-one 
• 936253-56-4 4-benzyloxy-17-methoxy-2-oxatricyclo[13.2.2.1^3,7]eicosa-1⁽¹⁸⁾,3⁽²⁰⁾,4,6,15⁽¹⁹⁾,16-hexaen-10-one 

Relevant academic research and scientific papers

Linear diarylheptanoids as potential anticancer therapeutics: synthesis, biological evaluation, and structure–activity relationship studies

In efforts to develop effective anticancer therapeutics with greater selectivity toward cancerous cell and reduced side-effects, such as emetic effects due to detrimental action of the drug toward the intestinal flora, a series of linear diarylheptanoids (LDHs) were designed and synthesized in 7 steps with good-to-moderate yields. All synthesized compounds were evaluated for their antibacterial, antiproliferative, and topoisomerase-I and -IIα inhibitory activity. Overall, all compounds showed little to no activity against the bacterial strains tested. Most of the synthesized compounds showed good antiproliferative activity against human breast cancer cell lines (T47D); specifically, the IC50 values of compounds 6a, 6d, 7j, and 7e were 0.09, 0.64, 0.67, and 0.99 μM, respectively. Among the tested compounds, 7b inhibited topo-I by 9.3% (camptothecin 68.8%), 7e and 7h inhibited topo-IIα by 38.4 and 47.4% (etoposide 76.9%), respectively, at the concentration of 100 μM. These results suggest that a set of promising anticancer agents can be obtained by reducing inhibitory actions on different microbes to provide enhanced selectivity against cancerous cells.

Microwave-assisted synthesis of macrocycles via intramolecular and/or bimolecular Ullmann coupling

Microwave-assisted synthesis of macrocyclic diaryl ethers via intramolecular and/or bimolecular Ullmann coupling is described. Using the optimized conditions, a panel of macrocycles, with different substitution patterns, ring sizes, and linkers, has been successfully synthesized using microwave irradiation. To the best of our knowledge, this work represents the first examples of the microwave-assisted synthesis of macrocyclic diaryl ethers via intramolecular and/or bimolecular Ullmann coupling.

Total synthesis and structural revision of engelhardione

The total synthesis of the macrocyclic natural product engelhardione is reported. This effort led to the structural revision of the published structure of engelhardione to that of pterocarine. The revision reflects the change of the substitution pattern of one phenyl ether ring from the meta to the para position. To confirm, pterocarine (2) and its close regioisomer 3 were subsequently synthesized for comparison. Moreover, to the best of our knowledge, our synthesis of 1 represents the first example of a 14-membered macrocyclic diarylheptanoid with a meta-meta substitution pattern at the diphenyl ether moiety.

First total synthesis of cytotoxic diarylheptanoids, galeon, and pterocarine

The first total synthesis of cytotoxic diphenyl ether-type diarylheptanoids, galeon and pterocarine, was described in which the Ullmann reaction was employed at the final step for the diaryl ether formation of key intermediate, 1-(3-bromo-4-benzyloxypheny

A versatile synthesis of cyclic diphenyl ether-type diarylheptanoids: Acerogenins, (±)-galeon, and (±)-pterocarine

A versatile method for the total synthesis of cyclic diphenyl ether-type diarylheptanoids, acerogenin C, acerogenin L, (±)-galeon, and (±)-pterocarine was described. The Ullmann reaction of suitably substituted linear diphenylheptanoids was employed for t