Synthesis and Cytotoxic Evaluation of Sanjoseolide and Representative Analogues

Abstract

The first total synthesis of sanjoseolide (1), which was originally obtained from Dalea frutescens A, was achieved via an efficient route with a longest linear sequence of six steps from the commercially available 2,4-dihydroxyacetophenone in 8.6% overall yield. Meanwhile, a series of sanjoseolide representative analogues were synthesized and assessed for their antiproliferative potency against cancer cells of different origins. Compound 8e inhibited the survival of all tested cancer cell lines in a dose-dependent manner, the IC 50 values of the treatment were about 12.8 μM for human cholangiocarcinoma cell lines RBE and 12.7 μM for human cholangiocarcinoma cell lines HCCC-9810, which was more active than sanjoseolide (1). Analysis of the structure−activity relationships revealed that the presence of a trifluoromethyl group may be beneficial in terms of both RBE and HCCC-9810 inhibition.

Sharpless Asymmetric Dihydroxylation: An Impressive Gadget for the Synthesis of Natural Products: A Review

“…Sanjoseolide, a natural product containing an isoprenylated chalcone skeleton, obtained from Dalea frustecens , has wide pharmacological significance, as it has been found to be effective against inflammation, cancer and diabetes [ 100 ]. Owing to its huge medicinal importance, Tian et al [ 101 ] in 2020 reported an efficient method for the synthesis of sanjoseolide by carrying out Sharpless asymmetric dihydroxylation, Stille coupling and Claisen–Schmidt condensation. In the first step, 2,4-dihydroxyacetophenone 208 was treated with I 2 and KIO 3 followed by protection with a methoxymethyl group, leading to the synthesis of compound 209 in 90% yield.…”

Study on the Synthesis of Dihydroflavonol Compounds

“…10 Another fragment focused on the formation of aryl iodine. 11 Compound 9 was used as a raw material to generate compound 12. It is worth noting that introducing aryl iodide was innovative in the designed synthetic route, because it provides the possibility of adding side chains in the total synthesis of natural products.…”

Solubility Determination, Thermodynamic Modeling, and Solvent Effect of 2′,4′-Dihydroxyacetophenone in 10 Monosolvents and Two Binary Solvents from 293.15 to 333.15 K

“…(2) Six thermodynamic equations were applied to regress the solid−liquid equilibrium data to obtain model parameters, and the regression effects were evaluated. (3) The KAT-LSER model was employed to study the dissolution rule of 2′,4′-DHAP in monosolvents at room temperature and analyze the relative contribution of various forces to the dissolution process.…”

“…In the pharmaceuticals industry, 2′,4′-DHAP can be used as a material to synthesize Schiff bases, paeonol, and efloxate, which have the function of treatment of antiangina pectoris. In the organic synthesis field, 2′,4′-DHAP is applied to synthesize chalcone as an indicator of the organic synthesis process. In addition, 2′,4′-DHAP can be used as an iron ion detection reagent to give ferric chloride solutions a red color …”