544711-79-7

Upstream product

• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 854737-54-5 (E)‐3‐(4‐((tert‐butyldimethylsilyl)oxy)‐3‐methoxyphenyl)acrylic acid 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 1135-23-5 3-(4-hydroxy-3-methoxyphenyl)propionic acid 

Downstream Products

• 544711-78-6 (1R,6R,7aR)-6-{3-[(4-(tert-butyldimethylsilanyloxy)-3-methoxyphenyl)propionyloxy]}hexahydropyrrolizine-1-carboxylic acid methyl ester 
• 210173-60-7 3-(4′-tert-butyldimethylsilyloxy-3′-methoxyphenyl)propanal 

Relevant academic research and scientific papers

The total syntheses of JBIR-94 and two synthetic analogs and their cytotoxicities against A549 (CCL-185) human small lung cancer cells

We here disclose the total syntheses of the natural polyphenol JBIR-94 and two nonnatural analogs, whose structures are of interest for their bioactivity potential as radical scavengers. Although we initially attempted this by dually acylating both of putrecine's amine nitrogens in a single pot, our endeavors with this method (which has been successfully reported by other groups) proved ineffectual. We accordingly opted for the lengthier approach of acylating each amine individually, which gratuitously prevailed and also aligns with separate literature precedent. Moreover, we here share our analysis of these target compounds’ cytotoxicities and IC50 values against A549 (CCL-185) human small lung cancer cells.

(-)-Tarchonanthuslactone: Design of New Analogues, Evaluation of their Antiproliferative Activity on Cancer Cell Lines, and Preliminary Mechanistic Studies

Natural products containing the α,β-unsaturated δ-lactone skeleton have been shown to possess a variety of biological activities. The natural product (-)-tarchonanthuslactone (1) possessing this privileged scaffold is a popular synthetic target, but its biological activity remains underexplored. Herein, the total syntheses of dihydropyran-2-ones modeled on the structure of 1 were undertaken. These compounds were obtained in overall yields of 17-21 % based on the Keck asymmetric allylation reaction and were evaluated in vitro against eight different cultured human tumor cell lines. We further conducted initial investigation into the mechanism of action of selected analogues. Dihydropyran-2-one 8 [(S,E)-(6-oxo-3,6-dihydro-2H-pyran-2-yl)methyl 3-(3,4-dihydroxyphenyl)acrylate], a simplified analogue of (-)-tarchonanthuslactone (1) bearing an additional electrophilic site and a catechol system, was the most cytotoxic and selective compound against six of the eight cancer cell lines analyzed, including the pancreatic cancer cell line. Preliminary studies on the mechanism of action of compound 8 on pancreatic cancer demonstrated that apoptotic cell death takes place mediated by an increase in the level of reactive oxygen species. It appears as though compound 8, possessing two Michael acceptors and a catechol system, may be a promising scaffold for the selective killing of cancer cells, and thus, it deserves further investigation to determine its potential for cancer therapy. Fighting the big C: We describe the synthesis of a new family of analogues based on the scaffold of the natural product (-)-tarchonanthuslactone; these compounds were evaluated in vitro against tumor cell lines. We further conducted an initial investigation into the mechanism of action, including the inhibition of phosphatases and glutathione-S-transferase and the production of reactive oxygen species.

N-(pyridinylamino) isoindolines and related compounds

Novel N-(pyridinylamino)isoindolines and related compounds, intermediates and processes for the preparation thereof, and methods of relieving memory dysfunction and treating depression utilizing the N-(pyridinylamino)isoindolines and related compounds, the intermediates or compositions thereof are disclosed.