60423-21-4

Usage

InChI:InChI=1/C17H18O5/c1-19-14-9-6-11(5-8-13(14)18)12-7-10-15(20-2)17(22-4)16(12)21-3/h5-10H,1-4H3

Upstream product

• 33816-51-2 5-bromo-2-methoxycyclohepta-2,4,6-trien-1-one 
• 118062-05-8 2,3,4-trimethoxyphenylboronic acid 
• 102119-62-0 trimethoxyphenyllithium 
• 125102-15-0 2-methoxy-5-<<(trifluoromethyl)sulfonyl>oxy>tropone 
• 343962-18-5 5-iodo-2-methoxytropone 
• 869653-86-1 4-(triethoxysilyl)-1,2,3-trimethoxybenzene 
• 634-36-6 1,2,3-trimethoxybenzene 
• 3172-00-7 5-bromotropolone 
• 2297-94-1 5-nitrosotropolone 
• 7021-46-7 5-aminotropolone 
• 125102-14-9 Trifluoro-methanesulfonic acid 7-oxo-4-trifluoromethanesulfonyloxy-cyclohepta-1,3,5-trienyl ester 
• 15852-34-3 2,5-dihydroxycyclohepta-2,4,6-trien-1-one 
• 10385-36-1 2,3,4-trimethoxybromobenzene 
• 3084-13-7 5-nitrotropolone 

Relevant academic research and scientific papers

Discovery of structurally simplified analogs of colchicine as an immunosuppressant

We have discovered a new class of colchicine-derived therapeutic agents for immune diseases including rejection of organ-transplantation and autoimmune disease. Compound 2, which had been developed to overcome poor pharmacokinetic properties of compound 1, a first-generation colchicine analog, turned out to show toxicity such as intestinal toxicity and loss of weight during in vivo tests. The deletion of 7-carboxamide group and middle ring-truncation in colchicine allowed us to have structurally simplified analogs with strong immunosuppressive activity. Herein, we report non-alkaloid tricyclic compound 7 and 12 as immunosuppressants which exhibited a strong immunosuppressive in vivo efficacy on the T-dependent antibody response, the Zymosan A-induced arthritis model and the Carrageenan-induced edema model. Compound 7 and 12 revealed less toxicity than the previous lead compound 2, and their minimum lethal doses (MLD) were proved to exceed 100 mg/kg.

Improved and highly versatile synthesis of 5-aryltropones

The use of 5-iodo-2-methoxytropone in palladium(0)-catalyzed coupling reactions with a variety of arylboronic acids has resulted in significantly improved reaction yields and times for a sterically and electronically diverse series of novel 5-aryltropones

Efforts directed toward the synthesis of colchicine: Application of palladium-catalyzed siloxane cross-coupling methodology

Colchicine is an important and synthetically challenging natural product. The key synthetic step in this approach to the synthesis of colchicine involved a palladium-catalyzed cross-coupling reaction between 5-bromotropolone (4) and an aryl siloxane to form the aryl-tropolone bond. The coupling of a variety of highly functionalized aryl siloxane derivatives was investigated and optimized coupling conditions were developed. It was discovered that a palladium catalyst with a high degree of phosphine ligand coordination (5 equiv of phosphine/mol Pd) was necessary to efficiently couple aryl siloxanes with 5-bromotropolone (4). In addition, the coupling approach has provided a direct comparison between siloxane and boronic acid coupling technologies that demonstrated that aryl siloxanes and boronic acids produce similar yields of highly functionalized biaryl products.

A CONVENIENT SYNTHESIS OF 5-ARYLTROPONES

2-methoxy-5-oxy>tropone was coupled to a variety of arylzinc chlorides in the presence of a palladium catalyst to furnish 5-aryltropones in good to excelent yields.