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 
• 869653-86-1 4-(triethoxysilyl)-1,2,3-trimethoxybenzene 
• 3172-00-7 5-bromotropolone 
• 22057-94-9 5-iodotropolone 
• 3084-13-7 5-nitrotropolone 
• 10385-36-1 2,3,4-trimethoxybromobenzene 
• 15852-34-3 2,5-dihydroxycyclohepta-2,4,6-trien-1-one 
• 343962-18-5 5-iodo-2-methoxytropone 
• 2297-94-1 5-nitrosotropolone 
• 125102-14-9 Trifluoro-methanesulfonic acid 7-oxo-4-trifluoromethanesulfonyloxy-cyclohepta-1,3,5-trienyl ester 
• 7021-46-7 5-aminotropolone 

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.

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.

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

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.