88909-07-3

Upstream product

• 2316-26-9 3,4-dimethoxycinnamic acid 
• 14737-89-4 3,4-dimethoxy-trans-cinnamic acid 
• 1135-24-6 3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 121-33-5 vanillin 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 77-95-2 D-(-)-quinic acid 
• 39856-08-1 3,4-dimethoxy-cinnamoyl chloride 

Downstream Products

• 68622-78-6 (+)-subcosine I 
• 89771-50-6 (+/-)-2-episubcosine II 
• 88931-06-0 (+/-)-subcosine I 

Relevant academic research and scientific papers

Substituted cinnamic anhydrides act as selective inhibitors of acetylcholinesterase

Cinnamic anhydrides have been shown to be more than reactive reagents, but they also act as inhibitors of the enzyme acetylcholinesterease (AChE). Thus, out of a set of 33 synthesised derivatives, several of them were mixed type inhibitors for AChE (from electric eel). Thus, (E)-3-(2,4-dimethoxyphenyl)acrylic anhydride (2c) showed Ki = 8.30 ± 0.94 μM and Ki′ = 9.54 ± 0.38 μM, and for (E)-3-(3-chlorophenyl)acrylic anhydride (2u) Ki = 8.23 ± 0.93 μM and Ki′ = 13.07 ± 0.46 μM were measured. While being not cytotoxic to many human cell lines, these compounds showed an unprecedented and noteworthy inhibitory effect for AChE but not for butyrylcholinesterase (BChE).

One-pot synthesis of cinnamic anhydrides from cinnamic acids and 6-chloro-2,4-dimethoxy-sec-triazine (CDMT) at room temperature

Symmetric cinnamic anhydrides were prepared by the reactions of cinnamic acid substrates with 6-chloro-2,4-dimethoxy-sec-triazine. The reactions were performed at room temperature for 15 h. Diverse cinnamic acid substrates bearing electron-withdrawing or -donating groups worked well, providing the corresponding cinnamic anhydrides in moderate-to-good yields.

Synthesis of Mono-, Di-, and Tri-3,4-dimethoxycinnamoyl-1,5-γ-quinides

Tri-3,4-dimethoxycinnamoyl-1,5-γ-quinide was synthesized and fully characterized by a direct synthesis from quinic acid and a large excess of 3,4-dimethoxycinnamoyl chloride. Mono- and di-3,4-dimethoxycinnamoyl-1,5-γ-quinides were also obtained from the direct coupling of 1,5-γ-quinide and 3,4-dimethoxycinnamoyl chloride in different molar ratios. Moreover, a hypothetical mechanism of the direct lactonization is proposed.

Synthesis of (+/-)-Lasubine I and II and (+/-)-Subcosine I

The first total synthesis of lasubine I and II and subcosine I has been achieved.A crucial step of this synthesis involves thermal dipolar cycloaddition of 1-(3,4-dimethoxyphenyl)butadiene with 2,3,4,5-tetrahydropyridine 1-oxide, affording the E and