77784-62-4Relevant academic research and scientific papers
Preparation method of 2-trifluoromethyl substituted quinazolinone compound and application of 2-trifluoromethyl substituted quinazolinone compound in synthesis of pharmaceutical molecules
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Paragraph 0042; 0043, (2021/07/01)
The invention discloses a preparation method of a 2-trifluoromethyl substituted quinazolinone compound. The preparation method comprises the following steps: adding a palladium catalyst, a ligand, a carbon monoxide substitute, an additive, trifluoroethylimido acyl chloride and amine into an organic solvent, reacting at 110 DEG C for 16-30 hours, and after the reaction is completed, carrying out post-treatment to obtain the 2-trifluoromethyl substituted quinazolinone compound. The preparation method has the advantages of simple operation, cheap and easily available initial raw materials, high reaction efficiency, good substrate compatibility, synthesis of trifluoromethyl quinazolinone compounds substituted by different groups through substrate design, convenient operation, and broadening of the practicality of the method. The method is also successfully applied to the high-yield synthesis of the drug molecule Rutaecarpine.
Optimization of rutaecarpine as ABCA1 up-regulator for treating atherosclerosis
Li, Yongzhen,Feng, Tingting,Liu, Peng,Liu, Chang,Wang, Xiao,Li, Dongsheng,Li, Ni,Chen, Minghua,Xu, Yanni,Si, Shuyi
supporting information, p. 884 - 888 (2014/09/17)
ATP-binding cassette transporter A1 (ABCA1) is a key transporter and receptor in promoting cholesterol efflux, and increasing the expression level of ABCA1 is antiatherogenic. In our previous study, rutaecarpine (RUT) was found to protect ApoE-/- mice from developing atherosclerosis through preferentially up-regulating ABCA1 expression. In the present work, a series of RUT derivatives were synthesized and examined as ABCA1 expression up-regulators. Compounds CD1, CD6, and BCD1-2 were found to possess the most potential activity as antiatherosclerotic agents among all compounds tested.
Synthesis and vasodilator effects of rutaecarpine analogues which might be involved transient receptor potential vanilloid subfamily, member 1 (TRPV1)
Chen, Zhuo,Hu, Gaoyun,Li, Dai,Chen, Jun,Li, Yuanjian,Zhou, Huayong,Xie, Ye
experimental part, p. 2351 - 2359 (2009/09/08)
Rutaecarpine is the major alkaloid component of Wu-Chu-Yu, a well known Chinese herbal drug. It has been reported that rutaecarpine causes the vasodilator, hypotensive effects by stimulation of CGRP synthesis and release via activation of TRPV1. In present study, 23 rutaecarpine analogues were designed and synthesized. Then, the vasodilator effects of theses compounds were screened by rat aortic ring experiment. The result showed that the 14-N atom of rutaecarpine might be the key site for the activity. The 5-carbonyl might make lower contribution to the effect. And simple substitute in indole-ring or quinazoline-ring would not enhance the vasodilator effect unless in proper position with proper group. One of these compounds, 10-methylrutaecarpine, exhibited similar effect with rutaecarpine. Further functional experiments showed its vasodilator and hypotensive effect were related to the stimulation of CGRP release via activation of TRPV1. The vasodilator effects of these compounds were evaluated and the structure-activity relationship was elucidated for the first time. The results suggested a new direction of valuable TRPV1 agonist as anti-hypertensive drugs.
Studies of Rutaecarpine and Related Quinazolinocarboline Alkaloids
Bergman, Jan,Bergman, Solveig
, p. 1246 - 1255 (2007/10/02)
Quinazolinocarboline alkaloids, e.g., rutaecarpine (1), can readily be synthesized by treating tryptamine with 2-(trifluoromethyl)-4H-3,1-benzoxazin-4-one (quickly generated in situ from trifluoroacetic anhydride (TFAA) and 2H-3,1-benzoxazine-2,4(1H)-dione.The product formed, 3--2-(trifluoromethyl)-4-(3H)-quinazolinone (5), is then cyclized (HCl/HOAc) to 13b-(trifluoromethyl)-13b,14-dihydrorutaecarpine (6), whereupon CF3H is eliminated by treatment with base.The sequence can conveniently be performed as a three-reaction one-pot procedure giving rutaecarpine (1) in 99percent yield within 3h.The approach can readily be extended to the synthesis of evodiamine (2), 13,13b-dehydroevodiamine (38a), and 13b,14-dihydrorutaecarpine (21).Thus treatment of 3--4(3H)-quinazolinone (19) with TFAA affected cyclization to 13b-(trifluoroacetyl)-13b,14-dihydrorutaecarpine (20), which can be readily hydrolyzed to 13b,14-dihydrorutaecarpine (21).
SYNTHESIS OF RUTECARPINE AND RELATED INDOLE ALKALOIDS
Bergman, Jan,Bergman, Solveig
, p. 347 - 350 (2007/10/02)
A new route to quinazolinocarboline alkaloids, involving elimination of CF3- in the final step has been developed.
