33284-02-5Relevant academic research and scientific papers
Bicyclic 1,2,3-triazolium ionic liquids: Synthesis, characterization, and application to rutaecarpine synthesis
Tseng, Ming-Chung,Cheng, Hui-Ting,Shen, Meng-Jane,Chu, Yen-Ho
, p. 4434 - 4437 (2011)
Starting with commercial reagents, bicyclic 1,2,3-triazolium ionic liquids [b-3C-tr][NTf2] (1) and [b-4C-tr][NTf2] (2) were synthesized in four steps with high overall isolated yields of 68% and 76%, respectively. Since the C-5 hydrogen is acidic, under basic condition ionic liquids 1 and 2 were readily methylated with methyl iodide to afford chemically stable ionic liquids 7 and 8 at room temperature (88% and 82%, respectively). Ionic liquid 1 was used as the ionic solvent to demonstrate its usefulness for the synthesis of rutaecarpine, a natural product.
Sustainable methine sources for the synthesis of heterocycles under metal- and peroxide-free conditions
Senadi, Gopal Chandru,Kudale, Vishal Suresh,Wang, Jeh-Jeng
supporting information, p. 979 - 985 (2019/03/12)
Alcohols and ethers were identified as sustainable methine sources for synthesizing quinazolinone and benzimidazole derivatives using a combination of TsOH·H2O/O2 and appropriate bis-nucleophiles for the first time. Deuterium labeling studies clearly proved that the C2 hydrogen of the synthesized heterocycles came from the methine source. These unique reaction conditions were successfully applied to the synthesis of echinozolinone (2e′), 2f′ (a common precursor of rutaecarpine and (±) evodiamine), and dimedazole (6d). Notable features of this method include its low toxicity, use of commercial feedstocks as substrates, low cost, broad functional group tolerance and suitability for a wide range of bis-nucleophilic starting materials.
Aryl substituted amide compounds and its preparation method, pharmaceutical composition containing the same and application thereof (by machine translation)
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Paragraph 0111; 0112; 0113, (2018/07/30)
The invention relates to an aryl-substituted amide compound in the formula (I), a preparing method thereof, a medicine composition comprising the same, and application of the amide compound and the medicine composition to pharmacy, wherein Arl, L1, M1, M2, L2 and Ar2 are defined as in the text. The aryl-substituted amide compound can excite TRPV1 and nuclear receptors (LXRs, PPARs and RXR), adjust expression of cholesterol excretion gap-associated protein ABCA1/G1, SR-BI, adjust expression of inflammation gap-associated protein TNF-alpha and the like, and play roles in promoting excretion of cholesterol and lipid, reducing sugar, adjusting blood lipid, resisting inflammation and reducing blood pressure, and can be used for treating and/or preventing and/or relieving cardiovascular and cerebrovascular diseases, adjusting blood lipid, and resisting atherosclerosis, diabetes mellitus, inflammation, pain and hypertension.
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.
Anthranilic acid based CCK1 receptor antagonists: Blocking the receptor with the same 'words' of the endogenous ligand
Lassiani, Lucia,Pavan, Michela V.,Berti, Federico,Kokotos, George,Markidis, Theodoros,Mennuni, Laura,Makovec, Francesco,Varnavas, Antonio
experimental part, p. 2336 - 2350 (2009/09/05)
The anthranilic acid diamides represent the more recent class of nonpeptide CCK1 receptor antagonists. This class is characterized by the presence of anthranilic acid, used as a molecular scaffold, and two pharmacophores selected from the C-terminal tetrapeptide of CCK. The lead compound coded VL-0395, endowed with sub-micromolar affinity towards CCK1 receptors, was characterized by the presence of Phe and 2-indole moiety at the C- and N-termini of anthranilic acid, respectively. Herein we describe the first step of the anthranilic acid C-terminal optimization using, instead of Phe, aminoacids belonging to the primary structure of CCK-8 and other not coded residues. Thus we demonstrate that the CCK1 receptor affinity depends on the nature of the aminoacidic side chain as well as that the free carboxy group of the alpha-aminoacids is crucial for the binding. The R enantiomers of the most active compounds represent the eutomers of this class of antagonists confirming thus the stereo preference of the receptor. Moreover this SAR study demonstrates that the receptor binding pocket, that host the aminoacidic side chain, results much more tolerant respect to that accommodating the indole ring. As a result, an appropriate variation of the aminoacidic side chain could provide a better CCK1 receptor affinity diorthosis.
C-terminal anthranoyl-anthranilic acid derivatives and their evaluation on CCK receptors
Varnavas, Antonio,Lassiani, Lucia,Luxich, Elena,Valenta, Valentina
, p. 293 - 302 (2007/10/03)
A series of C-terminal anthranoyl-anthranilic acid derivatives arising from a strict bond disconnection approach of asperlicin were synthesized and examined for their CCK receptor affinities. These compounds represent the second step of our investigation
Studies on quinazolines. VII. Reactions of anthranilamide with β- diketones; new approaches toward the synthesis of tetrahydropyrido[2,1- b]quinazolin-11-one derivatives
Chern, Ji-Wang,Chen, Hui-Ting,Lai, Nan-Yi,Wu, Kuo-Rong,Chern, Yu-Chin
, p. 928 - 933 (2007/10/03)
Condensation of anthranilamide and its derivatives with various 1,3- cyclohexanediones 5a,b or 2,4-pentanediones under acidic conditions produced a variety of heterocycles, leading to the synthesis of tetrahydropyridol[2,1- b]-quinazolin-11-one derivatives. Condensation of anthranilamide with 5a or 5b in the presence of p-toluenesulfonic acid at the reflux temperature of tetrahydrofuran (THF) afforded compound 6a (40%) and compound 7a (22%) or compound 6b (47%) and compound 7b (39%), respectively. However, reflux of anthranilamide with 5a or 5b in 6% ethanolic hydrogen chloride provided compounds 6a and 6b in 77% and 73% yields, respectively. Heating 7a with 5a in 6% ethanolic hydrogen chloride furnished 6a in 82.4% yield. Reaction of anthranilamide with 5c under the same conditions resulted in the formation of 11 (57%). Treatment of compounds 6a and 6b with NaBH4 furnished 8a,b (89, 87% yields), which were subsequently subjected to the Mitsunobu reaction to produce 6,7,8,9-tetrahydro-9-methyl-11H-pyrido[2,1-b]quinazolin-11-one (9a) and 6,7,8,9-tetrahydro-7,7,9-trimethyl-11H-pyrido[2,1-b]quinazolin-11-one (9b) in 56 and 72% yields, respectively. However, heating 14 with 15a in CH3CN in the presence of p-toluenesulfonic acid furnished 19 in 31% yield. Under similar conditions, treatment of 21 with 15a provided 23a (42.4% yield), a key intermediate for the synthesis of rutaecarpine. Analogous reaction of 21 with 15b, 15c and 5a provided 22b-d in 63-99.3% yield, respectively.
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).
ONE POT SYNTHESIS OF QUINAZOLINE DERIVATIVES BY USE OF PALLADIUM CATALYZED CARBONYLATION
Mori, Miwako,Kobayashi, Hiromi,Kimura, Masaya,Ban, Yoshio
, p. 2803 - 2806 (2007/10/02)
One pot synthesis of quinazoline derivatives from a mixture of o-iodoaniline 1a and five membered lactams or N-acyl-o-iodoaniline derivatives, 1b and 1c, and primary amines was effected through the palladium-catalyzed insertion of carbon monoxide.
