5990-67-0Relevant academic research and scientific papers
Novel total synthesis method of racemic tetrandrine
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Paragraph 0029; 0071; 0102-0105; 0136-0138; 0169-0170, (2021/07/01)
The invention discloses a novel total synthesis method of racemic tetrandrine, and belongs to the technical field of pharmaceutical chemical synthesis. 5-bromovanillin and 4-hydroxyphenylacetic acid which are low in price and easy to obtain are respectively used as starting materials to synthesize a compound 10, the compound 10 is used for synthesizing a compound 12 and a compound 14 through a simple route, and the two compounds are subjected to intermolecular and intramolecular Ullmann reaction to synthesize the racemic tetrandrine A. The key intermediates 12 and 14 are synthesized through the compound 10, the synthesis efficiency is greatly improved, the raw materials are utilized to the maximum extent, and the method is a racemic tetrandrine total synthesis route which is simplest in operation and lowest in cost so far.
Total synthesis method of optically pure Tetrandrine
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Paragraph 0052; 0057-0059; 0061; 0066-0068; 0069; 0074-0076, (2020/08/30)
The invention discloses a total synthesis method of optically pure tetrandrine, and belongs to the technical field of drug synthesis. The method comprises the following steps: (1) under the action ofa catalyst (1), carrying out intermolecular Ullmann reaction on a compound (1) and a compound (2) under alkaline and high-temperature conditions to synthesize a compound 3; (2) removing a hydroxyl protecting group from the compound (3) under an acidic condition to synthesize a compound (4); (3) carrying out intramolecular Ullmann reaction on the compound (4) under the action of a catalyst (2) under alkaline and high-temperature conditions to synthesize a compound (5), namely the optically pure tetrandrine. A convergent synthesis strategy is adopted, and only three steps are needed from the compound (1) to the synthesis of optically pure tetrandrine so that the reaction steps are greatly reduced, and the time and the material cost are saved; the yield can be as high as 28.7%-38.9%, and theyield is increased by dozens of times; the target product can be obtained on the gram scale, 1.3 g-1. 5 g of final optically pure product is synthesized, and the method has better industrialization potential.
Full-synthetic method of racemic tetrandrine
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, (2019/07/10)
The invention discloses a full-synthetic method of racemic tetrandrine, and belongs to the technical field of drug synthesis. The full-synthetic method of the racemic tetrandrine comprises the steps that a synthetic route adopts a convergence synthesis method, a 5-bromovanillin, namely a compound 1 and 3-hydroxy-4-methoxyphenylacetic acid, namely a compound 5 are taken as starting materials to obtain a compound 4 and a compound 6 respectively, then the compound 4 and the compound 6 are taken as raw materials to synthesize a compound 11, a compound 19 is synthesized from the compound 11, and finally, the compound 11 reacts with the compound 19. The full-synthetic method of the racemic tetrandrine has the advantages that the synthetic efficiency is higher, the yield is higher, and the cost is lower; the reaction conditions are milder, the operation is simple and convenient, the industrial value is higher, and a reference is provided for the full-synthetic method of optical voidness tetrandrine.
Anti-inflammatory effects of the partially purified extract of radix stephaniae tetrandrae
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, (2008/06/13)
This invention relates to inflammatory responses in isolated peripheral human neutrophils that studied in the presence or absence of specially processed Radix Stephaniae tetrandrae (SPRST). We conclude that SPRST exerts anti-inflammatory effects by interf
A CHEMISTRY OF BISBENZYLISOQUINOLINE ALKALOID: ISOMERIZATION OF BERBAMINE TO PENDULINE IN METHANOL BY RADICAL REACTION
Kashiwaba, Noriaki,Morooka, Shigeo,Kimura, Michiko,Ono, Minoru,Murakoshi, Yoshie,et al.
, p. 2043 - 2048 (2007/10/03)
Berbamine (1), a bisbenzylisoquinoline alkaloid, when treated with methanol, was isomerized to penduline (2), the C-1 epimer of 1.This isomerization was proved to proceed via a radical reaction by a free radical generated from methanol and molecular oxyge
ALKALOIDS OF DEHAASIA TRIANDRA
Lu, Sheng-Teh,Tsai, Ian-Lih,Leou, Shiow-Piaw
, p. 615 - 620 (2007/10/02)
Separation of the basic fraction from Dehaasia triandra afforded two new bisbenzylisoquinoline alkaloids, dehatridine and dehatrine, along with six known alkaloids, isocorydine, corytuberine, atheroline, nantenine, obaberine and a quaternary aporphine alkaloid, xanthoplanine (5). - Keywords: Dehaasia triandra; Lauraceae; Iau-Guoo-Nan; bisbenzylisoquinoline alkaloids; dehatridine; dehatrine.
Alcaloides bisbenzylisoquinoleiques de Albertisia cf. A. papuana
Lavault, Marie,Bruneton, Jean,Cave, Adrien,Chan, Kai Cheong,Deverre, Jean Robert,et al.
, p. 343 - 347 (2007/10/02)
Four new bisbenzylisoquinoline alkaloids were obtained from Albertisia cf.A. papuana Becc. (Menispermaceae).These are (-)-2,2'-bisnorphaeanthine (5), (+)-pangkoramine (7), (+)-pangkorimine (9), and (+)-2'-norcocsuline (14).They are accompanied by the known (+)-daphnoline (2), which is the main alkaloid, and by seven known dimers with one, two, or three ether bridges
SYNTHESIS OF STEBISIMINE, (+/-)-OBABERINE, AND (+/-)-ISOTETRANDRINE BY WILLGERODT-KINDLER CYCLOBISCONDENSATION. II.
Nakova, E. P.,Tolkachev, O. N.
, p. 88 - 91 (2007/10/02)
A synthesis of stebisimine, (+/-)-obaberine, and (+/-)-isotetrandrine has been performed by the cyclocondensation of 5-acetyl-2-methoxyphenyl 4'-acetylphenyl ether and 5-(β-aminoethyl)-2,3-dimethoxyphenyl 4'-(β-aminoethyl)-2'-methoxyphenyl ether and sulfur through the stage of formation of the corresponding biscyclophenylthioacetamides which, by Bischler-Napieralski cyclization and reduction of the corresponding bismethiodides, have been converted into the desired compounds.
A NEW SYNTHESIS OF STEBISIMINE, (+/-)-OBABERINE, AND (+/-)-ISOTETRANDRINE FROM ENAMINO SULFIDES. I.
Nakova, E. P.,Tolkachev, O. N.
, p. 83 - 87 (2007/10/02)
The synthesis of stebisimine, (+/-)-obaberine, and (+/-)-isotetrandrine has been effected by the cyclocondensation of 5-acetyl-2-methoxyphenyl 4'-acetylphenyl ether with 5-(β-aminoethyl)-2,3-dimethoxyphenyl 4'-(β-aminoethyl)-2'-methoxyphenyl ether and sulfur through the stage of obtaining the corresponding biscyclophenylthioacetamides which were converted into the desired compounds by Bischler-Napieralski cyclization and reduction of the corresponding bismethiodides.
