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Cyclovirobuxine D derivative, and preparation and use thereof

A technology of cyclovirboxicin and its derivatives, which is applied in the field of cyclovirboxicin D derivatives and their preparation and application, can solve the problems of poor water solubility and narrow safety range of cyclovirboxicin D, and achieve low cost, The preparation method is simple and the effect of high yield

Inactive Publication Date: 2009-07-22
SICHUAN CHUANDA WEST CHINA PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Pharmacological experiments and clinical application studies have shown that the safety range of cyclovir buxicine D is relatively narrow, and its water solubility is poor.

Method used

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  • Cyclovirobuxine D derivative, and preparation and use thereof
  • Cyclovirobuxine D derivative, and preparation and use thereof
  • Cyclovirobuxine D derivative, and preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Take Cyclovirbuxine D (404mg) and p-nitrobenzaldehyde (155mg) in a 100mL round bottom flask, then add ethanol (40mL), stir and reflux for 1h; after the reaction is complete, recover the solvent under reduced pressure, recrystallize with ethanol, A yellow solid product (Ia) in which R in the structure of formula (I) is p-nitrophenyl was obtained, with a yield of 85%, m.p.228-230°C. Structural test results:

[0018] 1 HNMR (400MHz, CDCl 3 )δ: 7.67~8.21 (4H, dd, ArH), 5.10 (1H, s, OCHN), 3.89~3.93 (1H, septet, 16-H), 2.98~3.02 (1H, m, 20-H), 1.94 ~2.46(6H, m, 2NCH 3 ), 0.60~0.61 (1H, d, 19-βH), 0.34~0.35 (1H, d, 19-αH);

[0019] IR(KBr)ν: 3435, 2964, 2862, 1520, 1339, 1106, 989, 971, 856, 743;

[0020] HRMS (ESI) calcd for C 33 h 50 N 3 o 3 [M+H] + 536.3847, found 536.3855.

Embodiment 2

[0022] Using the same method as in Example 1, take Cyclovirubuxin D (404mg) and p-chlorobenzaldehyde (192mg) in a 100mL round bottom flask, then add isopropanol (40mL), stir and reflux for 4h; after the reaction, The solvent was recovered under reduced pressure, recrystallized with isopropanol alcohol, and the product (Ib) in which R in the structure of formula (I) was p-chlorophenyl was obtained, the yield was 82%, m.p.118-120°C. Structural test results:

[0023] 1HNMR (400MHz, CDCl3) δ: 7.29~7.43(4H, dd, ArH), 4.91(1H, s, OCHN), 3.85~3.89(1H, septet, 16-H), 2.87~2.90(1H, m, 20 -H), 1.96~2.46 (6H, m, 2NCH3), 0.59~0.60 (1H, d, 19-βH), 0.33~0.34 (1H, d, 19-αH);

[0024] IR (KBr) v: 3435, 2963, 2864, 1491, 1470, 1378, 1346, 1088, 970, 800, 722;

[0025] HRMS (ESI) calcd for C33H50ClN2O1 [M+H]+525.3606, found 525.3579.

Embodiment 3

[0027] Using the same method as in Example 1, take Cyclovirubuxin D (404mg) and benzaldehyde (140mg) in a 100mL round bottom flask, then add isopropanol (40mL), stir and reflux for 5h; after the reaction is complete, depressurize The solvent was recovered and recrystallized with isopropanol to obtain a white solid (Ic) in which R in the structure of formula (I) was phenyl, with a yield of 87%, m.p.194-196°C. Structural test results:

[0028] 1 HNMR (400MHz, CDCl 3 )δ: δ: 7.27~7.49(5H, m, ArH), 4.92(1H, s, OCHN), 3.87~3.92(1H, septet, 16-H), 2.85~2.90(1H, m, 20-H) , 1.99~2.46 (6H, m, 2NCH 3 ), 0.59~0.60 (1H, d, 19-βH), 0.33~0.34 (1H, d, 19-αH);

[0029] IR(KBr)ν: 3435, 2928, 2869, 1450, 1377, 1108, 990, 938, 742, 700;

[0030] HRMS (ESI) calcd for C 33 h 51 N 2 o 1 [M+H] + 491.3996, found 491.3980.

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Abstract

The invention discloses a cyclovirobuxine D derivative and a preparation method and the application thereof. The structure of the derivative is shown as formula (I): R in the formula is selected from H, C1-6alkyl, phenyl, p-nitrophenyl, para halogen phenyl, para-C1-6alkyl substituted phenyl, para-C1-6alkoxy, para-trifluoromethyl-phenyl, para-dimethylamino-benzene base, inter-nitrophenyl, 3, 4-dimethyl-phenyl, 3, 4, 5- trimethyl-phenyl, 3, 4-dimethoxy-phenyl, 3, 4, 5-trimethoxybenzaldehyde base, 3-thiazolyl, 2-furyl or 1-naphthyl. The derivative can be prepared by taking cyclovirobuxine D and aldehydes (II) as raw materials. The derivative has the same effect as the cyclovirobuxine D, can be combined with pharmaceutically-acceptable auxiliary components into injection agent which can be used for treating cardiovascular and cerebrovascular disease and various oral pharmaceutical preparations.

Description

technical field [0001] The present invention relates to a class of new compounds with medical use obtained by chemical modification, specifically a class of cyclovirbuxusine D derivatives, as well as the preparation method and medical use of the derivatives. Background technique [0002] Cyclovirobuxine D (CVB-D) A, whose structure is shown in formula (A), is derived from Buxus microphylla Sieb.et Zucc.Var.Sinica Rehd.et Wils. and its genus The active ingredient extracted and separated from the compound, also known as cyclo-evergreen epiphylline D, is a fat-soluble alkaloid compound, which has good anti-arrhythmia, anti-myocardial ischemia and cardiotonic effects, and has a good effect on acute cerebral ischemia. It has a protective effect. At present, it has been included in the 2000 and 2005 editions of the "Chinese Pharmacopoeia" under the drug name "Huang Yangning", and is widely used in the treatment of clinical coronary heart disease, arrhythmia and other diseases. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J71/00C07J75/00A61K31/58A61P9/00
Inventor 杨鸿均胡翠窦后松范辰华郜宁李颖尹述凡
Owner SICHUAN CHUANDA WEST CHINA PHARMA
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