9-O-lauroylberberrubine chloride

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 原小檗碱生物碱及其衍生物
• 英文名称: 9-O-lauroylberberrubine chloride
• 英文别名: 2,3-methenedioxy-9-lauroyloxy-10-methoxyprotoberberine chloride；(17-Methoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-16-yl) dodecanoate;chloride
• 化学式: C₃₁H₃₈NO₅*Cl
• 分子量: 540.099
• InChiKey: PLCDLGSMLOHXOM-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  57.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  盐酸小檗碱 在 尿素 作用下， 以 乙腈 为溶剂， 反应 1.5h， 生成 9-O-lauroylberberrubine chloride
  参考文献：
  名称：

  Antimicrobial Activity of 9-O-Acyl- and 9-O-Benzoyl-Substituted Berberrubines

  摘要：

  在对小檗碱衍生物进行结构-活性关系研究的过程中，合成了一系列带有 9-O-酰基（4-6）和 9-O-苯甲酰基（7）取代基的化合物，以期提高其抗菌活性。与目前临床上使用的抗生素小檗碱相比，小檗碱衍生物之一，9-月桂酰基氯化小檗碱对革兰氏阳性菌粪肠球菌、金黄色葡萄球菌、表皮葡萄球菌、黄体小球菌、枯草杆菌以及革兰氏阴性菌肺炎克雷伯氏菌的活性最强。这一结果表明，某些结构和大小的亲脂取代基的存在可能是获得最佳抗菌活性的关键。

  DOI：

  10.1055/s-2000-8536

文献信息

• Antimicrobial Activity of 9-<i>O</i>-Acyl- and 9-<i>O</i>-Benzoyl-Substituted Berberrubines
  作者：Sa Hong、Sung Kim、Jung Jeun、Sang Lee、Sung Kim、Jung Kim

  DOI：10.1055/s-2000-8536

  日期：——

  In the course of a structure-activity relationship study on berberrubine derivatives, a series of compounds bearing 9-O-acyl- (4 - 6) and 9-O-benzoyl- (7) substituents was synthesized with the expectation of increasing the antimicrobial activity. One of the berberrubine derivatives, 9-lauroylberberrubine chloride was the most active against Gram-positive bacteria Enterococcus faecalis, Staphylococcus aureus, Staphylococcus epidermidis, Micrococcus luteus, Bacillus subtilis as well as the Gram-negative bacterium Klebsiella pneumoniae in comparison to berberine, the currently used antibiotic in clinic. This result suggested that the presence of lipophilic substituents of certain structures and sizes might be crucial for the optimal antimicrobial activity.

  在对小檗碱衍生物进行结构-活性关系研究的过程中，合成了一系列带有 9-O-酰基（4-6）和 9-O-苯甲酰基（7）取代基的化合物，以期提高其抗菌活性。与目前临床上使用的抗生素小檗碱相比，小檗碱衍生物之一，9-月桂酰基氯化小檗碱对革兰氏阳性菌粪肠球菌、金黄色葡萄球菌、表皮葡萄球菌、黄体小球菌、枯草杆菌以及革兰氏阴性菌肺炎克雷伯氏菌的活性最强。这一结果表明，某些结构和大小的亲脂取代基的存在可能是获得最佳抗菌活性的关键。
• Design, synthesis, and cholesterol-lowering efficacy for prodrugs of berberrubine
  作者：Ying-Hong Li、Yi Li、Peng Yang、Wei-Jia Kong、Xue-Fu You、Gang Ren、Hong-Bin Deng、Yue-Ming Wang、Yan-Xiang Wang、Jian-Dong Jiang、Dan-Qing Song

  DOI：10.1016/j.bmc.2010.06.106

  日期：2010.9

  In order to enhance oral bioavailability of berberine (BBR) for its cholesterol-lowering efficacy in vivo, a series of ester or ether prodrugs of berberrubine (M1), which is an active metabolite of BBR after first-pass metabolism, were designed, semi-synthesized, and evaluated. Among these M1 prodrugs, compound 5g possessing palmitate at the 9-position showed a moderate Log P value and esterase hydrolysis rate for releasing M1 in blood. Its cholesterol-lowering efficacy in vivo was evaluated in hyperlipidemic SD rats. Compound 5g (100 mg/kg/d) reduced blood CHO and LDL-c by 35.8% and 45.5%, respectively, similar to that by BBR. It also exhibited a good safety in rats with no side-effect on liver and kidney function. Therefore, the design of M1 prodrug appears to be an effective strategy to improve pharmacokinetic feature of BBR for its lipid-lowering efficacy in vivo. (C) 2010 Elsevier Ltd. All rights reserved.
• Antimicrobial Activity of 9-O-Acyl- and 9-O-Alkylberberrubine Derivatives
  作者：Sung Han Kim、Sang Jun Lee、Joo Hyoung Lee、Won Suck Sun、Jung Han Kim

  DOI：10.1055/s-2002-23128

  日期：2002.3

  structure-activity relationship study on berberrubine derivatives, a series of compounds bearing 9-O-acyl- and 9-O-alkyl-substituents were synthesized and tested for antimicrobial activity against Gram-positive, Gram-negative bacteria and fungi. Octanoyl, decanoyl, lauroyl derivatives among the acyl analogs and hexyl, heptyl, octyl, nonyl, decyl, undecyl derivatives among the alkyl analogs showed strong antimicrobial

  为了研究小ber红素衍生物的构效关系，合成了一系列带有9-O-酰基和9-O-烷基取代基的化合物，并测试了它们对革兰氏阳性，革兰氏阴性细菌和真菌的抗菌活性。酰基类似物中的辛酰基，癸酰基，月桂酰基衍生物以及烷基类似物中的己基，庚基，辛基，壬基，癸基，十一烷基衍生物对革兰氏阳性细菌和真菌表现出较强的抗菌活性。总体而言，烷基类似物在抗菌活性方面比酰基类似物更具活性。合成的衍生物对革兰氏阴性细菌没有活性。取代基太短或太长都会降低活性。这些结果表明，中等大小的亲脂性取代基的存在可能对最佳抗菌活性至关重要。