Acetonpalmatin | 38699-74-0

• 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: Acetonpalmatin
• 英文别名: 1-(2,3,9,10-tetramethoxy-6,8-dihydro-5H-isoquinolino[2,1-b]isoquinolin-8-yl)propan-2-one
• CAS: 38699-74-0
• 化学式: C₂₄H₂₇NO₅
• 分子量: 409.482
• InChiKey: OZWNJOUTOSEZGP-UHFFFAOYSA-N

物化性质

• 沸点：
  598.0±50.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Acetonpalmatin 、 丁酰氯 在 sodium iodide 、 盐酸 作用下， 以 乙腈 、 水 为溶剂， 反应 5.0h， 以11.7%的产率得到13-butanoylpalmatine chloride
  参考文献：
  名称：

  Syntheses and structure-activity relationships on antibacterial and anti-ulcerative colitis properties of quaternary 13-substituted palmatines and 8-oxo-13-substituted dihydropalmatines

  摘要：

  In this study, quaternary palmatine is used as a lead compound to design and synthesize derivatives to evaluate bioactivities, with twenty-seven compounds of four series being obtained. Antibacterial activity was examined by determining the minimal inhibitory concentration (MIC) values on Staphylococcus aureus, Escherichia coli, and Candida albicans, three series of derivatives being found to exhibit activity in vitro with significant structure-activity relationship (SAR). Elongating the carbon chain led to the antibacterial activity increased, with quaternary 13-hexanoylpalmatine chloride, quaternary 13-(omega-ethoxycarbonyl)heptylpalmatine chloride, and 8-oxo-13-(N-n-nonyl) aminomethyldihydropalmatine, all of which possess the longest aliphatic carbon chain in the corresponding series of derivatives, showing the MIC values of 62.5, 7.81, and 15.63 mu g/ml against S. aureus, respectively. The property of anti-ulcerative colitis (anti-UC) was assessed at the levels of both in vitro and in vivo, with X-box-binding protein 1 (XBP1) being targeted in vitro. Seven compounds were found not only to be hypocytotoxic toward intestinal epithelial cells, but also to exhibit activity of activating the transcription of XBP1 in vitro. Five compounds were found to possess significant dose-effect relationship with EC50 values at a level of 10(-7) mu M in vitro. 8-Oxo-13-formyldihydropalmatine as an intermediate was found to display significant curative effect on UC in vivo based on the biomarkers of body weight change, colon length change, and calculated values of disease activity index and colon macroscopic damage index of the experimental animals, as well as the examination into the pathological changes of the colon tissue of the modeled animals. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2018.04.025
• 作为产物：
  描述：

  盐酸巴马汀 、 丙酮 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 3.0h， 以54.9%的产率得到Acetonpalmatin
  参考文献：
  名称：

  Syntheses and structure-activity relationships on antibacterial and anti-ulcerative colitis properties of quaternary 13-substituted palmatines and 8-oxo-13-substituted dihydropalmatines

  摘要：

  In this study, quaternary palmatine is used as a lead compound to design and synthesize derivatives to evaluate bioactivities, with twenty-seven compounds of four series being obtained. Antibacterial activity was examined by determining the minimal inhibitory concentration (MIC) values on Staphylococcus aureus, Escherichia coli, and Candida albicans, three series of derivatives being found to exhibit activity in vitro with significant structure-activity relationship (SAR). Elongating the carbon chain led to the antibacterial activity increased, with quaternary 13-hexanoylpalmatine chloride, quaternary 13-(omega-ethoxycarbonyl)heptylpalmatine chloride, and 8-oxo-13-(N-n-nonyl) aminomethyldihydropalmatine, all of which possess the longest aliphatic carbon chain in the corresponding series of derivatives, showing the MIC values of 62.5, 7.81, and 15.63 mu g/ml against S. aureus, respectively. The property of anti-ulcerative colitis (anti-UC) was assessed at the levels of both in vitro and in vivo, with X-box-binding protein 1 (XBP1) being targeted in vitro. Seven compounds were found not only to be hypocytotoxic toward intestinal epithelial cells, but also to exhibit activity of activating the transcription of XBP1 in vitro. Five compounds were found to possess significant dose-effect relationship with EC50 values at a level of 10(-7) mu M in vitro. 8-Oxo-13-formyldihydropalmatine as an intermediate was found to display significant curative effect on UC in vivo based on the biomarkers of body weight change, colon length change, and calculated values of disease activity index and colon macroscopic damage index of the experimental animals, as well as the examination into the pathological changes of the colon tissue of the modeled animals. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2018.04.025

文献信息

• Antifungal formulation comprising protoberberine derivatives and salts
  申请人：Hanwha Corporation

  公开号：US06030978A1

  公开（公告）日：2000-02-29

  The antifungal formulation comprising the novel compounds of the following chemical formulae (I) and (II) exhibit in vitro antifungal activity against fungi including cutaneous filamentous fungus, such as Epidermophyton, Microsporum, Trichophyton, Sporothrix schenckii, Aspergillus or Candida. The formulation of the present invention exhibit in vitro antifungal activity at the concentration of 1-100 .mu.g/ml. ##STR1## wherein R.sup.1, R.sup.2, and R.sup.4 may be the same or different, and represent C.sub.1 -C.sub.5 alkoxy, R.sup.3 represents hydrogen or C.sub.1 -C.sub.10 alkyl, A.sup.- represents inorganic acid ion, organic acid ion or halide, R.sup.5 represents hydrogen, pyridylmethyl, substituted pyridylmethyl or a group having the following chemical formula(XI) ##STR2## wherein Z.sup.1, Z.sup.2, Z.sup.3, Z.sup.4 and Z.sup.5 may be the same or different and represent hydrogen, halogen, C.sub.1 -C.sub.5 alkyl, trifluoromethyl, phenyl, substituted phenyl, nitro, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylamino, acetylamino, C.sub.1 -C.sub.8 trialkyl ammonium, guanidinyl, methylthio, ethylthio, trifluoromethoxy, hydroxy, phenoxy, vinyl, carboxyl and C.sub.1 -C.sub.2 alkoxycarbonyl group.

  抗真菌配方包括以下化学式(I)和(II)的新化合物，对包括表皮丝状真菌在内的真菌表现出体外抗真菌活性，例如表皮癣菌、癣菌、毛癣菌、斯波罗替克氏真菌、曲霉或念珠菌。本发明的配方在浓度为1-100μg/ml时表现出体外抗真菌活性。其中R.sup.1、R.sup.2和R.sup.4可以相同也可以不同，表示C.sub.1-C.sub.5烷氧基，R.sup.3表示氢或C.sub.1-C.sub.10烷基，A.sup.-表示无机酸离子、有机酸离子或卤素，R.sup.5表示氢、吡啶甲基、取代吡啶甲基或具有以下化学式(XI)的基团。
• Pharmaceutically available protoberberine salts derivatives, and
  申请人：Hanwha Corporation

  公开号：US06008356A1

  公开（公告）日：1999-12-28

  The novel compounds of the following chemical formulae (I) and (II) exhibit in vitro antifungal activity against fungi including cutaneous filamentous fungus, such as Epidermophyton, Microsporum, Trichophyton, Sporothrix schenckii, Aspergillus or Candida. The compounds of the present invention exhibit in vitro antifungal activity at the concentration of 1-100 .mu.g/ml. ##STR1## wherein R.sup.1, R.sup.2, and R.sup.4 may be the same or different, and represent C.sub.1 -C.sub.5 alkoxy, R.sup.3 represents hydrogen or C.sub.1 -C.sub.10 alkyl, A.sup.- represents inorganic acid ion, organic acid ion or halide, R.sup.5 represents hydrogen, pyridylmethyl, substituted pyridylmethyl or a group having the following chemical formula(XI) ##STR2## wherein Z.sup.1, Z.sup.2, Z.sup.3, Z.sup.4 and Z.sup.5 may be the same or different and represent hydrogen, halogen, C.sub.1 -C.sub.5 alkyl, trifluoromethyl, phenyl, substituted phenyl, nitro, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylamino, acetylamino, C.sub.1 -C.sub.8 trialkyl ammonium, guanidinyl, methylthio, ethylthio, trifluoromethoxy, hydroxy, phenoxy, vinyl, carboxyl and C.sub.1 -C.sub.2 alkoxycarbonyl group.

  以下化学公式(I)和(II)的新化合物对包括皮肤丝状真菌（如表皮癣菌、小孢子菌、毛癣菌、申克孢子丝菌、曲霉菌或念珠菌）在内的真菌具有体外抗真菌活性。本发明的化合物在1-100微克/毫升的浓度下表现出体外抗真菌活性。##STR1## 其中，R.sup.1、R.sup.2和R.sup.4可以相同或不同，表示C.sub.1-C.sub.5烷氧基，R.sup.3表示氢或C.sub.1-C.sub.10烷基，A.sup.-表示无机酸离子、有机酸离子或卤素，R.sup.5表示氢、吡啶甲基、取代的吡啶甲基或具有以下化学公式(XI)的基团##STR2## 其中，Z.sup.1、Z.sup.2、Z.sup.3、Z.sup.4和Z.sup.5可以相同或不同，表示氢、卤素、C.sub.1-C.sub.5烷基、三氟甲基、苯基、取代的苯基、硝基、C.sub.1-C.sub.4烷氧基、C.sub.1-C.sub.4烷基氨基、乙酰氨基、C.sub.1-C.sub.8三烷基铵、胍基、甲硫基、乙硫基、三氟甲氧基、羟基、苯氧基、乙烯基、羧基和C.sub.1-C.sub.2烷氧基羰基。
• PHARMACEUTICALLY AVAILABLE PROTOBERBERINE SALTS DERIVATIVES, AND PROTOBERBERINE DERIVATIVES AND SALTS THEREOF
  申请人：HANWHA CHEMICAL CORPORATION

  公开号：EP1073655B1

  公开（公告）日：2004-04-14
• Feist; Sandstede, Archiv der Pharmazie, 1918, vol. 256, p. 2,5
  作者：Feist、Sandstede

  DOI：——

  日期：——
• v.Bruchhausen, Archiv der Pharmazie, 1923, vol. 261, p. 32,33
  作者：v.Bruchhausen

  DOI：——

  日期：——