(+/-)-2,3,10,11-tetrademethylpseudotetrahydropalmatine hydrobromide

• 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: (+/-)-2,3,10,11-tetrademethylpseudotetrahydropalmatine hydrobromide
• 英文别名: 2,3,10,11-tetrademethyltetrahydropseudopalmatine hydrobromide；(+/-)2,3,10,11-tetrahydroxyprotoberberine hydrobromide；6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-2,3,10,11-tetrol;hydrobromide
• 化学式: BrH*C₁₇H₁₇NO₄
• 分子量: 380.238
• InChiKey: FCWILCJWGGHXJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  84.2
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  二氯甲烷 、 (+/-)-2,3,10,11-tetrademethylpseudotetrahydropalmatine hydrobromide 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 4.5h， 生成 (2,3,10,11)-dimethylenedioxytetrahydroprotoberberine
  参考文献：
  名称：

  LC–NMR and LC–MS analysis of 2,3,10,11-oxygenated protoberberine metabolites in Corydalis cell cultures

  摘要：

  The metabolism of 2,3, 10,1 I-oxygenated protoberberine alkaloids was studied in cell cultures of Corydalis species. Without prior isolation, the structures of the metabolites were determined by LC-MS and LC-NMR analyses. Tetrahydropseudocoptisine alpha-N-metho salt, pseudoprotopine, and pseudomuramine were identified for the first time, and preliminary evidence for metabolic pathways to the formation of these alkaloids were obtained. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(03)00497-7
• 作为产物：
  描述：

  四氢罂粟碱盐酸盐 在 氢溴酸 作用下， 以 水 为溶剂， 反应 37.0h， 生成 (+/-)-2,3,10,11-tetrademethylpseudotetrahydropalmatine hydrobromide
  参考文献：
  名称：

  LC–NMR and LC–MS analysis of 2,3,10,11-oxygenated protoberberine metabolites in Corydalis cell cultures

  摘要：

  The metabolism of 2,3, 10,1 I-oxygenated protoberberine alkaloids was studied in cell cultures of Corydalis species. Without prior isolation, the structures of the metabolites were determined by LC-MS and LC-NMR analyses. Tetrahydropseudocoptisine alpha-N-metho salt, pseudoprotopine, and pseudomuramine were identified for the first time, and preliminary evidence for metabolic pathways to the formation of these alkaloids were obtained. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(03)00497-7

文献信息

• Potential cancer chemopreventive activity of simple isoquinolines, 1-benzylisoquinolines, and protoberberines
  作者：Wenhua Cui、Kinuko Iwasa、Harukuni Tokuda、Akiko Kashihara、Yosuke Mitani、Tomoko Hasegawa、Yumi Nishiyama、Masataka Moriyasu、Hoyoku Nishino、Miyoji Hanaoka、Chisato Mukai、Kazuyoshi Takeda

  DOI：10.1016/j.phytochem.2005.10.007

  日期：2006.1

  inhibition at 1 x 10(3) mol ratio/TPA). These alkaloids were more active than the naturally occurring alkaloids, 23, 25, 33, 53, and 54. In addition, fifteen simple isoquinolines, eighteen 1-benzylisoquinolines and eight protoberberines were evaluated with respect to their ability to scavenge 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radicals. Nine simple isoquinolines, ten 1-benzylisoquinolines, and four protoberberines

  测试了 17 种简单的异喹啉、15 种 1-苄基异喹啉和 19 种原小檗碱对 Raji 细胞中由 12-O-十四烷酰佛波醇-13-乙酸酯 (TPA) 诱导的 Epstein-Barr 病毒早期抗原 (EBV-EA) 激活的抑制活性。在被测生物碱中，1-苄基异喹啉和11种原小檗碱的抑制活性均高于β-胡萝卜素。1-苄基异喹啉 19、21、22、29 和 34 和原小檗碱 41、47-49、51、52 ​​和 55 显示出对 EBV-EA 诱导的有效抑制作用（1 x 10(3) 时抑制率为 96-100%摩尔比/TPA）。这些生物碱比天然存在的生物碱 23、25、33、53 和 54 更活跃。 此外，还评估了 15 种简单异喹啉、18 种 1-苄基异喹啉和 8 种原小檗碱清除 1、1-diphenyl-2-picrylhydrazyl (DPPH) 自由基。九个简单的异喹啉、十个 1-苄基异喹啉和四个
• Geranyl Derivatives of Isoquinoline Alkaloids Show Increased Biological Activities
  作者：Kinuko Iwasa、Yumi Nishiyama、Suguru Okada、Sousuke Takeuchi、Masataka Moriyasu、Miyoko Kamigauchi、Junko Koyama、Atsuko Takeuchi、Harukuni Tokuda、Hye-Sook Kim、Yusuke Wataya、Kazuyoshi Takeda、Yi-Nan Liu、Pei-Chi Wu、Kenneth F. Bastow、Toshiyuki Akiyama、Kuo-Hsiung Lee

  DOI：10.3987/com-10-11912

  日期：——

  Three types of isoquinoline alkaloids were tested for antimicrobial, cytotoxic, anti-malarial, anti-oxidant, and anti-HIV activities, as well as inhibitory activity against Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells. N- or O-Geranylation contributed to increased potency in four types of activities except anti-HIV and anti-oxidant. Some types of alkaloids may be useful as lead compounds for developing potential chemotherapeutic agents. N,N-Geranylated salsolinol was significantly active in three different assays, antimicrobial, cytotoxic, and EBV-EA, and may be a most useful compound.
• Kametani, Tetsuji; Kanaya, Naoaki; Ohta, Yohko, Heterocycles, 1980, vol. 14, # 7, p. 963 - 970
  作者：Kametani, Tetsuji、Kanaya, Naoaki、Ohta, Yohko、Ihara, Masataka

  DOI：——

  日期：——