N-benzylcanadinium bromide

• 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: N-benzylcanadinium bromide
• 英文别名: 13-Benzyl-16,17-dimethoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15(20),16,18-hexaene;bromide
• 化学式: Br*C₂₇H₂₈NO₄
• 分子量: 510.428
• InChiKey: AXFBPAXIOSPCJO-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-benzylcanadinium bromide 在 sodium hydride 作用下， 以 苯 为溶剂， 反应 14.0h， 以10%的产率得到Benzyl-tetrahydro-berberin
  参考文献：
  名称：

  从 Berbines 到 Protopines：区域控制的霍夫曼消除/氢化/氧化 N-取代的铼盐

  摘要：

  基于 N-（芳甲基）铼盐的顺序 Hofmann 消除、硼氢化和氧化反应，设计了一种改进的 protopines 合成方法。通过使用氯化小檗碱作为起始原料，这一系列反应提供了两种新的非天然原

  DOI：

  10.1002/ejoc.200500573
• 作为产物：
  描述：

  溴甲苯 、 tetrahydroberberine hydrochloride 反应 4.0h， 以40%的产率得到N-benzylcanadinium bromide
  参考文献：
  名称：

  Compounds and methods for modulating Rho GTPases

  摘要：

  本发明涉及影响Rho家族GTP酶的GTP结合活性的方法和组合物，优选是Rac GTP酶（Rac1、Raclb、Rac2和/或Rac3）。

  公开号：

  EP2014651A1

文献信息

• Regio- and Stereoselective Stevens Rearrangement of Benzyltetrahydroprotoberberinium Salts
  作者：Maria Valpuesta、Amelia Diaz、Rafael Suau、Gregorio Torres

  DOI：10.1002/ejoc.200400443

  日期：2004.11

  8-(Arylmethyl)berbines are conveniently obtained through a Stevens rearrangement of the corresponding N-arylmethylberbinium salts with sodium methylsulfinylmethylide in DMSO. This procedure has provided two new nonnatural 8-benzylcanadines stereoselectively, without competition from the Hofmann elimination. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  8-(芳甲基)小檗碱可以通过相应的N-芳甲基小檗盐与甲基亚磺酰基甲基化钠在DMSO中的Stevens重排方便地获得。该过程提供了两种新的非天然 8-苄基卡那丁立体选择性，没有来自霍夫曼消除的竞争。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• COMPOUNDS AND METHODS FOR MODULATING RHO GTPASES
  申请人：Leblond Bertrand

  公开号：US20100120810A1

  公开（公告）日：2010-05-13

  The present invention relates to methods and compositions that affect the GTP-binding activity of members of the Rho family GTPases, preferably Rac GTPases (Rac1, Rac1b, Rac2 and/or Rac3).

  本发明涉及影响Rho家族GTP酶成员的GTP结合活性的方法和组合物，优选是Rac GTP酶（Rac1，Rac1b，Rac2和/或Rac3）。
• Berberine Analogues as a Novel Class of the Low-Density-Lipoprotein Receptor Up-Regulators: Synthesis, Structure−Activity Relationships, and Cholesterol-Lowering Efficacy
  作者：Ying-Hong Li、Peng Yang、Wei-Jia Kong、Yan-Xiang Wang、Chang-Qin Hu、Zeng-Yan Zuo、Yue-Ming Wang、Hong Gao、Li-Mei Gao、Yan-Chun Feng、Na-Na Du、Ying Liu、Dan-Qing Song、Jian-Dong Jiang

  DOI：10.1021/jm801157z

  日期：2009.1.22

  Twenty-nine derivatives of berberine (1) or pseudoberberine (2) were designed, semisynthesized, and evaluated for their up-regulatory activity on the low-density-lipoprotein receptor (LDLR) expression. SAR analysis revealed that (i) the methylenedioxy group at the 2- and 3-position is an essential element to keep the activity, (ii) the 7-position quaternary ammonium and planar structure of the compound are activity-required, and (iii) addition of electron-donating groups at the 7- or 13-position reduced the activity. Of the compound I analogues, compound 2 exhibited an increased activity on LDLR expression compared to 1. In the hyperlipidemic rats, compound 2 (100 (mg/kg)/day) reduced blood CHO and LDL-c by 42.6% and 49.4%, respectively, more efficient than I did (p < 0.01 for both). The results were confirmed in the hyperlipidemic mice. LD50 of 2 in mice was over 5000 mg/kg (oral). We consider compound 2 a promising cholesterol-lowering drug candidate.
• Identification of N-benzyltetrahydroisoquinolines as novel anti-neuroinflammatory agents
  作者：Brian Gabet、Ping-Chang Kuo、Steven Fuentes、Yamini Patel、Ahmed Adow、Mary Alsakka、Paula Avila、Teri Beam、Jui-Hung Yen、Dennis A. Brown

  DOI：10.1016/j.bmc.2018.10.020

  日期：2018.11

  A series of simplified berberine analogs was designed, synthesized, and evaluated for anti-inflammatory activity. SAR studies identified N-benzyltetrahydroisoquinoline 7d as a potent berberine analog. 7d suppressed LPS-induced inflammatory cytokine levels in both BV2 cells and primary microglia. Taken together, our results suggest that simplified BB analogs have therapeutic potential as a novel class of anti-neuroinflammatory agents.
• US3932384A
  申请人：——

  公开号：US3932384A

  公开（公告）日：1976-01-13