(+/-)-6,7-Dimethoxy-1,2,2-trimethyl-1,2,3,4-tetrahydro-isochinolinium; Jodid | 5911-58-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (+/-)-6,7-Dimethoxy-1,2,2-trimethyl-1,2,3,4-tetrahydro-isochinolinium; Jodid
• 英文别名: 1,2,2-Trimethyl-6,7-dimethoxy-1,2,3,4-tetrahydroisochinoliniumjodid；Carnegin Iodmethylat；1,2,2-Trimethyl-6,7-dimethoxy-1,2,3,4-tetrahydroisochinoliniumjodid, Carneginmethojodid；(+/-)-6,7-dimethoxy-1,2,2-trimethyl-1,2,3,4-tetrahydro-isoquinolinium; iodide；Carnegine methyliodide；6,7-dimethoxy-1,2,2-trimethyl-3,4-dihydro-1H-isoquinolin-2-ium;iodide
• CAS: 5911-58-0
• 化学式: C₁₄H₂₂NO₂*I
• 分子量: 363.239
• InChiKey: FHNHMFLAPXSGDH-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-6,7-Dimethoxy-1,2,2-trimethyl-1,2,3,4-tetrahydro-isochinolinium; Jodid 在 氢溴酸 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 2.25h， 以98.5%的产率得到(+/-)-N,N-dimethylsalsolinol bromide
  参考文献：
  名称：

  Geranyl Derivatives of Isoquinoline Alkaloids Show Increased Biological Activities

  摘要：

  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.

  DOI：

  10.3987/com-10-11912
• 作为产物：
  描述：

  6,7-二甲氧基-1-甲基-1,2,3,4-四氢异喹啉 、 碘甲烷 在 甲醇 作用下， 生成 (+/-)-6,7-Dimethoxy-1,2,2-trimethyl-1,2,3,4-tetrahydro-isochinolinium; Jodid
  参考文献：
  名称：

  Orechoff; Proskurnina, Chemische Berichte, 1934, vol. 67, p. 878,880, 882, 883

  摘要：

  DOI：

文献信息

• Synthesis and biological evaluation of N-methyl-laudanosine iodide analogues as potential SK channel blockers
  作者：A. Graulich、F. Mercier、J. Scuvée-Moreau、V. Seutin、J.-F. Liégeois

  DOI：10.1016/j.bmc.2004.11.025

  日期：2005.2

  Neuronal action potentials are followed by an afterhyperpolarisation (AHP), which is mediated by small conductance Ca2+-activated K+ channels (SK channels or KCa2 channels). This AHP plays an important role in regulating neuronal activity and agents modulating AHP amplitude could have a potential therapeutic interest. It was previously shown that N-methyl-bicuculline iodide blocks SK channels but its GABA(A) activity represents a serious drawback. In view of the structural analogy between bicuculline and laudanosine 14, several N-quaternary analogues of the latter were developed. It was shown that N-methyl-laudanosine 15 (NML) and N-ethyl-laudanosine 16 induce a reversible and relatively specific blockade of the apamin sensitive AHP in dopaminergic neurones with mean IC(50)s of 15, and 47 muM, respectively. Laudanosine 14, N-butyl-17 and N-benzyl-18 derivatives were less potent. In order to find pharmacophore elements, modifications were performed at different positions such as C-1, C-6 and C-7. Intracellular recordings on rat midbrain dopaminergic neurones were made in order to evaluate the putative blockade of SK channels by these molecules. Simplified structures such as tetrahydroisoquinoline derivatives with H or Me at C-I 1-6 presented no significant activity at 300 muM. The presence of a 1-(3,4-dimethoxybenzy]) moiety seems an important feature. Indeed, compound 8 showed a blockade of the AHP of only 33% at 300 muM while compound 13 blocked it by 67%, respectively, at the same concentration. Binding experiments were also performed. Binding affinities for SK channels are in good agreement with electrophysiological data. These results indicate that the presence of a charged nitrogen group is an essential point for the affinity on SK channels. Finally, because of the similar activity of both enantionters of NML 19 and 20, the interaction site may present a symmetrical configuration. (C) 2004 Elsevier Ltd. All rights reserved.
• 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.
• Orechoff; Proskurnina, Chemische Berichte, 1934, vol. 67, p. 878,880, 882, 883
  作者：Orechoff、Proskurnina

  DOI：——

  日期：——