dimethyl N-[2-(3,4-dimethoxyphenyl)ethyl]iminodiacetate | 570402-50-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: dimethyl N-[2-(3,4-dimethoxyphenyl)ethyl]iminodiacetate
• 英文别名: Methyl 2-[2-(3,4-dimethoxyphenyl)ethyl-(2-methoxy-2-oxoethyl)amino]acetate
• CAS: 570402-50-5
• 化学式: C₁₆H₂₃NO₆
• 分子量: 325.362
• InChiKey: FTXLLVXPORFKEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dimethyl N-[2-(3,4-dimethoxyphenyl)ethyl]iminodiacetate 在 四(三苯基膦)钯 氢氧化钾 、 sodium methylate 、 sodium carbonate 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 为溶剂， 反应 47.5h， 生成 7,8-dimethoxy-3-(2-(3,4-dimethoxyphenyl)ethyl)-1-(3,4-dimethoxyphenyl)-[1]-benzopyrano[3,4-b]pyrrol-4(3H)-one-2-carboxylic acid
  参考文献：
  名称：

  制备3,4-二芳基吡咯海洋生物碱的短而灵活的途径：合成全甲基斯托尼酰胺A，宁格灵B和层状甘油三甲基醚

  摘要：

  使用Hinsberg型吡咯合成和钯催化3,4-二羟基吡咯双三氟甲磺酸酯衍生物的Suzuki交叉偶联，已经开发出一种高效的3,4-二芳基吡咯海洋生物碱途径。基于这种方法，已经实现了全甲基间苯二甲酰胺A和宁格灵B的正式合成，以及层状蛋白G三甲基醚的全合成。

  DOI：

  10.1016/s0040-4039(03)01031-1
• 作为产物：
  描述：

  3,4-二甲氧基苯乙胺 、 溴乙酸甲酯 在 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 2.5h， 以91%的产率得到dimethyl N-[2-(3,4-dimethoxyphenyl)ethyl]iminodiacetate
  参考文献：
  名称：

  制备3,4-二芳基吡咯海洋生物碱的短而灵活的途径：合成全甲基斯托尼酰胺A，宁格灵B和层状甘油三甲基醚

  摘要：

  使用Hinsberg型吡咯合成和钯催化3,4-二羟基吡咯双三氟甲磺酸酯衍生物的Suzuki交叉偶联，已经开发出一种高效的3,4-二芳基吡咯海洋生物碱途径。基于这种方法，已经实现了全甲基间苯二甲酰胺A和宁格灵B的正式合成，以及层状蛋白G三甲基醚的全合成。

  DOI：

  10.1016/s0040-4039(03)01031-1

文献信息

• The first total synthesis of lamellarin α 20-sulfate, a selective inhibitor of HIV-1 integrase
  作者：Tomohiro Yamaguchi、Tsutomu Fukuda、Fumito Ishibashi、Masatomo Iwao

  DOI：10.1016/j.tetlet.2006.03.121

  日期：2006.5

  The first total synthesis of lamellarin alpha 20-sulfate (1), a selective inhibitor of HIV-1 integrase, has been completed. The lamellarin alpha core in which 13-OH and 20-OH were differentially protected by isopropyl and benzyl groups, respectively, was constructed by using Hinsberg-type pyrrole synthesis and Suzuki-Miyaura coupling as the key reactions. The 20-sulfate was prepared by a sequence including debenzylation of 20-OBn, 2,2,2-trichloroethylsulfation of the resulting 20-OH deprotection of 13-Oi-Pr, and final reductive cleavage of the 2,2,2-trichloroethyl ester. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis, structure–activity relationships, and mechanism of action of anti-HIV-1 lamellarin α 20-sulfate analogues
  作者：Haruka Kamiyama、Yoshinao Kubo、Hironori Sato、Naoki Yamamoto、Tsutomu Fukuda、Fumito Ishibashi、Masatomo Iwao

  DOI：10.1016/j.bmc.2011.10.030

  日期：2011.12

  Lamellarin a and six different types of lamellarin alpha 20-sulfate analogues were synthesized and their structure-activity relationships were investigated using a single round HIV-1 vector infection assay. All lamellarin sulfates having pentacyclic lamellarin core exhibited anti-HIV-1 activity at a 10 mu M concentration range regardless of the number and position of the sulfate group. On the other hand, non-sulfated lamellarin alpha and ring-opened lamellarin sulfate analogues did not affect HIV-1 vector infection in similar concentrations. The lamellarin sulfates utilized in this study did not exhibit unfavorable cytotoxic effect under the concentrations tested (IC50 > 100 mu M). Confocal laser scanning microscopic analysis indicated that hydrophilic lamellarin sulfates were hardly incorporated in the cell. HIV-1 Env-mediated cell-cell fusion was suppressed by lamellarin sulfates. These results suggested that lamellarin sulfates have a novel anti-HIV-1 activity besides the previously reported integrase activity inhibition, possibly at a viral entry step of HIV-1 replication. (C) 2011 Elsevier Ltd. All rights reserved.
• Short and flexible route to 3,4-diarylpyrrole marine alkaloids: syntheses of permethyl storniamide A, ningalin B, and lamellarin G trimethyl ether
  作者：Masatomo Iwao、Toshiro Takeuchi、Naotaka Fujikawa、Tsutomu Fukuda、Fumito Ishibashi

  DOI：10.1016/s0040-4039(03)01031-1

  日期：2003.6

  4-diarylpyrrole marine alkaloids has been developed using Hinsberg-type pyrrole synthesis and palladium-catalyzed Suzuki cross-coupling of the 3,4-dihydroxypyrrole bis-triflate derivatives as key reactions. Based on this approach, formal syntheses of permethyl storniamide A and ningalin B, and a total synthesis of lamellarin G trimethyl ether have been achieved.

  使用Hinsberg型吡咯合成和钯催化3,4-二羟基吡咯双三氟甲磺酸酯衍生物的Suzuki交叉偶联，已经开发出一种高效的3,4-二芳基吡咯海洋生物碱途径。基于这种方法，已经实现了全甲基间苯二甲酰胺A和宁格灵B的正式合成，以及层状蛋白G三甲基醚的全合成。