N-methoxy-N-methyl-3,4-ethylenedioxybenzamide | 1293408-36-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: N-methoxy-N-methyl-3,4-ethylenedioxybenzamide
• 英文别名: N-methoxy-N-methyl-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamide；N-methoxy-N-methyl-2,3-dihydro-1,4-benzodioxine-6-carboxamide
• CAS: 1293408-36-2
• 化学式: C₁₁H₁₃NO₄
• mdl: MFCD18535145
• 分子量: 223.229
• InChiKey: CLKOLKBESIFUGE-UHFFFAOYSA-N

物化性质

• 熔点：
  49-50 °C
• 沸点：
  399.6±41.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-methoxy-N-methyl-3,4-ethylenedioxybenzamide 在 正丁基锂 、 tetra-n-butylammoniumfluoride trihydrate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 生成 (3-hydroxy-4-methoxyphenyl)(3,4-ethylenedioxyphenyl)methanone
  参考文献：
  名称：

  Application of plant allylpolyalkoxybenzenes in synthesis of antimitotic phenstatin analogues

  摘要：

  Phenstatin and its derivatives with the modified ring A have been synthesized, using plant allylpolyalkoxybenzenes as a starting material. The targeted molecules were evaluated in a phenotypic sea urchin embryo assay for antiproliferative activity. It was found that phenstatin ring A modifications yielded antimitotic compounds. The most effective myristicin derivative 7d (combretastatin A-2 analogue) was determined to be ca. 10 times more potent than phenstatin, displaying antimitotic tubulin-destabilizing activity at the same concentration range as combretastatins. In contrast to combretastatins, 7d featured the steric stability with potential for further design as anticancer agent. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.124
• 作为产物：
  描述：

  2,3-二氢-1,4-苯并二噁烷-6-羧酸 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 20.33h， 生成 N-methoxy-N-methyl-3,4-ethylenedioxybenzamide
  参考文献：
  名称：

  Application of plant allylpolyalkoxybenzenes in synthesis of antimitotic phenstatin analogues

  摘要：

  Phenstatin and its derivatives with the modified ring A have been synthesized, using plant allylpolyalkoxybenzenes as a starting material. The targeted molecules were evaluated in a phenotypic sea urchin embryo assay for antiproliferative activity. It was found that phenstatin ring A modifications yielded antimitotic compounds. The most effective myristicin derivative 7d (combretastatin A-2 analogue) was determined to be ca. 10 times more potent than phenstatin, displaying antimitotic tubulin-destabilizing activity at the same concentration range as combretastatins. In contrast to combretastatins, 7d featured the steric stability with potential for further design as anticancer agent. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.124

文献信息

• INHIBITORS OF THE ENZYME UDP-GLUCOSE: N-ACYL-SPHINGOSINE GLUCOSYLTRANSFERASE
  申请人：Concert Pharmaceuticals, Inc.

  公开号：US20160068519A1

  公开（公告）日：2016-03-10

  This invention relates to novel inhibitors of UDP-glucose: N-acyl-sphingosine glucosyltransferase and pharmaceutically acceptable salts thereof. This invention also provides compositions comprising a compound of this invention and the use of such compositions in methods of treating diseases and conditions that are beneficially treated by administering inhibitors of UDP-glucose: N-acyl-sphingosine glucosyltransferase.

  本发明涉及新型UDP葡萄糖：N-酰基鞘氨醇葡萄糖基转移酶抑制剂及其药学上可接受的盐。本发明还提供包含本发明化合物的组合物，并使用这种组合物治疗通过给予UDP葡萄糖：N-酰基鞘氨醇葡萄糖基转移酶抑制剂有益治疗的疾病和病况的方法。
• Inhibitors of the enzyme UDP-glucose: N-acyl-sphingosine glucosyltransferase
  申请人：Concert Pharmaceuticals, Inc.

  公开号：US10385042B2

  公开（公告）日：2019-08-20

  This invention relates to novel inhibitors of UDP-glucose: N-acyl-sphingosine glucosyltransferase and pharmaceutically acceptable salts thereof. This invention also provides compositions comprising a compound of this invention and the use of such compositions in methods of treating diseases and conditions that are beneficially treated by administering inhibitors of UDP-glucose: N-acyl-sphingosine glucosyltransferase.

  本发明涉及 UDP-葡萄糖的新型抑制剂：及其药学上可接受的盐。本发明还提供了包含本发明化合物的组合物，以及这些组合物在治疗疾病和病症的方法中的用途，这些疾病和病症可通过施用 UDP-葡萄糖：N-乙酰-鞘氨醇葡萄糖基转移酶抑制剂得到有益治疗：N-acyl-sphingosine 葡糖基转移酶的抑制剂。
• 10.3390/molecules29112459
  作者：Li, Shiyun、Wen, Bin、Zhao, Wei、Wang, Lulu、Chen, Xingquan

  DOI：10.3390/molecules29112459

  日期：——

  exert antidepressant effects by blocking NMDAR ion channels, but its anesthetic and psychotomimetic side effects limit its application. Here, we report efforts to design and synthesize a novel series of ketamine derivatives of NMDAR antagonists, among which compounds 23 and 24 have improved activity compared with ketamine, introducing a new direction for the development of rapid-acting antidepressant drugs

  抑郁症是一种慢性、严重且常常危及生命的神经系统疾病。不仅导致患者抑郁、影响日常生活，严重时还可能导致自杀行为，给家庭和社会带来不良影响。近年来发现，亚麻醉剂量的氯胺酮对难治性抑郁症患者具有快速的抗抑郁作用，并能显着降低重度抑郁症患者的自杀倾向。目前的研究表明，氯胺酮可能通过阻断NMDAR离子通道发挥抗抑郁作用，但其麻醉和拟精神病副作用限制了其应用。在这里，我们报道了设计和合成一系列新型NMDAR拮抗剂氯胺酮衍生物的努力，其中化合物23和24与氯胺酮相比具有提高的活性，为速效抗抑郁药物的开发提供了新的方向。
• US9783528B2
  申请人：——

  公开号：US9783528B2

  公开（公告）日：2017-10-10
• Application of plant allylpolyalkoxybenzenes in synthesis of antimitotic phenstatin analogues
  作者：Ilia Y. Titov、Irina K. Sagamanova、Roman T. Gritsenko、Irina B. Karmanova、Olga P. Atamanenko、Marina N. Semenova、Victor V. Semenov

  DOI：10.1016/j.bmcl.2011.01.124

  日期：2011.3

  Phenstatin and its derivatives with the modified ring A have been synthesized, using plant allylpolyalkoxybenzenes as a starting material. The targeted molecules were evaluated in a phenotypic sea urchin embryo assay for antiproliferative activity. It was found that phenstatin ring A modifications yielded antimitotic compounds. The most effective myristicin derivative 7d (combretastatin A-2 analogue) was determined to be ca. 10 times more potent than phenstatin, displaying antimitotic tubulin-destabilizing activity at the same concentration range as combretastatins. In contrast to combretastatins, 7d featured the steric stability with potential for further design as anticancer agent. (C) 2011 Elsevier Ltd. All rights reserved.