1-(spiro[1,3-benzodioxole-2,4’-piperidine]-1-yl)ethan-1one | 185316-84-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 1-(spiro[1,3-benzodioxole-2,4’-piperidine]-1-yl)ethan-1one
• 英文别名: 1'-acetyl-spiro[1,3-benzodioxolo-2,4'-piperidine]；1-Spiro[1,3-benzodioxole-2,4'-piperidine]-1'-ylethanone
• CAS: 185316-84-1
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: YTVPXRUZOFDCOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(spiro[1,3-benzodioxole-2,4’-piperidine]-1-yl)ethan-1one 在 水 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 20.0h， 生成 spiro[1,3-benzodioxole-2,4’-piperidine]
  参考文献：
  名称：

  Synthesis of 5-oxyquinoline derivatives for reversal of multidrug resistance

  摘要：

  ABC（ATP结合盒）转运蛋白的抑制被认为是逆转多药耐药的有力工具。发现了一种具有二氟环丙基环戊二苯亚基结构的佐苏奎达，它被发现是P-糖蛋白的抑制剂，后者是研究最充分的多药外流泵之一。已合成了十二种5-氧异喹啉衍生物，它们是佐苏奎达的类似物，其中二苯亚基-哌嗪结构被二芳胺哌啶或哌啶酮衍生的缩醛或硫缩醛基团替代，这些衍生物均为纯对映异构体。它们的抑制力已经针对细菌多药耐药ABC转运蛋白LmrCD和真菌Pdr5进行了评估。新合成的四种化合物中有四种比佐苏奎达更有效地降低了转运活性，在LmrCD的情况下高达四倍，对于Pdr5则提高了约两倍。

  DOI：

  10.3762/bjoc.8.193
• 作为产物：
  描述：

  N-乙酰基-4-哌啶酮 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 生成 1-(spiro[1,3-benzodioxole-2,4’-piperidine]-1-yl)ethan-1one
  参考文献：
  名称：

  Novel tricyclic spiropiperidines. Synthesis and adrenergic activity of spiro[1,3-benzodioxolopiperidines] and spiro[1,3-benzodioxanepiperidines]

  摘要：

  The synthesis of new series of spiropiperidines is reported. Some of these compounds showed interesting adrenergic activity. The biological activities of the new compounds were evaluated on-guinea pig atria (beta 1), guinea-pig trachea (beta 2) and rat vas deferens (alpha). Compounds 6a, 6c and 6f showed activity comparable to propranolol, in spite of being tertiary amines.

  DOI：

  10.1016/s0223-5234(97)89851-0

文献信息

• Amino-substituted dihydropyrimido[4,5-D]pyrimidinone derivatives
  申请人：——

  公开号：US20040087600A1

  公开（公告）日：2004-05-06

  Compounds of formula I 1 are described. These compounds are protein kinase inhibitors, in particular they inhibit the src family tyrosine kinases. Thus, these compounds are useful for the treatment of diseases mediated by src tyrosine kinases, including cell proliferative disorders such as cancer. Also described are methods of making and using compounds of formula I as well as pharmaceutical compositions containing these compounds.

  描述了化学式I1的化合物。这些化合物是蛋白激酶抑制剂，特别是它们抑制src家族酪氨酸激酶。因此，这些化合物对于治疗由src酪氨酸激酶介导的疾病，包括癌症等细胞增殖性疾病，具有用途。还描述了制备和使用化学式I的化合物的方法，以及含有这些化合物的药物组合物。
• Synthesis of 5-oxyquinoline derivatives for reversal of multidrug resistance
  作者：Torsten Dittrich、Nils Hanekop、Nacera Infed、Lutz Schmitt、Manfred Braun

  DOI：10.3762/bjoc.8.193

  日期：——

  The inhibition of ABC (ATP binding cassette) transporters is considered a powerful tool to reverse multidrug resistance. Zosuquidar featuring a difluorocyclopropyl-annulated dibenzosuberyl moiety has been found to be an inhibitor of the P-glycoprotein, one of the best-studied multidrug efflux pumps. Twelve 5-oxyisoquinoline derivatives, which are analogues of zosuquidar wherein the dibenzosuberyl-piperazine moiety is replaced by either a diarylaminopiperidine or a piperidone-derived acetal or thioacetal group, have been synthesized as pure enantiomers. Their inhibitory power has been evaluated for the bacterial multidrug-resistance ABC transporter LmrCD and fungal Pdr5. Four of the newly synthesized compounds reduced the transport activity to a higher degree than zosuquidar, being up to fourfold more efficient than the lead compound in the case of LmrCD and about two times better for Pdr5.

  ABC（ATP结合盒）转运蛋白的抑制被认为是逆转多药耐药的有力工具。发现了一种具有二氟环丙基环戊二苯亚基结构的佐苏奎达，它被发现是P-糖蛋白的抑制剂，后者是研究最充分的多药外流泵之一。已合成了十二种5-氧异喹啉衍生物，它们是佐苏奎达的类似物，其中二苯亚基-哌嗪结构被二芳胺哌啶或哌啶酮衍生的缩醛或硫缩醛基团替代，这些衍生物均为纯对映异构体。它们的抑制力已经针对细菌多药耐药ABC转运蛋白LmrCD和真菌Pdr5进行了评估。新合成的四种化合物中有四种比佐苏奎达更有效地降低了转运活性，在LmrCD的情况下高达四倍，对于Pdr5则提高了约两倍。
• Novel tricyclic spiropiperidines. Synthesis and adrenergic activity of spiro[1,3-benzodioxolopiperidines] and spiro[1,3-benzodioxanepiperidines]
  作者：MD Pujol、G Rosell、G Guillaumet

  DOI：10.1016/s0223-5234(97)89851-0

  日期：1996.1

  The synthesis of new series of spiropiperidines is reported. Some of these compounds showed interesting adrenergic activity. The biological activities of the new compounds were evaluated on-guinea pig atria (beta 1), guinea-pig trachea (beta 2) and rat vas deferens (alpha). Compounds 6a, 6c and 6f showed activity comparable to propranolol, in spite of being tertiary amines.