螺[1,3-苯并二氧戊环-2,1'-环己烷]-5-胺 | 64179-41-5

• 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
• 中文名称: 螺[1,3-苯并二氧戊环-2,1'-环己烷]-5-胺
• 中文别名: 螺[1,3-苯并二恶唑-2,1'-环己基]-5-胺
• 英文名称: 5-aminospiro<1,3-benzodioxole-2,1'-cyclohexane>
• 英文别名: 5-aminospiro(1,3-benzodioxole-2,1'-cyclohexane)；4-aminocatechol cyclohexylidene ketal；Spiro[1,3-benzodioxole-2,1'-cyclohexan]-5-amine；spiro[1,3-benzodioxole-2,1'-cyclohexane]-5-amine
• CAS: 64179-41-5
• 化学式: C₁₂H₁₅NO₂
• mdl: MFCD02019003
• 分子量: 205.257
• InChiKey: ZGUHEEOHWIVGOA-UHFFFAOYSA-N

物化性质

• 溶解度：
  19.1 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  螺[1,3-苯并二氧戊环-2,1'-环己烷]-5-胺 在 盐酸 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 sodium t-butanolate 作用下， 以 甲醇 、 乙醇 、 氯仿 、 甲苯 为溶剂， 反应 55.5h， 生成
  参考文献：
  名称：

  FerriIridium：靶向溶酶体的铁（III）活化铱（III）前药，用于胃癌细胞的化学治疗。

  摘要：

  据报道，FeIII激活的靶向溶酶体的前药FerriIridium可用于胃癌治疗。它包含一个亚亚氨基儿茶酚基团，该基团可以选择性地与细胞内的游离FeIII结合并被其氧化。随后的氧化重排释放FeII，并在酸性条件下水解胺键，形成氨基联吡啶Ir配合物和2-羟基苯醌。因此，FeII催化Fenton反应，将过氧化氢转化为羟基自由基，苯醌化合物干扰呼吸链，并且前药向Ir络合物的转化导致磷光和毒性增加。这些特性，再加上癌细胞具有较高的FeIII含量和酸性，使得FerriIridium成为选择性和高效的治疗剂（对于AGS细胞，IC50 = 9.22μm，而> 对于LO2电池为200μm）。FerriIridium是第一种基于金属的化合物，已开发出用于使用FeIII进行化学疗法以增强选择性和效力的化合物。

  DOI：

  10.1002/anie.201915828
• 作为产物：
  描述：

  环己酮缩邻苯二酚 在 palladium on activated charcoal 氢气 、 硝酸 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 3.75h， 生成 螺[1,3-苯并二氧戊环-2,1'-环己烷]-5-胺
  参考文献：
  名称：

  Comparative toxicities and analgesic activities of three monomethylated analogs of acetaminophen

  摘要：

  Three monomethylated derivatives of 4'-hydroxyacetanilide (acetaminophen) were prepared in order to compare their cytotoxic potential and analgesic activity with that of acetaminophen. Only 4'-hydroxy-N-methylacetanilide (N-methylacetaminophen) was devoid of cytotoxic effects to hepatic tissue of mice. Results of comparative tissue distribution studies and metabolism studies both in vivo and in vitro in mice indicate that the disposition of N-methylacetaminophen is similar to that of acetaminophen except that it is not oxidized to a toxic metabolite. In contrast, 3'-methyl-4'-hydroxyacetanilide (3-methylacetaminophen) is as hepatotoxic as acetaminophen in mice while 2'-methyl-4'-hydroxyacetanilide (2-methylacetaminophen) is less hepatotoxic. The analgesic potency of the analogues seems to parallel their hepatotoxic potential, and both activities parallel the oxidation potentials in this series of compounds.

  DOI：

  10.1021/jm00159a029

文献信息

• FerriNaphth: A fluorescent chemodosimeter for redox active metal ions
  作者：Randy K. Jackson、Yu Shi、Xudong Yao、Shawn C. Burdette

  DOI：10.1039/c000248h

  日期：——

  FerriNaphth, a fluorescent chemodosimeter for FeIII, has been prepared and characterized. The probe consists of a catechol ligand linked to a naphthalimide fluorophore by an aniline nitrogen linker. Upon exposure to FeIII, the aminocatechol of FerriNaphth is oxidized to the corresponding quinone, which in its imine-one tautomer, is hydrolyzed to liberate a fluorescent aminonaphthalimide derivative. The fluorescence behavior is consistent with oxidation being promoted by metal coordination.

  FerriNaphth，一种用于FeIII的荧光化学传感器，已经制备并进行了表征。该探针由一个儿茶酚配体通过一个苯胺氮连接子与萘酞菁荧光团相连。在暴露于FeIII时，FerriNaphth的氨基儿茶酚被氧化为相应的醌，其亚胺一型互变异构体在水中水解，释放出一个荧光氨基萘酞菁衍生物。荧光行为与金属配位促进的氧化作用一致。
• WO2007/10085
  申请人：——

  公开号：——

  公开（公告）日：——
• CLARK R. L.; PESSOLANO A. A.; SHEN T.-Y.; JACOBUS D. P.; JONES H.; LOTTI +, J. MED. CHEM., 1978, 21, NO 9, 965-978
  作者：CLARK R. L.、 PESSOLANO A. A.、 SHEN T.-Y.、 JACOBUS D. P.、 JONES H.、 LOTTI +

  DOI：——

  日期：——
• COMPOUNDS, COMPOSITIONS, AND METHODS FOR MODULATING FERROPTOSIS AND TREATING EXCITOTOXIC DISORDERS
  申请人：THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK

  公开号：US20210299107A1

  公开（公告）日：2021-09-30

  The present disclosure provides, inter alia, a compound having the structure: Also provided are compositions containing a pharmaceutically acceptable carrier and one or more compounds according to the present disclosure. Further provided are methods for treating or ameliorating the effects of an excitotoxic disorder in a subject, methods of modulating ferroptosis in a subject, methods of reducing reactive oxygen species (ROS) in a cell, methods for treating or ameliorating the effects of a neurodegenerative disease, methods for alleviating side effects in a subject undergoing radiotherapy and/or immunotherapy, and methods for treating or ameliorating the effects of an infection associated with ferroptosis in a subject.