4-Hydroxy-7-[3-(oxan-2-yloxy)propyl]bicyclo[4.2.0]octa-1(6),2,4-triene-7-carbonitrile | 917967-27-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-Hydroxy-7-[3-(oxan-2-yloxy)propyl]bicyclo[4.2.0]octa-1(6),2,4-triene-7-carbonitrile
• CAS: 917967-27-2
• 化学式: C₁₇H₂₁NO₃
• 分子量: 287.359
• InChiKey: IAVGZFCIHIZIQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  62.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-Hydroxy-7-[3-(oxan-2-yloxy)propyl]bicyclo[4.2.0]octa-1(6),2,4-triene-7-carbonitrile 在 正丁基锂 、 四丙基高钌酸铵 、 4-甲基苯磺酸吡啶 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 4.92h， 生成 7-[3-(Furan-3-yl)-3-oxopropyl]-4-tri(propan-2-yl)silyloxybicyclo[4.2.0]octa-1(6),2,4-triene-7-carbonitrile
  参考文献：
  名称：

  Synthesis and biological evaluation of dihydrofuran-fused perhydrophenanthrenes as a new anti-influenza agent having novel structural characteristic

  摘要：

  Dihydrofuran-fused perhydrophenanthrenes were synthesized by means of o-quinodimethane chemistry with high generality and stereoselectivity, and found to exhibit potent anti-influenza activity. These compounds exerted an inhibitory effect on various strains of influenza virus growth, including influenza A and B, with a concentration dependent manner, and direct cytotoxicity was low. Several biological experiments suggested that these new drugs affected a virus replication process before mRNA synthesis stage. Novel rigid cage-type of structural characteristic of the compounds has not been found in hitherto anti-influenza drugs, and will provide new basis and motif for exploring promising and unprecedented anti-influenza agents. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.046
• 作为产物：
  描述：

  1-cyano-5-methoxybenzocyclobutane 在 碘代三甲硅烷 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 18.67h， 生成 4-Hydroxy-7-[3-(oxan-2-yloxy)propyl]bicyclo[4.2.0]octa-1(6),2,4-triene-7-carbonitrile
  参考文献：
  名称：

  Synthesis and biological evaluation of dihydrofuran-fused perhydrophenanthrenes as a new anti-influenza agent having novel structural characteristic

  摘要：

  Dihydrofuran-fused perhydrophenanthrenes were synthesized by means of o-quinodimethane chemistry with high generality and stereoselectivity, and found to exhibit potent anti-influenza activity. These compounds exerted an inhibitory effect on various strains of influenza virus growth, including influenza A and B, with a concentration dependent manner, and direct cytotoxicity was low. Several biological experiments suggested that these new drugs affected a virus replication process before mRNA synthesis stage. Novel rigid cage-type of structural characteristic of the compounds has not been found in hitherto anti-influenza drugs, and will provide new basis and motif for exploring promising and unprecedented anti-influenza agents. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.046

文献信息

• Synthesis of dihydrofuran-fused perhydrophenanthrenes having a phenolic hydroxyl group as a novel anti-Alzheimer’s disease agent
  作者：Kenji Sugimoto、Kosuke Tamura、Naoki Ohta、Chihiro Tohda、Naoki Toyooka、Hideo Nemoto、Yuji Matsuya

  DOI：10.1016/j.bmcl.2011.10.127

  日期：2012.1

  As a part of our research program on developing novel anti-Alzheimer’s disease medicines, several dihydrofuran-fused perhydrophenanthrenes (DFs) possessing a phenolic hydroxyl group were found to exhibit potent dendritic and axonal regeneration activities. Introduction of a methoxy group into the perhydrophenanthrene skeleton was successfully achieved via a PhI(OAc)2-mediated phenolic oxidation of

  作为我们开发新型抗阿尔茨海默氏病药物的研究计划的一部分，发现一些具有酚羟基的二氢呋喃稠合的过氢菲（DFs）具有有效的树突和轴突再生活性。通过PhI（OAc）2介导的苯并环丁烯核的酚氧化以及随后基于邻喹二甲烷化学的串联分子内电环反应，成功地将甲氧基引入到全氢菲骨架中。我们可以发现，在这项研究中研究的DF中，具有酚羟基的新甲氧基衍生物对受损神经元的树突和轴突延伸发挥了最显着的作用。
• NEURONAL CELL DEATH INHIBITOR
  申请人：Nemoto Hideo

  公开号：US20110021625A1

  公开（公告）日：2011-01-27

  There is provided a neuronal cell death inhibitor having a high efficacy. A neuronal cell death inhibitor comprising a compound of general formula (1) below: (where R 1 is a hydrogen atom or an optionally substituted hydroxy group; R 2 is a hydrogen atom; R 3 is a hydrogen atom or an optionally substituted hydroxy group; R 4 is a hydrogen atom or an optionally substituted hydroxy group, R 3 together with R 4 is optionally an oxo group or a group of —O—(CH 2 ) n —O— (where n is an integer of 2 to 4), or R 2 together with R 4 optionally forms an unsaturated bond between carbon atoms, the respective carbon atoms being attached to R 2 and R 4 ; R 5 is a hydrogen atom or an optionally substituted lower alkyl group; each of R 6 , R 7 , and R 8 is the same as or different from each other and is a hydrogen atom, an optionally substituted hydroxy group, an optionally substituted alkyl group, an optionally substituted aryl group, or an optionally substituted heteroaryl group); or a salt thereof.

  提供了一种高效的神经元细胞死亡抑制剂。该神经元细胞死亡抑制剂包括以下通式（1）的化合物：（其中，R1是氢原子或可选取代羟基；R2是氢原子；R3是氢原子或可选取代羟基；R4是氢原子或可选取代羟基，R3与R4可选取为氧代基或—O—（CH2）n—O—（其中n是2到4的整数）的基团，或R2与R4可选形成碳原子之间的不饱和键，相应的碳原子附着于R2和R4；R5是氢原子或可选取代的较低烷基基团；R6、R7和R8中的每一个都与其他相同或不同，是氢原子、可选取代的羟基、可选取代的烷基、可选取代的芳基或可选取代的杂芳基）；或其盐。
• EP2253636
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and biological evaluation of dihydrofuran-fused perhydrophenanthrenes as a new anti-influenza agent having novel structural characteristic
  作者：Yuji Matsuya、Kazushige Sasaki、Hiroshi Ochiai、Hideo Nemoto

  DOI：10.1016/j.bmc.2006.09.046

  日期：2007.1.1

  Dihydrofuran-fused perhydrophenanthrenes were synthesized by means of o-quinodimethane chemistry with high generality and stereoselectivity, and found to exhibit potent anti-influenza activity. These compounds exerted an inhibitory effect on various strains of influenza virus growth, including influenza A and B, with a concentration dependent manner, and direct cytotoxicity was low. Several biological experiments suggested that these new drugs affected a virus replication process before mRNA synthesis stage. Novel rigid cage-type of structural characteristic of the compounds has not been found in hitherto anti-influenza drugs, and will provide new basis and motif for exploring promising and unprecedented anti-influenza agents. (c) 2006 Elsevier Ltd. All rights reserved.