7-亚苄基纳曲酮 | 129468-28-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 7-亚苄基纳曲酮
• 英文名称: 7-benzylidene-7-dehydronaltrexonee
• 英文别名: 7-benzylidene naltrexone；7-benzylidenenaltrexone；BNTX；(4R,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-6-(phenylmethylene)-1,2,4,5,7a,13-hexahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one；(4R,4aS,7aR,12bS)-6-benzylidene-3-(cyclopropylmethyl)-4a,9-dihydroxy-1,2,4,5,7a,13-hexahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
• CAS: 129468-28-6
• 化学式: C₂₇H₂₇NO₄
• 分子量: 429.516
• InChiKey: WXOUFNFMPVMGFZ-NVSKSXHLSA-N

物化性质

• 沸点：
  661.2±55.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-亚苄基纳曲酮 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 以68%的产率得到17-(cyclopropylmethyl)-7α-benzyl-4,5α-epoxy-3,14-dihydromorphinan-6-one
  参考文献：
  名称：

  Investigation of 7-benzylidenenaltrexone derivatives as resistance reverser for chloroquine-resistant Plasmodium chabaudi

  摘要：

  Derivatives of 7-benzylidenenaltrexone (BNTX), which was recently reported to be an effective chloroquine (CQ)-resistance reverser, were synthesized and evaluated for their CQ-resistance reversing activities. The synthesized derivatives showed CQ-resistance reversing effects. They also reacted with glutathione (GSH) both enzymatically and chemically, and inhibited glutathione reductase activity. 7-Benzyl derivative, which was obtained by reduction of the olefin group in alpha,beta-unsaturated ketone structure of BNTX, also exhibited CQ-resistance reversing effect, but its potency was significantly lower than that of BNTX. These outcomes suggested that the decrease in GSH level could be one of the mechanisms of CQ-resistance reversing effects induced by BNTX derivatives. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.085
• 作为产物：
  描述：

  盐酸纳曲酮 、 苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 14.0h， 以50%的产率得到7-亚苄基纳曲酮
  参考文献：
  名称：

  间隔基在赋予κ阿片受体对与降冰片碱相关的二价配体的选择性中的作用。

  摘要：

  合成并测试了κ选择性阿片拮抗剂norbinaltorphimine（1a，norBNI）的噻吩2和吡喃3类似物，以测定间隔物对不同阿片受体类型的二价配体相互作用的贡献。发现2和3都是平滑肌制剂中的选择性kappa阿片受体拮抗剂，并且它们选择性结合kappa识别位点。噻吩类似物2的结合选择性与1a的数量级相同，而3对κ位的选择性低得多。这与以下事实一致：1a和2中的第二个药效团比1a和3具有更高的叠加度。

  DOI：

  10.1021/jm00108a008

文献信息

• Favorskii-Type Rearrangement of the 4,5-Epoxymorphinan Skeleton
  作者：Noriki Kutsumura、Yasuaki Koyama、Yuko Suzuki、Ken-ichi Tominaga、Naoshi Yamamoto、Tsuyoshi Saitoh、Yasuyuki Nagumo、Hiroshi Nagase

  DOI：10.1021/acs.orglett.8b00288

  日期：2018.3.16

  The aldol condensation of naltrexone with various aryl aldehydes gives the corresponding 7-benzylidenenaltrexone derivatives in high yields. However, novel C-ring-contracted morphinan compounds were produced when 2-pyridinecarboxaldehyde or its related analogues were used as a coupling partner. The key structural feature was the existence of the tetrahydrofuran ring (4,5-epoxy ring, E-ring) of the

  纳曲酮与各种芳基醛的醛醇缩合以高收率得到相应的7-亚苄基纳曲酮衍生物。但是，当将2-吡啶甲醛或其相关类似物用作偶联伴侣时，会产生新颖的C环缩合的吗啡喃化合物。主要的结构特征是吗啡喃骨架的四氢呋喃环（4,5-环氧环，E环）的存在。反应系统的时间分辨原位红外光谱表明，扭曲的环丙烷酮中间体的吸收时间很短。
• Investigation of 7-benzylidenenaltrexone derivatives as a novel structural antitrichomonal lead compound
  作者：Noriki Kutsumura、Ryo Nakajima、Yasuaki Koyama、Yoshiyuki Miyata、Tsuyoshi Saitoh、Naoshi Yamamoto、Satoshi Iwata、Hideaki Fujii、Hiroshi Nagase

  DOI：10.1016/j.bmcl.2015.06.002

  日期：2015.11

  We evaluated antitrichomonal effects of delta opioid receptor (DOR) agonists and antagonists. Although all the agonists were inactive, the DOR antagonists BNTX (2a) and its derivatives 2b-d showed antitrichomonal activity with MIC of 20-40 mu M. In addition, the development of a more effective synthetic method for the BNTX derivatives was achieved by using the Knoevenagel condensation. (C) 2015 Elsevier Ltd. All rights reserved.