(E)-5-nonen-2-yn-1-ol | 76896-83-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-5-nonen-2-yn-1-ol
• 英文别名: trans-5-nonen-2-yne-1-ol；(E)-non-5-en-2-yn-1-ol
• CAS: 76896-83-8
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: VQRJBYPXPJTYRK-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-5-nonen-2-yn-1-ol 在 lithium aluminium tetrahydride 、 sodium hydride 、 2-碘酰基苯甲酸 作用下， 以 甲醇 、 乙醚 、 二甲基亚砜 、 苯 为溶剂， 反应 48.5h， 生成 4-((2E,4E,7E)-undeca-2,4,7-trienylamino)benzoic acid
  参考文献：
  名称：

  Novel triacsin C analogs as potential antivirals against rotavirus infections

  摘要：

  Recently our group has demonstrated that cellular triglyceride (TG) levels play an important role in rotavirus replication. In this study, we further examined the roles of the key enzymes for TG synthesis (lipogenesis) in the replication of rotaviruses by using inhibitors of fatty acid synthase, long chain fatty acid acyl-CoA synthetase (ACSL), and diacylglycerol acyltransferase and acyl-CoA:cholesterol acyltransferase in association with lipid droplets of which TG is a major component. Triacsin C, a natural ACSL inhibitor from Streptomyces aureofaciens, was found to be highly effective against rotavirus replication. Thus, novel triacsin C analogs were synthesized and evaluated for their efficacies against the replication of rotaviruses in cells. Many of the analogs significantly reduced rotavirus replication, and one analog (1e) was highly effective at a nanomolar concentration range (ED50 0.1 mu M) with a high therapeutic index in cell culture. Our results suggest a crucial role of lipid metabolism in rotavirus replication, and triacsin C and/or its analogs as potential therapeutic options for rotavirus infections. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.010
• 作为产物：
  描述：

  反式-2-已烯-1-醇 在 乙基溴化镁 、 copper(l) cyanide 、 草酸 、 三溴化磷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (E)-5-nonen-2-yn-1-ol
  参考文献：
  名称：

  Novel triacsin C analogs as potential antivirals against rotavirus infections

  摘要：

  Recently our group has demonstrated that cellular triglyceride (TG) levels play an important role in rotavirus replication. In this study, we further examined the roles of the key enzymes for TG synthesis (lipogenesis) in the replication of rotaviruses by using inhibitors of fatty acid synthase, long chain fatty acid acyl-CoA synthetase (ACSL), and diacylglycerol acyltransferase and acyl-CoA:cholesterol acyltransferase in association with lipid droplets of which TG is a major component. Triacsin C, a natural ACSL inhibitor from Streptomyces aureofaciens, was found to be highly effective against rotavirus replication. Thus, novel triacsin C analogs were synthesized and evaluated for their efficacies against the replication of rotaviruses in cells. Many of the analogs significantly reduced rotavirus replication, and one analog (1e) was highly effective at a nanomolar concentration range (ED50 0.1 mu M) with a high therapeutic index in cell culture. Our results suggest a crucial role of lipid metabolism in rotavirus replication, and triacsin C and/or its analogs as potential therapeutic options for rotavirus infections. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.010

文献信息

• Alkyl, alkenyl, and aryl substituted triazene compounds, their salts and
  申请人：Fujisawa Pharmaceutical Co. Ltd.

  公开号：US04297096A1

  公开（公告）日：1981-10-27

  A new triazene compound of the formula: R--CH.dbd.N--N.dbd.N--OH wherein R is alkyl, alkenyl or aryl and its pharmaceutically acceptable salts thereof. The production and use of such compounds are also disclosed. The compounds are useful as smooth muscle relaxants and hypotensives.

  一种新的三氮烯化合物，化学式为：R--CH.dbd.N--N.dbd.N--OH，其中R为烷基，烯基或芳基及其药学上可接受的盐。本发明还公开了该化合物的制备和使用。该化合物可用作平滑肌松弛剂和降压药。
• New triazene compound, process for the preparation thereof, and pharmaceutical composition comprising the same
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0015540A2

  公开（公告）日：1980-09-17

  A new triazene compound of the formula: wherein R is alkyl, alkenyl or aryl and its pharmaceutically acceptable salt, and processes for their preparation, and a pharmaceutical composition comprising as an effective ingredient, the above compound. '

  一种新的三嗪化合物，其式如下 式中 R 为烷基、烯基或芳基的新型三嗪化合物及其药学上可接受的盐，及其制备方法，以及包含上述化合物作为有效成分的药物组合物。'
• Structure and synthesis of a new hypotensive vasodilator isolated from
  作者：Hirokazu Tanaka、Keizo Yoshida、Yoshikuni Itoh、Hiroshi Imanaka

  DOI：10.1016/s0040-4039(01)81921-3

  日期：1981.1
• An efficient cyclopentenone formation via an allene oxide
  作者：Seong Jin Kim、Jin K. Cha

  DOI：10.1016/s0040-4039(00)80826-6

  日期：1988.1
• YOSHIDA, KEIZO;TANAKA, HIROKAZU;OKAMOTO, MASANORI;IGUCHI, EIKO;KOHSAKA, M+
  作者：YOSHIDA, KEIZO、TANAKA, HIROKAZU、OKAMOTO, MASANORI、IGUCHI, EIKO、KOHSAKA, M+

  DOI：——

  日期：——