nonadienal | 128701-56-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: nonadienal
• 英文别名: 2E,5E-nonadienal；(E,E)-2,5-nanodienal；(2E,5E)-nona-2,5-dienal
• CAS: 128701-56-4；138558-80-2；76896-85-0
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: RCVGYIQDISIYJQ-AOSYACOCSA-N

物化性质

• 沸点：
  212.8±19.0 °C(Predicted)
• 密度：
  0.855±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  nonadienal 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 20.5h， 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 lithium aluminium tetrahydride 、 乙基溴化镁 、 copper(l) cyanide 、 草酸 、 三溴化磷 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 34.0h， 生成 nonadienal
  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

• Asymmetric Formal <i>trans</i>-Dihydroxylation and <i>trans</i>-Aminohydroxylation of α,β-Unsaturated Aldehydes via an Organocatalytic Reaction Cascade
  作者：Łukasz Albrecht、Hao Jiang、Gustav Dickmeiss、Björn Gschwend、Signe Grann Hansen、Karl Anker Jørgensen

  DOI：10.1021/ja103538s

  日期：2010.7.7

  study demonstrates the first formal asymmetric trans-dihydroxylation and trans-aminohydroxylation of alpha,beta-unsaturated aldehydes in an organocatalytic multibond forming one-pot reaction cascade. This efficient process converts alpha,beta-unsaturated aldehydes into optically active trans-2,3-dihydroxyaldehydes and trans-3-amino-2-hydroxyaldehydes with the aldehyde moiety protected as an acetal. The

  这项研究证明了在有机催化多键形成一锅反应级联中，α、β-不饱和醛的第一次正式不对称反式二羟基化和反式氨基羟基化。这种有效的过程将 α,β-不饱和醛转化为光学活性的反式-2,3-二羟基醛和反式-3-氨基-2-羟基醛，醛部分被保护为缩醛。精心设计的一锅法通过形成 2,3-环氧和 2,3-氮丙啶醛中间体进行，随后参与新的 NaOMe 引发的重排反应，导致形成缩醛保护的反式-2,3-二羟基醛和反式-3-氨基-2-羟基醛以高度立体选择性的方式。有利地，该多键形成反应级联可以一锅法进行，从而最大限度地减少获得产品所需的手动操作和纯化程序的数量。此外，为了 α、β-不饱和醛的反式氨基羟基化，开发了一种使用 4-甲基-N-（甲苯磺酰氧基）苯磺酰胺作为氮源的新的对映选择性氮丙啶化方案。α，β-不饱和醛的正式反式二羟基化和反式氨基羟基化的机制通过各种调查（包括同位素标记研究）阐明。最后，获得的产品被用于合成许多重要的分子。开发了一种使用
• 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。'
• Inhibition of long chain fatty acyl-CoA synthetase (ACSL) and ischemia reperfusion injury
  作者：Allan M. Prior、Man Zhang、Nina Blakeman、Palika Datta、Hung Pham、Qian Chen、Lindon H. Young、Margaret T. Weis、Duy H. Hua

  DOI：10.1016/j.bmcl.2014.01.016

  日期：2014.2

  Various triacsin C analogs, containing different alkenyl chains and carboxylic acid bioisoteres including 4-aminobenzoic acid, isothiazolidine dioxide, hydroxylamine, hydroxytriazene, and oxadiazolidine dione, were synthesized and their inhibitions of long chain fatty acyl-CoA synthetase (ACSL) were examined. Two methods, a cell-based assay of ACSL activity and an in situ [C-14]-palmitate incorporation into extractable lipids were used to study the inhibition. Using an in vivo leukocyte recruitment inhibition protocol, the translocation of one or more cell adhesion molecules from the cytoplasm to the plasma membrane on either the endothelium or leukocyte or both was inhibited by inhibitors 1, 9, and triacsin C. The results suggest that inhibition of ACSL may attenuate the vascular inflammatory component associated with ischemia reperfusion injury and lead to a decrease of infarct expansion. (C) 2014 Elsevier Ltd. All rights reserved.
• 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
• Carbostyril derivatives
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP0382185B1

  公开（公告）日：1994-06-15