octadeca-9,12,15-trienoyl chloride | 112498-02-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: octadeca-9,12,15-trienoyl chloride
• 英文别名: Linolensaeurechlorid；9,12,15-Octadecatrienoyl chloride, (9Z,12Z,15Z)-
• CAS: 112498-02-9
• 化学式: C₁₈H₂₉ClO
• 分子量: 296.881
• InChiKey: MRKXCQPDRPTZCG-UHFFFAOYSA-N

物化性质

• 沸点：
  382.9±21.0 °C(Predicted)
• 密度：
  0.942±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  20
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.611
• 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：

  异烟肼 、 octadeca-9,12,15-trienoyl chloride 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以0.35 g的产率得到(9Z,12Z,15Z)-N'-octadeca-9,12,15-trienoylisonicotinohydrazide
  参考文献：
  名称：

  Synthesis and antimycobacterial activity of isoniazid derivatives from renewable fatty acids

  摘要：

  This work describes the synthesis of a series of fatty acid hydrazide derivatives of isoniazid (INH). The compounds were tested against Mycobacterium tuberculosis H37Rv (ATCC 27294) as well as INH-resistant (ATCC 35822 and 1896 HF) and rifampicin-resistant (ATCC 35338) M. tuberculosis strains. The fatty acid derivatives of INH showed high antimycobacterial potency against the studied strains, which is desirable for a pharmaceutical compound, suggesting that the increased lipophilicity of isoniazid plays an important role in its antimycobacterial activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.09.034
• 作为产物：
  描述：

  Γ-十八碳三烯酸 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 octadeca-9,12,15-trienoyl chloride
  参考文献：
  名称：

  Synthesis and antimycobacterial activity of isoniazid derivatives from renewable fatty acids

  摘要：

  This work describes the synthesis of a series of fatty acid hydrazide derivatives of isoniazid (INH). The compounds were tested against Mycobacterium tuberculosis H37Rv (ATCC 27294) as well as INH-resistant (ATCC 35822 and 1896 HF) and rifampicin-resistant (ATCC 35338) M. tuberculosis strains. The fatty acid derivatives of INH showed high antimycobacterial potency against the studied strains, which is desirable for a pharmaceutical compound, suggesting that the increased lipophilicity of isoniazid plays an important role in its antimycobacterial activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.09.034

文献信息

• Method of treating hyperlipemia
  申请人：Terumo Corporation

  公开号：US04794115A1

  公开（公告）日：1988-12-27

  A method of treating or preventing hyperlipemia by administering ethanolamine derivatives. As preferable ethanolamine derivatives are mentioned N-(9,12,15,-octadecatrienoyl)-2-aminoethyl nicotinate, N-(5,8,11,14,17-eicosapentaenoyl)-2-aminoethyl nicotinate and the like. Hyperlipemia is effectively prevented or treated by administering 300-2000 mg per day of said ethanolamine derivative for adults.

  一种通过给予乙醇胺衍生物治疗或预防高脂血症的方法。优选的乙醇胺衍生物包括N-(9,12,15,-octadecatrienoyl)-2-aminoethyl nicotinate、N-(5,8,11,14,17-eicosapentaenoyl)-2-aminoethyl nicotinate等。通过给予成人每天300-2000毫克的该乙醇胺衍生物，可以有效地预防或治疗高脂血症。
• Fatty acid derivatives of aminoalkyl nicotinic acid esters and platelet
  申请人：Terumo Kabushiki Kaisha

  公开号：US04619938A1

  公开（公告）日：1986-10-28

  Alkanolamine derivatives and platelet aggregation inhibitors containing the same as an active ingredient are disclosed. The alkanolamine derivatives are novel compounds which possess potent platelet aggregation inhibitory activities and effective in preventing diseases such as thrombosis. As typical compounds are mentioned N-5,8,11,14,17-eicosapentaenoyl-2-aminoethanol, N-nicotinoyl-2-aminoethyl-5,8,11,14,17-eicosapentaenoate, N-ethyl-N-5,8,11,14,17-eicosapentaenoyl-2-aminoethanol, N-butyl-N-5,8,11,14,17-eicosapentaenoyl-2-aminoethanol, N-5,8,11,14,17-3-aminopropylnicotinate, (N-ethyl-N-nicotinoyl-2-aminoethyl)-5,8,11,14,17-eicosapentaenoate and the like.

  本发明公开了含有烷基醇胺衍生物和血小板聚集抑制剂的药物，其中烷基醇胺衍生物是新化合物，具有强效的血小板聚集抑制活性，可有效预防血栓等疾病。典型的化合物包括N-5,8,11,14,17-二十碳五烯酰-2-氨基乙醇、N-烟酰基-2-氨基乙基-5,8,11,14,17-二十碳五烯酸酯、N-乙基-N-5,8,11,14,17-二十碳五烯酰-2-氨基乙醇、N-丁基-N-5,8,11,14,17-二十碳五烯酰-2-氨基乙醇、N-5,8,11,14,17-3-氨基丙基烟酸酯、(N-乙基-N-烟酰基-2-氨基乙基)-5,8,11,14,17-二十碳五烯酸酯等。
• Holan, George; Wernert, Gregory T., Australian Journal of Chemistry, 1987, vol. 40, # 5, p. 873 - 881
  作者：Holan, George、Wernert, Gregory T.

  DOI：——

  日期：——
• Coenzyme Q. 124. New substituted 2,3-dimethoxy-1,4-benzoquinones as inhibitors of coenzyme Q systems
  作者：Karl Folkers、Joseph C. Catlin、G. Doyle Daves

  DOI：10.1021/jm00283a012

  日期：1971.1
• Synthesis and antimycobacterial activity of isoniazid derivatives from renewable fatty acids
  作者：Marieli O. Rodrigues、Jéssica B. Cantos、Caroline R. Montes D’Oca、Karina L. Soares、Tatiane S. Coelho、Luciana A. Piovesan、Dennis Russowsky、Pedro A. da Silva、Marcelo G. Montes D’Oca

  DOI：10.1016/j.bmc.2013.09.034

  日期：2013.11

  This work describes the synthesis of a series of fatty acid hydrazide derivatives of isoniazid (INH). The compounds were tested against Mycobacterium tuberculosis H37Rv (ATCC 27294) as well as INH-resistant (ATCC 35822 and 1896 HF) and rifampicin-resistant (ATCC 35338) M. tuberculosis strains. The fatty acid derivatives of INH showed high antimycobacterial potency against the studied strains, which is desirable for a pharmaceutical compound, suggesting that the increased lipophilicity of isoniazid plays an important role in its antimycobacterial activity. (C) 2013 Elsevier Ltd. All rights reserved.