(Z,Z)-heptadeca-8,11-dien-1-yl bromide | 155614-06-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: (Z,Z)-heptadeca-8,11-dien-1-yl bromide
• 英文别名: (6Z,9Z)-17-bromo-heptadeca-6,9-diene；(8Z,11Z)-1-bromoheptadiene；17-bromo-hepta-6c,9c-diene；17-Brom-hepta-6c,9c-dien；(6Z,9Z)-17-Bromo-6,9-heptadecadiene；(6Z,9Z)-17-bromoheptadeca-6,9-diene
• CAS: 155614-06-5
• 化学式: C₁₇H₃₁Br
• 分子量: 315.337
• InChiKey: VCGKGVAPRBVZDT-HZJYTTRNSA-N

物化性质

• 沸点：
  364.9±21.0 °C(Predicted)
• 密度：
  1.018±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于二氯甲烷；己烷;醚

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  18
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (Z,Z)-heptadeca-8,11-dien-1-yl bromide 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以80%的产率得到(Z,Z)-heptadeca-8,11-dien-1-yl iodide
  参考文献：
  名称：

  Bull, Steven D.; Carman, Raymond M., Australian Journal of Chemistry, 1994, vol. 47, # 9, p. 1661 - 1672

  摘要：

  DOI：
• 作为产物：
  描述：

  (Z,Z)-9,12-十八烷二烯酸二聚物 在 4-二甲氨基吡啶 、 草酰氯 、 三氯溴甲烷 、 sodium salt hydrate 、 2-巯基吡啶-N-氧化物 作用下， 以 甲苯 为溶剂， 生成 (Z,Z)-heptadeca-8,11-dien-1-yl bromide
  参考文献：
  名称：

  脂肪酸的[1-14C]-单-E异构体的发散合成。

  摘要：

  描述了使用烯烃转化作为关键步骤方便地合成[1-14C]-单反式脂肪酸的方法。这种方法可以轻松合成油酸，亚油酸和亚麻酸的[1-14C]标记的单反式类似物。例如，仅需十一个步骤即可从其商业全Z形式获得亚麻酸的[1-14C]-单-E异构体。在第一步中，Barton的脱羧过程产生了溴中间体。该化合物的环氧化导致形成三个单环氧化物，可以通过HPLC进行分离。通过1 H NMR和MS鉴定后，然后对纯单环氧化物进行转化，该转化包括立体定向脱氧，然后进行β消除步骤。最后，

  DOI：

  10.1016/s0009-3084(03)00054-9

文献信息

• LIPIDIC FURAN, PYRROLE, AND THIOPHENE COMPOUNDS FOR USE IN THE TREATMENT OF ATROPHIC VAGINITIS
  申请人：Avoscience, LLC

  公开号：US20170312246A1

  公开（公告）日：2017-11-02

  Provided herein are lipidic furan, pyrrole, and thiophene compounds, compositions, and methods using such compounds and compositions for the treatment of atrophic vaginitis. Specifically, the invention includes administering an effective amount of a compound of Formula I, I′, or I″, or a pharmaceutically acceptable composition, salt, isotopic analog, prodrug, or combination thereof, to a subject suffering from atrophic vaginitis.

  本文提供了脂质类呋喃、吡咯和噻吩化合物、组合物以及使用这些化合物和组合物治疗萎缩性阴道炎的方法。具体而言，本发明包括向患有萎缩性阴道炎的受试者投与化合物I、I'或I"的有效量，或者药学上可接受的组合物、盐、同位素类似物、前药或其组合物。
• Synthesis and Evaluation of Tetraarylethylene-based Mono-, Bis-, and Tris(pyridinium) Derivatives for Image-Guided Mitochondria-Specific Targeting and Cytotoxicity of Metastatic Melanoma Cells
  作者：Jessica L. Reedy、Devin K. Hedlund、Moustafa T. Gabr、Grant M. Henning、F. Christopher Pigge、Michael K. Schultz

  DOI：10.1021/acs.bioconjchem.6b00394

  日期：2016.10.19

  Metastatic melanoma is the most aggressive and lethal form of skin cancer. Emerging evidence suggests that differences in melanoma metabolism relative to nonmalignant cells represent potential targets for improved therapy for melanoma. Specifically, melanoma cells exhibit increased mitochondrial electron transport chain (ETC) activity and concomitant hyperpolarized mitochondrial membrane potential

  转移性黑色素瘤是皮肤癌中最具侵袭性和致死性的形式。越来越多的证据表明，黑色素瘤相对于非恶性细胞的代谢差异代表了改善黑色素瘤治疗的潜在靶标。特别地，相对于非恶性细胞，黑素瘤细胞表现出增加的线粒体电子传输链（ETC）活性和伴随的超极化线粒体膜电位。我们已经合成了一些新的荧光亲脂性乙烯基吡啶鎓阳离子，这些阳离子是由四芳基乙烯支架构建的，该支架通过吸引超极化线粒体膜电位来靶向线粒体。使用共聚焦荧光显微镜法证实了相对于正常人成纤维细胞，黑色素瘤细胞中的线粒体特异性积累，并导致氧化代谢的破坏，导致体外黑色素瘤特异性细胞死亡。因此，吡啶鎓四芳基乙烯平台代表具有潜在的成像和治疗特性的有希望的新的线粒体靶向递送载体。
• Lipidic Furan, Pyrrole, and Thiophene Compounds for Treatment of Cancer, Neurological Disorders, and Fibrotic Disorders
  申请人：Avoscience, LLC

  公开号：US20140309274A1

  公开（公告）日：2014-10-16

  Compounds, methods, and compositions are provided for the treatment of cancer, neurological disorders, and fibrotic disorders. Specifically, the invention includes administering an effective amount of a compound of Formula I, II, or III, or a pharmaceutically acceptable composition, salt, isotopic analog, prodrug, or combination thereof, to a subject suffering from a cancer, neurological disorder, or fibrotic disorder.

  本发明提供了用于治疗癌症、神经系统疾病和纤维化疾病的化合物、方法和组合物。具体而言，该发明包括向患有癌症、神经系统疾病或纤维化疾病的受试者施用公式I、II或III的化合物、药学上可接受的组合物、盐、同位素类似物、前药或其组合的有效量。
• LIPIDIC FURAN, PYRROLE, AND THIOPHENE COMPOUNDS FOR TREATMENT OF CANCER, NEUROLOGICAL DISORDERS, AND FIBROTIC DISORDERS
  申请人：Avoscience, LLC

  公开号：US20160263080A1

  公开（公告）日：2016-09-15

  Compounds, methods, and compositions are provided for the treatment of cancer, neurological disorders, and fibrotic disorders. Specifically, the invention includes administering an effective amount of a compound of Formula I, II, or III, or a pharmaceutically acceptable composition, salt, isotopic analog, prodrug, or combination thereof, to a subject suffering from a cancer, neurological disorder, or fibrotic disorder.

  本发明提供了用于治疗癌症、神经系统疾病和纤维化疾病的化合物、方法和组合物。具体而言，本发明包括向患有癌症、神经系统疾病或纤维化疾病的受试者施用公式I、II或III的化合物或其药学上可接受的组合物、盐、同位素类似物、前药或其组合物的有效量。
• ——
  作者：Cesar Rodriguez-Saona、Jocelyn G. Millar、David F. Maynard、John T. Trumble

  DOI：10.1023/a:1022325601724

  日期：——

  Several insecticidal compounds have been identified by bioassay-driven fractionation of avocado, Persea americana Mill, idioblast cell oil. A flash chromatography fraction of the oil showed substantial toxicity to early instars of the generalist insect herbivore, Spodoptera exigua (Hubner) (100% mortality after seven days). Following further fractionation, five biologically active compounds, 2-(pentadecyl)furan, 2-(heptadecyl)furan, 2-(1E-penta-decenyl)furan, 2-(8Z,11Z-heptadecadienyl)furan, and the triglyceride triolein, were identified. Several minor components were also tentatively identified, including 2-(1Z-pentadecenyl)furan, 2-(1E-heptadecenyl)furan, and 2-(1E,8Z,11Z-heptadecatrienyl)furan. Several 2-alkylfurans of this type have been reported previously from avocado (Persea spp.) and have received the common name of avocadofurans. The major compounds were tested individually for toxic and growth inhibitory effects. Individually, the compounds had low to moderate toxicity. Of these, 2-(pentadecyl)furan had the greatest effects, with an LC50 value of 1031 mu g/g. At concentrations of 600 mu g/g or higher in diets, larval growth was inhibited by >70% compared to controls. The analogous 2-(heptadecyl)furan had an LC50 value of 1206 mu g/g, and also significantly reduced larval growth (>75% versus controls) at concentrations of > 600 mu g/g. The unsaturated analogs 2-(1E-pentadecenyl)furan and 2-(8Z, 11Z-heptadecadienyl)furan were less toxic. Triolein was only weakly toxic, with an LC50 value of 10,364 mu g/g diet. Larval growth was inhibited only at concentrations of 7000 mu g/g or higher. The potential of avocadofurans in insect control is discussed.