N-(4-aminobutyl)-2-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)thio)benzamide | 1402249-28-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: N-(4-aminobutyl)-2-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)thio)benzamide
• 英文别名: N-(4-aminobutyl)-2-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]sulfanylbenzamide
• CAS: 1402249-28-8
• 化学式: C₂₆H₄₀N₂OS
• 分子量: 428.682
• InChiKey: LACNTPHPFVABJE-FQLUOEGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.67
• 重原子数：
  30.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.12
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-(4-aminobutyl)-2-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)thio)benzamide 、 氯磷酸二乙酯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以83.7%的产率得到N-[4-(diethoxyphosphorylamino)butyl]-2-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]sulfanylbenzamide
  参考文献：
  名称：

  [EN] ANTI-INFLAMMATORY, ANTI-CANCER, AND ANTI-ANGIOGENIC COMPOUNDS, PHARMACEUTICAL COMPOSITIONS, AND METHODS OF MAKING AND USING THEREOF
  [FR] COMPOSÉS ANTI-INFLAMMATOIRES, ANTICANCÉREUX ET ANTI-ANGIOGÉNIQUES, COMPOSITIONS PHARMACEUTIQUES ET LEURS PROCÉDÉS DE FABRICATION ET D'UTILISATION

  摘要：

  公开号：

  WO2019067974A8
• 作为产物：
  描述：

  反,反-法呢基溴 在 N-甲基吗啉 、 水 、 氯甲酸乙酯 、 potassium carbonate 、 三氟乙酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 18.0h， 生成 N-(4-aminobutyl)-2-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)thio)benzamide
  参考文献：
  名称：

  Hybrid Molecule from Farnesylthiosalicylic Acid-diamine and Phenylpropenoic Acid as Ras-related Signaling Inhibitor with Potent Antitumor Activities

  摘要：

  Novel series of Farnesylthiosalicylic acid‐diamine/phenylpropenoic acid hybrids were designed and synthesized. Their in vitro growth inhibitory assays showed that most compounds displayed strong antiproliferation activity against seven cancer cells. Especially, the new hybrid 12f, by the conjugation of 10a with ferulic acid, could selectively suppress the proliferation of tumor cells and display significantly lower toxicities to normal cells than its intermediate 10a. Furthermore, 12f dose‐dependently induced SMMC‐7721 cell apoptosis. Additionally, our observations demonstrated that 12f inhibited both Ras‐related signaling and phosphorylated NF‐κB synergistically, which may be advantageous to the strong antitumor activities of 12f. Our findings suggest that these novel hybrids may hold a great promise as therapeutic agents for the intervention of human cancers.

  DOI：

  10.1111/cbdd.12393

文献信息

• Synthesis and biological evaluation of farnesylthiosalicylamides as potential anti-tumor agents
  作者：Yong Ling、Zhiqiang Wang、Hongyan Zhu、Xuemin Wang、Wei Zhang、Xinyang Wang、Li Chen、Zhangjian Huang、Yihua Zhang

  DOI：10.1016/j.bmc.2013.11.013

  日期：2014.1

  Fourteen hybrids of farnesylthiosalicylic acid (FTS) with various diamines were synthesized and biologically evaluated. It was found that FTS-monoamide molecules (10a-g) displayed strong anti-proliferative activity against seven human cancer cell lines, superior to FTS and FTS-bisamide compounds (11a-g). The mono-amide 10f was the most active, with IC(50)s of 3.78-7.63 mu M against all tested cancer cells, even more potent than sorafenib (9.12-22.9 mu M). In addition, 10f induced SMMC-7721 cell apoptosis, down-regulated the expression of Bcl-2 and up-regulated Bax and caspase-3. Furthermore, 10f had the improved aqueous solubility relative to FTS. Finally, treatment with 10f dose-dependently inhibited the Ras-related signaling pathways in SMMC-7721 cells. Collectively, 10f could be a promising candidate for the intervention of human cancers. (C) 2013 Elsevier Ltd. All rights reserved.
• ANTI-INFLAMMATORY, ANTI-CANCER, AND ANTI-ANGIOGENIC COMPOUNDS, PHARMACEUTICAL COMPOSITIONS, AND METHODS OF MAKING AND USING THEREOF
  申请人：MEDICON PHARMACEUTICALS, INC.

  公开号：US20200246330A1

  公开（公告）日：2020-08-06

  Compounds of the general Formula A-D-Y are disclosed with activity towards treating diseases related to inflammation, cancer, neurodegenerative diseases, and cardiovascular diseases. Pharmaceutical compositions, methods of making, and methods of use thereof are also described.
• [EN] ANTI-INFLAMMATORY, ANTI-CANCER, AND ANTI-ANGIOGENIC COMPOUNDS, PHARMACEUTICAL COMPOSITIONS, AND METHODS OF MAKING AND USING THEREOF<br/>[FR] COMPOSÉS ANTI-INFLAMMATOIRES, ANTICANCÉREUX ET ANTI-ANGIOGÉNIQUES, COMPOSITIONS PHARMACEUTIQUES ET LEURS PROCÉDÉS DE FABRICATION ET D'UTILISATION
  申请人：MEDICON PHARMACEUTICALS INC

  公开号：WO2019067974A8

  公开（公告）日：2020-04-23
• Hybrid Molecule from Farnesylthiosalicylic Acid-diamine and Phenylpropenoic Acid as Ras-related Signaling Inhibitor with Potent Antitumor Activities
  作者：Yong Ling、Zhiqiang Wang、Xuemin Wang、Xianghua Li、Xinyang Wang、Wei Zhang、Hong Dai、Li Chen、Yihua Zhang

  DOI：10.1111/cbdd.12393

  日期：2015.2

  Novel series of Farnesylthiosalicylic acid‐diamine/phenylpropenoic acid hybrids were designed and synthesized. Their in vitro growth inhibitory assays showed that most compounds displayed strong antiproliferation activity against seven cancer cells. Especially, the new hybrid 12f, by the conjugation of 10a with ferulic acid, could selectively suppress the proliferation of tumor cells and display significantly lower toxicities to normal cells than its intermediate 10a. Furthermore, 12f dose‐dependently induced SMMC‐7721 cell apoptosis. Additionally, our observations demonstrated that 12f inhibited both Ras‐related signaling and phosphorylated NF‐κB synergistically, which may be advantageous to the strong antitumor activities of 12f. Our findings suggest that these novel hybrids may hold a great promise as therapeutic agents for the intervention of human cancers.