methoxymethyl S-trans,trans-farnesylthiosalicylate | 1092521-71-5

• 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: methoxymethyl S-trans,trans-farnesylthiosalicylate
• 英文别名: methoxymethyl S-farnesylthiosalicylate；methoxymethyl 2-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]sulfanylbenzoate
• CAS: 1092521-71-5
• 化学式: C₂₄H₃₄O₃S
• 分子量: 402.598
• InChiKey: WPYKJACQQNTKNZ-FJNYLYSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  氯甲基甲基醚 、 法尼基硫代水杨酸 在 sodium hydride 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 4.0h， 以78%的产率得到methoxymethyl S-trans,trans-farnesylthiosalicylate
  参考文献：
  名称：

  ALKOXYALKYL S-PRENYLTHIOSALICYLATES FOR TREATMENT OF CANCER

  摘要：

  本发明涉及烷氧基烷基S-异戊烯硫基水杨酸酯及含有其的制药组合物和药用载体。还公开了通过向需要治疗癌症，包括实体肿瘤或血液恶性肿瘤的患者施用有效量的烷氧基烷基S-异戊烯硫基水杨酸酯来治疗人类的方法。

  公开号：

  US20100189781A1

文献信息

• New Derivatives of Farnesylthiosalicylic Acid (Salirasib) for Cancer Treatment: Farnesylthiosalicylamide Inhibits Tumor Growth in Nude Mice Models
  作者：Liat Goldberg、Roni Haklai、Victor Bauer、Aaron Heiss、Yoel Kloog

  DOI：10.1021/jm801165r

  日期：2009.1.8

  The Ras inhibitor S-trans, trans-farnesylthiosalicylic acid (FTS, Salirasib) interferes with Ras membrane interactions that are crucial for Ras-dependent transformation. It remains unknown whether modifications of the carboxyl group of FTS can affect its activity. Here we show that specific modifications of the FrS carboxyl group by esterification or amidation yield compounds with improved growth inhibitory activity, compared to FTS, as shown in Panc-1 and U87 cells. The most potent compounds were FTS-methoxymethyl ester and FTS-amide. However, selectivity toward active Ras-GTP, as known for FrS, was apparent with the amide derivatives of FTS. FTS-amide exhibited the overall highest efficacy in inhibition of Ras-GTP and cell growth. This new compound significantly inhibited growth of both Panc-1 tumors and U87 brain tumors. Thus amide derivatives of the FTS carboxyl group provide potent cell-growth inhibitors without loss of selectivity toward the active Ras protein and may serve as new candidates in cancer therapy.
• TREATMENT OF MULTIPLE SCLEROSIS
  申请人：Ramot at Tel-Aviv University Ltd

  公开号：EP2523668A1

  公开（公告）日：2012-11-21
• TREATMENT OF DELAYED CUTANEOUS HYPERSENSITIVITY CONDITIONS WITH S-FARNESYLTHIOSALICYLIC ACID AND ANALOGS THEREOF
  申请人：Ramot at Tel-Aviv University Ltd.

  公开号：EP2590639A1

  公开（公告）日：2013-05-15
• USE OF FTS AND ANALOGS TO TREAT NON-AUTOIMMUNE-ALLERGIC AND NON-ALLERGIC INFLAMMATORY CONDITIONS
  申请人：Ramot at Tel-Aviv University Ltd.

  公开号：EP2590640A1

  公开（公告）日：2013-05-15
• US8338481B2
  申请人：——

  公开号：US8338481B2

  公开（公告）日：2012-12-25