5,9,13-trimethyl-4(E),8(E),12-tetradecatriene-1-thiol | 162132-08-3

• 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: 5,9,13-trimethyl-4(E),8(E),12-tetradecatriene-1-thiol
• 英文别名: (4E,8E)-5,9,13-trimethyltetradeca-4,8,12-triene-1-thiol
• CAS: 162132-08-3
• 化学式: C₁₇H₃₀S
• 分子量: 266.491
• InChiKey: RIYSFBACZPZKEJ-QKXOVSGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5,9,13-trimethyl-4(E),8(E),12-tetradecatriene-1-thiol 在 sodium hydroxide 、 oxone 、 四正辛基溴化铵 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 10.03h， 生成 7,8-epoxy-4,8-dimethyl-3(E)-nonenyl 5',9',13'-trimethyl-4'(E),8'(E),12'-tetradecatrienyl sulfoxide
  参考文献：
  名称：

  Synthesis of Sulfur- and Sulfoxide-Substituted 2,3-Oxidosqualenes and Their Evaluation as Inhibitors of 2,3-Oxidosqualene-Lanosterol Cyclase

  摘要：

  2,3-Oxidosqualene (23-OS) analogs that contain thioether (52-55) and sulfoxide (56-60) at positions normally occupied by carbons considered to be cationic during 2,3-oxidosqualene-lanosterol cyclase (OSC) cyclization (C-6, C-10, C-14, and C-19) were synthesized and tested as substrate mimic inhibitors of fungal and mammalian OSC. The analogs were found to be potent inhibitors of cyclase in cell-free extracts of Candida albicans and rat liver. Thioether analogs were more potent than the corresponding sulfoxides. In both series, those 2,3-OS analogs containing a sulfur at the position normally occupied by C-19 were the most potent. With C. albicans cyclase, the IC50 for thioether 55 was 0.0023 mu M while 60 exhibited an IC50 of 0.065 mu M, which are the lowest values reported for a inhibitor of this enzyme. Similarly, thioether 55 displayed an IC50 of 0.00082 mu M for rat liver cyclase which is the best inhibitor up to date for this enzyme. These results suggest that mimics with modification in the region of C-19 of 2,3-OS have a high affinity for the active site of these enzymes. The same series of analogs (52-60) were also tested for inhibition of cholesterol biosynthesis in intact MDBK (Madin Darbin bovine kidney) cells and for in vitro antifungal activity against C. albicans.

  DOI：

  10.1021/ja00107a011
• 作为产物：
  描述：

  (4E,8E)-5,9,13-trimethyl-4,8,12-tetradecatrien-1-ol 在 lithium aluminium tetrahydride 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.0h， 生成 5,9,13-trimethyl-4(E),8(E),12-tetradecatriene-1-thiol
  参考文献：
  名称：

  Synthesis of Sulfur- and Sulfoxide-Substituted 2,3-Oxidosqualenes and Their Evaluation as Inhibitors of 2,3-Oxidosqualene-Lanosterol Cyclase

  摘要：

  2,3-Oxidosqualene (23-OS) analogs that contain thioether (52-55) and sulfoxide (56-60) at positions normally occupied by carbons considered to be cationic during 2,3-oxidosqualene-lanosterol cyclase (OSC) cyclization (C-6, C-10, C-14, and C-19) were synthesized and tested as substrate mimic inhibitors of fungal and mammalian OSC. The analogs were found to be potent inhibitors of cyclase in cell-free extracts of Candida albicans and rat liver. Thioether analogs were more potent than the corresponding sulfoxides. In both series, those 2,3-OS analogs containing a sulfur at the position normally occupied by C-19 were the most potent. With C. albicans cyclase, the IC50 for thioether 55 was 0.0023 mu M while 60 exhibited an IC50 of 0.065 mu M, which are the lowest values reported for a inhibitor of this enzyme. Similarly, thioether 55 displayed an IC50 of 0.00082 mu M for rat liver cyclase which is the best inhibitor up to date for this enzyme. These results suggest that mimics with modification in the region of C-19 of 2,3-OS have a high affinity for the active site of these enzymes. The same series of analogs (52-60) were also tested for inhibition of cholesterol biosynthesis in intact MDBK (Madin Darbin bovine kidney) cells and for in vitro antifungal activity against C. albicans.

  DOI：

  10.1021/ja00107a011

文献信息

• CYCLISATION PROCESS OF FORMING A MULTIPLE RING COMPOUND
  申请人：Loh Teck Peng

  公开号：US20100228058A1

  公开（公告）日：2010-09-09

  The present invention relates to a cyclisation process of forming a multiple ring compound from an isoprenoid compound. The cyclisation process involves reacting the isoprenoid compound with an acetal initiator under conditions sufficient to form the multiple ring compound. The isoprenoid compound is contacted with an initiator an optionally with a catalyst. Cyclisation occurs by reaction of the initiator with the isoprenoid compound. Cyclic acetal compounds wherein the acetal forms part of 6-membered unsaturated ring are also defined.

  本发明涉及一种从异戊二烯化合物形成多环化合物的环化过程。该环化过程涉及将异戊二烯化合物与缩醛引发剂在足够的条件下反应以形成多环化合物。异戊二烯化合物与引发剂接触，可选择地与催化剂接触。环化是通过引发剂与异戊二烯化合物的反应发生的。还定义了其中缩醛部分形成6元不饱和环的环状缩醛化合物。
• US8227645B2
  申请人：——

  公开号：US8227645B2

  公开（公告）日：2012-07-24
• US8629268B2
  申请人：——

  公开号：US8629268B2

  公开（公告）日：2014-01-14
• [EN] CYCLISATION PROCESS OF FORMING A MULTIPLE RING COMPOUND<br/>[FR] PROCÉDÉ DE CYCLISATION DESTINE A FORMER UN COMPOSE A CYCLES MULTIPLES
  申请人：UNIV NANYANG

  公开号：WO2007097719A1

  公开（公告）日：2007-08-30

  [EN] The present invention relates to a cyclisation process of forming a multiple ring compound from an isoprenoid compound. The cyclisation process involves reacting the isoprenoid compound with an acetal initiator under conditions sufficient to form the multiple ring compound. The isoprenoid compound is contacted with an initiator an optionally with a catalyst. Cyclisation occurs by reaction of the initiator with the isoprenoid compound. Cyclic aceta compounds wherein the acetal forms part of 6-membered unsaturated ring are also defined.
  [FR] La présente invention concerne un procédé de cyclisation destiné à former un composé à cycles multiples à partir d'un composé d'isoprénoïde. Le procédé de cyclisation comprend la mise en réaction du composé d'isoprénoïde avec un amorceur acétalique dans des conditions suffisantes pour former le composé à cycles multiples. Le composé d'isoprénoïde est mis en contact avec un amorceur, et éventuellement, avec un catalyseur. La cyclisation a lieu par réaction de l'amorceur avec le composé d'isoprénoïde. L'invention concerne également des composés cycliques d'acétal, l'acétal faisant partie d'un cycle insaturé à 6 chaînons.
• Synthesis of Sulfur- and Sulfoxide-Substituted 2,3-Oxidosqualenes and Their Evaluation as Inhibitors of 2,3-Oxidosqualene-Lanosterol Cyclase
  作者：Yi Feng Zheng、Allan C. Oehlschlager、Nafsika H. Georgopapadakou、Peter G. Hartman、Petra Scheliga

  DOI：10.1021/ja00107a011

  日期：1995.1

  2,3-Oxidosqualene (23-OS) analogs that contain thioether (52-55) and sulfoxide (56-60) at positions normally occupied by carbons considered to be cationic during 2,3-oxidosqualene-lanosterol cyclase (OSC) cyclization (C-6, C-10, C-14, and C-19) were synthesized and tested as substrate mimic inhibitors of fungal and mammalian OSC. The analogs were found to be potent inhibitors of cyclase in cell-free extracts of Candida albicans and rat liver. Thioether analogs were more potent than the corresponding sulfoxides. In both series, those 2,3-OS analogs containing a sulfur at the position normally occupied by C-19 were the most potent. With C. albicans cyclase, the IC50 for thioether 55 was 0.0023 mu M while 60 exhibited an IC50 of 0.065 mu M, which are the lowest values reported for a inhibitor of this enzyme. Similarly, thioether 55 displayed an IC50 of 0.00082 mu M for rat liver cyclase which is the best inhibitor up to date for this enzyme. These results suggest that mimics with modification in the region of C-19 of 2,3-OS have a high affinity for the active site of these enzymes. The same series of analogs (52-60) were also tested for inhibition of cholesterol biosynthesis in intact MDBK (Madin Darbin bovine kidney) cells and for in vitro antifungal activity against C. albicans.