(5E,9E)-6,10,14-trimethylpentadeca-5,9,13-trien-1-ol | 129121-66-0

• 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: (5E,9E)-6,10,14-trimethylpentadeca-5,9,13-trien-1-ol
• 英文别名: (E,E)-6,10,14-Trimethyl-5,9,13-pentadeca-trien-1-ol；6,10,14-Trimethyl-5,9,13-pentadecatrien-1-ol；(E,E)-6,10,14-Trimethyl-5,9,13-pentadecatriene-1-ol；(E,E)-6,10,14-Trimethyl-5,9,13-pentadecatrien-1-ol
• CAS: 129121-66-0
• 化学式: C₁₈H₃₂O
• 分子量: 264.451
• InChiKey: CMOKAOLTCLWPKW-CBXDKUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (5E,9E)-6,10,14-trimethylpentadeca-5,9,13-trien-1-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 6,10,14-trimethylpentadeca-5E,9E,13-trien-1-al
  参考文献：
  名称：

  Inhibitors of Protein:Farnesyl Transferase and Protein:Geranylgeranyl Transferase I: Synthesis of Homologous Diphosphonate Analogs of Isoprenylated Pyrophosphate

  摘要：

  Novel diphosphonate homologs 7a-7c, and their cyclic counterparts 8a-8c, of the previously synthesized farnesyl pyrophosphate analogs 1 and 2 were prepared and tested for their inhibition potency and specificity of the enzymes PFT and PGGT-I. Compound 2 was shown to be the most potent inhibitor of PFT (IC50 = 0.58 +/- 0.45 mu M) in this series. The novel compound 7a, the one carbon homolog of 2, proved to be the most potent inhibitor of PGGT-I (IC50 = 0.98 +/- 0.01 mu M). The cyclic analogs 8a-8c are generally less biologically active. The compounds 2 and 7a are nonspecific toward inhibition of PFT and PGGT-I: and may inhibit both farnesylation and geranylgeranylation processing of oncogenic proteins. (C) 1998 Academic Press.

  DOI：

  10.1006/bioo.1998.1101
• 作为产物：
  描述：

  1-chloro-3,7,11-trimethyldodeca-2(E),6(Z),10-triene 在 六甲基磷酰三胺 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 生成 (5E,9E)-6,10,14-trimethylpentadeca-5,9,13-trien-1-ol
  参考文献：
  名称：

  Isoprenoid phosphinylformic acid squalene synthetase inhibitors

  摘要：

  提供了一种抑制胆固醇生物合成（通过抑制新生角鲨烯生物合成）的化合物，因此可用作降胆固醇药物和抗动脉粥样硬化药物，其结构为##STR1##其中R.sup.2是金属离子、低碳烷基或H；R.sup.3是金属离子或低碳烷基；R是R.sup.1--(CH.sub.2).sub.n--、R.sup.1--(CH.sub.2).sub.m--O--或R.sup.1--(CH.sub.2).sub.m--OCH.sub.2--，其中n为1至4，m为0至3，R.sup.1是R.sup.5--Q.sup.1--Q.sup.2--Q.sup.3--其中R.sup.5、Q.sup.1、Q.sup.2和Q.sup.3如本文所定义。还提供了新的中间体、新的制备方法和一种使用这些化合物抑制胆固醇生物合成的方法。

  公开号：

  US05025003A1

文献信息

• Methods of using .alpha.-phosphonosulfonate squalene synthetase
  申请人：Bristol-Myers Squibb Company

  公开号：US05470845A1

  公开（公告）日：1995-11-28

  .alpha.-Phosphonosulfonate compounds are provided which inhibit the enzyme squalene synthetase and thereby inhibit cholesterol biosynthesis. These compounds have the formula ##STR1## wherein R.sup.2 is OR.sup.5 or R.sup.5a ; R.sup.3 and R.sup.5 are independently H, alkyl, arylalkyl, aryl or cycloalkyl; R.sup.5a is H, alkyl, arylalkyl or aryl; R.sup.4 is H, alkyl, aryl, arylalkyl, or cycloalkyl;, Z is H, halogen, lower alkyl or lower alkenyl; and R.sup.1 is a lipophilic group which contains at least 7 carbons and is alkyl, alkenyl, alkynyl, mixed alkenyl-alkynyl, aryl, arylalkyl, cycloalkyl, cycloalkylalkyl, heteroaryl, heteroarylalkyl, cycloheteroalkyl, cycloheteroalkylalkyl; as further defined above; including pharmaceutically acceptable salts and or prodrug esters of the phosphonic (phosphinic) and/or sulfonic acids.

  提供了抑制酶角鲨烯合酶并从而抑制胆固醇生物合成的.alpha.-磷酸磺酸酯化合物。这些化合物的化学式为##STR1##其中R.sup.2为OR.sup.5或R.sup.5a；R.sup.3和R.sup.5独立地为H、烷基、芳基烷基、芳基或环烷基；R.sup.5a为H、烷基、芳基烷基或芳基；R.sup.4为H、烷基、芳基、芳基烷基或环烷基；Z为H、卤素、低烷基或低烯基；R.sup.1为至少含有7个碳原子的疏水基团，为烷基、烯基、炔基、混合烯基-炔基、芳基、芳基烷基、环烷基、环烷基烷基、杂环芳基、杂环芳基烷基、环杂环烷基、环杂环烷基烷基；如上所述；包括磷酸(亚磷酸)和/或磺酸的药用可接受盐和/或前药酯。
• Phosphorus-containing squalene synthetase inhibitors
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US05212164A1

  公开（公告）日：1993-05-18

  Compounds which are inhibitors of cholesterol biosynthesis (by inhibiting de novo squalene biosynthesis), and thus are useful as hypocholesterolemic agents and antiatherosclerotic agents are provided which have the structure ##STR1## wherein m is 0, 1, 2 or 3; n is 0, 1, 2, 3 or 4; Y.sup.1 and Y.sup.2 are H or halogen; R.sup.2, R.sup.3 and R.sup.4 may be the same or different and are independently H, metal ion, C.sub.1 to C.sub.8 alkyl or C.sub.3 to C.sub.12 alkenyl; X is O, S, NH or NCH.sub.2 R.sup.15 wherein R.sup.15 is H or C.sub.1 to C.sub.5 alkyl; and R.sup.1 is R.sup.5 --Q.sup.1 --Q.sup.2 --Q.sup.3 -- wherein R.sup.5, Q.sup.1, Q.sup.2 and Q.sup.3 are as defined herein; and when m is o, X is other than S; and if m is o and X is 0, then n is 1, 2, 3 or 4; including all stereoisomers thereof.

  提供了抑制胆固醇生物合成（通过抑制新生角鲨烯生物合成）的化合物，因此可用作降胆固醇药物和抗动脉粥样硬化药物，其结构为##STR1##其中m为0、1、2或3；n为0、1、2、3或4；Y.sup.1和Y.sup.2为H或卤素；R.sup.2、R.sup.3和R.sup.4可以相同也可以不同，独立地为H、金属离子、C.sub.1到C.sub.8烷基或C.sub.3到C.sub.12烯基；X为O、S、NH或NCH.sub.2R.sup.15，其中R.sup.15为H或C.sub.1到C.sub.5烷基；R.sup.1为R.sup.5--Q.sup.1--Q.sup.2--Q.sup.3--其中R.sup.5、Q.sup.1、Q.sup.2和Q.sup.3如本文所定义；当m为o时，X不是S；如果m为o且X为0，则n为1、2、3或4；包括所有立体异构体。
• Bisphosphonate squalene synthetase inhibitors and method
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US05157027A1

  公开（公告）日：1992-10-20

  Compounds which are inhibitors of cholesterol biosynthesis (by inhibiting de novo squalene biosynthesis), and thus are useful as hypocholesterolemic agents and antiatherosclerotic agents are provided which have the structure ##STR1## and analogs thereof, wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same or different and are H, lower alkyl, a metal ion or a prodrug ester; R.sup.5 is H, halogen or lower alkyl; Zq is substituted alkenyl, substituted alkynyl, mixed alkenyl-alkynyl or substituted phenylalkyl or, phenylalkenyl or phenylalkynyl, or alkyl, including all stereoisomers thereof. New methods for using such compounds to inhibit cholesterol biosynthesis are also provided.

  提供了一种抑制胆固醇生物合成（通过抑制新生角鲨烯生物合成）的化合物，因此可用作降胆固醇药物和抗动脉粥样硬化药物，其结构为##STR1##及其类似物，其中R.sup.1、R.sup.2、R.sup.3和R.sup.4相同或不同，为H、较低烷基、金属离子或前药酯；R.sup.5为H、卤素或较低烷基；Zq为取代烯基、取代炔基、混合烯基-炔基或取代苯基烷基、苯基烯基或苯基炔基，或烷基，包括其所有立体异构体。还提供了使用这些化合物抑制胆固醇生物合成的新方法。
• Matteson Reaction under Flow Conditions: Iterative Homologations of Terpenes
  作者：Conrad Kuhwald、Andreas Kirschning

  DOI：10.1021/acs.orglett.1c01222

  日期：2021.6.4

  The Matteson reaction is ideally suited for flow chemistry since it allows iterative homologation of boronate esters. The present study provides accurate data on reaction times of the individual steps of the Matteson reaction, which occurs in less than 10 s in total. The protocol allows terpenes to be (per-)homologated in a controlled manner to yield homo-, bishomo-, and trishomo-terpenols after oxidative

  Matteson 反应非常适合流动化学，因为它允许硼酸酯的迭代同系化。本研究提供了有关马特森反应各个步骤的反应时间的准确数据，该反应总共发生在 10 秒以内。该协议允许萜烯以受控方式进行 (per-) homologated, 以在氧化处理后产生 homo-、bishomo-和 trishomo-terpenols。新萜醇的嗅觉特性得到验证。
• Method for lowering cholesterol employing a phosphonomethylphosphinate
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US05428028A1

  公开（公告）日：1995-06-27

  A method is provided for inhibiting cholesterol biosynthesis by inhibiting de novo squalene production employing methylene phosphonoalkylphosphinate compounds.

  提供了一种通过抑制脱新生角鲨烯产生来抑制胆固醇生物合成的方法，采用亚甲基膦酸烷基膦酸酯化合物。