(2E,6Z)-1-bromo-3,7,11-trimethyl-2,6,10-dodecatriene | 24163-94-8

• 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: (2E,6Z)-1-bromo-3,7,11-trimethyl-2,6,10-dodecatriene
• 英文别名: (E,Z)-farnesyl bromide；(2E,6Z)-farnesyl bromide；(2E,6Z)-1-bromo-3,7,11-trimethyl-dodeca-2,6,10-triene；farnesyl bromide；trans-farnesyl bromide；Farnesylbromid；(2E,6Z)-1-bromo-3,7,11-trimethyldodeca-2,6,10-triene
• CAS: 24163-94-8
• 化学式: C₁₅H₂₅Br
• 分子量: 285.267
• InChiKey: FOFMBFMTJFSEEY-GNESMGCMSA-N

物化性质

• 沸点：
  333.3±21.0 °C(Predicted)
• 密度：
  1.058±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  (2E,6Z)-1-bromo-3,7,11-trimethyl-2,6,10-dodecatriene 在 盐酸 、 氢氧化钾 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 5.5h， 生成 (5E,9Z)-6,10,14-trimethylpentadeca-5,9,13-trien-2-one
  参考文献：
  名称：

  Synthesis and pheromone activities of optically active neocembrenes and their geometrical isomers, (E,Z,E)- and (E,E,Z)-neocembrenes

  摘要：

  DOI：

  10.1021/jo01294a041
• 作为产物：
  描述：

  (E,Z)-金合欢醇 在 三溴化磷 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 (2E,6Z)-1-bromo-3,7,11-trimethyl-2,6,10-dodecatriene
  参考文献：
  名称：

  合成胡萝卜素-端基和（Z）-修饰末端的多巴宾登根

  摘要：

  末端共轭双键具有ψ-端基和（Z）-构型的胡萝卜素的合成

  DOI：

  10.1002/hlca.19850680604

文献信息

• Inhibitors of farnesyl-protein transferase
  申请人：Merck & Co., Inc.

  公开号：US05627202A1

  公开（公告）日：1997-05-06

  The present invention comprises analogs of the CA.sup.1 A.sup.2 X motif of the protein Ras that is modified by farnesylation in vivo. These CA.sup.1 A.sup.2 X analogs inhibit the farnesyl-protein transferase and the farnesylation of certain proteins. Furthermore, these CA.sup.1 A.sup.2 X analogs differ from those previously described as inhibitors of farnesyl-protein transferase in that they do not have a thiol moiety. The lack of the thiol offers unique advantages in terms of improved pharmacokinetic behavior in animals, prevention of thiol-dependent chemical reactions, such as rapid autoxidation and disulfide formation with endogenous thiols, and reduced systemic toxicity. The compounds of the instant invention also incorporate a cyclic amine moiety in the A.sup.2 position of the motif. Further contained in this invention are chemotherapeutic compositions containing these farnesyl transferase inhibitors and methods for their production.

  本发明包括蛋白质Ras的CA.sup.1 A.sup.2 X基序的类似物，该基序在体内通过法尼酰化进行修饰。这些CA.sup.1 A.sup.2 X类似物抑制法尼酰蛋白转移酶和某些蛋白质的法尼酰化。此外，这些CA.sup.1 A.sup.2 X类似物与先前描述的抑制法尼酰蛋白转移酶的类似物不同，因为它们不具有硫醇基团。缺乏硫醇基团在改善动物的药代动力学行为、预防依赖硫醇的化学反应（如快速自氧化和与内源硫醇形成二硫键）以及减少全身毒性方面提供了独特优势。本发明的化合物还在该基序的A.sup.2位置包含一个环胺基团。本发明还包括含有这些法尼酰转移酶抑制剂的化疗组合物以及其生产方法。
• 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。
• 11-(Piperazino-acetyl)-5,11-di
  申请人：Boehringer Ingelheim GmbH

  公开号：US04213984A1

  公开（公告）日：1980-07-22

  Compounds of the formula ##STR1## wherein R.sub.1 is alkyl of 3 to 12 carbon atoms; unsaturated aliphatic hydrocarbyl of 3 to 20 carbon atoms comprising 1 to 3 double bonds and/or one triple bond; phenyl(alkyl of 2 to 4 carbon atoms); methylenedioxybenzyl; chlorobenzyl; indan-5-ylmethyl; indan-3-ylmethyl; phenyl(alkenyl of 2 to 4 carbon atoms); cycloalkyl of 5 to 7 carbon atoms; (cycloalkyl of 3 to 10 carbon atoms)methyl; (methylcycloalkyl of 4 to 11 carbon atoms)methyl; morpholino(alkyl of 2 to 3 carbon atoms); pyrrolidino(alkyl of 2 to 3 carbon atoms); piperidino (alkyl of 2 to 3 carbon atoms); 4-methylpiperazino(alkyl of 2 to 3 carbon atoms); or, when R.sub.3 and/or R.sub.4 are methyl or ethyl, also methyl or ethyl; R.sub.2 is hydrogen, methyl or ethyl; and R.sub.3 and R.sub.4 are each hydrogen, methyl or ethyl; and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as the salts are useful as anti-ulcerogenics and secretion inhibitors.

  式为##STR1##的化合物，其中R.sub.1是3到12个碳原子的烷基；不饱和脂肪烃基，碳原子数为3到20，包括1到3个双键和/或一个三键；苯基（2到4个碳原子的烷基）；亚甲二氧基苯甲基；氯苯甲基；茚-5-基甲基；茚-3-基甲基；苯基（2到4个碳原子的烯基）；5到7个碳原子的环烷基；（3到10个碳原子的环烷基）甲基；（4到11个碳原子的甲基环烷基）甲基；吗啉（2到3个碳原子的烷基）；吡咯啉（2到3个碳原子的烷基）；哌啶（2到3个碳原子的烷基）；4-甲基哌嗪（2到3个碳原子的烷基）；或者，当R.sub.3和/或R.sub.4是甲基或乙基时，也可以是甲基或乙基；R.sub.2是氢、甲基或乙基；R.sub.3和R.sub.4分别是氢、甲基或乙基；以及其非毒性、药理学上可接受的酸盐。这些化合物以及盐可用作抗溃疡剂和分泌抑制剂。
• Protein farnesyl transferase inhibitors
  申请人：Bristol-Myers Squibb Company

  公开号：US05523430A1

  公开（公告）日：1996-06-04

  Inhibition of farnesyl transferase, which is an enzyme involved in ras oncogene expression, and inhibition of cholesterol biosynthesis, are effected by compounds of the formula ##STR1## their enantiomers, diastereomers, and pharmaceutically acceptable salts, prodrugs, and solvates, wherein: X is --ONR.sup.1 C(O)--, --N(OR.sup.1)C(O)--, --NR.sup.1 C(O)--, --C(O)NR.sup.1 --, --NR.sup.1 S(O.sub.2)--, --C(O)O--, --OC(O)--, --O--, --NR.sup.1 -- or --(S)q; Y and Z are each independently --CO.sub.2 R.sup.2, --SO.sub.3 R.sup.2 or --P(O)(OR.sup.2)(OR.sup.3); R is alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkenylene or aryl; R.sup.1, R.sup.2 and R.sup.3 are each independently hydrogen, alkyl, aryl or aralkyl; m and n are each independently 0 or an integer from 1 to 5; p is 0 or 1; and q is an integer from 1 to 2.

  抑制法尼基转移酶，该酶参与ras癌基因表达，以及抑制胆固醇生物合成，由式##STR1##及其对映异构体、顺异构体和药学上可接受的盐、前药和溶剂所影响，其中：X为--ONR.sup.1 C(O)--，--N(OR.sup.1)C(O)--，--NR.sup.1 C(O)--，--C(O)NR.sup.1 --，--NR.sup.1 S(O.sub.2)--，--C(O)O--，--OC(O)--，--O--，--NR.sup.1 --或--(S)q；Y和Z分别独立为--CO.sub.2 R.sup.2，--SO.sub.3 R.sup.2或--P(O)(OR.sup.2)(OR.sup.3)；R为烷基，取代烷基，烯基，取代烯基，烯亚基或芳基；R.sup.1，R.sup.2和R.sup.3分别独立为氢，烷基，芳基或芳基烷基；m和n分别独立为0或1到5之间的整数；p为0或1；q为1到2之间的整数。
• .alpha.-phosphonocarboxylate squalene synthetase inhibitors
  申请人：Bristol-Myers Squibb Co.

  公开号：US05312814A1

  公开（公告）日：1994-05-17

  .alpha.- Phosphonocarboxylate compounds are provided which inhibit the enzyme squalene synthetase and thereby inhibit cholesterol biosynthesis. These compounds have the formula ##STR1## wherein R.sup.1 is a lipophilic group which contains at least 7 carbons and is substituted alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted arylalkyl or optionally substituted aryl; Z is H, halogen, hydroxy, hydroxyalkyl or lower alkyl; R.sup.2 and R.sup.3 are independently H, metal ion or other pharmaceutically acceptable cation, or a prodrug ester; R.sup.4 is H, metal ion or other pharmaceutically acceptable cation, lower alkyl, lower alkenyl, arylalkyl, aryl or a prodrug ester.

  提供了抑制齐墩果酸合酶并从而抑制胆固醇生物合成的磷酸羧酸化合物。这些化合物的化学式为##STR1##其中R.sup.1是至少含有7个碳且为取代烷基、可选择取代环烷基、可选择取代环烷基烷基、可选择取代烯基、可选择取代炔基、可选择取代芳基烷基或可选择取代芳基的亲脂基团；Z为H、卤素、羟基、羟基烷基或较低烷基；R.sup.2和R.sup.3独立地为H、金属离子或其他药用可接受阳离子，或为一种前药酯；R.sup.4为H、金属离子或其他药用可接受阳离子、较低烷基、较低烯基、芳基烷基、芳基或一种前药酯。