[(2E,6E)-3,7-dimethyl-8-(3-methylphenyl)octa-2,6-dienyl] 2-bromoacetate

• 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,6E)-3,7-dimethyl-8-(3-methylphenyl)octa-2,6-dienyl] 2-bromoacetate
• 化学式: C₁₉H₂₅BrO₂
• 分子量: 365.3
• InChiKey: MCBFYRZFHWKRHQ-HRYPAVBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

文献信息

• Anticancer agents based on regulation of protein prenylation
  申请人：Arizona Biomedical Research Commission

  公开号：EP1798217A1

  公开（公告）日：2007-06-20

  Oncoproteins such as Ras and RhoB are known to induce cell division in an unrestrained manner when such proteins are localized at the inner surface of a cancer cell membrane. The localization is effected by the prenylation reaction, whereby a hydrophobic group (e.g. a farnesyl group) is attached to the protein in the presence of an enzyme (e.g. farnesyl protein transferase). Deactivation of the prenylation enzyme through covalent modification can therefore ultimately result in the mitigation and/or cessation of cancer cell growth. Various prenylation inhibitors having the necessary structural groups to bond covalently, or essentially irreversibly, to the prenylation enzyme include carbonyl or thiocarbonyl compounds (or masked versions of these compounds) and alpha oxo-epoxides bonded to a hydrophobic, substrate-mimicking group. The carbonyl or thiocarbonyl compounds also contain a nucleofugal atom or group to enhance the tendency to form covalent bonds.

  众所周知，当 Ras 和 RhoB 等肿瘤蛋白定位于癌细胞膜的内表面时，就会以无限制的方式诱导细胞分裂。这种定位是通过预炔化反应实现的，即在一种酶（如法炔基蛋白转移酶）存在的情况下，疏水基团（如法炔基）被连接到蛋白质上。因此，通过共价修饰使前酰化酶失活，最终可减轻和/或停止癌细胞的生长。各种具有与前酰化酶共价键合或基本不可逆键合的必要结构基团的前酰化抑制剂包括羰基或硫代羰基化合物（或这些化合物的掩蔽型）以及与疏水基、底物模拟基键合的α-氧代环氧化物。羰基或硫代羰基化合物还含有一个核糖原子或基团，以增强形成共价键的趋势。
• ANTICANCER AGENTS BASED ON REGULATION OF PROTEIN PRENYLATION
  申请人：Rose Seth D.

  公开号：US20090143467A1

  公开（公告）日：2009-06-04

  Oncoproteins such as Ras and RhoB are known to induce cell division in an unrestrained manner when such proteins are localized at the inner surface of a cancer cell membrane. The localization is effected by the prenylation reaction, whereby a hydrophobic group (e.g. a farnesyl group) is attached to the protein in the presence of an enzyme (e.g. farnesyl protein transferase). Deactivation of the prenylation enzyme through covalent modification can therefore ultimately result in the mitigation and/or cessation of cancer cell growth. Various prenylation inhibitors having the necessary structural groups to bond covalently, or essentially irreversibly, to the prenylation enzyme include carbonyl or thiocarbonyl compounds (or masked versions of these compounds) and alpha oxo-epoxides bonded to a hydrophobic, substrate-mimicking group. The carbonyl or thiocarbonyl compounds also contain a nucleofugal atom or group to enhance the tendency to form covalent bonds.
• US7423170B2
  申请人：——

  公开号：US7423170B2

  公开（公告）日：2008-09-09
• US7943665B2
  申请人：——

  公开号：US7943665B2

  公开（公告）日：2011-05-17