1-methyl 2-phenylselenyl-succinate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-methyl 2-phenylselenyl-succinate
• 英文别名: 2-phenylselanyl-succinic acid-1-methyl ester；2-phenylselanyl-succinic acid methyl ester；4-Methoxy-4-oxo-3-phenylselanylbutanoic acid；4-methoxy-4-oxo-3-phenylselanylbutanoic acid
• 化学式: C₁₁H₁₂O₄Se
• 分子量: 287.174
• InChiKey: DPCMVXNQKQKAMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.45
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-phenylselanyl-succinic acid 4-methyl ester 、 1-methyl 2-phenylselenyl-succinate 在 盐酸 作用下， 以 水 为溶剂， 以82%的产率得到2-phenylselanyl-succinic acid
  参考文献：
  名称：

  Tocopherol ester compounds

  摘要：

  揭示了一种新的生育酚酯化合物，其公式为：其中X是2或3个碳原子的链，例如乙烯和三亚甲基，将它们连接到它们所结合的2个羰基基团; R1是具有公式-Y-R4的基团，其中Y是硒、碲或硫原子，而R4是烷基、环烷基或芳基基团。公式（I）的生育酚酯化合物在乳腺癌细胞系上表现出抗增殖和生长抑制作用。

  公开号：

  US06716873B1
• 作为产物：
  描述：

  甲醇 、 3-溴四氢呋喃-2,5-二酮 、 二苯基二硒醚 在 sodium tetrahydroborate 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 3.5h， 生成 2-phenylselanyl-succinic acid 4-methyl ester 、 1-methyl 2-phenylselenyl-succinate
  参考文献：
  名称：

  Tocopherol ester compounds

  摘要：

  揭示了一种新的生育酚酯化合物，其公式为：其中X是2或3个碳原子的链，例如乙烯和三亚甲基，将它们连接到它们所结合的2个羰基基团; R1是具有公式-Y-R4的基团，其中Y是硒、碲或硫原子，而R4是烷基、环烷基或芳基基团。公式（I）的生育酚酯化合物在乳腺癌细胞系上表现出抗增殖和生长抑制作用。

  公开号：

  US06716873B1

文献信息

• Tocopherol ester compounds
  申请人：Yasoo Health Inc.

  公开号：US06716873B1

  公开（公告）日：2004-04-06

  Disclosed are novel tocopherol ester compounds having the formula wherein X is a chain of 2 or 3 carbon atoms, e.g., ethylene and trimethylene, joining the 2 carbonyl groups to which they are bonded; and R1 is a group having the formula —Y—R4 wherein Y is a selenium, tellurium or sulfur atom and R4 is an alkyl, cycloalkyl or aryl radical. The tocopherol ester compounds of formula (I) exhibit antiproliferative and growth inhibitory effects on breast cancer cell lines.

  揭示了一种新的生育酚酯化合物，其公式为：其中X是2或3个碳原子的链，例如乙烯和三亚甲基，将它们连接到它们所结合的2个羰基基团; R1是具有公式-Y-R4的基团，其中Y是硒、碲或硫原子，而R4是烷基、环烷基或芳基基团。公式（I）的生育酚酯化合物在乳腺癌细胞系上表现出抗增殖和生长抑制作用。
• Synthesis and study of the cancer cell growth inhibitory properties of α-, γ-tocopheryl and γ-tocotrienyl 2-phenylselenyl succinates
  作者：Panayiota S. Vraka、Chryssoula Drouza、Maria P. Rikkou、Andreani D. Odysseos、Anastasios D. Keramidas

  DOI：10.1016/j.bmc.2005.11.045

  日期：2006.4

  Vitamin E succinate selenium-conjugated molecules were synthesized and their apoptogenic properties were evaluated. 4-Methyl-2-phenylselenyl succinate (4) was prepared by the reaction of sodium benzeneselenolate with 2-bromosuccinic anhydrite in methanol solution. The methyl ester was converted to the acid (5) by hydrolysis with aqueous hydrochloric acid. Reaction of the 2-phenylselenyl succinic anhydrite (6) with alpha-tocopherol (1a), gamma-tocopherol (le), and gamma-tocotrienol (2c) in acidic conditions gave the respective esters. The free radical scavenging properties of alpha-tocopheryl-2-phenylselenyl succinate (7), gamma-tocopheryl-2-phenylselenyl succinate (8), and gamma-tocotrienyl-2-phenylselenyl succinate (9) were evaluated in comparison with those of alpha-tocopheryl succinate (10). gamma-tocopheryl succinate (11), and gamma-tocotrienyl succinate (12), respectively, and the free tocopherols and gamma-tocotrienol. Compounds 7-9 induced a statistically significant decrease in prostate cancer cell viability compared to 10-12, respectively, or 5, exhibiting features of apoptotic cell death and associated with caspase-3 activation. These data show that structural modifications of vitamin E components by 5 enhance their apoptogenic properties in cancer cells. (c) 2005 Elsevier Ltd. All rights reserved.