(4,6-ditert-butylspiro[3H-1-benzofuran-2,1'-cycloheptane]-5-yl) acetate | 1026287-74-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (4,6-ditert-butylspiro[3H-1-benzofuran-2,1'-cycloheptane]-5-yl) acetate
• CAS: 1026287-74-0
• 化学式: C₂₄H₃₆O₃
• 分子量: 372.548
• InChiKey: WZMJXMJWFARCFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4,6-ditert-butylspiro[3H-1-benzofuran-2,1'-cycloheptane]-5-yl) acetate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 4,6-ditert-butylspiro[3H-1-benzofuran-2,1'-cycloheptane]-5-ol
  参考文献：
  名称：

  Design and Synthesis of 4,6-Di-tert-butyl-2,3-dihydro-5-benzofuranols as a Novel Series of Antiatherogenic Antioxidants

  摘要：

  Antioxidants have been considered as potential antiatherogenic agents by inhibiting oxidation of low-density lipoprotein (LDL), albeit vitamin E, a natural antioxidant, has failed to show reduction on atherosclerosis in clinical trials. We have rationally designed and synthesized a novel series of antioxidants, 4,6-di-tert-butyl-2,3-dihydro-5-benzofuranols, to overcome the clinical limitation of vitamin E. In vitro, the compounds showed a potent inhibitory effect on lipid peroxidation detected as 2-methyl-6-(p-methoxyphenyl)-3,7-dihydroimidazo[1,2-a]pyrazin3-one (MCLA)-dependent chemiluminescence in linoleic acid autoxidation. They also inhibited the LDL oxidation induced by Cu2+, and the inhibition is more potent than that of vitamin E and probucol. In vivo, 4,6-di-tert-butyl-2,3-dihydro-2,2-dipentyl-5-benzofuranoI (BO-653, 1f), an optimal compound, showed the highest concentration in plasma and LDL fraction in Watanabe heritable hyperlipidemic rabbits, due to its high affinity to LDL. The isolated LDL samples from the If-treated rabbits showed potent resistibility to LDL oxidation. Compound If has been taken into clinical trials.

  DOI：

  10.1021/jm030062a
• 作为产物：
  描述：

  2,6-二叔丁基-4-甲氧基苯酚 在 碘代三甲硅烷 、 (CH₂)6N₄ 、 硫酸 、 三氟化硼乙醚 、 magnesium 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 110.5h， 生成 (4,6-ditert-butylspiro[3H-1-benzofuran-2,1'-cycloheptane]-5-yl) acetate
  参考文献：
  名称：

  Design and Synthesis of 4,6-Di-tert-butyl-2,3-dihydro-5-benzofuranols as a Novel Series of Antiatherogenic Antioxidants

  摘要：

  Antioxidants have been considered as potential antiatherogenic agents by inhibiting oxidation of low-density lipoprotein (LDL), albeit vitamin E, a natural antioxidant, has failed to show reduction on atherosclerosis in clinical trials. We have rationally designed and synthesized a novel series of antioxidants, 4,6-di-tert-butyl-2,3-dihydro-5-benzofuranols, to overcome the clinical limitation of vitamin E. In vitro, the compounds showed a potent inhibitory effect on lipid peroxidation detected as 2-methyl-6-(p-methoxyphenyl)-3,7-dihydroimidazo[1,2-a]pyrazin3-one (MCLA)-dependent chemiluminescence in linoleic acid autoxidation. They also inhibited the LDL oxidation induced by Cu2+, and the inhibition is more potent than that of vitamin E and probucol. In vivo, 4,6-di-tert-butyl-2,3-dihydro-2,2-dipentyl-5-benzofuranoI (BO-653, 1f), an optimal compound, showed the highest concentration in plasma and LDL fraction in Watanabe heritable hyperlipidemic rabbits, due to its high affinity to LDL. The isolated LDL samples from the If-treated rabbits showed potent resistibility to LDL oxidation. Compound If has been taken into clinical trials.

  DOI：

  10.1021/jm030062a

文献信息

• Design and Synthesis of 4,6-Di-<i>tert</i>-butyl-2,3-dihydro-5-benzofuranols as a Novel Series of Antiatherogenic Antioxidants
  作者：Kunio Tamura、Yoshiaki Kato、Akira Ishikawa、Yasuharu Kato、Motomu Himori、Mitsutaka Yoshida、Yoshiaki Takashima、Tsukasa Suzuki、Yoshiki Kawabe、Osamu Cynshi、Tatsuhiko Kodama、Etsuo Niki、Makoto Shimizu

  DOI：10.1021/jm030062a

  日期：2003.7.1

  Antioxidants have been considered as potential antiatherogenic agents by inhibiting oxidation of low-density lipoprotein (LDL), albeit vitamin E, a natural antioxidant, has failed to show reduction on atherosclerosis in clinical trials. We have rationally designed and synthesized a novel series of antioxidants, 4,6-di-tert-butyl-2,3-dihydro-5-benzofuranols, to overcome the clinical limitation of vitamin E. In vitro, the compounds showed a potent inhibitory effect on lipid peroxidation detected as 2-methyl-6-(p-methoxyphenyl)-3,7-dihydroimidazo[1,2-a]pyrazin3-one (MCLA)-dependent chemiluminescence in linoleic acid autoxidation. They also inhibited the LDL oxidation induced by Cu2+, and the inhibition is more potent than that of vitamin E and probucol. In vivo, 4,6-di-tert-butyl-2,3-dihydro-2,2-dipentyl-5-benzofuranoI (BO-653, 1f), an optimal compound, showed the highest concentration in plasma and LDL fraction in Watanabe heritable hyperlipidemic rabbits, due to its high affinity to LDL. The isolated LDL samples from the If-treated rabbits showed potent resistibility to LDL oxidation. Compound If has been taken into clinical trials.