4-O-[6-(hydroxymethyl)-4-oxopyran-3-yl] 1-O-[(1S,6R,8R,11R,12S,15S,16R,19S,21R)-19-methoxy-1,7,7,11,16,20,20-heptamethyl-8-pentacyclo[13.8.0.03,12.06,11.016,21]tricos-3-enyl] butanedioate | 1186389-68-3

• 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: 4-O-[6-(hydroxymethyl)-4-oxopyran-3-yl] 1-O-[(1S,6R,8R,11R,12S,15S,16R,19S,21R)-19-methoxy-1,7,7,11,16,20,20-heptamethyl-8-pentacyclo[13.8.0.03,12.06,11.016,21]tricos-3-enyl] butanedioate
• CAS: 1186389-68-3
• 化学式: C₄₁H₆₀O₈
• 分子量: 680.923
• InChiKey: XHIMTYYAXNBQRC-JVPKMNBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  49
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  曲酸 、 4-[[(1S,6R,8R,11R,12S,15S,16R,19S,21R)-19-methoxy-1,7,7,11,16,20,20-heptamethyl-8-pentacyclo[13.8.0.03,12.06,11.016,21]tricos-3-enyl]oxy]-4-oxobutanoic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以30%的产率得到4-O-[6-(hydroxymethyl)-4-oxopyran-3-yl] 1-O-[(1S,6R,8R,11R,12S,15S,16R,19S,21R)-19-methoxy-1,7,7,11,16,20,20-heptamethyl-8-pentacyclo[13.8.0.03,12.06,11.016,21]tricos-3-enyl] butanedioate
  参考文献：
  名称：

  Novel 3α-methoxyserrat-14-en-21β-ol (PJ-1) and 3β-methoxyserrat-14-en-21β-ol (PJ-2)-curcumin, kojic acid, quercetin, and baicalein conjugates as HIV agents

  摘要：

  Sixteen novel compounds; 3 alpha-methoxyserrat-14-en-21 beta-ol (1) and 3 beta-methoxyserrat-14-en-21 beta-ol (2) and their curcumin, kojic acid, quercetin, and baicalein conjugates (3)-(18) were designed, synthesized, and evaluated for in vitro anti-HIV-1 reverse transcriptase (RT) activity in infected C8166-CCR5 cells, a human CD4(+) T-lymphocyte cell line. Among them, kojic acid derivatives, 9-12 showed significant biological activity. In particular, the compound 13, the conjugate of two molecules of 3 alpha-methoxyserrat-14-en-21 beta-ol (1) and one molecule of kojic acid, exerted significant anti-HIV activity with an EC50 value of 0.12 mu g/mL. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.05.049

文献信息

• Novel 3α-methoxyserrat-14-en-21β-ol (PJ-1) and 3β-methoxyserrat-14-en-21β-ol (PJ-2)-curcumin, kojic acid, quercetin, and baicalein conjugates as HIV agents
  作者：Reiko Tanaka、Hiroko Tsujii、Takeshi Yamada、Tetsuya Kajimoto、Fumio Amano、Junya Hasegawa、Yoshio Hamashima、Manabu Node、Kayoko Katoh、Yutaka Takebe

  DOI：10.1016/j.bmc.2009.05.049

  日期：2009.7

  Sixteen novel compounds; 3 alpha-methoxyserrat-14-en-21 beta-ol (1) and 3 beta-methoxyserrat-14-en-21 beta-ol (2) and their curcumin, kojic acid, quercetin, and baicalein conjugates (3)-(18) were designed, synthesized, and evaluated for in vitro anti-HIV-1 reverse transcriptase (RT) activity in infected C8166-CCR5 cells, a human CD4(+) T-lymphocyte cell line. Among them, kojic acid derivatives, 9-12 showed significant biological activity. In particular, the compound 13, the conjugate of two molecules of 3 alpha-methoxyserrat-14-en-21 beta-ol (1) and one molecule of kojic acid, exerted significant anti-HIV activity with an EC50 value of 0.12 mu g/mL. (C) 2009 Elsevier Ltd. All rights reserved.