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 | 1186389-76-3

• 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-[[(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
• CAS: 1186389-76-3
• 化学式: C₃₅H₅₆O₅
• 分子量: 556.827
• InChiKey: RMNPKMCCZFVCHZ-KWJFKFLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  40
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  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 、 染料木素 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以41%的产率得到4-O-[5-hydroxy-3-(4-hydroxyphenyl)-4-oxochromen-7-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：

  Conjugates of 3α-methoxyserrat-14-en-21β-ol (PJ-1) and 3β-methoxyserrat-14-en-21β-ol (PJ-2) as cancer chemopreventive agents

  摘要：

  3 alpha-Methoxyserrat-14-en-21 beta-ol (PJ-1) and 3 beta-methoxyserrat-14-en-21 beta-ol (PJ-2) were conjugated with well-known phenolic compounds, narigenin, hesperetin, genistein, and daidzein (1-8). Other conjugates of PJ-2-3,5-dihydroxy-4-methoxybenzoic acid (9), PJ-2 pyrogallol (10), and derivatives of PJ-1, PJ-2-3,3-dimethyl-succinates (11, 12), PJ-1, PJ-2 succinates (13, 14), PJ-2 glycine (15), PJ-2 piperidine acetic acid (16), and PJ-1 epoxy-3,3-dimethyl-succinate (17) were tested for their inhibitory effects on Epstein Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). The inhibitory effects of 11 (IC50 = 251),12 (IC50 = 248), and 17 (IC50= 230 mol ratio/32 pmol/TPA), were 2-fold stronger than those of the other compounds such as oleanolic acid (IC50 = 449). Compounds 10, 11, and 17 inhibited mouse skin tumor promotion in an in vivo two-stage carcinogenesis model. The in vivo two-stage mouse-skin carcinogenesis test employed 7,12-dimethylbenz[a]anthracene (DMBA) as an initiator and TPA as a promoter. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.062
• 作为产物：
  描述：

  丁二酸酐 、 3β-methoxyserrat-14-en-21β-ol 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 22.5h， 以65%的产率得到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
  参考文献：
  名称：

  Conjugates of 3α-methoxyserrat-14-en-21β-ol (PJ-1) and 3β-methoxyserrat-14-en-21β-ol (PJ-2) as cancer chemopreventive agents

  摘要：

  3 alpha-Methoxyserrat-14-en-21 beta-ol (PJ-1) and 3 beta-methoxyserrat-14-en-21 beta-ol (PJ-2) were conjugated with well-known phenolic compounds, narigenin, hesperetin, genistein, and daidzein (1-8). Other conjugates of PJ-2-3,5-dihydroxy-4-methoxybenzoic acid (9), PJ-2 pyrogallol (10), and derivatives of PJ-1, PJ-2-3,3-dimethyl-succinates (11, 12), PJ-1, PJ-2 succinates (13, 14), PJ-2 glycine (15), PJ-2 piperidine acetic acid (16), and PJ-1 epoxy-3,3-dimethyl-succinate (17) were tested for their inhibitory effects on Epstein Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). The inhibitory effects of 11 (IC50 = 251),12 (IC50 = 248), and 17 (IC50= 230 mol ratio/32 pmol/TPA), were 2-fold stronger than those of the other compounds such as oleanolic acid (IC50 = 449). Compounds 10, 11, and 17 inhibited mouse skin tumor promotion in an in vivo two-stage carcinogenesis model. The in vivo two-stage mouse-skin carcinogenesis test employed 7,12-dimethylbenz[a]anthracene (DMBA) as an initiator and TPA as a promoter. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.062

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.
• Conjugates of 3α-methoxyserrat-14-en-21β-ol (PJ-1) and 3β-methoxyserrat-14-en-21β-ol (PJ-2) as cancer chemopreventive agents
  作者：Reiko Tanaka、Hiroko Tsujii、Takeshi Yamada、Tetsuya Kajimoto、Harukuni Tokuda、Takanari Arai、Nobutaka Suzuki、Junya Hasegawa、Yoshio Hamashima、Manabu Node

  DOI：10.1016/j.ejmech.2011.04.062

  日期：2011.8

  3 alpha-Methoxyserrat-14-en-21 beta-ol (PJ-1) and 3 beta-methoxyserrat-14-en-21 beta-ol (PJ-2) were conjugated with well-known phenolic compounds, narigenin, hesperetin, genistein, and daidzein (1-8). Other conjugates of PJ-2-3,5-dihydroxy-4-methoxybenzoic acid (9), PJ-2 pyrogallol (10), and derivatives of PJ-1, PJ-2-3,3-dimethyl-succinates (11, 12), PJ-1, PJ-2 succinates (13, 14), PJ-2 glycine (15), PJ-2 piperidine acetic acid (16), and PJ-1 epoxy-3,3-dimethyl-succinate (17) were tested for their inhibitory effects on Epstein Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). The inhibitory effects of 11 (IC50 = 251),12 (IC50 = 248), and 17 (IC50= 230 mol ratio/32 pmol/TPA), were 2-fold stronger than those of the other compounds such as oleanolic acid (IC50 = 449). Compounds 10, 11, and 17 inhibited mouse skin tumor promotion in an in vivo two-stage carcinogenesis model. The in vivo two-stage mouse-skin carcinogenesis test employed 7,12-dimethylbenz[a]anthracene (DMBA) as an initiator and TPA as a promoter. (C) 2011 Elsevier Masson SAS. All rights reserved.