bis(methyl 3-dioxy-7α,12α-diacetoxy-5β-cholan-24-oate) | 300542-84-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: bis(methyl 3-dioxy-7α,12α-diacetoxy-5β-cholan-24-oate)
• CAS: 300542-84-1
• 化学式: C₅₈H₈₈O₁₆
• 分子量: 1041.33
• InChiKey: IJYOAPGHZWFQRH-XVQUDYIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.95
• 重原子数：
  74.0
• 可旋转键数：
  12.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  194.72
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  bis(methyl 3-dioxy-7α,12α-diacetoxy-5β-cholan-24-oate) 在 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 72.0h， 以72%的产率得到
  参考文献：
  名称：

  Cholic Acid Derivatives as 1,2,4,5-Tetraoxane Carriers:  Structure and Antimalarial and Antiproliferative Activity

  摘要：

  Cholic acid-derived 1,2,4,5-tetraoxanes were synthesized in order to explore the influence of steroid carrier on its antimalarial and antiproliferative activity in vitro. Starting with chiral ketones, cis and trans series of diastereomeric tetraoxanes were obtained, and the cis series was found to be similar to 2 times as active as the trans against Plasmodium falciparum DG and W2 clones. The same tendency was observed against human melanoma (Fem-X) and human cervix carcinoma (HeLa) cell lines. The amide C(24) termini, for the first time introduced into the carrier molecule of a tetraoxane pharmacophore, significantly enhanced both antimalarial and antiproliferative activity, as compared to the corresponding methyl esters, with cis-bis(N-propylamide) being most efficient against the chloroquine-susceptible D6 clone (IC50 = 9.29 nM). cis- and trans-bis(N-propylamides) were also screened against PBMC, and PRA-stimulated PBMC, showing a cytotoxicity/antimalarial potency ratio of 1/10 000.

  DOI：

  10.1021/jm000952f
• 作为产物：
  描述：

  胆酸甲酯 在 chromium(VI) oxide 、 甲醇 、 三氟甲磺酸三甲基硅酯 、 硫酸 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 4.33h， 生成 bis(methyl 3-dioxy-7α,12α-diacetoxy-5β-cholan-24-oate)
  参考文献：
  名称：

  Cholic Acid Derivatives as 1,2,4,5-Tetraoxane Carriers:  Structure and Antimalarial and Antiproliferative Activity

  摘要：

  Cholic acid-derived 1,2,4,5-tetraoxanes were synthesized in order to explore the influence of steroid carrier on its antimalarial and antiproliferative activity in vitro. Starting with chiral ketones, cis and trans series of diastereomeric tetraoxanes were obtained, and the cis series was found to be similar to 2 times as active as the trans against Plasmodium falciparum DG and W2 clones. The same tendency was observed against human melanoma (Fem-X) and human cervix carcinoma (HeLa) cell lines. The amide C(24) termini, for the first time introduced into the carrier molecule of a tetraoxane pharmacophore, significantly enhanced both antimalarial and antiproliferative activity, as compared to the corresponding methyl esters, with cis-bis(N-propylamide) being most efficient against the chloroquine-susceptible D6 clone (IC50 = 9.29 nM). cis- and trans-bis(N-propylamides) were also screened against PBMC, and PRA-stimulated PBMC, showing a cytotoxicity/antimalarial potency ratio of 1/10 000.

  DOI：

  10.1021/jm000952f

文献信息

• Antimalarial and antiproliferative evaluation of Bis-Steroidal tetraoxanes
  作者：Dejan Opsenica、Goran Angelovski、Gabriella Pocsfalvi、Zorica Juranić、Željko Žižak、Dennis Kyle、Wilbur K Milhous、Bogdan A Šolaja

  DOI：10.1016/s0968-0896(03)00224-4

  日期：2003.7

  Several cis and trans bis-steroidal 1,2,4,5-tetraoxanes possessing amide terminus were synthesised and evaluated as antimalarials and antiproliferatives. The compounds exhibited submicromolar antimalarial activity against Plasmodium falciparum D6 and W2 strains. The existence of HN-C(O) moiety was found necessary for pronounced antimalarial and antiproliferative activity. In antiproliferative screen, the trans tetraoxane 6 was found to exhibit a pronounced cytotoxicity on 14 cancer cell lines. In addition, tetraoxanes 11 and 12 exhibited significant cytotoxic activity too; microscopic examination of treated HeLa cells showed morphological appearance reminiscent for apoptosis (condensed and/or fragmented nuclei). (C) 2003 Elsevier Science Ltd. All rights reserved.