(3E)-hydroxyiminocholest-6-one | 1056028-46-6

• 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: (3E)-hydroxyiminocholest-6-one
• 英文别名: (3E)-hydroximinocholest-6-one
• CAS: 1056028-46-6
• 化学式: C₂₇H₄₅NO₂
• 分子量: 415.66
• InChiKey: MYCFAUYZGMJOHQ-BMJUKOHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.12
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  49.66
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3E)-hydroxyiminocholest-6-one 在 氯化亚砜 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 3.0h， 生成 4-aza-A-homocholest-3,6-dione-6-thiosemicarbazone
  参考文献：
  名称：

  Synthesis and antiproliferative activity of some steroidal lactams

  摘要：

  Using cholesterol as starting material, a series of 6-substituted-3-aza-A-homo-3-oxycholestanes and 6-substituted-4-aza-A-homo-3-oxycholestanes were synthesized by the oxidation, reduction, oximation, Beckman rearrangement and condensation reaction. These synthesized compounds displayed a distinct cytotoxicity against MGC 7901, HeLa and SMMC 7404 cancer cells. Our results revealed that the structures of functional groups at position-6 on the steroidal ring are crucial for the IC50 value of antiproliferative activities of these compounds and the cytotoxic activity against MGC 7901 and SMMC 7404 cells was not significantly different between 4-N-lactams and 3-N-lactams when its 6-substituted group was a carbonyl or a hydroximino, but all 3-N-lactams showed a higher cytotoxicity against HeLa cells than 4-N-lactams. In particular, compounds 6, 8, 9 (IC50 6: 6.5 mu mol/L; 8: 7.7 mu mol/L; 9: 5.6 mu mol/L) were even more cytotoxic than cisplatin to HeLa cells (positive contrast, 10.1 mu mol/L). The information obtained from the studies may be useful for the design of novel chemotherapeutic drugs. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.06.013
• 作为产物：
  描述：

  5-胆甾烯-3-酮 在 sodium tetrahydroborate 、 Jones reagent 、 nickel(II) chloride hexahydrate 、 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 2.5h， 生成 (3E)-hydroxyiminocholest-6-one
  参考文献：
  名称：

  Syntheses and antiproliferative activity of some sulfated hydroximinosterols

  摘要：

  Four new sulfated steroidal compounds, sodium 3-hydroxy-6-hydroximinocholestane 3-sulfate (7a), sodium 3-hydroxy-6-hydroximinostigmastane 6-sulfate (7b), sodium 3-hydroxy-6-hydroximinocholest-4-ene 3-sulfate (10a), and sodium 6-hydroxy-3-hydroximinocholestane 6-sulfate (16) had been synthesized using cholesterol or stigmasterol as starting materials by different synthetic methods. The synthetic compounds were characterized by their analytical and spectral data, and their antiproliferative activity against MGC 7901 (human gastric carcinoma cell line), HeLa (human cervical carcinoma cell line), and SMMC 7404 (human liver carcinoma cell line) were investigated. The results showed that the compounds exhibited a remarkable cytotoxicity against HeLa tumor cells in vitro and 7a displayed a better cytotoxicity than cisplatin (a positive contrast).

  DOI：

  10.1007/s00044-012-0047-5

文献信息

• Synthesis and evaluation of some steroidal oximes as cytotoxic agents: Structure/activity studies (II)
  作者：Jianguo Cui、Lei Fan、Yanmin Huang、Yi Xin、Aimin Zhou

  DOI：10.1016/j.steroids.2009.07.009

  日期：2009.11

  side chain at position 17 is required for the biological activity of the compounds as we previously confirmed, elimination of the 4,5-double bond augmented the cytotoxic activity for the steroidal oximes. In addition, the presence of a hydroxy on 3- or 6-position of the steroidal nucleus resulted in a remarkable increase of cytotoxic activity. Our findings present more evidence showing the relationship

  从海洋海绵中分离出的羟氨基甾类化合物表现出多种生物学功能，包括细胞毒性和抗病毒功能。在这项研究中，我们合成了一系列在环A或B上具有不同官能团且在位置17处具有不同侧链的氢氧甾类衍生物，并分析了这些化合物对sk-Hep-1，H-292，PC-的细胞毒性3和Hey-1B癌细胞。我们的研究结果表明，尽管如我们先前所确认的，化合物17的胆固醇活性侧链对于化合物的生物学活性是必需的，但4,5双键的消除增强了甾体肟的细胞毒活性。另外，甾体核的3-或6-位上羟基的存在导致细胞毒性活性的显着增加。
• Synthesis and antiproliferative activity of some steroidal thiosemicarbazones, semicarbazones and hydrozones
  作者：Chunfang Gan、Jianguo Cui、Shaoyang Su、Qifu Lin、Linyi Jia、Lianghua Fan、Yanmin Huang

  DOI：10.1016/j.steroids.2014.05.026

  日期：2014.9

  Steroidal thiosemicarbazones, semicarbazones and hydrazones have received extensive attention of scientists recently because they exhibit some biological activities such as antibacterial, antiviral and anticancer. Using different steroids as starting materials, through different chemical methods, 24 steroidal compounds with thiosemicarbazone, semicarbazone or hydrazone groups in their structures, were

  甾类硫代半脲，半脲和类化合物由于它们具有一定的生物学活性，如抗菌，抗病毒和抗癌作用，最近受到了科学家的广泛关注。以不同的类固醇为原料，通过不同的化学方法，合成了24个结构上具有硫代半碳carb，半碳zone或or的甾族化合物，并通过红外，核磁共振和质谱进行了表征。评估了化合物对人胃癌（SGC-7901）和人肝癌（Bel-7404）细胞的抗增殖活性。讨论了这些化合物的构效关系。结果显示化合物3和12a-12c对Bel-7404细胞表现出显着的抑制活性，它们的IC50值分别为4.2、11.0、7.4和15.0μM（Cisplatin，IC50：