(22E)-3β-hydroxystigmast-22-en-6-one | 323180-22-9

• 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: (22E)-3β-hydroxystigmast-22-en-6-one
• 英文别名: 3-hydroxy-24-ethylcholest-22-en-6-one；(3S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-3-hydroxy-10,13-dimethyl-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-6-one
• CAS: 323180-22-9
• 化学式: C₂₉H₄₈O₂
• 分子量: 428.699
• InChiKey: OBHXMPNLHXYZMO-DCCDKXNDSA-N

物化性质

• 熔点：
  237 °C
• 沸点：
  521.0±33.0 °C(Predicted)
• 密度：
  0.997±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.06
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (22E)-3β-hydroxystigmast-22-en-6-one 在 sodium azide 、 TEA 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 17.0h， 生成 (22E)-stigmasta-2,22-dien-6-one
  参考文献：
  名称：

  New brassinosteroid analogs having nitrogenated functionalities at C3 to provide more information about the brassinosteroid–receptor interaction

  摘要：

  An efficient synthesis of different brassinosteroid derivatives with an azide or an amine function at C3 without any function at C2 and their biological activity evaluation in the rice lamina inclination test is described. The key step in the synthetic strategy involves a nucleophilic substitution by azide of an activated 3beta-OH followed by reduction to amine. The activity elicited by 7 and 9 having an azide group, in contrast with the residual ones elicited by their corresponding amines, suggests that the 3alpha-OH group of an active brassinosteroid could act as acceptor in the putative hydrogen bonding interaction with the receptor/s. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.126
• 作为产物：
  描述：

  stigmasterone 在 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 作用下， 以 甲醇 为溶剂， 反应 0.08h， 生成 (22E)-3β-hydroxystigmast-22-en-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 bioactivity of natural and C-3 fluorinated biosynthetic precursors of 28-homobrassinolide
  作者：Lydia R Galagovsky、Eduardo G Gros、Javier A Ramı́rez

  DOI：10.1016/s0031-9422(01)00379-x

  日期：2001.11

  paper we describe the synthesis of two new fluorinated brassinosteroids: (22R,23R)-22,23-dihydroxy-3alpha-fluorostigmastan-6-one and (22R,23R)-22,23-dihydroxy-3beta-fluorostigmastan-6-one. Their bioactivities were evaluated in the rice lamina inclination test and compared with that of 28-homocastasterone, 28-homotyphasterol and 28-homoteasterone, possible biosynthetic precursors of 28-homobrassinolide

  在本文中，我们描述了两种新的氟化油菜素类固醇的合成：(22R,23R)-22,23-dihydroxy-3alpha-fluorostigmastan-6-one 和 (22R,23R)-22,23-dihydroxy-3beta-fluorostigmastan-6 -一。在水稻叶片倾斜试验中评估了它们的生物活性，并与 28-高芥子酮、28-高豆蔻甾醇和 28-高油甾酮（28-高芸苔素内酯的可能生物合成前体）的生物活性进行了比较。结果证实了 24-乙基油菜素类固醇（称为 28-同源系列）的生物合成与 24-甲基油菜素类固醇的生物合成之间的预期相似性，并且还表明这些前体可能表现出本身的活性。