3β-acetoxy-5,20-dioxo-5,6-seco-5β-pregnan-6-oic acid | 96737-70-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3β-acetoxy-5,20-dioxo-5,6-seco-5β-pregnan-6-oic acid
• 英文别名: 2-[(1S,3aS,4S,5S,7aS)-1-acetyl-5-[(1R,4S)-4-acetyloxy-1-methyl-2-oxocyclohexyl]-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-4-yl]acetic acid
• CAS: 96737-70-1
• 化学式: C₂₃H₃₄O₆
• 分子量: 406.519
• InChiKey: CDQQKSIUKWHMBQ-DLIVVPPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  97.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-5,20-dioxo-5,6-seco-5β-pregnan-6-oic acid 在 吡啶 、 盐酸 、 sodium azide 、 草酰氯 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 、 苯 为溶剂， 生成 3β-hydroxy-6,22,25-triaza-cholestane
  参考文献：
  名称：

  Structure–activity relationship of Aza-steroids as PI-PLC inhibitors

  摘要：

  A number of aza-steroids were synthesized as potent phosphatidylinositol phospholipase C (PI-PLC) inhibitors. The epimeric mixtures 22,25-diazacholesterol (8a) and 3 beta -hydroxy-22,25-diazacholestane (8b) were among the most active of these inhibitors, with IC50 values of 7.4 and 7.5 muM, respectively. The 20 alpha epimer, 8a2 (IC50 = 0.64 muM), whose stereochemistry at C-20 coincides with that of cholesterol, was found 50 times more potent than the 20 beta epimer, 8a1 (IC50 = 32.2 muM). In diaza-estrone derivatives, the 3-methoxy group on the aromatic A-ring of 23 exhibited moderate PI-PLC inhibitory activity (IC50 = 19.7 muM), while compound with a free hydroxyl group (21) was inactive. However, in diaza-pregnane derivatives, epimers with a 3-hydroxyl group (8a, IC50 = 7.4 muM) exhibited more potent PI-PLC inhibitory activity than their counterparts with 3-methoxyl group on the non-aromatic A-ring (26, IC50 = 17.4 muM). We have illustrated in our previous publication that 3-hydroxyl-6-aza steroids are potent PI-PLC inhibitors.(3) However, simultaneous presence of the 6-aza and 22,25-diaza moieties in one molecule as in 13, led to loss of activity. Epimeric mixture 8a showed selective growth inhibition effects in the NCI in vitro tumor cell screen with a mean GI(50) value (MG-MID) of 5.75 muM for 54 tumors. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(00)00302-3
• 作为产物：
  描述：

  孕烯醇酮醋酸酯 在 哌啶 、 臭氧 作用下， 以 乙酸乙酯 、 Petroleum ether 为溶剂， 反应 2.0h， 以60%的产率得到3β-acetoxy-5,20-dioxo-5,6-seco-5β-pregnan-6-oic acid
  参考文献：
  名称：

  类固醇衍生酸作为人类Cdc25A蛋白磷酸酶的抑制剂。

  摘要：

  合成了一组类固醇衍生酸，发现它们是人Cdc25A抑制剂。它们的效力范围从1.1到> 100 microM。最好的是与我们最近报道的新型含氰基的含氰基的5,6-seco-胆固醇1（IC50 = 2.2microM）相比非常有利的（Peng，H .; Zalkow，LH; Abraham，RT; Powis，GJ Med.Chem.1998，41，4677）。这些化合物的构效关系表明，疏水性胆固醇侧链和游离羧基对活性至关重要。这两个药效基团之间的距离对于这些化合物的效力也很重要。几种化合物在NCI体外癌细胞系中显示出选择性的生长抑制作用。

  DOI：

  10.1016/s0968-0896(99)00284-9

文献信息

• Epalons: 6-Substituted Derivatives of 7-Norepiallopregnanolone
  作者：Alexander Kasal

  DOI：10.1016/s0040-4020(00)00263-5

  日期：2000.5

  The target compounds (3 alpha-hydroxy-5,6-epoxy-7-nor-5 alpha-pregnan-20-one, 3 alpha-hydroxy-5,6 beta-epoxy-7-nor-5 beta-pregnan-20-one and 3 alpha-hydroxy-7-nor-5 alpha-pregnane-6,20-dione) were prepared from 5,6 beta-dihydroxy-20-oxo-5 alpha-pregnan-3 beta-yl acetate via the corresponding 5,6-seco acid and 3 beta-acetoxy-20-oxo-7-nor-5 beta,6 alpha-pregnane-6,5-carbolactone-actone. Intermediate 3 beta-hydroxy-7-norpregn-5-en-20-one was converted into the corresponding 5 alpha,6 alpha and 5 beta,6 beta epoxides. The latter was isomerized into 3 beta-hydroxy-7-nor-5 alpha-pregnane-6,20-dione. The configuration of the 3 beta-hydroxy group in these compounds was inverted by Mitsunobu reactions. (C) 2000 Elsevier Science Ltd. All rights reserved.