4α-isocyanato-19-nor-ent-16-ketobeyeran | 953017-88-4

• 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: 4α-isocyanato-19-nor-ent-16-ketobeyeran
• 英文别名: 4-isocyanato-19-nor-ent-16-oxobeyeran
• CAS: 953017-88-4
• 化学式: C₂₀H₂₉NO₂
• 分子量: 315.456
• InChiKey: MQVQWWMGXRMLCJ-UMBUOUCESA-N

物化性质

• 熔点：
  118-120 °C(Solv: ligroine (8032-32-4))
• 沸点：
  414.1±38.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.5
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4α-isocyanato-19-nor-ent-16-ketobeyeran 在 水 、 氢溴酸 作用下， 以70%的产率得到4α-amino-19-nor-ent-16-ketobeyerane
  参考文献：
  名称：

  Synthesis and anti-hepatitis B virus activity of C4 amide-substituted isosteviol derivatives

  摘要：

  A series of novel isosteviol derivatives having C4-amide substituents were synthesized in order to test for antiviral effects against the hepatitis B virus (HBV) in vitro. Among them, IN-4 [N-(propylcarbonyl)-4 alpha-amino- 19-nor-ent-16-ketobeyeran] (5) exhibited inhibitory activity against secretion of HBsAg and HBeAg as well as inhibition of HBV DNA replication. Therefore, the mechanism of its antiviral activity was further analyzed using HBV-transfected Huh7 cells. Exposure to IN-4 produced minimal inhibitory effects on viral precore/pregenomic RNA expression. However, expression levels of the 2.4/2.1-kb preS/major S RNA of the viral surface gene significantly decreased, along with intracellular levels of HBV DNA. A promoter activity analysis demonstrated that IN-4 significantly inhibited viral X, S, and preS expression levels but not viral core promoter activities. In particular, IN-4 was observed to significantly inhibit HBV gene regulation by disrupting nuclear factor (NF)-kappa B-associated promoter activity. In addition, the nuclear expression of p65/p50 NF-kappa B member proteins was attenuated following IN-4 treatment, while cytoplasmic I kappa B alpha protein levels were enhanced. Meanwhile, IN-4 was observed to inhibit the binding activity of NF-kappa B to putative DNA elements. Furthermore, transfection of a p65 expression plasmid into Huh7 cells significantly reversed the inhibitory effect of IN-4 on HBV DNA levels, providing further evidence of the central role of NF-kappa B in its antiviral mechanism. It is therefore suggested that IN-4 inhibits HBV by interfering with the NF-kappa B signaling pathway, resulting in downregulation of viral gene expression and DNA replication. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.12.064
• 作为产物：
  描述：

  4α-azido-19-nor-ent-16-ketobeyeran 以 甲苯 为溶剂， 反应 5.0h， 以65%的产率得到4α-isocyanato-19-nor-ent-16-ketobeyeran
  参考文献：
  名称：

  聚醚脲桥连手性分子钳及其制备和应用

  摘要：

  本发明公开了聚醚脲桥连手性分子钳及其制备和应用。所述聚醚脲桥连手性分子钳的结构如式(I)或式(II)所示。本发明提供了所述的聚醚脲桥连手性分子钳在识别手性分子客体中的应用，所述的手性分子客体为D/L‑氨基酸酯盐酸盐。本发明合成的分子钳对D/L‑氨基酸酯盐酸盐具有一定的手性识别性能，可用于手性识别分离对映异构体。

  公开号：

  CN108727227B

文献信息

• Synthesis and antiviral effects of isosteviol-derived analogues against the hepatitis B virus
  作者：Tsurng-Juhn Huang、Bo-Hon Chou、Cheng-Wen Lin、Jen-Hsien Weng、Chang-Hung Chou、Li-Ming Yang、Shwu-Jiuan Lin

  DOI：10.1016/j.phytochem.2013.12.014

  日期：2014.3

  Among several isosteviol-derived analogues, NC-8 (ent-16-oxobeyeran-19-N-methylureido) showed inhibitory potency against the hepatitis B virus (HBV) in HepG2 2.2.15 cells. Its anti-HBV mechanism was then next investigated in a human hepatoma cell culture system. Results showed that it specifically inhibited viral gene expression and reduced the level of encapsidated viral DNA intermediates in Huh7 cells that expressed replicating HBV. It also potently attenuated all viral promoter activity in HBV-expressing Huh7 cells, but not in cells lacking HBV expression. By examining its antiviral mechanism in cellular signaling pathways, NC-8 was found to inhibit the activity of the nuclear factor (NF)-kappa B element-containing promoter, but only slightly enhanced activities of activator protein (AP)-1-and interferon-sensitive response element (ISRE)-containing promoters in HBV-expressing cells. NC-8 also significantly eliminated NE-kappa B (p65/p50) and Toll-like receptor (TLR)2 proteins, but increased the I kappa B alpha protein level in a dose-dependent manner in HBV-transfected Huh7 cells, while these protein levels were apparently unchanged in non-transfected cells. Meanwhile, NC-8-treated nuclear extracts that co-expressed HBV inhibited the binding of NF-kappa B to the CSI site of HBV major surface gene and specifically attenuated CS1-containing promoter activity. Taken together, this study suggests that the antiviral mechanism of NC-8 appears to be mediated by disturbing replication and gene expression of HBV and by inhibiting the host TLR2/NF-kappa B signaling pathway. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis of Schiff bases on the basis of the isosteviol terpenoid
  作者：O. I. Militsina、I. Yu. Strobykina、G. I. Kovylyaeva、G. A. Bakaleinik、V. E. Kataev、A. T. Gubaidullin、R. Z. Musin、A. G. Tolstikov

  DOI：10.1134/s1070363207020168

  日期：2007.2

  The transformation of the carboxy and keto groups of the isosteviol (ent-16-ketobeyeran-19-oic acid) diterpenoid was used to synthesize its new nitrogen-containing derivatives, including Schiff bases by the C-4 and C-16 atoms of the isosteviol frame. The structure of the resulting compounds was established by X-ray diffraction.