lupeone oxime | 3607-91-8

• 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: lupeone oxime
• 英文别名: lupenone oxime；3‐hydroxyiminolup‐20(29)‐ene；Lup-20-en-3-on-oxim；Lupenon-oxim；lup-20(29)-en-3-oxime；Lupeon-oxim；N-[(1R,3aR,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-9-ylidene]hydroxylamine
• CAS: 3607-91-8
• 化学式: C₃₀H₄₉NO
• 分子量: 439.725
• InChiKey: IBHLVHLIYYDTRV-BHMAJAPKSA-N

物化性质

• 熔点：
  263 °C
• 沸点：
  512.4±19.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  32
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  lupeone oxime 在 Montmorillonite K-10 clay 、 pyridinium chlorochromate 作用下， 反应 0.03h， 以90%的产率得到羽扇烯酮
  参考文献：
  名称：

  Ganguly, Nemai C.; Datta, Mrityunjoy; De, Prithwiraj, Journal of the Indian Chemical Society, 2004, vol. 81, # 4, p. 308 - 312

  摘要：

  DOI：
• 作为产物：
  描述：

  羽扇豆醇 在 吡啶 、 盐酸羟胺 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 lupeone oxime
  参考文献：
  名称：

  新齐墩果酸和羽扇豆醇衍生物对抗白血病细胞系的合成、体外和计算机分析：NF-κB 通路的参与

  摘要：

  齐墩果酸 (OA) 和羽扇豆醇 (LU) 属于天然三萜类，具有广泛的生物活性，包括对几种癌细胞系的细胞毒性。在这种情况下，我们研究了从两种天然前体中获得的一组化合物，它们对白血病 HL60 细胞和耐多药 (MDR) 变体 HL60R 具有细胞毒性。六种新的半合成三萜已被合成、充分表征，并与其他三萜化合物一起研究了它们的药理作用机制。还借助对接评估了更具细胞毒性的化合物与核因子 kappa B (NF-κB) 途径的相互作用。羽扇烷类化合物比前体更活跃，而齐墩果烷类化合物表现出更复杂的行为。OA 和 LU 衍生物都与 NF-kB 的 p65 亚基具有相似的相互作用模式，证明了它们抑制 p65 与 DNA 结合的能力具有相似的趋势。此外，一些测试的衍生物能够增加 IκB-α 水平，防止 NF-kB 易位到细胞核。总之，这项研究为三萜类化合物对白血病细胞的药理作用提供了更深入的了解，并改善了对开发新的抗癌药物有用的背景。

  DOI：

  10.3390/ijms23126594

文献信息

• Synthesis and Anti-HIV Activity of Lupane and Olean-18-ene Derivatives. Absolute Configuration of 19,20-Epoxylupanes by VCD
  作者：Fátima Gutiérrez-Nicolás、Bárbara Gordillo-Román、Juan C. Oberti、Ana Estévez-Braun、Ángel G. Ravelo、Pedro Joseph-Nathan

  DOI：10.1021/np200910u

  日期：2012.4.27

  Lupane triterpenoids 2 and 5-12 and oleanene derivatives 13 and 14 were prepared from lupeol (1), betulin (3), and germanicol (4). They were tested for anti-HIV activity, and some structure-activity relationships were outlined. The 20-(S) absolute configuration of epoxylupenone (8) was assessed by comparison of the observed and DFT-calculated vibrational circular dichroism spectra. The CompareVOA algorithm was employed to support the C-20 configuration assignment. The 20,29 double bond in lupenone (2) and 3-epilupeol (15) was stereoselectively epoxidized to produce 20-(S)-8 and 20-(S)-16, respectively, an assignment in agreement with their X-ray diffraction structures.
• Misra, Namita; Kumar, Satish; Raj, Kanwal, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2011, vol. 50, # 3, p. 275 - 283
  作者：Misra, Namita、Kumar, Satish、Raj, Kanwal

  DOI：——

  日期：——
• Zur Kenntnis der Triterpene (51. Mitteilung). Die Umwandlung von Betulin in Lupeol
  作者：L. Ruzieka、M. Brenner

  DOI：10.1002/hlca.193902201190

  日期：——
• Synthesis of new heterocyclic lupeol derivatives as nitric oxide and pro-inflammatory cytokine inhibitors
  作者：Pamita Bhandari、Neeraj Kumar Patel、Kamlesh Kumar Bhutani

  DOI：10.1016/j.bmcl.2014.05.032

  日期：2014.8

  A series of heterocyclic derivatives including indoles, pyrazines along with oximes and esters were synthesized from lupeol and evaluated for anti-inflammatory activity through inhibition of lipopolysaccharide (LPS) induced nitric oxide (NO) production in RAW 264.7 and J774A.1 cells. All the synthesized molecules of lupeol were found to be more active in inhibiting NO production with an IC50 of 18.4-48.7 mu M in both the cell lines when compared to the specific nitric oxide synthase (NOS) inhibitor, L-NAME (IC50 = 69.21 and 73.18 mu M on RAW 264.7 and J774A.1 cells, respectively). The halogen substitution at phenyl ring of indole moiety leads to potent inhibition of NO production with half maximal concentration ranging from 18.4 to 41.7 mu M. Furthermore, alkyl (11, 12) and p-bromo/iodo (15, 16) substituted compounds at a concentration of 20 mu g/mL exhibited mild inhibition (29-42%) of LPS-induced tumor necrosis factor alpha (TNF-alpha) and weak inhibition (10-22%) towards interleukin 1-beta (IL-1 beta) production in both the cell lines. All the derivatives were found to be non-cytotoxic when tested at their IC50 (mu M). These findings suggest that the derivatives of lupeol could be a lead to potent inhibitors of NO. (C) 2014 Elsevier Ltd. All rights reserved.
• Über die Harzalkohole der Mistel. (9. Mitteilung über die Chemie der Harzbestandteile.)
  作者：K. H. Bauer、U. Gerloff

  DOI：10.1002/ardp.19362740804

  日期：——