3-hydroxyimino-urs-12-en-28-oic acid methyl ester | 42447-82-5

• 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: 3-hydroxyimino-urs-12-en-28-oic acid methyl ester
• 英文别名: methyl (1S,2R,4aS,6aR,6aS,6bR,8aR,12aR,14bS)-10-hydroxyimino-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,5,6,6a,7,8,8a,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• CAS: 42447-82-5
• 化学式: C₃₁H₄₉NO₃
• 分子量: 483.735
• InChiKey: FEHYPMHEQKXLSP-ZOPQKVJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-hydroxyimino-urs-12-en-28-oic acid methyl ester 在 丙醇 、 sodium 作用下， 反应 2.0h， 以0.6 g的产率得到3β-Amino-18β-H-urs-12-en-28-oic acid methyl ester
  参考文献：
  名称：

  Jain, S. M.; Atal, C. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 427 - 428

  摘要：

  DOI：
• 作为产物：
  描述：

  熊果酸 在 盐酸羟胺 、 pyridinium chlorochromate 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 2.0h， 生成 3-hydroxyimino-urs-12-en-28-oic acid methyl ester
  参考文献：
  名称：

  Hyaluronidase Inhibitory Activity of Pentacylic Triterpenoids from Prismatomeris tetrandra (Roxb.) K. Schum: Isolation, Synthesis and QSAR Study

  摘要：

  哺乳动物透明质酸酶通过裂解 β-1,4-糖苷键来降解透明质酸，提供四糖分子作为主要产物，四糖分子是高度血管生成和炎性细胞因子的有效诱导剂。熊果酸 1 是从 Prismatomeris tetrandra 中分离出来的，被鉴定为具有开发透明质酸酶抑制剂的潜力。通过熊果酸1的结构修饰合成了一系列熊果酸类似物，或者通过商业途径获得。评价这些化合物对透明质酸酶的抑制活性。使用半经验量子化学方法计算了这些化合物的几种结构、拓扑和量子化学描述符。进行定量结构活性关系研究 (QSAR)，将这些描述符与透明质酸酶抑制活性相关联。最佳多线性模型（BML）（R2 = 0.9717，R2cv = 0.9506）提供的统计特征表明所开发模型具有令人满意的稳定性和预测能力。用于确定结合相互作用的计算机分子对接研究表明，熊果酸类似物22对人透明质酸酶具有很强的亲和力。

  DOI：

  10.3390/ijms17020143

文献信息

• Oxidation by mercuric acetate of some triterpenoid derivatives containing an isopropenyl group
  作者：J. J. H. Simes、T. G. Watson

  DOI：10.1039/j39690002352

  日期：——

  The oxidation of the A-secolanosterol derivative 3-nitrilo-3,4-secolanosta-4(30),8-diene (IV) by mercuric acetate has produced the aromatic compound A-seco-1,2,3-trisnorlanosta-4(30),5(10),6,8-tetraene (VIII). When the cyanide group in (IV) was replaced by CO2H, CO2Me, or CONH2, the reaction did not occur. The aromatisation reaction also failed if the isopropenyl group was reduced [as in (IX)] or when

  乙酸汞氧化A-癸香油甾醇衍生物3-nitrilo-3,4-secolanosta-4（30），8-二烯（IV）产生了芳族化合物A-seco-1,2,3-trisnorlanosta-4 （30），5（10），6，8-四烯（VIII）。当（IV）中的氰化物基团被CO 2 H，CO 2 Me或CONH 2取代时，该反应没有发生。如果异丙烯基被还原[如（IX）中]或当环B中没有双键[如（XII）中]时，芳构化反应也将失败。
• Jacobs; Fleck, Journal of Biological Chemistry, 1931, vol. 92, p. 487,492
  作者：Jacobs、Fleck

  DOI：——

  日期：——
• The cytotoxic activity of ursolic acid derivatives
  作者：Chao-Mei Ma、Shao-Qing Cai、Jing-Rong Cui、Rui-Qing Wang、Peng-Fei Tu、Masao Hattori、Mohsen Daneshtalab

  DOI：10.1016/j.ejmech.2005.01.001

  日期：2005.6

  Ursolic acid and 2a-hydroxyursolic acid isolated from apple peels were found to show growth inhibitory activity against four tumor cell lines, HL-60, BGC, Bel-7402 and Hela. Structural modifications were performed on the C-3, C-28 and C-11 positions of ursolic acid and the cytotoxicity of the derivatives was evaluated. The SAR revealed that the triterpenes possessing two hydrogen-bond forming groups (an H-donor and a carbonyl group) at positions 3 and 28 exhibit cytotoxic activity. The configuration at C-3 was found to be important for the activity. Introduction of an amino group increased the cytotoxicity greatly. A 3 beta-amino derivative was 20 times more potent than the parent ursolic acid. The 28-aminoalkyl dimer compounds showed selective cytotoxicity. (c) 2005 Elsevier SAS. All rights reserved.
• Comparison of combined spinal-epidural and low dose epidural for labour analgesia
  作者：David L. Hepner、Robert R. Gaiser、Theodore G. Cheek、Brett B. Gutsche

  DOI：10.1007/bf03018918

  日期：2000.3

  Purpose: To compare the combined spinal-epidural (CSE) technique with the epidural technique with regard to time to initiate and manage, motor block, onset of analgesia and satisfaction during labour.Methods: Upon requesting analgesia, 50 healthy term parturients were randomized in a prospective, double-blind fashion to receive either CSE analgesia or lumbar epidural analgesia in the labour floor of a university hospital at an academic medical centre. The epidural group (n=24) received bupivacaine 0.0625%-fentanyl 0.0002% with 0.05 ml in 10 ml local anesthetic sodium bicarbonate 8.4% and epinephrine 1:200, 000. The CSE group (n=26) received intrathecal 25 mu g fentanyl and 2.5 mg bupivacaine. Additional analgesia was provided upon maternal request.Results: There were no differences (P > 0.05) in time to perform either technique, motor blockade, or parturient satisfaction or in the number of times that the anesthesiologist was called to perform any intervention, Although the first sign of analgesia was not different between the two groups, the onset of complete analgesia was more rapid with the CSE technique (Visual Analogue Pain Score (VAPS) at five minutes < three: 26/26 vs 17/24, P +/- 0.001).Conclusion: Although epidural analgesia with a tow concentration of local anesthetic and opioid mixture takes longer to produce complete analgesia, it is a satisfactory alternative to CSE.
• Hyaluronidase Inhibitory Activity of Pentacylic Triterpenoids from Prismatomeris tetrandra (Roxb.) K. Schum: Isolation, Synthesis and QSAR Study
  作者：Nor Abdullah、Noel Thomas、Yasodha Sivasothy、Vannajan Lee、Sook Liew、Ibrahim Noorbatcha、Khalijah Awang

  DOI：10.3390/ijms17020143

  日期：——

  The mammalian hyaluronidase degrades hyaluronic acid by the cleavage of the β-1,4-glycosidic bond furnishing a tetrasaccharide molecule as the main product which is a highly angiogenic and potent inducer of inflammatory cytokines. Ursolic acid 1, isolated from Prismatomeris tetrandra, was identified as having the potential to develop inhibitors of hyaluronidase. A series of ursolic acid analogues were either synthesized via structure modification of ursolic acid 1 or commercially obtained. The evaluation of the inhibitory activity of these compounds on the hyaluronidase enzyme was conducted. Several structural, topological and quantum chemical descriptors for these compounds were calculated using semi empirical quantum chemical methods. A quantitative structure activity relationship study (QSAR) was performed to correlate these descriptors with the hyaluronidase inhibitory activity. The statistical characteristics provided by the best multi linear model (BML) (R2 = 0.9717, R2cv = 0.9506) indicated satisfactory stability and predictive ability of the developed model. The in silico molecular docking study which was used to determine the binding interactions revealed that the ursolic acid analog 22 had a strong affinity towards human hyaluronidase.

  哺乳动物透明质酸酶通过裂解 β-1,4-糖苷键来降解透明质酸，提供四糖分子作为主要产物，四糖分子是高度血管生成和炎性细胞因子的有效诱导剂。熊果酸 1 是从 Prismatomeris tetrandra 中分离出来的，被鉴定为具有开发透明质酸酶抑制剂的潜力。通过熊果酸1的结构修饰合成了一系列熊果酸类似物，或者通过商业途径获得。评价这些化合物对透明质酸酶的抑制活性。使用半经验量子化学方法计算了这些化合物的几种结构、拓扑和量子化学描述符。进行定量结构活性关系研究 (QSAR)，将这些描述符与透明质酸酶抑制活性相关联。最佳多线性模型（BML）（R2 = 0.9717，R2cv = 0.9506）提供的统计特征表明所开发模型具有令人满意的稳定性和预测能力。用于确定结合相互作用的计算机分子对接研究表明，熊果酸类似物22对人透明质酸酶具有很强的亲和力。