N-(2α,3β-dihydroxyolean-12-ene-28-amido)-L-valine | 1137728-61-0

• 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: N-(2α,3β-dihydroxyolean-12-ene-28-amido)-L-valine
• 英文别名: N-[2α, 3β-dihydroxy-ole-12-en-28-oyl]-L-valine acid；N-(2α,3β-dihydroxy-12-oleanen-28-oyl)-L-valine；N-(2,3-dihydroxy-12-oleanen-28-oyl)-L-valine；(2S)-2-[[(4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-10,11-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carbonyl]amino]-3-methylbutanoic acid
• CAS: 1137728-61-0
• 化学式: C₃₅H₅₇NO₅
• 分子量: 571.841
• InChiKey: FCCWJFJXXNCGHS-QWNKRHSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  41
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  山楂酸 在 吡啶 、 草酰氯 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 47.0h， 生成 N-(2α,3β-dihydroxyolean-12-ene-28-amido)-L-valine
  参考文献：
  名称：

  Synthesis of water soluble pentacyclic dihydroxyterpene carboxylic acid derivatives coupled amino acids and their inhibition activities on α-glucosidase

  摘要：

  Twenty maslinic acid and corosolic acid derivatives were obtained by coupling with L-amino acids at C-28 position. The alpha-glucosidase inhibitory activities of the present compounds were evaluated in vitro. Results reveal that some of the derivatives exhibit a better a-glucosidase inhibitory activity than that of acarbose in the test conditions of ethanol-water solution and DMSO. It is worth noting that maslinic acid and corosolic acid derivatives coupled aspartic acid (9f: IC50 = 382 mu m and 10f: IC50 = 364 mu m, respectively) have the best water solubility and thus presented higher inhibitory activity than that of acarbose (IC50 = 484 mu m). Unfortunately, all of the derivatives possess lower inhibitory properties of a-glucosidase than those of the parent compounds in the measurement system of DMSO solution, even if the derivatives exhibit better water solubility than that of the parent compounds.

  DOI：

  10.1016/j.bioorg.2019.02.001

文献信息

• Solution- and solid-phase synthesis and anti-HIV activity of maslinic acid derivatives containing amino acids and peptides
  作者：Andres Parra、Francisco Rivas、Pilar E. Lopez、Andres Garcia-Granados、Antonio Martinez、Fernando Albericio、Nieves Marquez、Eduardo Muñoz

  DOI：10.1016/j.bmc.2008.12.041

  日期：2009.2

  Maslinic acid (1) has been coupled at C-28 with several α- and ω-amino acids by using solution- and solid-phase synthetic procedures. Twelve derivatives (2–13) with a single amino acid residue were prepared in solution phase, whereas a dipeptide (14), a tripeptide (15), and a series of conjugate dipeptides (16–24) were synthesized in solid phase. The anti-HIV activity of these compounds was assessed

  通过使用溶液和固相合成方法，山酸（1）在C-28处与几种α-和ω-氨基酸偶联。十二衍生物（2 - 13）与单一的氨基酸残基在溶液相中制备，而二肽（14），三肽（15），和一系列共轭二肽（16 - 24）在固相合成。在携带荧光素酶基因作为报告基因的病毒克隆感染的MT-2细胞上评估了这些化合物的抗HIV活性。虽然在山梨酸中（1）同时具有细胞毒性和抗病毒活性，但只有衍生物13和24 具有抗HIV-1活性，因此代表了一类新型的抗HIV-1化合物。
• Synthesis of water soluble pentacyclic dihydroxyterpene carboxylic acid derivatives coupled amino acids and their inhibition activities on α-glucosidase
  作者：Zhen Zeng、Xiaoli Yin、Xueyuan Wang、Wuying Yang、Xiaoqin Liu、Yanping Hong

  DOI：10.1016/j.bioorg.2019.02.001

  日期：2019.5

  Twenty maslinic acid and corosolic acid derivatives were obtained by coupling with L-amino acids at C-28 position. The alpha-glucosidase inhibitory activities of the present compounds were evaluated in vitro. Results reveal that some of the derivatives exhibit a better a-glucosidase inhibitory activity than that of acarbose in the test conditions of ethanol-water solution and DMSO. It is worth noting that maslinic acid and corosolic acid derivatives coupled aspartic acid (9f: IC50 = 382 mu m and 10f: IC50 = 364 mu m, respectively) have the best water solubility and thus presented higher inhibitory activity than that of acarbose (IC50 = 484 mu m). Unfortunately, all of the derivatives possess lower inhibitory properties of a-glucosidase than those of the parent compounds in the measurement system of DMSO solution, even if the derivatives exhibit better water solubility than that of the parent compounds.