2-hydroxymethylene-3-oxoolean-12-en-28-oic acid methyl ester | 42273-01-8

• 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: 2-hydroxymethylene-3-oxoolean-12-en-28-oic acid methyl ester
• 英文别名: methyl 2-hydroxymethine-3-oxooleanate；methyl 2-hydroxymethylene-3-oxoolean-12-en-28-oate；methyl (4aS,6aR,6aS,6bR,8aR,12aR,14bS)-11-(hydroxymethylidene)-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,3,4,5,6,6a,7,8,8a,12,13,14b-dodecahydropicene-4a-carboxylate
• CAS: 42273-01-8
• 化学式: C₃₂H₄₈O₄
• 分子量: 496.731
• InChiKey: UUNHONFHQDYGRZ-QROXQBBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  36
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydroxymethylene-3-oxoolean-12-en-28-oic acid methyl ester 在 sodium dichromate 、 溶剂黄146 、 锌 作用下， 反应 53.0h， 生成 methyl 2,3-dinor-1,4-lactone-11α-hydroxy-12-oleanen-28-oate
  参考文献：
  名称：

  Zaprutko, L., Polish Journal of Chemistry, 1995, vol. 69, # 7, p. 1003 - 1012

  摘要：

  DOI：
• 作为产物：
  描述：

  齐墩果酸 在 Jones reagent 、 sodium methylate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 、 苯 为溶剂， 生成 2-hydroxymethylene-3-oxoolean-12-en-28-oic acid methyl ester
  参考文献：
  名称：

  Synthesis of novel heterocyclic oleanolic acid derivatives with improved antiproliferative activity in solid tumor cells

  摘要：

  合成了一系列新的齐墩果烷咪唑碳酸酯、N-酰基咪唑或N-烷基咪唑，并对其在AsPC-1胰腺癌细胞中的抗增殖活性进行了表征和评估。构效关系分析显示，N-烷基咪唑27是最具活性的化合物，其诱导凋亡的能力与NOXA的上调和Bcl-xL的下调相关。进一步测试了化合物27在更多实体瘤细胞系中的抗增殖活性，其IC50值低于1 μM。

  DOI：

  10.1039/c3ob00011g

文献信息

• Identification of a Strigoterpenoid with Dual Nrf2 and Nf-κB Modulatory Activity
  作者：Federica Rogati、Estrella Millán、Giovanni Appendino、Alejandro Correa、Diego Caprioglio、Alberto Minassi、Eduardo Muñoz

  DOI：10.1021/acsmedchemlett.8b00604

  日期：2019.4.11

  The sesquiterpene–coumarin ether samarcandone provided a suitable framework to replace the apocarotenoid A–C ring system of strigol (1), replicating, after linking to a butenolide moiety, the activity of the natural phytohormone on Nrf2 and also showing potent NF-kB inhibitory activity, overall modulating two critical pathways of inflammation and cancer.

  倍半萜烯-香豆素醚三烯酸酮提供了一个合适的框架来替代strigol（1）的类胡萝卜素A-C环系统，在连接到丁烯醇内酯部分后，复制了天然植物激素在Nrf2上的活性，并且还显示出有效的NF-kB抑制活性，全面调节炎症和癌症的两个关键途径。
• Triterpenoide. XIV. [2,3-<i>d</i>]Isoxazoltriterpenderivate
  作者：A. Gzella、E. Linkowska、L. Zaprutko、U. Wrzeciono

  DOI：10.1107/s010827019900013x

  日期：1999.6.15

  The X-ray crystal structure analyses of two triterpene isoxazoles, namely olean-2,12-dieno[2,3-d]isoxazol-28-oic acid methyl ester methyl isoxazolo[4,5-b]olean-2,12-dien-28-oate, C32H47NO3, (2a)} and 19 beta,28-epoxy-18 alpha-olean-2-eno[2,3-d]isoxazole 19 beta,28-epoxy-isoxazolo[4,5-b]-18 alpha-olean-2-ene, C31H47NO2, (4a)} are described. These compounds were obtained by treatment of 2-formyl- or 2-hydroxymethylene derivatives of 3-oxoolean-12-en-28-oic methyl ester, (la) and (Ib), and 19 beta,28-epoxy-18H alpha-oleanan-3-one, (3a) and (3b), with hydroxylamine hydrochloride according to the method described by Govardhan, Reddy, Ramaiah & Rao [J. Indian Chem. Sac. (1983), pp. 858-860] for the synthesis of ring-A-fused triterpene [3,2-c]isoxazoles. The structures of the obtained [2,3-d]isoxazoles, (2a) and (4a), were confirmed by the comparison of the bond lengths and bond angles found for the isoxazole rings of compounds (2a) and (4a) with the corresponding data given in the literature. The isoxazole rings in both compounds are planar. Ring A in (2a) and (4a) has a conformation between the half-chair and sofa form. Rings B, D and E in (2a), and B, C, D and E in (4a) have the chair conformation. Ring C in (2a) has a distorted sofa form. In (2a), the rings A/B, B/C and C/D are trans-fused and the rings D/E cis-fused, In (4a), the A/B, B/C, C/D and D/E ring junctions are trans. The axial O2 and C28 atoms in (4a) are beta oriented and form, together with the C17, C18 and C19 atoms, the five-membered ring F, which has an envelope conformation.