methyl 4-oxycyanobenzoate | 72331-27-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-oxycyanobenzoate
• CAS: 72331-27-2
• 化学式: C₉H₇NO₃
• 分子量: 177.159
• InChiKey: HBEBGARDDOHLLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.65
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  53.72
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 4-oxycyanobenzoate 在 lithium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 三乙胺 作用下， 以 甲醇 、 四氯化碳 、 氯仿 、 水 为溶剂， 反应 27.33h， 生成 4-[5-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-isoxazol-3-yl]-benzoic acid
  参考文献：
  名称：

  Heterocycle-Containing Retinoids. Discovery of a Novel Isoxazole Arotinoid Possessing Potent Apoptotic Activity in Multidrug and Drug-Induced Apoptosis-Resistant Cells

  摘要：

  In a search for retinoic acid (RA) receptor ligands endowed with potent apoptotic activity, a series of novel arotinoids were prepared. Because the stereochemistry of the CS-alkenyl portion of natural 9-cis-RA and the olefinic moiety of the previously synthesized isoxazole retinoid 4 seems to have particular importance for their apoptotic activity, novel retinoid analogues with a restricted or, vice versa, a larger flexibility in this region were designed and prepared. The new compounds were evaluated in vitro for their ability to activate natural retinoid receptors and for their differentiation-inducing activity. Cytotoxic and apoptotic activities were, in addition, evaluated. In general, these analogues showed low cytotoxicity, with the restricted structures being slightly more active than the more flexible ones. As an exception, however, the isoxazole retinoid 15b proved to be particularly able to induce apoptosis at concentrations <5 muM, showing a higher activity than the classical retinoids such as all-trans-RA, 13-cis-RA, and 9-cis-RA and the previously described synthetic retinoid 4. 15b also exhibited a good affinity for the retinoid receptors. Interestingly, another important property of 15b was its ability to induce apoptosis in the HL60R multidrug-resistant (MDR) cell line, at the same concentration as is effective in HL60. Therefore, 15b represents a new retinoid possessing high apoptotic activity in an MDR cell line. The ability of 15b to act on K562 and HL60R cells suggests that this compound may have important implications in the treatment of different leukemias, and its structure could offer an interesting model for the design of new compounds endowed with apoptotic activity on MDR- and retinoid-resistant malignancies.

  DOI：

  10.1021/jm0010320
• 作为产物：
  描述：

  methyl (E)-4-((hydroxyimino)methyl)benzoate 在 吡啶 、 N-氯代丁二酰亚胺 作用下， 以 氯仿 为溶剂， 反应 1.0h， 生成 methyl 4-oxycyanobenzoate
  参考文献：
  名称：

  硼化镍介导的5-（2-硝基苯基）异恶唑的还原环转化新方法获得2-取代的喹啉-4-酮

  摘要：

  3取代的5-（2-硝基苯基）异恶唑的还原环转化很容易通过2-乙炔基硝基苯与腈的氧化物进行1,3-偶极环加成而获得，为2取代的喹啉-4-酮的开发提供了一种新途径。由氯化镍和硼氢化钠原位生成的硼化镍可以通过同时还原硝基和异恶唑环的还原性裂解，一步一步转化为目标喹啉-4-酮。该方案耐受除烯烃以外的各种官能团，因此与铁/乙酸的还原环转化互补，铁/乙酸主要耐受烯烃。

  DOI：

  10.1016/j.tetlet.2019.151327

文献信息

• SASAKI T.; MANABE T.; NISHIDA S., J. ORG. CHEM., 1980, 45, NO 3, 479-482
  作者：SASAKI T.、 MANABE T.、 NISHIDA S.

  DOI：——

  日期：——