2-acetoxy-6-allylbenzoic acid | 851594-66-6

• 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: 2-acetoxy-6-allylbenzoic acid
• 英文别名: 2-Acetyloxy-6-prop-2-enylbenzoic acid；2-acetyloxy-6-prop-2-enylbenzoic acid
• CAS: 851594-66-6
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: AAXAZZBJICAXCT-UHFFFAOYSA-N

物化性质

• 熔点：
  94-95 °C
• 沸点：
  320.2±30.0 °C(Predicted)
• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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-acetoxy-6-allylbenzoic acid 在 吡啶 、 4-二甲氨基吡啶 、 copper(l) iodide 、 caesium carbonate 、 三苯基膦 、 N,N'-二甲基乙二胺 、 偶氮二甲酸二乙酯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 13.5h， 生成 (4S,6S,E)-6-(tert-butyldimethylsilyloxy)-1-(3-phenylpropiolamido)deca-1,9-dien-4-yl 2-acetoxy-6-allylbenzoate
  参考文献：
  名称：

  Synthesis and structure–activity studies of the V-ATPase inhibitor saliphenylhalamide (SaliPhe) and simplified analogs

  摘要：

  An efficient total synthesis of the potent V-ATPase inhibitor saliphenylhalamide (SaliPhe), a synthetic variant of the natural product salicylihalamide A (SaliA), has been accomplished aimed at facilitating the development of SaliPhe as an anticancer and antiviral agent. This new approach enabled facile access to derivatives for structure-activity relationship studies, leading to simplified analogs that maintain SaliPhe's biological properties. These studies will provide a solid foundation for the continued evaluation of SaliPhe and analogs as potential anticancer and antiviral agents. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.09.021
• 作为产物：
  描述：

  2,6-二羟基苯甲酸 在 吡啶 、 4-二甲氨基吡啶 、 tris-(dibenzylideneacetone)dipalladium(0) 、 氯化亚砜 、 tri(3-furyl)phosphine 、 水 、 lithium chloride 、 potassium hydroxide 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 43.0h， 生成 2-acetoxy-6-allylbenzoic acid
  参考文献：
  名称：

  Synthesis and structure–activity studies of the V-ATPase inhibitor saliphenylhalamide (SaliPhe) and simplified analogs

  摘要：

  An efficient total synthesis of the potent V-ATPase inhibitor saliphenylhalamide (SaliPhe), a synthetic variant of the natural product salicylihalamide A (SaliA), has been accomplished aimed at facilitating the development of SaliPhe as an anticancer and antiviral agent. This new approach enabled facile access to derivatives for structure-activity relationship studies, leading to simplified analogs that maintain SaliPhe's biological properties. These studies will provide a solid foundation for the continued evaluation of SaliPhe and analogs as potential anticancer and antiviral agents. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.09.021

文献信息

• Evaluating the potential of Vacuolar ATPase inhibitors as anticancer agents and multigram synthesis of the potent salicylihalamide analog saliphenylhalamide
  作者：Sylvain Lebreton、Janis Jaunbergs、Michael G. Roth、Deborah A. Ferguson、Jef K. De Brabander

  DOI：10.1016/j.bmcl.2008.07.003

  日期：2008.11

  The natural product salicylihalamide is a potent inhibitor of the Vacuolar ATPase (V-ATPase), a potential target for antitumor chemotherapy. We generated salicylihalamide-resistant tumor cell lines typified by an overexpansion of lysosomal organelles. We also found that many tumor cell lines upregulate tissue-specific plasmalemmal V-ATPases, and hypothesize that tumors that derive their energy from

  天然产物水杨酰胺是液泡 ATP 酶 (V-ATPase) 的有效抑制剂，是抗肿瘤化疗的潜在靶点。我们产生了以溶酶体细胞器过度扩张为代表的抗水杨酰胺的肿瘤细胞系。我们还发现许多肿瘤细胞系上调组织特异性质膜 V-ATP 酶，并假设从糖酵解中获得能量的肿瘤依赖于这些亚型来维持中性细胞质 p​​H。为了进一步验证 V-ATPase 抑制剂作为癌症化疗先导物的潜力，我们开发了有效的水杨酰卤酰胺类似物 saliphenylhalamide 的多克合成。
• Synthesis of Functionalized Salicylate Esters and Amides by Photochemical Acylation
  作者：Omid Soltani、Jef K. De Brabander

  DOI：10.1002/anie.200462577

  日期：2005.3.4
• Synthesis and structure–activity studies of the V-ATPase inhibitor saliphenylhalamide (SaliPhe) and simplified analogs
  作者：Jose Garcia-Rodriguez、Saurabh Mendiratta、Michael A. White、Xiao-Song Xie、Jef K. De Brabander

  DOI：10.1016/j.bmcl.2015.09.021

  日期：2015.10

  An efficient total synthesis of the potent V-ATPase inhibitor saliphenylhalamide (SaliPhe), a synthetic variant of the natural product salicylihalamide A (SaliA), has been accomplished aimed at facilitating the development of SaliPhe as an anticancer and antiviral agent. This new approach enabled facile access to derivatives for structure-activity relationship studies, leading to simplified analogs that maintain SaliPhe's biological properties. These studies will provide a solid foundation for the continued evaluation of SaliPhe and analogs as potential anticancer and antiviral agents. (C) 2015 Elsevier Ltd. All rights reserved.