4-benzyloxy-2-methoxy-3,6-dimethylbenzoic acid | 125304-84-9

• 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: 4-benzyloxy-2-methoxy-3,6-dimethylbenzoic acid
• 英文别名: 2-methoxy-3,6-dimethyl-4-phenylmethoxybenzoic acid
• CAS: 125304-84-9
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: VCHWHRJVTPXCMI-UHFFFAOYSA-N

物化性质

• 沸点：
  440.5±40.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-benzyloxy-2-methoxy-3,6-dimethylbenzoic acid 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 23.0h， 以89%的产率得到4-hydroxy-2-methoxy-3,6-dimethylbenzoic acid
  参考文献：
  名称：

  Elix, John A.; Chester, Douglas O.; Wardlaw, Judith H., Australian Journal of Chemistry, 1990, vol. 43, # 1, p. 191 - 196

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 4-benzyloxy-2-methoxy-3,6-dimethylbenzoate 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 以71%的产率得到4-benzyloxy-2-methoxy-3,6-dimethylbenzoic acid
  参考文献：
  名称：

  Depsides as non-redox inhibitors of leukotriene B4 biosynthesis and HaCaT cell growth. 1. Novel analogues of barbatic and diffractaic acid

  摘要：

  A series of barbatic and diffractaic acid analogues has been synthesized and evaluated as inhibitors of leukotriene B-4 (LTB4) biosynthesis and as antiproliferative agents. The 4-O-demethyl barbatic and diffractaic acid derivatives were among the most active compounds in both assays. In particular, ethyl 4-O-demethylbarbatate was the most potent LTB4 biosynthesis inhibitor of this series, with an IC50 value in the submicromolar range. Because the compounds did not show appreciable reactivity against a stable free radical, 2,2-diphenyl-1-picrylhydrazyl, and did not produce appreciable amounts of deoxyribose degradation as a measure of their potency to generate hydroxyl radicals, a simple redox effect could not explain their biological activity. Also, there was no nonspecific cytotoxicity as documented by the activity of lactate dehydrogenase released from the cytoplasm of keratinocytes, which was in the control range. (C) 1999 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(99)00132-4

文献信息

• Depsides as non-redox inhibitors of leukotriene B4 biosynthesis and HaCaT cell growth, 2. Novel analogues of obtusatic acid
  作者：S Kumar KC

  DOI：10.1016/s0223-5234(00)00132-x

  日期：2000.4

  acid analogues has been synthesized and evaluated as inhibitors of leukotriene B(4) (LTB(4)) biosynthesis and as antiproliferative agents. The 4-O-benzylated and the 4-O-demethylated congeners were the most potent inhibitors of LTB(4) production of the depside class of compounds, with IC(50) values in the submicromolar range. Furthermore, these compounds do not function as redox-based inhibitors because

  已合成了一系列的tus酸类似物，并被评估为白三烯B（4）（LTB（4））生物合成的抑制剂和抗增殖剂。4-O-苄基化和4-O-去甲基化同类物是最有效的Lpp（4）产生的深度类化合物的抑制剂，IC（50）值在亚微摩尔范围内。此外，这些化合物不能用作基于氧化还原的抑制剂，因为它们对稳定的自由基2,2,2-二苯基-1-吡啶并肼基不具有反应性，并且不产生可观量的脱氧核糖降解（作为衡量其生成潜力的量度）羟基自由基。一些钝化酸同源物也是角质形成细胞生长的有效抑制剂。生长抑制不是通过破坏细胞膜来介导的，
• Elix, John A.; Chester, Douglas O.; Gaul, Kim L., Australian Journal of Chemistry, 1989, vol. 42, # 7, p. 1191 - 1200
  作者：Elix, John A.、Chester, Douglas O.、Gaul, Kim L.、Parker, John L.、Wardlaw, Judith H.

  DOI：——

  日期：——
• ELIX, JOHN A.;CHESTER, DOUGLAS O.;WARDLAW, JUDITH H.;WILKINS, ALISTAIR L., AUSTRAL. J. CHEM., 43,(1990) N, C. 191-196
  作者：ELIX, JOHN A.、CHESTER, DOUGLAS O.、WARDLAW, JUDITH H.、WILKINS, ALISTAIR L.

  DOI：——

  日期：——
• Depsides as non-redox inhibitors of leukotriene B4 biosynthesis and HaCaT cell growth. 1. Novel analogues of barbatic and diffractaic acid
  作者：Sunil Kumar KC、Klaus Müller

  DOI：10.1016/s0223-5234(99)00132-4

  日期：1999.12

  A series of barbatic and diffractaic acid analogues has been synthesized and evaluated as inhibitors of leukotriene B-4 (LTB4) biosynthesis and as antiproliferative agents. The 4-O-demethyl barbatic and diffractaic acid derivatives were among the most active compounds in both assays. In particular, ethyl 4-O-demethylbarbatate was the most potent LTB4 biosynthesis inhibitor of this series, with an IC50 value in the submicromolar range. Because the compounds did not show appreciable reactivity against a stable free radical, 2,2-diphenyl-1-picrylhydrazyl, and did not produce appreciable amounts of deoxyribose degradation as a measure of their potency to generate hydroxyl radicals, a simple redox effect could not explain their biological activity. Also, there was no nonspecific cytotoxicity as documented by the activity of lactate dehydrogenase released from the cytoplasm of keratinocytes, which was in the control range. (C) 1999 Editions scientifiques et medicales Elsevier SAS.
• Elix, John A.; Chester, Douglas O.; Wardlaw, Judith H., Australian Journal of Chemistry, 1990, vol. 43, # 1, p. 191 - 196
  作者：Elix, John A.、Chester, Douglas O.、Wardlaw, Judith H.、Wilkins, Alistair L.

  DOI：——

  日期：——