Bis(3-carboxy-4,6-dimethoxy-2,5-dimethylphenyl) Methane | 148014-10-2

• 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: Bis(3-carboxy-4,6-dimethoxy-2,5-dimethylphenyl) Methane
• 英文别名: 5-[(5-Carboxy-2,4-dimethoxy-3,6-dimethylphenyl)methyl]-2,4-dimethoxy-3,6-dimethylbenzoic acid
• CAS: 148014-10-2
• 化学式: C₂₃H₂₈O₈
• 分子量: 432.471
• InChiKey: CKNQWLIPGZWTSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Bis(3-carboxy-4,6-dimethoxy-2,5-dimethylphenyl) Methane 在 正丁基锂 、 草酰氯 、 苯甲醚 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 1.5h， 生成 (5-carboxy-2,4-dimethoxy-3,6-dimethylphenyl)[5-({4-[(4-carboxy-3-methoxy-2,5,6-trimethylphenoxy)carbonyl]-3-methoxy-2,5,6-trimethylphenoxy}carbonyl)-2,4-dimethoxy-3,6-dimethylphenyl]methane
  参考文献：
  名称：

  Synthesis and Phospholipase A₂ Inhibitory Activity of Thielocin B3 Derivatives

  摘要：

  We prepared several types of derivatives of thielocin B3, a very potent naturally occurring inhibitor for human nonpancreatic secretory PLA(2) (sPLA(2)-II), and conducted a structure-activity relationship study to identify potent sPLA(2)-II inhibitors with the aim of developing antiinflammatory drugs. The total number of aromatic rings is critical for sPLA(2)-II inhibition, and the best result was obtained in the case of six rings. The structure of the central part of the inhibitors was not specific, and potent inhibitors were found among the sulfide, sulfone, ether, methylene, and amino derivatives. Although a diester of the terminal carboxylic acid lost its inhibitory activity, having both of the carboxylic acids was not necessary for expression of activity, as illustrated by a glycine derivative with the benzyl ester group 36. Among the newly synthesized derivatives, 18, 20, 29, and 36 showed very potent human sPLA(2)-II inhibitory activity comparable to that of natural thielocin B3. Their IC50 values are in the range 0.069-0.14 mu M, and they are a class of compounds showing the most potent sPLA(2)-II inhibition to date.

  DOI：

  10.1021/jm960437a
• 作为产物：
  描述：

  formyl-3-dimethoxy-4,6-dimethyl-2,5-benzoate de methyle 在 吡啶 、 4-二甲氨基吡啶 、 氢氧化钾 、 sodium tetrahydroborate 、 三氟化硼乙醚 、 potassium carbonate 作用下， 以 二氯甲烷 、 二甲基亚砜 、 异丙醇 、 丙酮 、 甲苯 为溶剂， 反应 2.25h， 生成 Bis(3-carboxy-4,6-dimethoxy-2,5-dimethylphenyl) Methane
  参考文献：
  名称：

  Synthesis and Phospholipase A₂ Inhibitory Activity of Thielocin B3 Derivatives

  摘要：

  We prepared several types of derivatives of thielocin B3, a very potent naturally occurring inhibitor for human nonpancreatic secretory PLA(2) (sPLA(2)-II), and conducted a structure-activity relationship study to identify potent sPLA(2)-II inhibitors with the aim of developing antiinflammatory drugs. The total number of aromatic rings is critical for sPLA(2)-II inhibition, and the best result was obtained in the case of six rings. The structure of the central part of the inhibitors was not specific, and potent inhibitors were found among the sulfide, sulfone, ether, methylene, and amino derivatives. Although a diester of the terminal carboxylic acid lost its inhibitory activity, having both of the carboxylic acids was not necessary for expression of activity, as illustrated by a glycine derivative with the benzyl ester group 36. Among the newly synthesized derivatives, 18, 20, 29, and 36 showed very potent human sPLA(2)-II inhibitory activity comparable to that of natural thielocin B3. Their IC50 values are in the range 0.069-0.14 mu M, and they are a class of compounds showing the most potent sPLA(2)-II inhibition to date.

  DOI：

  10.1021/jm960437a

文献信息

• PHOSPHOLIPASE A2 INHIBITOR
  申请人：SHIONOGI & CO., LTD.

  公开号：EP0547231A1

  公开（公告）日：1993-06-23

  A novel thielocin derivative having a phospholipase A2 inhibitory activity, represented by general formula (I), or a salt thereof, wherein R1 to R8 represent each independently hydrogen, lower alkyl, lower alkoxy, hydroxy or halogen; E1 and E2 represent each independently hydrogen or an ester residue; m and n represent each independently an integer of 0 to 4; and -Y- represents a divalent group selected among those represented by the following formulae -CH2CH2-, -CH = CH-, (II), (III), (IV), (V), (VI), (VII).

  一种具有磷脂酶 A2 抑制活性的新型噻罗菌素衍生物，由通式 (I) 表示，或其盐，其中 R1 至 R8 各自独立地代表氢、低级烷基、低级烷氧基、羟基或卤素；E1和E2各自独立地代表氢或酯残基；m和n各自独立地代表0至4的整数；以及-Y-代表选自下式-CH2CH2-、-CH＝CH-、(II)、(III)、(IV)、(V)、(VI)、(VII)代表的二价基团。
• US5597943A
  申请人：——

  公开号：US5597943A

  公开（公告）日：1997-01-28