4-(N,N-双(2-甲氧基乙基)氨磺酰基)苯甲酸 | 328038-28-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(N,N-双(2-甲氧基乙基)氨磺酰基)苯甲酸
• 英文名称: 4-[N,N-bis(2-methoxyethyl)aminosulfonyl]benzoic acid
• 英文别名: 4-[bis(2-methoxyethyl)sulfamoyl]benzoic Acid
• CAS: 328038-28-4
• 化学式: C₁₃H₁₉NO₆S
• mdl: MFCD02705288
• 分子量: 317.363
• InChiKey: FUBAFUGQTVAQJR-UHFFFAOYSA-N

物化性质

• 沸点：
  477.9±55.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(N,N-双(2-甲氧基乙基)氨磺酰基)苯甲酸 在 氯化亚砜 作用下， 以 吡啶 、 氯仿 为溶剂， 反应 1.0h， 生成 4-[N,N-bis-(2-methoxyethyl)aminosulfonyl]-N-[9-phenylmethyl-6-(3-pyrrolidin-1-yl-propylamino)-9H-purin-2-yl]benzenecarboxamide
  参考文献：
  名称：

  具有抗血小板活性的新型嘌呤

  摘要：

  四种嘌呤 - 2,6 - 二胺，4a, b, 5a, b，十九种 N-（嘌呤 - 2 - 基）苯甲酰胺 6a - q, 7b 和一种 N-（嘌呤 - 2 - 基） -2 - 呋喃甲酰胺 8首次制备并测试它们对血小板聚集的抑制作用。6a、b、h、m、o、p六种化合物在Born试验中抑制胶原诱导的血小板聚集，IC50值在3～10μmol/L之间。ADP、PAF和肾上腺素被用作特异性聚集诱导剂来检查抗聚集活性的机制。观察到惊人的纳米摩尔级活动模式，6m、7b、8 甚至亚纳摩尔范围（6b）。化合物6b以IC50 = 0.45 nM（6m：3.5 nM；8：30 nM）抑制ADP诱导的血小板聚集。化合物 7b 显示出对诱导剂肾上腺素的拮抗作用，IC 50 = 1.8 nM (6o: 20 nM; 8: 30 nM)。

  DOI：

  10.1002/ardp.200500189
• 作为产物：
  描述：

  双(2-甲氧基乙基)胺 、 4-(氯磺酰)苯甲酸 以 甲醇 为溶剂， 反应 3.0h， 生成 4-(N,N-双(2-甲氧基乙基)氨磺酰基)苯甲酸
  参考文献：
  名称：

  Discovery and initial development of a novel class of antibacterials: Inhibitors of Staphylococcus aureus transcription/translation

  摘要：

  The novel bacterial transcription/translation (TT) inhibitor 1 was identified through a combination of high throughput screening and exploratory medicinal chemistry. Initial optimization of the anthranilic acid moiety and sulfonamide amine diversity was accomplished via 1- and two-dimensional solution phase libraries, resulting in an improvement in the MIC of the lead from 64 to 8 mu g/mL (compound 4I). Subsequent modification of the central aromatic ring and further refinement of the sulfonamide amines required the development of a solid phase route on Wang resin. The resulting libraries generated a number of potent antibacterials with MICs of <= 1 mu g/mL (e.g., 10b, 12, and 13). During the course of this work, it became apparent that the antibacterial activity of the series is not fully correlated with TT inhibition, suggesting that at least one additional mechanism of action is operative. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.044

文献信息

• Discovery and initial development of a novel class of antibacterials: Inhibitors of Staphylococcus aureus transcription/translation
  作者：Scott D. Larsen、Matthew R. Hester、J. Craig Ruble、Gregg M. Kamilar、Donna L. Romero、Brian Wakefield、Earline P. Melchior、Michael T. Sweeney、Keith R. Marotti

  DOI：10.1016/j.bmcl.2006.09.044

  日期：2006.12

  The novel bacterial transcription/translation (TT) inhibitor 1 was identified through a combination of high throughput screening and exploratory medicinal chemistry. Initial optimization of the anthranilic acid moiety and sulfonamide amine diversity was accomplished via 1- and two-dimensional solution phase libraries, resulting in an improvement in the MIC of the lead from 64 to 8 mu g/mL (compound 4I). Subsequent modification of the central aromatic ring and further refinement of the sulfonamide amines required the development of a solid phase route on Wang resin. The resulting libraries generated a number of potent antibacterials with MICs of <= 1 mu g/mL (e.g., 10b, 12, and 13). During the course of this work, it became apparent that the antibacterial activity of the series is not fully correlated with TT inhibition, suggesting that at least one additional mechanism of action is operative. (c) 2006 Elsevier Ltd. All rights reserved.
• New Purines with Antiplatelet Activity
  作者：Katrin Märschenz、Klaus Rehse

  DOI：10.1002/ardp.200500189

  日期：2006.3

  collagen with IC50 values between 3 and 10 μmol/L in the Born test. ADP, PAF, and adrenaline were used as specific aggregation inducers to examine the mechanism of the anti‐aggregating activity. An astonishing pattern of activities in the nanomolar, with 6m, 7b, 8 and even subnanomolar range, with 6b, was observed. Compound 6b inhibited the platelet aggregation induced by ADP with an IC50 = 0.45 nM (6m: 3

  四种嘌呤 - 2,6 - 二胺，4a, b, 5a, b，十九种 N-（嘌呤 - 2 - 基）苯甲酰胺 6a - q, 7b 和一种 N-（嘌呤 - 2 - 基） -2 - 呋喃甲酰胺 8首次制备并测试它们对血小板聚集的抑制作用。6a、b、h、m、o、p六种化合物在Born试验中抑制胶原诱导的血小板聚集，IC50值在3～10μmol/L之间。ADP、PAF和肾上腺素被用作特异性聚集诱导剂来检查抗聚集活性的机制。观察到惊人的纳米摩尔级活动模式，6m、7b、8 甚至亚纳摩尔范围（6b）。化合物6b以IC50 = 0.45 nM（6m：3.5 nM；8：30 nM）抑制ADP诱导的血小板聚集。化合物 7b 显示出对诱导剂肾上腺素的拮抗作用，IC 50 = 1.8 nM (6o: 20 nM; 8: 30 nM)。