4-[4-[双(2-羟乙基)氨基]苯基]丁酸 | 34677-78-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 4-[4-[双(2-羟乙基)氨基]苯基]丁酸
• 英文名称: 4-phenyl>butyric acid
• 英文别名: N,N-bis(2-hydroxyethyl)-p-aminophenylbutyric acid；chlorambucil diol；4-[4-(Bis(2-hydroxyethyl)amino)phenyl]butanoic acid；4-[4-[bis(2-hydroxyethyl)amino]phenyl]butanoic acid
• CAS: 34677-78-6
• 化学式: C₁₄H₂₁NO₄
• 分子量: 267.325
• InChiKey: QTGUQAIGQHYVHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  81
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯丁酸氮芥 在 sodium hydroxide 作用下， 反应 96.0h， 生成 4-[4-[双(2-羟乙基)氨基]苯基]丁酸
  参考文献：
  名称：

  Cullis, Paul M.; Green, Ruth E.; Malone, Mark E., Journal of the Chemical Society. Perkin transactions II, 1995, # 7, p. 1503 - 1512

  摘要：

  DOI：

文献信息

• Reactions of <i>N</i>,<i>N</i>-Bis(2-chloroethyl)-<i>p</i>-aminophenylbutyric Acid (Chlorambucil) with 2‘-Deoxyguanosine
  作者：Elina Haapala、Kristo Hakala、Eeva Jokipelto、Juhani Vilpo、Jari Hovinen

  DOI：10.1021/tx000249u

  日期：2001.8.1

  N,N-Bis(2-chloroethyl)-p-aminophenylbutyric acid (chlorambucil, 1) was allowed to react in the presence of 2'-deoxyguanosine (16 mM) at physiological pH (cacodylic acid, 50% base), and the reactions were followed by HPLC/MS/MS techniques. Although the predominant reaction observed was chlorambucil hydrolysis, ca. 24% of 1 reacted with different heteroatoms of the nucleoside. As expected, the principal

  使N，N-双（2-氯乙基）-对氨基苯基丁酸（苯丁酸氮芥，1）在2'-脱氧鸟苷（16 mM）的存在下于生理pH（草酸，50％碱）下反应，用HPLC / MS / MS技术跟踪反应。尽管观察到的主要反应是苯丁酸氮芥水解，但是。1的24％与不同的核苷杂原子反应。不出所料，2'-脱氧鸟苷烷基化的主要位点是N7。N7的烷基化导致自然的去嘌呤，N-（7-胍基乙基）-N-羟乙基-对氨基苯基丁酸（5）和相应的N7，N7-双加合物（6）是主要的稳定dGuo衍生物。还检测了其他几种加合物，并通过MS / MS和UV进行了初步鉴定。从它们来看，O（6-），N1-，N（2-）和O5'衍生物可能具有生物学意义。
• Degradation of Chlorambucil in Aqueous Solution
  作者：Hans Ehrsson、Staffan Eksborg、Inger Wallin、Sten-Ove Nilsson

  DOI：10.1002/jps.2600690928

  日期：1980.9

  The stability of chlorambucil and its degradation product 4-[p-(2-chloroethyl-2-hydroxyethylamino)phenyl]butyric acid (I) was studied using reversed-phase high-pressure liquid chromatography. The degradation rate of chlorambucil was unaffected by pH between pH 5 and 10 but decreased at lower pH. The degradation rates of chlorambucil and I differed only slightly (pH < 6). The proteolytic properties

  使用反相高压液相色谱法研究了苯丁酸氮芥及其降解产物4- [对-（（2-氯乙基-2-羟乙基氨基）苯基]丁酸（I）的稳定性。苯丁酸氮芥的降解速率不受pH介于5和10之间的pH的影响，但在较低的pH时会降低。苯丁酸氮芥和I的降解率仅略有不同（pH <6）。使用分光光度法和分配技术研究了这些化合物的蛋白水解性能。
• Kinetics of Chlorambucil Hydrolysis Using High-Pressure Liquid Chromatography
  作者：Dulal C. Chatterji、Russell L. Yeager、Joseph F. Gallelli

  DOI：10.1002/jps.2600710113

  日期：1982.1

  stability-specific high-pressure liquid chromatographic (HPLC) method was developed to assay intact chlorambucil (I) in the presence of its hydrolytic decomposition products. The HPLC method was used to follow the degradation kinetics of I over pH 1.0-10.0 in the presence of various buffers with and without added chloride ion. In the absence of chloride ion, the hydrolysis of I followed first-order kinetics and the

  建立了一种特定于稳定性的高压液相色谱（HPLC）方法，以测定完整的苯丁酸氮芥（I）在其水解分解产物存在下的含量。在存在和不存在添加氯离子的各种缓冲液的存在下，使用HPLC方法跟踪pH超过1.0-10.0时I的降解动力学。在不存在氯离子的情况下，I的水解遵循一级动力学，pH速率分布图显示，由于氮芥子的离子化，pH值在2.5左右发生了急剧的变化；由于羧酸的离子化，pH值在5.0左右发生了较浅的变化。团体。该速率在pH 6.0-10.0范围内与pH无关，并且在不存在氯离子的情况下与缓冲液种类无关。在存在氯离子的情况下，I水解的动力学仍然是一阶的。然而，在特定的pH和缓冲液浓度下，降解半衰期随氯化物浓度线性增加。动力学证据表明，氯稳定机制涉及氯离子对不稳定的环状亚乙基铵中间体的进攻，以返还I。讨论了动力学数据对口服I命运的影响。
• Chatterji, Dulal C., Journal of Pharmaceutical Sciences, 1980, vol. 69, # 7, p. 858 - 861
  作者：Chatterji, Dulal C.

  DOI：——

  日期：——
• Role of Thiocyanate Ion in Detoxification of the Anticancer Agent Chlorambucil
  作者：Jari Hovinen、Toni Pettersson-Fernholm、Markku Lahti、Juhani Vilpo

  DOI：10.1021/tx980122t

  日期：1998.11.1

  N,N-Bis(2-chloroethyl)-p-aminophenylbutyric acid(chlorambucil, 1)is an orally administrated drug widely used in the chemotherapy of chronic lymphocytic leukemia. We have recently described a new metabolic path for the decomposition of 1 in human gastric juice based on its reactions with saliva-derived thiocyanate ion. We report here our quantitative data on the reactions of thiocyanate ion with CLB in various fluid matrixes at 37 degrees C. The rate of decomposition of 1 is zero-order with respect to SCN- concentration up to 100 mM. However, thiocyanate ion reacts ca. 18 300 times faster than water with the aziridinium ion derived from 1 at neutral and acidic pH. When the SCN- concentration was greater than 10 mM, practically no N,N-bis(2-hydroxyethyl)-p-aminophenylbutyric acid, 4, the product of chlorambucil hydrolysis, could be detected. Thiocyanate ion also effectively overcompensates for the rate retardation caused by Cl-; 10 mM SCN- is enough to decrease the effect of 0.5 Prl chloride ion to one-half. This is an important factor in human gastric juice where the chloride ion concentration is normally high.