3-[(2,4,5-三氯苯氧基)甲基]苯胺 | 88253-93-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-[(2,4,5-三氯苯氧基)甲基]苯胺
• 英文名称: 3-aminobenzyl 2,4,5-trichlorophenyl ether
• 英文别名: 3-[(2,4,5-Trichlorophenoxy)methyl]aniline
• CAS: 88253-93-4
• 化学式: C₁₃H₁₀Cl₃NO
• mdl: MFCD11119014
• 分子量: 302.588
• InChiKey: IUJPGCHKIONUJB-UHFFFAOYSA-N

物化性质

• 沸点：
  442.3±40.0 °C(Predicted)
• 密度：
  1.425±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  丙酮 、 二聚氰胺 、 3-[(2,4,5-三氯苯氧基)甲基]苯胺 在 盐酸 作用下， 反应 24.0h， 以53%的产率得到
  参考文献：
  名称：

  Comparative structure-activity relationships of antifolate triazines inhibiting murine tumor cells sensitive and resistant to methotrexate

  摘要：

  The inhibitory effect of 108 4,6-diamino-1,2-dihydro-2,2-dimethyl-1-(substituted-phenyl)-s-triazines on murine L5178Y tumor cells, resistant and sensitive to methotrexate (MTX), has been studied. From the pI50 values, quantitative structure-activity relationships have been formulated which show that the lipophilic triazines are much more inhibitory against resistant cells than methotrexate or hydrophilic triazines. The results are compared with the behavior of other antifolate drugs that have been used in chemotherapy, as well as with eight antitumor drugs that are not antifolates. The acquired resistance of these cells toward hydrophilic antifolates may be attributed to the combined effect of an impaired active-transport system, a change in the conformation of dihydrofolate reductase in the resistant cells, and an amplified production of dihydrofolate reductase in the resistant cells.

  DOI：

  10.1021/jm00369a019
• 作为产物：
  描述：

  2,4,5-三氯苯酚 在 氢氧化钾 、 铁粉 、 溶剂黄146 作用下， 以 乙醇 、 二乙二醇二甲醚 、 水 为溶剂， 反应 48.0h， 生成 3-[(2,4,5-三氯苯氧基)甲基]苯胺
  参考文献：
  名称：

  Comparative structure-activity relationships of antifolate triazines inhibiting murine tumor cells sensitive and resistant to methotrexate

  摘要：

  The inhibitory effect of 108 4,6-diamino-1,2-dihydro-2,2-dimethyl-1-(substituted-phenyl)-s-triazines on murine L5178Y tumor cells, resistant and sensitive to methotrexate (MTX), has been studied. From the pI50 values, quantitative structure-activity relationships have been formulated which show that the lipophilic triazines are much more inhibitory against resistant cells than methotrexate or hydrophilic triazines. The results are compared with the behavior of other antifolate drugs that have been used in chemotherapy, as well as with eight antitumor drugs that are not antifolates. The acquired resistance of these cells toward hydrophilic antifolates may be attributed to the combined effect of an impaired active-transport system, a change in the conformation of dihydrofolate reductase in the resistant cells, and an amplified production of dihydrofolate reductase in the resistant cells.

  DOI：

  10.1021/jm00369a019

文献信息

• Dihydrofolate reductase inhibitors
  申请人：——

  公开号：US20030203908A1

  公开（公告）日：2003-10-30

  A compound of formula (I) or (II), wherein X is hydrogen, halogen, alkyl, aralkyl,aryloxy, arylalkoxy or alkoxy, Y is hydrogen, halogen, alkyl, aralkyl, aryloxy, arylalkoxy or alkoxy, or formula (a) wherein A and B are different and one of A and B is CH 2 and the other is O, NH, or S or A and B are both CH 2 or CH═, and R a , R b , and R c are the same or different and are hydrogen, halogen, alkyl, alkoxy, aryloxy, aralkyl or arylalkoxy. R 1 is hydrogen, and R 2 is hydrogen, C 1 -C 6 alkyl or aryl which is unsubstituted or substituted by halogen, cyano, hydroxy, C 1 -C 6 alkyl, which is unsubstituted or substituted by halogen, cyano, hydroxy, C 1 -C 6 alkoxy, aralkyl, aryloxy or aryl, C 1 -C 6 alkoxy, aralkyl, arylalkoxy, aryloxy or aryl, which is unsubstituted or substituted by halogen, cyano, hydroxy, C 1 -C 6 alkyl or C 1 -C 6 alkoxy; and pharmaceutically acceptable salts thereof; with the proviso that when R 2 is phenyl and Y is hydrogen, X is not chlorine. 1

  化合物的化学式(I)或(II)，其中X为氢、卤素、烷基、芳基烷基、芳氧基、芳基烷氧基或烷氧基，Y为氢、卤素、烷基、芳基烷基、芳氧基、芳基烷氧基或烷氧基，或者化学式(a)中A和B不同，A和B中之一为CH2，另一个为O、NH或S，或者A和B都为CH2或CH═，而Ra、Rb和Rc相同或不同，分别为氢、卤素、烷基、烷氧基、芳氧基、芳基烷基或芳基烷氧基。R1为氢，R2为氢、C1-C6烷基或芳基，未被卤素、氰基、羟基、C1-C6烷基（未被卤素、氰基、羟基、C1-C6烷氧基、芳基烷基、芳氧基或芳基取代）取代或取代的烷基、芳基烷基、芳基烷氧基、芳氧基或芳基，未被卤素、氰基、羟基、C1-C6烷基或C1-C6烷氧基取代或取代的烷基、芳基烷基、芳基烷氧基、芳氧基或芳基；以及其药学上可接受的盐；但当R2为苯基且Y为氢时，X不为氯。
• [EN] DIHYDROFOLATE REDUCTASE INHIBITORS<br/>[FR] INHIBITEURS DE LA DIHYDROFOLATE REDUCTASE
  申请人：ISIS INNOVATION

  公开号：WO2001053276A1

  公开（公告）日：2001-07-26

  A compound of formula (I) or (II), wherein X is hydrogen, halogen, alkyl, aralkyl,aryloxy, arylalkoxy or alkoxy, Y is hydrogen, halogen, alkyl, aralkyl, aryloxy, arylalkoxy or alkoxy, or formula (a) wherein A and B are different and one of A and B is CH2 and the other is O, NH, or S or A and B are both CH2 or CH=, and R?a, Rb, and Rc¿ are the same or different and are hydrogen, halogen, alkyl, alkoxy, aryloxy, aralkyl or arylalkoxy. R1 is hydrogen, and R2 is hydrogen, C¿1?-C6 alkyl or aryl which is unsubstituted or substituted by halogen, cyano, hydroxy, C1-C6 alkyl, which is unsubstituted or substituted by halogen, cyano, hydroxy, C1-C6 alkoxy, aralkyl, aryloxy or aryl, C1-C6 alkoxy, aralkyl, arylalkoxy, aryloxy or aryl, which is unsubstituted or substituted by halogen, cyano, hydroxy, C1-C6 alkyl or C1-C6 alkoxy; and pharmaceutically acceptable salts thereof; with the proviso that when R?2¿ is phenyl and Y is hydrogen, X is not chlorine.
• Comparative structure-activity relationships of antifolate triazines inhibiting murine tumor cells sensitive and resistant to methotrexate
  作者：Cynthia Dias Selassie、Corwin Hansch、Tasneem A. Khwaja、Cecilia B. Dias、Stephanie Pentecost

  DOI：10.1021/jm00369a019

  日期：1984.3

  The inhibitory effect of 108 4,6-diamino-1,2-dihydro-2,2-dimethyl-1-(substituted-phenyl)-s-triazines on murine L5178Y tumor cells, resistant and sensitive to methotrexate (MTX), has been studied. From the pI50 values, quantitative structure-activity relationships have been formulated which show that the lipophilic triazines are much more inhibitory against resistant cells than methotrexate or hydrophilic triazines. The results are compared with the behavior of other antifolate drugs that have been used in chemotherapy, as well as with eight antitumor drugs that are not antifolates. The acquired resistance of these cells toward hydrophilic antifolates may be attributed to the combined effect of an impaired active-transport system, a change in the conformation of dihydrofolate reductase in the resistant cells, and an amplified production of dihydrofolate reductase in the resistant cells.