1-(2-氨基-4-甲基苯基)-2-氯乙烷酮 | 109532-23-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2-氨基-4-甲基苯基)-2-氯乙烷酮
• 中文别名: 乙酮,1-(2-氨基-4-甲基苯基)-2-氯-(9CI)
• 英文名称: 2-Amino-α-chlor-4-methylacetophenon
• 英文别名: 1-(2-Amino-4-methylphenyl)-2-chloroethanone
• CAS: 109532-23-2
• 化学式: C₉H₁₀ClNO
• 分子量: 183.637
• InChiKey: BEZVNVUGWZWWDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2922399090

反应信息

• 作为反应物：
  描述：

  1-(2-氨基-4-甲基苯基)-2-氯乙烷酮 在 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 以76%的产率得到6-甲基吲哚
  参考文献：
  名称：

  Nimtz, Manfred; Haefelinger, Guenter, Liebigs Annalen der Chemie, 1987, p. 765 - 770

  摘要：

  DOI：
• 作为产物：
  描述：

  氯乙腈 、 3-甲基苯胺 在 三氯化铝 、 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 生成 1-(2-氨基-4-甲基苯基)-2-氯乙烷酮
  参考文献：
  名称：

  New homocamptothecins: Synthesis, antitumor activity, and molecular modeling

  摘要：

  Homocamptothecins (hCPTs) represent a class of new emerging antitumor agents, which contains a seven-membered beta-hydroxylactone in place of the conventional six-membered alpha-hydroxylactone ring (E ring) of camptothecins. Some novel 7-substituted hCPTs were designed and synthesized based on a newly developed synthetic route which couples ring A with ring C, E and D. Most of the synthesized compounds exhibit very high cytotoxic activity on tumor cell line A549. Some compounds, such as 9b, 91, and 9y, show broad in vitro antitumor spectrum and are more potent than topotecan. Three-dimensional quantitative structure-activity relationship (3D-QSAR) methods, CoMFA and CoMSIA, were applied to explain the structure-activity relationship (SAR) of the synthesized compounds. Furthermore, molecular docking was used to clarify the binding mode of the synthesized compounds to human DNA topoisomerase I. The important hydrophobic, base-pair stacking, and hydrogen-bonding interactions were observed between the hCPT derivatives and their receptor. The results from molecular modeling will guide the design of novel hCPTs with higher antitumor activity. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.10.046

文献信息

• NIMTZ, MANFRED;HAFELINGER, GUNTER, LIEBIGS ANN. CHEM.,(1987) N 9, 765-770
  作者：NIMTZ, MANFRED、HAFELINGER, GUNTER

  DOI：——

  日期：——
• New homocamptothecins: Synthesis, antitumor activity, and molecular modeling
  作者：Zhenyuan Miao、Chunquan Sheng、Wannian Zhang、Haitao Ji、Jing Zhang、Lücheng Shao、Liang You、Min Zhang、Jianzhong Yao、Xiaoyin Che

  DOI：10.1016/j.bmc.2007.10.046

  日期：2008.2.1

  Homocamptothecins (hCPTs) represent a class of new emerging antitumor agents, which contains a seven-membered beta-hydroxylactone in place of the conventional six-membered alpha-hydroxylactone ring (E ring) of camptothecins. Some novel 7-substituted hCPTs were designed and synthesized based on a newly developed synthetic route which couples ring A with ring C, E and D. Most of the synthesized compounds exhibit very high cytotoxic activity on tumor cell line A549. Some compounds, such as 9b, 91, and 9y, show broad in vitro antitumor spectrum and are more potent than topotecan. Three-dimensional quantitative structure-activity relationship (3D-QSAR) methods, CoMFA and CoMSIA, were applied to explain the structure-activity relationship (SAR) of the synthesized compounds. Furthermore, molecular docking was used to clarify the binding mode of the synthesized compounds to human DNA topoisomerase I. The important hydrophobic, base-pair stacking, and hydrogen-bonding interactions were observed between the hCPT derivatives and their receptor. The results from molecular modeling will guide the design of novel hCPTs with higher antitumor activity. (C) 2007 Elsevier Ltd. All rights reserved.
• Nimtz, Manfred; Haefelinger, Guenter, Liebigs Annalen der Chemie, 1987, p. 765 - 770
  作者：Nimtz, Manfred、Haefelinger, Guenter

  DOI：——

  日期：——