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1-(2-氨基-4-氟苯基)-2-氯乙酮 | 68438-32-4

中文名称
1-(2-氨基-4-氟苯基)-2-氯乙酮
中文别名
——
英文名称
4-Fluor-2-amino-α-chloracetophenon
英文别名
1-(2-Amino-4-fluorophenyl)-2-chloroethan-1-one;1-(2-amino-4-fluorophenyl)-2-chloroethanone
1-(2-氨基-4-氟苯基)-2-氯乙酮化学式
CAS
68438-32-4
化学式
C8H7ClFNO
mdl
——
分子量
187.601
InChiKey
YXSDQKCCWFHABG-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

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:
    0.12
  • 拓扑面积:
    43.1
  • 氢给体数:
    1
  • 氢受体数:
    3

反应信息

  • 作为反应物:
    描述:
    9-ethyl-9-hydroxy-2,3,8,9-tetrahydro-5H-6-oxa-3a-azacyclohepta[f]indene-1,4,7-trione1-(2-氨基-4-氟苯基)-2-氯乙酮对甲苯磺酸 作用下, 以 甲苯 为溶剂, 生成 12-(chloromethyl)-5-ethyl-9-fluoro-5-hydroxy-1,4,5,13-tetrahydro-3H,15H-oxepino[3',4':6,7]indolizino[1,2-b]quinoline-3,15-dione
    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
  • 作为产物:
    描述:
    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
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文献信息

  • SUGASAWA T.; ADACHI M.; SASAKURA K.; KITAGAWA A., J. ORG. CHEM. 1979, 44, NO 4, 578-586
    作者:SUGASAWA T.、 ADACHI M.、 SASAKURA K.、 KITAGAWA A.
    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.
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