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2-Dimethylaminomethyl-cyclobutanon-(1) | 17714-44-2

中文名称
——
中文别名
——
英文名称
2-Dimethylaminomethyl-cyclobutanon-(1)
英文别名
2-[(Dimethylamino)methyl]cyclobutan-1-one
2-Dimethylaminomethyl-cyclobutanon-(1)化学式
CAS
17714-44-2
化学式
C7H13NO
mdl
MFCD09927445
分子量
127.186
InChiKey
OVJNCWZZTNZEDV-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):
    0.1
  • 重原子数:
    9
  • 可旋转键数:
    2
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.857
  • 拓扑面积:
    20.3
  • 氢给体数:
    0
  • 氢受体数:
    2

反应信息

  • 作为反应物:
    参考文献:
    名称:
    2,3-Ethylene- and 2,3-trimethylene-bridged analogues of the group III metabotropic glutamate receptor ligand 2-amino-4-phosphonobutanoic acid
    摘要:
    The estrogen receptor alpha (ER alpha) is understood to play an important role in the progression of breast cancer. Therefore, pure antiestrogens with a preference for this receptor form are of interest as new agents for the treatment of this malignancy. Several chemical structures with selective binding affinity for ER alpha have been identified and might be useful for the synthesis of ER alpha-selective pure antiestrogens. In this study we applied the 2,5-diphenyifuran system which is closely related to the triphenylfurans described by others. Various side chains with amino and/or sulfur functions were linked to C3 to convert the furans to estrogen antagonists without residual estrogenic activity. The degree of alpha-selectivity which ranges from 2.5- to 236-fold is strongly influenced by the alkyl group at C4. Antiestrogenic potency was determined in MCF-7/2a breast cancer cells stably transfected with a luciferase gene under the control of an ERE. The 2,5-bis(4-hydroxyphenyl)furan with an ethyl substituent and a 6-[N-methyl-N-(3-pentylthiopropyi)amino]hexyl side chain exerted the strongest antiestrogenic effect in this series with an IC50 value of 50 nM in cells stimulated with 1 nM estradiol. The RBA values of this derivative were 18% (ER alpha) and 3.4% (ER beta) of estradiol, respectively. It inhibited the growth of wild-type MCF-7 cells with an IC50 value of 22 nM. The data show that the 2,5-diphenylfuran system is appropriate for the development of pure antiestrogens with preference for ER alpha. (c) 2004 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.bmcl.2004.10.040
  • 作为产物:
    参考文献:
    名称:
    2,3-Ethylene- and 2,3-trimethylene-bridged analogues of the group III metabotropic glutamate receptor ligand 2-amino-4-phosphonobutanoic acid
    摘要:
    The estrogen receptor alpha (ER alpha) is understood to play an important role in the progression of breast cancer. Therefore, pure antiestrogens with a preference for this receptor form are of interest as new agents for the treatment of this malignancy. Several chemical structures with selective binding affinity for ER alpha have been identified and might be useful for the synthesis of ER alpha-selective pure antiestrogens. In this study we applied the 2,5-diphenyifuran system which is closely related to the triphenylfurans described by others. Various side chains with amino and/or sulfur functions were linked to C3 to convert the furans to estrogen antagonists without residual estrogenic activity. The degree of alpha-selectivity which ranges from 2.5- to 236-fold is strongly influenced by the alkyl group at C4. Antiestrogenic potency was determined in MCF-7/2a breast cancer cells stably transfected with a luciferase gene under the control of an ERE. The 2,5-bis(4-hydroxyphenyl)furan with an ethyl substituent and a 6-[N-methyl-N-(3-pentylthiopropyi)amino]hexyl side chain exerted the strongest antiestrogenic effect in this series with an IC50 value of 50 nM in cells stimulated with 1 nM estradiol. The RBA values of this derivative were 18% (ER alpha) and 3.4% (ER beta) of estradiol, respectively. It inhibited the growth of wild-type MCF-7 cells with an IC50 value of 22 nM. The data show that the 2,5-diphenylfuran system is appropriate for the development of pure antiestrogens with preference for ER alpha. (c) 2004 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.bmcl.2004.10.040
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文献信息

  • Muehlstaedt,M.; Meinhold,H., Journal fur praktische Chemie (Leipzig 1954), 1968, vol. 37, p. 162 - 167
    作者:Muehlstaedt,M.、Meinhold,H.
    DOI:——
    日期:——
  • STRATEN J. W.; NORDEN J. J.; SCHAIK T. A. M.; FRANKE G. TH.; WOLF W. H.; +, REC. TRAV. CHIM., 1978, 97, NO 4, 105-106
    作者:STRATEN J. W.、 NORDEN J. J.、 SCHAIK T. A. M.、 FRANKE G. TH.、 WOLF W. H.、 +
    DOI:——
    日期:——
  • US7507816B2
    申请人:——
    公开号:US7507816B2
    公开(公告)日:2009-03-24
  • 2,3-Ethylene- and 2,3-trimethylene-bridged analogues of the group III metabotropic glutamate receptor ligand 2-amino-4-phosphonobutanoic acid
    作者:Rodney L. Johnson、Kolluri S.S.P. Rao
    DOI:10.1016/j.bmcl.2004.10.040
    日期:2005.1
    The estrogen receptor alpha (ER alpha) is understood to play an important role in the progression of breast cancer. Therefore, pure antiestrogens with a preference for this receptor form are of interest as new agents for the treatment of this malignancy. Several chemical structures with selective binding affinity for ER alpha have been identified and might be useful for the synthesis of ER alpha-selective pure antiestrogens. In this study we applied the 2,5-diphenyifuran system which is closely related to the triphenylfurans described by others. Various side chains with amino and/or sulfur functions were linked to C3 to convert the furans to estrogen antagonists without residual estrogenic activity. The degree of alpha-selectivity which ranges from 2.5- to 236-fold is strongly influenced by the alkyl group at C4. Antiestrogenic potency was determined in MCF-7/2a breast cancer cells stably transfected with a luciferase gene under the control of an ERE. The 2,5-bis(4-hydroxyphenyl)furan with an ethyl substituent and a 6-[N-methyl-N-(3-pentylthiopropyi)amino]hexyl side chain exerted the strongest antiestrogenic effect in this series with an IC50 value of 50 nM in cells stimulated with 1 nM estradiol. The RBA values of this derivative were 18% (ER alpha) and 3.4% (ER beta) of estradiol, respectively. It inhibited the growth of wild-type MCF-7 cells with an IC50 value of 22 nM. The data show that the 2,5-diphenylfuran system is appropriate for the development of pure antiestrogens with preference for ER alpha. (c) 2004 Elsevier Ltd. All rights reserved.
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