trimethyl-(2-oxo-cyclopentylmethyl)-ammonium; iodide | 93226-89-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: trimethyl-(2-oxo-cyclopentylmethyl)-ammonium; iodide
• 英文别名: Trimethyl-(2-oxo-cyclopentylmethyl)-ammonium; Jodid；Trimethyl-[(2-oxocyclopentyl)methyl]azanium;iodide
• CAS: 93226-89-2
• 化学式: C₉H₁₈NO*I
• 分子量: 283.153
• InChiKey: XGYPQXHXWPLYIF-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.93
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trimethyl-(2-oxo-cyclopentylmethyl)-ammonium; iodide 在 ammonium hydroxide 、 氯化铵 作用下， 以 甲醇 、 苯 为溶剂， 生成 (2-Amino-2-cyano-cyclopentylmethyl)-phosphonic acid diethyl ester
  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：
  描述：

  2-((dimethylamino)methylene)cyclopentanone 在 lithium aluminium tetrahydride 作用下， 以 1,4-二氧六环 、 乙醚 为溶剂， 反应 12.0h， 生成 trimethyl-(2-oxo-cyclopentylmethyl)-ammonium; iodide
  参考文献：
  名称：

  经由烯胺酮从酮和酯合成曼尼希碱。

  摘要：

  描述了一系列活化的亚甲基化合物与酰胺缩醛的反应以形成高产率的烯胺酮。还涵盖了通过用氢化锂铝还原而进一步转化为曼尼希碱的方法。

  DOI：

  10.1016/s0040-4039(00)84586-4

文献信息

• Further exploration of 1-{2-[Bis-(4-fluorophenyl)methoxy]ethyl}piperazine (GBR 12909): role of N-aromatic, N-heteroaromatic, and 3-oxygenated N-phenylpropyl substituents on affinity for the dopamine and serotonin transporter
  作者：David Lewis、Ying Zhang、Thomas Prisinzano、Christina M. Dersch、Richard B. Rothman、Arthur E. Jacobson、Kenner C. Rice

  DOI：10.1016/s0960-894x(03)00108-2

  日期：2003.4

  N-phenylpropyl derivatives of 1-(2-benzhydryloxyethyl)-piperazine and 1-[2-[bis-(4-fluorophenyl)methoxy]ethyl]piperazine, analogues of GBR 12909 (1a) and 12935 (1b), was synthesized and examined for their dopamine (DAT) and serotonin (SERT) transporter binding properties. One of these compounds, racemic 3-[4-(2-benzhydryloxyethyl)piperazin-1-yl]-1-(3-fluorophenyl)-propan-1-ol (33), had DAT affinity as good as

  1-（2-苯甲酰氧基乙基）-哌嗪和1- [2- [双-（双-（4-氟苯基）甲氧基]乙基]哌嗪的一系列N-芳族，N-杂芳族和氧化的N-苯基丙基衍生物，GBR的类似物合成了12909（1a）和12935（1b）并检查了它们的多巴胺（DAT）和血清素（SERT）转运蛋白结合特性。这些化合物中的一种，即外消旋的3- [4-（2-苯甲氧基氧基乙基）哌嗪-1-基] -1-（3-氟苯基）-丙-1-醇（33），其DAT亲和力与或优于，GBR 12909和12935，并且比GBR化合物对SAT的DAT更具选择性。反式（43）和顺式（47）（+/-）-2-（4- [2- [双-（4-氟苯基）-甲氧基]乙基]哌嗪-1-基甲基）-6-甲氧基- 1,2,3,4-四氢萘-1-醇具有相对较好的SERT选择性，并且对SERT也具有很高的亲和力。
• The synthesis of mannich bases from ketones and esters via enaminones.
  作者：Paul Francis Schuda、Cynthia B. Ebner、Tina M. Morgan

  DOI：10.1016/s0040-4039(00)84586-4

  日期：1986.1

  The reactions of a series of activated methylene compounds with amide acetals to form high yields of enaminones is described. Further conversion to the Mannich Bases via reduction with lithium aluminum hydride is also covered.

  描述了一系列活化的亚甲基化合物与酰胺缩醛的反应以形成高产率的烯胺酮。还涵盖了通过用氢化锂铝还原而进一步转化为曼尼希碱的方法。
• 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.