4-(2-Piperidino-ethoxy)-benzophenon | 102156-42-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(2-Piperidino-ethoxy)-benzophenon
• 英文别名: Methanone, phenyl[4-[2-(1-piperidinyl)ethoxy]phenyl]-；phenyl-[4-(2-piperidin-1-ylethoxy)phenyl]methanone
• CAS: 102156-42-3
• 化学式: C₂₀H₂₃NO₂
• 分子量: 309.408
• InChiKey: GXMUDWKDBJHGNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-苯基-2-丁酮 、 4-(2-Piperidino-ethoxy)-benzophenon 在 四氯化钛 、 锌 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以24%的产率得到2-benzyl-1-phenyl-1-[4-(piperidinylethoxy)phenyl]but-1-ene
  参考文献：
  名称：

  Flexible Estrogen Receptor Modulators:  Design, Synthesis, and Antagonistic Effects in Human MCF-7 Breast Cancer Cells

  摘要：

  Although many series of estrogen receptor antagonists continue to be produced, the majority are direct structural analogues of existing modulators. To examine the tolerance of the estrogen receptor toward flexible ligands, a series of novel flexible estrogen receptor antagonists were prepared and their antiproliferative effects on human MCF-7 breast tumor cells investigated. Each of these compounds deviated from the traditional triphenylethylene backbone associated with common tamoxifen analogues through the introduction of a flexible methylene (benzylic) spacing group between one of the aryl rings and the ethylene group and through variations in the basic side chain moiety. The compounds prepared, when assayed in conjunction with a tamoxifen standard, demonstrated high potency in antiproliferative assays against an MCF-7 human breast cancer cell line with low cytotoxicity and high binding affinity. A computational study was undertaken to investigate the compounds ' potential interactions with specific residues within the human estrogen receptor a ligand-binding domain (ER-LBD), predicting these compounds bind in an antiestrogenic fashion within the ER-LBD and interact with those important residues previously identified in the structures of ER-LBD agonist/antagonist cocrystals. These compounds further illustrate the eclectic nature of the estrogen receptor in terms of ligand flexibility tolerance.

  DOI：

  10.1021/jm001119l
• 作为产物：
  描述：

  1-(2-氯乙基)哌啶盐酸盐 、 4-羟基-二苯甲酮 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 6.0h， 以89%的产率得到4-(2-Piperidino-ethoxy)-benzophenon
  参考文献：
  名称：

  Flexible Estrogen Receptor Modulators:  Design, Synthesis, and Antagonistic Effects in Human MCF-7 Breast Cancer Cells

  摘要：

  Although many series of estrogen receptor antagonists continue to be produced, the majority are direct structural analogues of existing modulators. To examine the tolerance of the estrogen receptor toward flexible ligands, a series of novel flexible estrogen receptor antagonists were prepared and their antiproliferative effects on human MCF-7 breast tumor cells investigated. Each of these compounds deviated from the traditional triphenylethylene backbone associated with common tamoxifen analogues through the introduction of a flexible methylene (benzylic) spacing group between one of the aryl rings and the ethylene group and through variations in the basic side chain moiety. The compounds prepared, when assayed in conjunction with a tamoxifen standard, demonstrated high potency in antiproliferative assays against an MCF-7 human breast cancer cell line with low cytotoxicity and high binding affinity. A computational study was undertaken to investigate the compounds ' potential interactions with specific residues within the human estrogen receptor a ligand-binding domain (ER-LBD), predicting these compounds bind in an antiestrogenic fashion within the ER-LBD and interact with those important residues previously identified in the structures of ER-LBD agonist/antagonist cocrystals. These compounds further illustrate the eclectic nature of the estrogen receptor in terms of ligand flexibility tolerance.

  DOI：

  10.1021/jm001119l

文献信息

• SMALL MOLECULE COMPOUNDS FOR STEM CELL DIFFERENTIATION
  申请人：Mercola Mark

  公开号：US20100159596A1

  公开（公告）日：2010-06-24

  Methods and small molecule compounds for stem cell differentiation are provided. One example of a class of compounds that may be used is represented by the compound having the structure IA or IB in the form of free base or a pharmaceutically acceptable salt, hydrate, solvate or N-oxide thereof: R 1 is independently hydrogen or (C 1 -C 6 )alkyl; R 2 is independently hydrogen, (C 1 -C 6 )alkyl, aryl, or heteroaryl; R 2′ is independently hydrogen, (C 1 -C 6 )alkyl, CF 3 or C 2 F 5 ; R 3 is independently (C 1 -C 6 )alkyl, aryl, 2-tetrahydrofurylmethyl, an aliphatic tertiary amine, or 4-methoxybenzyl; or R 2 and R 3 may be joined together to form a 5 or 6 member ring lactone; R 4 is independently hydrogen, (C 1 -C 6 )alkyl, a 2- or 4-R 5 -substituted aromatic ring selected from a 4-R 5 -phenyl or a 2-R 5 -5-pyridyl, aryl, heteroaryl, aliphatic tertiary amine or halogen; and R 5 , R 5′ , R 6 , R 6′ , R 7 , R 7′ , are each independently hydrogen, (C 1 -C 6 )alkyl, aryl, optionally substituted phenyl, heteroaryl, a heterocyclic ring, an aliphatic tertiary amine, or halogen.

  提供干细胞分化的方法和小分子化合物。可以使用的一类化合物的一个示例由结构IA或IB表示，以自由碱基或其药学上可接受的盐，水合物，溶剂或N-氧化物的形式存在：R1独立地是氢或（C1-C6）烷基; R2独立地是氢，（C1-C6）烷基，芳基或杂环芳基; R2'独立地是氢，（C1-C6）烷基，CF3或C2F5; R3独立地是（C1-C6）烷基，芳基，2-四氢呋喃甲基，脂肪族三级胺或4-甲氧基苄基; 或者R2和R3可以结合形成5或6元环内酯; R4独立地是氢，（C1-C6）烷基，2-或4-R5-取代的芳环，选自4-R5-苯基或2-R5-5-吡啶基，芳基，杂环芳基，脂肪族三级胺或卤素; R5，R5'，R6，R6'，R7，R7'独立地是氢，（C1-C6）烷基，芳基，可选取代的苯基，杂环芳基，杂环环，脂肪族三级胺或卤素。
• HL 752: A potent and long-acting antispasmodic agent
  作者：Swati Bal-Tembe、Dilip N. Bhedi、Anil K. Mishra、Ramanujam Rajagopalan、Anil V. Ghate、Palakodety Subbarayan、Narayan S. Punekar、Anjali V. Kulkarni

  DOI：10.1016/s0968-0896(97)00067-9

  日期：1997.7

  Ester analogues of methyl-2-(4-(2-piperidinoethoxy)benzoyl)-benzoate hydrochloride (pitofenone) (2) were prepared with an aim to find a more potent and metabolically stable antispasmodic compound. The compounds were evaluated for their in vitro and in vivo antispasmodic activity, and stability to in vitro enzymatic hydrolysis. Of the compounds synthesised, HL 752 (21) showed the most potent and long-lasting antispasmodic activity and was selected as the candidate for clinical development. (C) 1997 Elsevier Science Ltd.
• US7432268B2
  申请人：——

  公开号：US7432268B2

  公开（公告）日：2008-10-07
• US9012217B2
  申请人：——

  公开号：US9012217B2

  公开（公告）日：2015-04-21
• Flexible Estrogen Receptor Modulators:  Design, Synthesis, and Antagonistic Effects in Human MCF-7 Breast Cancer Cells
  作者：Mary J. Meegan、Rosario B. Hughes、David G. Lloyd、D. Clive Williams、Daniela M. Zisterer

  DOI：10.1021/jm001119l

  日期：2001.3.1

  Although many series of estrogen receptor antagonists continue to be produced, the majority are direct structural analogues of existing modulators. To examine the tolerance of the estrogen receptor toward flexible ligands, a series of novel flexible estrogen receptor antagonists were prepared and their antiproliferative effects on human MCF-7 breast tumor cells investigated. Each of these compounds deviated from the traditional triphenylethylene backbone associated with common tamoxifen analogues through the introduction of a flexible methylene (benzylic) spacing group between one of the aryl rings and the ethylene group and through variations in the basic side chain moiety. The compounds prepared, when assayed in conjunction with a tamoxifen standard, demonstrated high potency in antiproliferative assays against an MCF-7 human breast cancer cell line with low cytotoxicity and high binding affinity. A computational study was undertaken to investigate the compounds ' potential interactions with specific residues within the human estrogen receptor a ligand-binding domain (ER-LBD), predicting these compounds bind in an antiestrogenic fashion within the ER-LBD and interact with those important residues previously identified in the structures of ER-LBD agonist/antagonist cocrystals. These compounds further illustrate the eclectic nature of the estrogen receptor in terms of ligand flexibility tolerance.