1-(4-chloromethyl-2-phenyl-[1,3]dioxolan-2-ylmethyl)piperidine-2-one | 221198-16-9

• 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: 1-(4-chloromethyl-2-phenyl-[1,3]dioxolan-2-ylmethyl)piperidine-2-one
• CAS: 221198-16-9
• 化学式: C₁₆H₂₀ClNO₃
• 分子量: 309.793
• InChiKey: CYSABIPOGFZWKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(4-chloromethyl-2-phenyl-[1,3]dioxolan-2-ylmethyl)piperidine-2-one 以 乙醚 为溶剂， 反应 36.0h， 生成 Trimethyl-[(2R,4S)-2-(2-oxo-piperidin-1-ylmethyl)-2-phenyl-[1,3]dioxolan-4-ylmethyl]-ammonium; iodide
  参考文献：
  名称：

  Malmusi, Luca; Franchini, Silvia; Mucci, Adele, Medicinal Chemistry Research, 1998, vol. 8, # 9, p. 499 - 509

  摘要：

  DOI：
• 作为产物：
  描述：

  N-phenacyl piperidin-2-one 在 三甲基氯硅烷 、 对甲苯磺酸 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 27.0h， 生成 1-(4-chloromethyl-2-phenyl-[1,3]dioxolan-2-ylmethyl)piperidine-2-one
  参考文献：
  名称：

  Malmusi, Luca; Franchini, Silvia; Mucci, Adele, Medicinal Chemistry Research, 1998, vol. 8, # 9, p. 499 - 509

  摘要：

  DOI：

文献信息

• 1,3-Dioxolane-based ligands incorporating a lactam or imide moiety: Structure–affinity/activity relationship at α1-adrenoceptor subtypes and at 5-HT1A receptors
  作者：Silvia Franchini、Adolfo Prandi、Annamaria Baraldi、Claudia Sorbi、Annalisa Tait、Michela Buccioni、Gabriella Marucci、Antonio Cilia、Lorenza Pirona、Paola Fossa

  DOI：10.1016/j.ejmech.2010.05.023

  日期：2010.9

  A series of 1,3-dioxolane-based compounds incorporating a lactam (2-4) or imide (5-7) moiety was synthesized and the pharmacological profile at alpha(1)-adrenoceptor subtypes and 5-HT1A receptor was assessed through binding and functional experiments. Starting from the 2,2-diphenyl-1,3-dioxolane derivative 1, previously shown to be a selective alpha(1a(A))/alpha(1d(D))-adrenoceptor subtype antagonist, over alpha(1b(B)) subtype and 5-HT1A receptor, and replacing one phenyl ring with lactam or imide moiety a reduction of alpha(1)/5-H-1A selectivity is observed, mainly due to the increase in 5-H-1A affinity. In functional experiments lactam derivatives seems to favour 5-HT1A receptor antagonism (pKb = 7.20-7.80) and alpha(1B)-adrenoceptor antagonist selectivity (alpha(1B)/alpha(1A) and alpha(1B)/alpha(1D) of about 10-fold). The most interesting of the various imide derivatives is compound 7t, which is a selective alpha(1D)-adrenoceptor antagonist (pKb = 8.1 and alpha(1D)/alpha(1A) and alpha(1D)/alpha(1B) selectivity ratios of 16 and 11 respectively) whereas at 5-HT1A receptor it is a potent partial agonist (pD2 = 7.98, E-max = 60%).]. Given that as and trans diastereomer pairs for 2-7 are possible, a computational strategy based on molecular docking studies was used to elucidate the atomic details of the 5-HT1A/agonist and 5-HT1A/antagonist interaction. (C) 2010 Elsevier Masson SAS. All rights reserved.