5-[methyl(phenylmethyl)amino]-5-oxopentanoic acid | 940100-44-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-[methyl(phenylmethyl)amino]-5-oxopentanoic acid
• 英文别名: 5-[Benzyl(methyl)amino]-5-oxopentanoic acid
• CAS: 940100-44-7
• 化学式: C₁₃H₁₇NO₃
• mdl: MFCD11175299
• 分子量: 235.283
• InChiKey: WQKZLCDADWIIOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.384
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-amino-3-[2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl][1]benzothieno[3,2-d]pyrimidine-2,4(1H,3H)-dione 、 5-[methyl(phenylmethyl)amino]-5-oxopentanoic acid 、 氯甲酸乙酯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 31.08h， 以22%的产率得到N¹-methyl-N⁵-[3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-2,4-dioxo-1,2,3,4-tetrahydro[1]benzothieno[3,2-d]pyrimidin-8-yl]-N¹-(phenylmethyl)pentanediamide
  参考文献：
  名称：

  High affinity ligands and potent antagonists for the α1D-adrenergic receptor. Novel 3,8-disubstituted [1]benzothieno[3,2-d]pyrimidine derivatives

  摘要：

  A new series of high affinity ligands and antagonists for the α1D-adrenergic receptor (AR) has been discovered. New molecules present a [1]benzothieno[3,2-d]pyrimidin-2,4(1H,3H)-dione or a [1]benzothieno[3,2-d]pyrimidin-4(3H)-one scaffold and bear a 2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl moiety in the 3-position and various amide substituents in the 8-position. In binding assays at the three human cloned α1A-, α1B-, and α1D-AR subtypes, they showed high affinity values, particularly for the α1D-AR subtype. Compound 22 (RX18), N(1)-methyl-N(5)-[3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-2,4-dioxo-1,2,3,4-tetrahydro[1]benzothieno[3,2-d]pyrimidin-8-yl]-N(1)-(phenylmethyl)pentanediamide, was the most interesting in the series displaying very high affinity (pKi = 10.25) and potent antagonism (pKb = 9.15) when tested in a functional assay at the α1D-AR.

  DOI：

  10.1016/j.ejmech.2014.06.057
• 作为产物：
  描述：

  丁二酸酐 、 N-甲基苄胺 以 甲苯 为溶剂， 反应 42.0h， 以0.54 g的产率得到5-[methyl(phenylmethyl)amino]-5-oxopentanoic acid
  参考文献：
  名称：

  High affinity ligands and potent antagonists for the α1D-adrenergic receptor. Novel 3,8-disubstituted [1]benzothieno[3,2-d]pyrimidine derivatives

  摘要：

  A new series of high affinity ligands and antagonists for the α1D-adrenergic receptor (AR) has been discovered. New molecules present a [1]benzothieno[3,2-d]pyrimidin-2,4(1H,3H)-dione or a [1]benzothieno[3,2-d]pyrimidin-4(3H)-one scaffold and bear a 2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl moiety in the 3-position and various amide substituents in the 8-position. In binding assays at the three human cloned α1A-, α1B-, and α1D-AR subtypes, they showed high affinity values, particularly for the α1D-AR subtype. Compound 22 (RX18), N(1)-methyl-N(5)-[3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-2,4-dioxo-1,2,3,4-tetrahydro[1]benzothieno[3,2-d]pyrimidin-8-yl]-N(1)-(phenylmethyl)pentanediamide, was the most interesting in the series displaying very high affinity (pKi = 10.25) and potent antagonism (pKb = 9.15) when tested in a functional assay at the α1D-AR.

  DOI：

  10.1016/j.ejmech.2014.06.057

文献信息

• Cyclohexyl-1, 4-diamine compounds
  申请人：Sundermann Corinna

  公开号：US20070112007A1

  公开（公告）日：2007-05-17

  Novel cyclohexyl-1,4-diamine compounds corresponding to formula I, processes for the production thereof, pharmaceutical compositions containing these compounds, methods of producing pharmaceutical compositions including these compounds and related methods of treating or inhibiting certain diseases or conditions.

  新型环己基-1,4-二胺化合物对应于式I，其生产方法，包含这些化合物的药物组合物，制备包含这些化合物的药物组合物的方法以及相关的治疗或抑制某些疾病或状况的方法。
• SUBSTITUIERTE CYCLOHEXYL-1,4-DIAMIN-DERIVATE
  申请人：Grünenthal GmbH

  公开号：EP1745010B1

  公开（公告）日：2009-08-05
• High affinity ligands and potent antagonists for the α1D-adrenergic receptor. Novel 3,8-disubstituted [1]benzothieno[3,2-d]pyrimidine derivatives
  作者：Giuseppe Romeo、Loredana Salerno、Valeria Pittalà、Maria N. Modica、Maria A. Siracusa、Luisa Materia、Michela Buccioni、Gabriella Marucci、Kenneth P. Minneman

  DOI：10.1016/j.ejmech.2014.06.057

  日期：2014.8

  A new series of high affinity ligands and antagonists for the α1D-adrenergic receptor (AR) has been discovered. New molecules present a [1]benzothieno[3,2-d]pyrimidin-2,4(1H,3H)-dione or a [1]benzothieno[3,2-d]pyrimidin-4(3H)-one scaffold and bear a 2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl moiety in the 3-position and various amide substituents in the 8-position. In binding assays at the three human cloned α1A-, α1B-, and α1D-AR subtypes, they showed high affinity values, particularly for the α1D-AR subtype. Compound 22 (RX18), N(1)-methyl-N(5)-[3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-2,4-dioxo-1,2,3,4-tetrahydro[1]benzothieno[3,2-d]pyrimidin-8-yl]-N(1)-(phenylmethyl)pentanediamide, was the most interesting in the series displaying very high affinity (pKi = 10.25) and potent antagonism (pKb = 9.15) when tested in a functional assay at the α1D-AR.