4-(1-amino-1-cyclopropyl-methylene)-pent-2-enedioic acid dimethyl ester | 862695-72-5

• 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: 4-(1-amino-1-cyclopropyl-methylene)-pent-2-enedioic acid dimethyl ester
• 英文别名: 4-(1-Amino-1-cyclopropyl-methylene)-pent-2-enedioic acid dimethyl ester；dimethyl 4-[amino(cyclopropyl)methylidene]pent-2-enedioate
• CAS: 862695-72-5
• 化学式: C₁₁H₁₅NO₄
• 分子量: 225.244
• InChiKey: YNSQMJLYIZKYAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  78.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(1-amino-1-cyclopropyl-methylene)-pent-2-enedioic acid dimethyl ester 在 二氯磷酸苯酯 、 sodium hydroxide 、 sodium t-butanolate 作用下， 以 甲醇 、 水 为溶剂， 反应 33.17h， 生成 6-氯-2-环丙基烟酸
  参考文献：
  名称：

  Optimisation of pharmacokinetic properties in a neutral series of 11β-HSD1 inhibitors

  摘要：

  11 beta-HSD1 is increasingly seen as an attractive target for the treatment of type II diabetes and other elements of the metabolic syndrome. In this program of work we describe how a series of neutral 2-thioalkyl-pyridine 11 beta-HSD1 inhibitors were optimized in terms of their pharmacokinetic properties to give compounds with excellent bioavailability in both rat and dog through a core change to pyrimidine. A potential reactive metabolite issue with 4-thioalkyl-pyrimidines was circumvented by a switch from sulfur to carbon substitution. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.070
• 作为产物：
  描述：

  3-环丙基-3-氧代丙酸甲酯 在 ammonium acetate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 68.0h， 生成 4-(1-amino-1-cyclopropyl-methylene)-pent-2-enedioic acid dimethyl ester
  参考文献：
  名称：

  Optimisation of pharmacokinetic properties in a neutral series of 11β-HSD1 inhibitors

  摘要：

  11 beta-HSD1 is increasingly seen as an attractive target for the treatment of type II diabetes and other elements of the metabolic syndrome. In this program of work we describe how a series of neutral 2-thioalkyl-pyridine 11 beta-HSD1 inhibitors were optimized in terms of their pharmacokinetic properties to give compounds with excellent bioavailability in both rat and dog through a core change to pyrimidine. A potential reactive metabolite issue with 4-thioalkyl-pyrimidines was circumvented by a switch from sulfur to carbon substitution. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.070

文献信息

• [EN] PYRIDINE DERIVATIVES AS CONNABINOID RECEPTOR MODULATORS<br/>[FR] DERIVES DE LA PYRIDINE UTILISES COMME MODULATEURS DU RECEPTEUR CANNABINOIDE
  申请人：GLAXO GROUP LTD

  公开号：WO2005075464A1

  公开（公告）日：2005-08-18

  The present invention relates to novel pyridine derivatives such as compounds of the formula (I): and the use of such compounds or pharmaceutical compositions thereof in the treatment of diseases, particularly pain, which are mediated by the activity of the cannabinoid 2 receptor.

  本发明涉及新颖的吡啶衍生物，如式(I)的化合物，以及这些化合物或其药物组合物在治疗疾病中的应用，特别是通过大麻素2受体活性介导的疼痛。
• Pyridine Derivatives and Their Use as Cb2 Receptor Modulators
  申请人：Eatherton Andrew John

  公开号：US20080280868A1

  公开（公告）日：2008-11-13

  The present invention relates to novel pyridine derivatives such as compounds of the formula (I): and the use of such compounds or pharmaceutical compositions thereof in the treatment of diseases, particularly pain, which are mediated by the activity of the cannabinoid 2 receptor.

  本发明涉及新型吡啶衍生物，例如式（I）化合物，以及使用这些化合物或其制药组合物治疗疾病，特别是由大麻素2受体活性介导的疼痛。
• Pyridine Derivatives as Connabinoid Receptor Modulators
  申请人：Giblin Gerard Martin Paul

  公开号：US20080280952A1

  公开（公告）日：2008-11-13

  The present invention relates to novel pyridine derivatives such as compounds of the formula (I): and the use of such compounds or pharmaceutical compositions thereof in the treatment of diseases, particularly pain, which are mediated by the activity of the cannabinoid 2 receptor.

  本发明涉及新型吡啶衍生物，例如公式（I）所示的化合物，以及这些化合物或其制药组合物在治疗疾病，特别是通过大麻素2受体活性介导的疼痛方面的应用。
• Optimisation of pharmacokinetic properties in a neutral series of 11β-HSD1 inhibitors
  作者：James S. Scott、Adrian L. Gill、Linda Godfrey、Sam D. Groombridge、Amanda Rees、John Revill、Paul Schofield、Pernilla Sörme、Andrew Stocker、John G. Swales、Paul R.O. Whittamore

  DOI：10.1016/j.bmcl.2012.08.070

  日期：2012.11

  11 beta-HSD1 is increasingly seen as an attractive target for the treatment of type II diabetes and other elements of the metabolic syndrome. In this program of work we describe how a series of neutral 2-thioalkyl-pyridine 11 beta-HSD1 inhibitors were optimized in terms of their pharmacokinetic properties to give compounds with excellent bioavailability in both rat and dog through a core change to pyrimidine. A potential reactive metabolite issue with 4-thioalkyl-pyrimidines was circumvented by a switch from sulfur to carbon substitution. (C) 2012 Elsevier Ltd. All rights reserved.