4-环丙基-2-甲基-5-嘧啶羧酸乙酯 | 887410-59-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 4-环丙基-2-甲基-5-嘧啶羧酸乙酯
• 英文名称: ethyl 4-cyclopropyl-2-methyl-pyrimidine-5-carboxylate
• 英文别名: ethyl 4-cyclopropyl-2-methylpyrimidine-5-carboxylate
• CAS: 887410-59-5
• 化学式: C₁₁H₁₄N₂O₂
• 分子量: 206.244
• InChiKey: DVNVPMSBZFMCPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-环丙基-2-甲基-5-嘧啶羧酸乙酯 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 4-cyclopropyl-N-[(2r,5s)-5-hydroxyadamantan-2-yl]-2-methylpyrimidine-5-carboxamide
  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-羰基-丙酸乙酯 在 sodium methylate 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 11.0h， 生成 4-环丙基-2-甲基-5-嘧啶羧酸乙酯
  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
• 作为试剂：
  描述：

  sodium ethoxide-ethanol 、 盐酸乙脒 、 2-环丙基羰基-3-二甲基氨基丙烯酸甲酯 在 水 、 乙酸乙酯 、 Brine 、 Sodium sulfate-III 、 silica gel 、 ethyl acetate n-hexane 、 4-环丙基-2-甲基-5-嘧啶羧酸乙酯 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以to obtain a mixture (1.897 g) of methyl 4-cyclopropyl-2-methyl-pyrimidine-5-carboxylate and ethyl 4-cyclopropyl-2-methyl-pyrimidine-5-carboxylate as a yellow oily matter的产率得到methyl 4-cyclopropyl-2-methyl-pyrimidine-5-carboxylate
  参考文献：
  名称：

  PYRAZOLE COMPOUNDS AND USE THEREOF

  摘要：

  本发明的吡唑化合物由以下一般式（I）表示。本发明的吡唑化合物或其盐或溶剂化物强烈抑制肝糖原磷酸化酶，因此可用作糖尿病的治疗或预防剂。其中每个符号如规范所述。

  公开号：

  US20090036450A1

文献信息

• PYRAZOLES AND USE THEREOF AS DRUGS
  申请人：Japan Tobacco Inc.

  公开号：EP2096111A1

  公开（公告）日：2009-09-02

  The pyrazole compound of the present invention is represented by the following general formula (I). The pyrazole compound of present invention or a salt thereof or a solvate thereof potently inhibits liver glycogen phosphorylase, and, therefore, is useful as a therapeutic or prophylactic agent for diabetes. wherein each symbol denotes as described in the specification.

  本发明的吡唑化合物由以下通式（I）表示。本发明的吡唑化合物或其盐或其溶液能有效抑制肝糖原磷酸化酶，因此可用作糖尿病的治疗或预防药物。 其中各符号表示如说明书所述。
• PYRAZOLE COMPOUNDS AND USE THEREOF
  申请人：Takagi Masaki

  公开号：US20090036450A1

  公开（公告）日：2009-02-05

  The pyrazole compound of the present invention is represented by the following general formula (I). The pyrazole compound of the present invention or a salt thereof or a solvate thereof potently inhibits liver glycogen phosphorylase, and, therefore, is useful as a therapeutic or prophylactic agent for diabetes. wherein each symbol denotes as described in the specifications.

  本发明的吡唑化合物由以下一般式（I）表示。本发明的吡唑化合物或其盐或溶剂化物强力抑制肝糖原磷酸化酶，因此，可用作糖尿病的治疗或预防剂。其中，每个符号如规范中所述。
• 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.