5-amino-2-cyclopropyl-4,6-dichloropyrimidine | 75438-70-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-amino-2-cyclopropyl-4,6-dichloropyrimidine
• 英文别名: 4,6-dichloro-2-cyclopropylpyrimidin-5-amine
• CAS: 75438-70-9
• 化学式: C₇H₇Cl₂N₃
• 分子量: 204.059
• InChiKey: OAIPRQSPYGPMAG-UHFFFAOYSA-N

物化性质

• 沸点：
  311.9±37.0 °C(Predicted)
• 密度：
  1.569±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-amino-2-cyclopropyl-4,6-dichloropyrimidine 在 氨 、 溶剂黄146 、 N,N-二异丙基乙胺 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 N-甲基吡咯烷酮 、 二氯甲烷 、 水 为溶剂， 反应 22.5h， 生成 5-Cyclopropyl-3-(oxan-2-ylmethyl)triazolo[4,5-d]pyrimidin-7-amine
  参考文献：
  名称：

  Discovery of triazolopyrimidine-based PDE8B inhibitors: Exceptionally ligand-efficient and lipophilic ligand-efficient compounds for the treatment of diabetes

  摘要：

  PDE8B is a cAMP-specific isoform of the broader class of phosphodiesterases (PDEs). As no selective PDE8B inhibitors had been reported, a high throughput screen was run with the goal of identifying selective tools for exploring the potential therapeutic utility of PDE8B inhibition. Of the numerous hits, one was particularly attractive since it was amenable to rapid deconstruction leading to inhibitors with very high ligand efficiency (LE) and lipophilic ligand efficiency (LLE). These triazolopyrimidines were optimized for potency, selectivity and ADME properties ultimately leading to compound 42. This compound was highly potent and selective with good bioavailability and advanced into pre-clinical development. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.079
• 作为产物：
  描述：

  4,6-二氯-2-环丙基-5-硝基嘧啶 在 镍 二氯甲烷 、 环己烷 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、1333.22 MPa 条件下， 反应 6.0h， 以41 g of 2-cyclopropyl-4,6-dichloro-5-amino-pyrimidine is obtained的产率得到5-amino-2-cyclopropyl-4,6-dichloropyrimidine
  参考文献：
  名称：

  Substituted aminopyrimidines

  摘要：

  本发明涉及一些通式为 ##STR1## 的氨基嘧啶，其中R.sup.1、R.sup.2和R.sup.3为氢、卤素、烷氧基、烷硫基或1至4个碳原子的烷基，或3至5个碳原子的环烷基，R.sup.4为氢或脂肪族或芳香族酰基，以及其生理兼容的酸加成盐。本发明的化合物可用作降血压剂和青光眼治疗剂。

  公开号：

  US04323570A1

文献信息

• Substituted aminopyrimidines
  申请人：Beiersdorf Aktiengesellschaft

  公开号：US04323570A1

  公开（公告）日：1982-04-06

  The present invention is directed to certain aminopyrimidines of the general formula ##STR1## wherein R.sup.1, R.sup.2, and R.sup.3 are hydrogen, halogen, alkoxy, alkylthio, or alkyl having 1 to 4 carbon atoms, or cycloalkyl having 3 to 5 carbon atoms and R.sup.4 is hydrogen or an aliphatic or aromatic acyl group, as well as physiologically compatible acid addition salts thereof. Compounds of the present invention are useful as blood pressure lowering agents and in the treatment of glaucoma.

  本发明涉及一些氨基嘧啶，其一般式为##STR1##其中R.sup.1、R.sup.2和R.sup.3为氢、卤素、烷氧基、烷基硫基或具有1至4个碳原子的烷基，或具有3至5个碳原子的环烷基，R.sup.4为氢或脂肪族或芳香族酰基，以及其生理兼容性酸盐。本发明的化合物可用作降血压剂和青光眼治疗。
• [EN] SUBSTITUTED TRIAZOLOPYRIMIDINES AS PDE8 INHIBITORS<br/>[FR] TRIAZOLOPYRIMIDINES SUBSTITUÉES COMME INHIBITEURS DE PDE8
  申请人：PFIZER

  公开号：WO2011058478A1

  公开（公告）日：2011-05-19

  Compounds of Formula (I): wherein R1 , R2, R3, R4, and R5 are as defined herein, are disclosed.

  式(I)的化合物：其中R1，R2，R3，R4和R5如本文所定义，已被披露。
• US4323570A
  申请人：——

  公开号：US4323570A

  公开（公告）日：1982-04-06
• Discovery of triazolopyrimidine-based PDE8B inhibitors: Exceptionally ligand-efficient and lipophilic ligand-efficient compounds for the treatment of diabetes
  作者：Michael P. DeNinno、Stephen W. Wright、John B. Etienne、Thanh V. Olson、Benjamin N. Rocke、Jeffrey W. Corbett、Daniel W. Kung、Kenneth J. DiRico、Kim M. Andrews、Michele L. Millham、Janice C. Parker、William Esler、Maria van Volkenburg、David D. Boyer、Karen L. Houseknecht、Shawn D. Doran

  DOI：10.1016/j.bmcl.2012.06.079

  日期：2012.9

  PDE8B is a cAMP-specific isoform of the broader class of phosphodiesterases (PDEs). As no selective PDE8B inhibitors had been reported, a high throughput screen was run with the goal of identifying selective tools for exploring the potential therapeutic utility of PDE8B inhibition. Of the numerous hits, one was particularly attractive since it was amenable to rapid deconstruction leading to inhibitors with very high ligand efficiency (LE) and lipophilic ligand efficiency (LLE). These triazolopyrimidines were optimized for potency, selectivity and ADME properties ultimately leading to compound 42. This compound was highly potent and selective with good bioavailability and advanced into pre-clinical development. (C) 2012 Elsevier Ltd. All rights reserved.