3,7-dimethyl-1-((tetrahydrofuran-2-yl)methyl)-1H-purin-2,6(3H,7H)-dione | 1305317-99-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 3,7-dimethyl-1-((tetrahydrofuran-2-yl)methyl)-1H-purin-2,6(3H,7H)-dione
• 英文别名: 3,7-dimethyl-1-((tetrahydrofuran-2-yl)methyl)-1H-purine-2,6(2H,6H)-dione；3,7-Dimethyl-1-(oxolan-2-ylmethyl)purine-2,6-dione；3,7-dimethyl-1-(oxolan-2-ylmethyl)purine-2,6-dione
• CAS: 1305317-99-0
• 化学式: C₁₂H₁₆N₄O₃
• 分子量: 264.284
• InChiKey: HSJYPHSHRSXMEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,7-dimethyl-1-((tetrahydrofuran-2-yl)methyl)-1H-purin-2,6(3H,7H)-dione 在 过氧化氢异丙苯 、 还原型辅酶II(NADPH)四钠盐 、 cytochrome P₄₅₀ 3A₄ 作用下， 反应 1.5h， 以100%的产率得到5-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)-4-hydroxypentanal
  参考文献：
  名称：

  Predictable Stereoselective and Chemoselective Hydroxylations and Epoxidations with P450 3A4

  摘要：

  Enantioselective hydroxylation of one specific methylene in the presence of many similar groups is debatably the most challenging chemical transformation. Although chemists have recently made progress toward the hydroxylation of inactivated C-H bonds, enzymes such as P450s (CYPs) remain unsurpassed in specificity and scope. The substrate promiscuity of many P450s is desirable for synthetic applications; however, the inability to predict the products of these enzymatic reactions is impeding advancement. We demonstrate here the utility of a chemical auxiliary to control the selectivity of CYP3A4 reactions. When linked to substrates, inexpensive, achiral theobromine directs the reaction to produce hydroxylation or epoxidation at the fourth carbon from the auxiliary with pro-R facial selectivity. This strategy provides a versatile yet controllable system for regio-, chemo-, and stereoselective oxidations at inactivated C-H bonds and demonstrates the utility of chemical auxiliaries to mediate the activity of highly promiscuous enzymes.

  DOI：

  10.1021/ja200551y
• 作为产物：
  描述：

  可可碱 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 0.33h， 以81%的产率得到3,7-dimethyl-1-((tetrahydrofuran-2-yl)methyl)-1H-purin-2,6(3H,7H)-dione
  参考文献：
  名称：

  Predictable Stereoselective and Chemoselective Hydroxylations and Epoxidations with P450 3A4

  摘要：

  Enantioselective hydroxylation of one specific methylene in the presence of many similar groups is debatably the most challenging chemical transformation. Although chemists have recently made progress toward the hydroxylation of inactivated C-H bonds, enzymes such as P450s (CYPs) remain unsurpassed in specificity and scope. The substrate promiscuity of many P450s is desirable for synthetic applications; however, the inability to predict the products of these enzymatic reactions is impeding advancement. We demonstrate here the utility of a chemical auxiliary to control the selectivity of CYP3A4 reactions. When linked to substrates, inexpensive, achiral theobromine directs the reaction to produce hydroxylation or epoxidation at the fourth carbon from the auxiliary with pro-R facial selectivity. This strategy provides a versatile yet controllable system for regio-, chemo-, and stereoselective oxidations at inactivated C-H bonds and demonstrates the utility of chemical auxiliaries to mediate the activity of highly promiscuous enzymes.

  DOI：

  10.1021/ja200551y

文献信息

• HYDROXYL PURINE COMPOUNDS AND USE THEREOF
  申请人：GUANGDONG ZHONGSHENG PHARMACEUTICAL CO., LTD

  公开号：US20180148451A1

  公开（公告）日：2018-05-31

  Disclosed are a series of hydroxyl purine compounds and the use thereof as PDE2 or TNFα inhibitors, in particular, the compounds as shown in formula (I), or tautomers or pharmaceutically acceptable salts thereof.

  揭示了一系列的羟基嘌呤化合物及其作为PDE2或TNFα抑制剂的用途，特别是如公式(I)所示的化合物，或其互变异构体或药用可接受的盐。
• Hydroxyl purine compounds and use thereof
  申请人：GUANGDONG RAYNOVENT BIOTECH CO., LTD.

  公开号：US10618898B2

  公开（公告）日：2020-04-14

  Disclosed are a series of hydroxyl purine compounds and the use thereof as PDE2 or TNFα inhibitors, in particular, the compounds as shown in formula (I), or tautomers or pharmaceutically acceptable salts thereof.

  公开了一系列羟基嘌呤化合物及其作为 PDE2 或 TNFα 抑制剂的用途，特别是如式 (I) 所示的化合物或其同系物或药学上可接受的盐。
• [EN] HYDROXYL PURINE COMPOUNDS AND USE THEREOF<br/>[FR] COMPOSÉS D'HYDROXYLE PURINE ET UTILISATION DE CEUX-CI<br/>[ZH] 羟基嘌呤类化合物及其应用
  申请人：MEDSHINE DISCOVERY INC

  公开号：WO2016184313A1

  公开（公告）日：2016-11-24

  本发明公开了一系列羟基嘌呤类化合物及其作为PDE2或TNFα抑制剂的应用，具体公开了式(Ⅰ)所示化合物、其互变异构体或其药学上可接受的盐。
• Predictable Stereoselective and Chemoselective Hydroxylations and Epoxidations with P450 3A4
  作者：Aaron T. Larsen、Erin M. May、Karine Auclair

  DOI：10.1021/ja200551y

  日期：2011.5.25

  Enantioselective hydroxylation of one specific methylene in the presence of many similar groups is debatably the most challenging chemical transformation. Although chemists have recently made progress toward the hydroxylation of inactivated C-H bonds, enzymes such as P450s (CYPs) remain unsurpassed in specificity and scope. The substrate promiscuity of many P450s is desirable for synthetic applications; however, the inability to predict the products of these enzymatic reactions is impeding advancement. We demonstrate here the utility of a chemical auxiliary to control the selectivity of CYP3A4 reactions. When linked to substrates, inexpensive, achiral theobromine directs the reaction to produce hydroxylation or epoxidation at the fourth carbon from the auxiliary with pro-R facial selectivity. This strategy provides a versatile yet controllable system for regio-, chemo-, and stereoselective oxidations at inactivated C-H bonds and demonstrates the utility of chemical auxiliaries to mediate the activity of highly promiscuous enzymes.