5-(benzo[1,3]dioxol-5-yl)pyrimidine-4,6-diol | 926008-54-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5-(benzo[1,3]dioxol-5-yl)pyrimidine-4,6-diol
• 英文别名: 5-(1,3-benzodioxol-5-yl)-4-hydroxy-1H-pyrimidin-6-one
• CAS: 926008-54-0
• 化学式: C₁₁H₈N₂O₄
• 分子量: 232.196
• InChiKey: OTGWDUKSLXORMA-UHFFFAOYSA-N

物化性质

• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  80.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(benzo[1,3]dioxol-5-yl)pyrimidine-4,6-diol 在 bis-triphenylphosphine-palladium(II) chloride ammonium hydroxide 、 copper(l) iodide 、 氢碘酸 、 三乙胺 、 sodium iodide 、 三氯氧磷 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 110.0h， 生成 5-(benzo[1,3]dioxol-5-yl)-6-trimethylsilanylethynylpyrimidin-4-ylamine
  参考文献：
  名称：

  4-Amino-5-aryl-6-arylethynylpyrimidines: Structure–activity relationships of non-nucleoside adenosine kinase inhibitors

  摘要：

  A series of non-nucleoside adenosine kinase (AK) inhibitors is reported. These inhibitors originated from the modification of 5-(3-bromophenyl)-7-(6-morpholin-4-ylpyridin-3-yl)pyrido[2,3-d]pyrimidin-4-ylamine (ABT-702). The identification of a linker that would approximate the spatial arrangement found between the pyrimidine ring and the aryl group at C(7) in ABT702 was a key element in this modification. A search of potential linkers led to the discovery of an acetylene moiety as a suitable scaffold. It was hypothesized that the aryl acetylenes, ABT-702, and adenosine bound to the active site of AK (closed form) in a similar manner with respect to the orientation of the heterocyclic base. Although potent acetylene analogs were discovered based on this assumption, an X-ray crystal structure of 5-(4-dimethylaminophenyl)-6-(6-morpholin-4-yipyridin-3-ylethynyl)pyrimidin-4-ylamine (16a) revealed a binding orientation contrary to adenosine. In addition, this compound bound tightly to a unique open conformation of AK. The structure-activity relationships and unique ligand orientation and protein conformation are discussed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.12.029
• 作为产物：
  描述：

  苯并[1,3]二氧代l-5-乙酸甲酯 在 sodium 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 46.0h， 生成 5-(benzo[1,3]dioxol-5-yl)pyrimidine-4,6-diol
  参考文献：
  名称：

  PYRIMIDINE SULFAMIDE DERIVATIVE AND PREPARATION METHOD AND MEDICAL APPLICATION THEREOF

  摘要：

  揭示了一系列嘧啶磺胺化合物及其在制备与ET受体拮抗剂相关疾病的药物中的应用。具体地，揭示了由式(I)表示的衍生化合物，或其互变异构体或药用可接受的组合物。

  公开号：

  US20200283425A1

文献信息

• Pyrimidine sulfamide derivative and preparation method and medical application thereof
  申请人：SHIJIAZHUANG SAGACITY NEW DRUG DEVELOPMENT CO., LTD.

  公开号：US11319305B2

  公开（公告）日：2022-05-03

  Disclosed are a series of pyrimidine sulfamide compounds and applications thereof in preparing a drug for a disease related to an ETA receptor antagonist. In particular, disclosed is a derived compound represented by formula (I) or a tautomer or pharmaceutically acceptable composition thereof.

  公开了一系列嘧啶硫酰胺化合物及其在制备与 ETA 受体拮抗剂有关的疾病药物中的应用。特别是公开了由式（I）代表的衍生化合物或其同系物或药学上可接受的组合物。
• [EN] AZOBENZENE COMPOUND AND APPLICATION THEREOF<br/>[FR] COMPOSÉ AZOBENZÈNE ET SON APPLICATION<br/>[ZH] 氮杂联苯类化合物及其应用
  申请人：[en]CHIA TAI TIANQING PHARMACEUTICAL GROUP CO., LTD.;[zh]正大天晴药业集团股份有限公司

  公开号：WO2023078463A1

  公开（公告）日：2023-05-11

  一种氮杂联苯类化合物及其应用，具体公开了式(A)所示化合物及其药学上可接受的盐。
• PYRIMIDINE SULFAMIDE DERIVATIVE AND PREPARATION METHOD AND MEDICAL APPLICATION THEREOF
  申请人：SHIJIAZHUANG SAGACITY NEW DRUG DEVELOPMENT CO., LTD.

  公开号：US20200283425A1

  公开（公告）日：2020-09-10

  Disclosed are a series of pyrimidine sulfamide compounds and applications thereof in preparing a drug for a disease related to an ET A receptor antagonist. In particular, disclosed is a derived compound represented by formula (I) or a tautomer or pharmaceutically acceptable composition thereof.

  揭示了一系列嘧啶磺胺化合物及其在制备与ET受体拮抗剂相关疾病的药物中的应用。具体地，揭示了由式(I)表示的衍生化合物，或其互变异构体或药用可接受的组合物。
• 4-Amino-5-aryl-6-arylethynylpyrimidines: Structure–activity relationships of non-nucleoside adenosine kinase inhibitors
  作者：Mark A. Matulenko、Ernest S. Paight、Robin R. Frey、Arthur Gomtsyan、Stanley DiDomenico、Meiqun Jiang、Chih-Hung Lee、Andrew O. Stewart、Haixia Yu、Kathy L. Kohlhaas、Karen M. Alexander、Steve McGaraughty、Joseph Mikusa、Kennan C. Marsh、Steven W. Muchmore、Clarissa L. Jakob、Elizabeth A. Kowaluk、Michael F. Jarvis、Shripad S. Bhagwat

  DOI：10.1016/j.bmc.2006.12.029

  日期：2007.2

  A series of non-nucleoside adenosine kinase (AK) inhibitors is reported. These inhibitors originated from the modification of 5-(3-bromophenyl)-7-(6-morpholin-4-ylpyridin-3-yl)pyrido[2,3-d]pyrimidin-4-ylamine (ABT-702). The identification of a linker that would approximate the spatial arrangement found between the pyrimidine ring and the aryl group at C(7) in ABT702 was a key element in this modification. A search of potential linkers led to the discovery of an acetylene moiety as a suitable scaffold. It was hypothesized that the aryl acetylenes, ABT-702, and adenosine bound to the active site of AK (closed form) in a similar manner with respect to the orientation of the heterocyclic base. Although potent acetylene analogs were discovered based on this assumption, an X-ray crystal structure of 5-(4-dimethylaminophenyl)-6-(6-morpholin-4-yipyridin-3-ylethynyl)pyrimidin-4-ylamine (16a) revealed a binding orientation contrary to adenosine. In addition, this compound bound tightly to a unique open conformation of AK. The structure-activity relationships and unique ligand orientation and protein conformation are discussed. (c) 2006 Elsevier Ltd. All rights reserved.