2-iodo-4-methoxy-6-methylpyrimidine | 69696-32-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-iodo-4-methoxy-6-methylpyrimidine
• CAS: 69696-32-8
• 化学式: C₆H₇IN₂O
• 分子量: 250.039
• InChiKey: SAQCUSKHXJPHBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  35
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-iodo-4-methoxy-6-methylpyrimidine 在 copper(l) iodide 、 正丁基锂 、 3,4,7,8-四甲基-1,10-菲罗啉 、 caesium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.75h， 生成 2-(azetidin-1-yl)-4-methoxy-6-hexadecylpyrimidine
  参考文献：
  名称：

  [EN] THERAPEUTIC COMPOUNDS
  [FR] COMPOSÉS THÉRAPEUTIQUES

  摘要：

  公开号：

  WO2016133959A9
• 作为产物：
  描述：

  2-氨基-4-甲氧基-6-甲基嘧啶 在 copper(l) iodide 、 二碘甲烷 、 碘 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以37%的产率得到2-iodo-4-methoxy-6-methylpyrimidine
  参考文献：
  名称：

  Optimization of pyrimidinol antioxidants as mitochondrial protective agents: ATP production and metabolic stability

  摘要：

  Previously we described a novel series of pyrimidinol antioxidants and their structural optimization as potential therapeutic agents for neurodegenerative and mitochondrial disorders. Our initial lead compound was a potent antioxidant in vitro, but was subsequently found to exhibit poor stability to oxidative metabolism. The current study focused on balancing potency with metabolic stability through structural modification, and involved modifications at positions 2 and 4 of the pyrimidinol redox core, likely sites of oxidative metabolism. Eight new analogues have been prepared and their ability to suppress lipid peroxidation and reactive oxygen species (ROS), and to preserve mitochondrial membrane potential (Delta psi(m)) and support ATP production, has been investigated. The metabolic stability of the prepared compounds was also assessed in vitro using bovine liver microsomes to obtain preliminary insight on this class of compounds. This study revealed the complexity of balancing reasonable metabolic stability with efficient antioxidant properties. While a few analogues appear promising, especially in terms of metabolic stability, a 4-isopropoxy derivative conserved the favorable biological activity and exhibited good metabolic stability. The favorable metabolic stability conferred by the combination of the azetidine and isopropoxy moieties in analogue 6 makes this compound an excellent candidate for further evaluation. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.08.039

文献信息

• PHARMACEUTICAL COMPOSITIONS COMPRISING DEUTERATED AND UNDEUTERATED 2-AMINO-PYRIMIDIN-5-OL DERIVATIVES FOR TREATING MITOCHONDRIAL DISEASES (E.G. OBESITY)
  申请人：Arizona Board of Regents on behalf of Arizona State University

  公开号：EP3719006A1

  公开（公告）日：2020-10-07

  Pharmaceutical compositions comprising Compounds of formula I and salts thereof are disclosed. Also disclosed are isotopes of compounds of formula I of the salts thereof, processes for preparing compounds of formula I, intermediates useful for preparing compounds of formula I and therapeutic methods using a compound of formula I or a pharmaceutical composition thereof.

  由式 I 化合物组成的药物组合物 及其盐类组成的药物组合物。 还公开了式 I 化合物及其盐的同位素、制备式 I 化合物的工艺、制备式 I 化合物的中间体以及使用式 I 化合物或其药物组合物的治疗方法。
• Therapeutic compounds
  申请人：ARIZONA BOARD OF REGENTS ON BEHALF OF ARIZONA STATE UNIVERSITY

  公开号：US10364227B2

  公开（公告）日：2019-07-30

  Compounds of formula (I) and salts are disclosed. Also disclosed are isotopes of compounds of formula I of the salts thereof. Pharmaceutical compositions comprising a compound of formula I, processes for preparing compounds of formula I, intermediates useful for preparing compounds of formula I and therapeutic methods using a compound of formula I are disclosed.

  公开了式 (I) 化合物及其盐类。还公开了式 I 化合物的同位素及其盐类。公开了包含式 I 化合物的药物组合物、制备式 I 化合物的工艺、用于制备式 I 化合物的中间体以及使用式 I 化合物的治疗方法。
• EDO KIYOTO; SAKAMOTO TAKAO; YAMANAKA HIROSHI, CHEM. AND PHARM. BULL., 1978, 26, NO 12, 3843-3850
  作者：EDO KIYOTO、 SAKAMOTO TAKAO、 YAMANAKA HIROSHI

  DOI：——

  日期：——
• THERAPEUTIC COMPOUNDS
  申请人：Arizona Board of Regents on behalf of Arizona State University

  公开号：EP3259254A1

  公开（公告）日：2017-12-27
• DEUTERATED AND UNDEUTERATED 2-AMINO-PYRIMIDIN-5-OL DERIVATIVES FOR TREATING MITOCHONDRIAL DISEASES (E.G. OBESITY)
  申请人：Arizona Board of Regents on behalf of Arizona State University

  公开号：EP3259254B1

  公开（公告）日：2020-07-01