N,N-diethyl-6-phenylthieno[2,3-d]pyrimidin-4-amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: N,N-diethyl-6-phenylthieno[2,3-d]pyrimidin-4-amine
• 化学式: C₁₆H₁₇N₃S
• 分子量: 283.397
• InChiKey: YAJMHFAINLVTDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-苯基-3H-噻吩并[2,3-d]嘧啶-4-酮 在 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 异丙醇 、 甲苯 为溶剂， 生成 N,N-diethyl-6-phenylthieno[2,3-d]pyrimidin-4-amine
  参考文献：
  名称：

  Subtle modifications to a thieno[2,3-d]pyrimidine scaffold yield negative allosteric modulators and agonists of the dopamine D2 receptor

  摘要：

  We recently described a structurally novel series of negative allosteric modulators (NAMs) of the dopamine D-2 receptor (D2R) based on thieno[2,3-d]pyrimidine 1, showing it can be structurally simplified to reveal low molecular weight, fragment-like NAMs that retain robust negative cooperativity, such as 3. Herein, we report the synthesis and functional profiling of analogues of 3, placing specific emphasis on examining secondary and tertiary amino substituents at the 4-position, combined with a range of substituents at the 5/6-positions (e.g. aromatic/aliphatic carbocycles). We identify analogues with diverse pharmacology at the D2R including NAMs with sub-mu M affinity (9h) and, surprisingly, low efficacy partial agonists (9d and 9i). (C) 2019 Published by Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.01.061

文献信息

• Rapid Access to Kinase Inhibitor Pharmacophores by Regioselective C–H Arylation of Thieno[2,3-<i>d</i>]pyrimidine
  作者：Shuya Yamada、Kaylin Nicole Flesch、Kei Murakami、Kenichiro Itami

  DOI：10.1021/acs.orglett.0c00143

  日期：2020.2.21

  Regioselective C-H arylations of thieno[2,3-d]pyrimidine are accomplished under palladium catalysis. Thieno[2,3-d]pyrimidines react with aryl iodides at the C6-position and with aryl boronic acids at the C5-position, showing excellent regioselectivity. Mechanistic investigations indicate that the regioselectivity is controlled by the nature of the palladium catalyst: the cationic palladium favorably

  噻吩并[2,3-d]嘧啶的区域选择性CH芳基化反应在钯催化下完成。噻吩并[2,3-d]嘧啶在C6位与芳基碘化物和在C5位与芳基硼酸反应，表现出出色的区域选择性。机理研究表明，区域选择性受钯催化剂的性质控制：阳离子钯有利地使C5-位芳基化。在激酶抑制剂及其衍生物的简化合成中，突出了这种直接芳基化的效用。
• ARYL HYDROCARBON RECEPTOR ANTAGONISTS AND METHODS OF USE
  申请人：Magenta Therapeutics Inc.

  公开号：US20210220408A1

  公开（公告）日：2021-07-22

  The disclosure relates to aryl hydrocarbon receptor antagonists as well as methods of modulating aryl hydrocarbon receptor activity and expanding hematopoietic stem cells by culturing hematopoietic stem or progenitor cells in the presence of these agents. Additionally, the disclosure provides methods of treating various pathologies, such as cancer, by administration of these aryl hydrocarbon receptor antagonists. Additionally, the disclosure provides methods of treating various pathologies in a patient by administration of expanded hematopoietic stem cells. The disclosure further provides kits containing aryl hydrocarbon receptor antagonists that can be used for the expansion of hematopoietic stem cells. The disclosure further relates to pharmaceutical compositions comprising the compounds and methods of treating or preventing a disease in which aryl hydrocarbon receptor plays a role.
• Subtle modifications to a thieno[2,3-d]pyrimidine scaffold yield negative allosteric modulators and agonists of the dopamine D2 receptor
  作者：Tim J. Fyfe、Barrie Kellam、Shailesh N. Mistry、Peter J. Scammells、J. Robert Lane、Ben Capuano

  DOI：10.1016/j.ejmech.2019.01.061

  日期：2019.4

  We recently described a structurally novel series of negative allosteric modulators (NAMs) of the dopamine D-2 receptor (D2R) based on thieno[2,3-d]pyrimidine 1, showing it can be structurally simplified to reveal low molecular weight, fragment-like NAMs that retain robust negative cooperativity, such as 3. Herein, we report the synthesis and functional profiling of analogues of 3, placing specific emphasis on examining secondary and tertiary amino substituents at the 4-position, combined with a range of substituents at the 5/6-positions (e.g. aromatic/aliphatic carbocycles). We identify analogues with diverse pharmacology at the D2R including NAMs with sub-mu M affinity (9h) and, surprisingly, low efficacy partial agonists (9d and 9i). (C) 2019 Published by Elsevier Masson SAS. All rights reserved.