2-[(pyridin-3-ylmethyl)amino]thieno[3,2-d]pyrimidine-4-carboxylic acid isopropylamide | 1135299-05-6

• 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: 2-[(pyridin-3-ylmethyl)amino]thieno[3,2-d]pyrimidine-4-carboxylic acid isopropylamide
• 英文别名: 2-[(Pyridin-3-ylmethyl)-amino]-thieno[3,2-d]pyrimidine-4-carboxylic acid iso-propylamide；N-propan-2-yl-2-(pyridin-3-ylmethylamino)thieno[3,2-d]pyrimidine-4-carboxamide
• CAS: 1135299-05-6
• 化学式: C₁₆H₁₇N₅OS
• 分子量: 327.41
• InChiKey: CDUCLUZYLNLKKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-[(pyridin-3-ylmethyl)amino]thieno[3,2-d]pyrimidine-4-carboxylic acid methyl ester 、 异丙胺 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以24%的产率得到2-[(pyridin-3-ylmethyl)amino]thieno[3,2-d]pyrimidine-4-carboxylic acid isopropylamide
  参考文献：
  名称：

  Discovery and optimization of potent and selective functional antagonists of the human adenosine A2B receptor

  摘要：

  We herein report the discovery of a novel class of antagonists of the human adenosine A2B receptor. This low molecular weight scaffold has been optimized to offer derivatives with potential utility for the alleviation of conditions associated with this receptor subtype, such as nociception, diabetes, asthma and COPD. Furthermore, preliminary pharmacokinetic analysis has revealed compounds with profiles suitable for either inhaled or systemic routes of administration. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.08.040

文献信息

• [EN] COMPOUNDS AND METHODS FOR MODULATING ADENOSINE A2B RECEPTOR AND ADENOSINE A2A RECEPTOR<br/>[FR] COMPOSÉS ET PROCÉDÉS DE MODULATION DU RÉCEPTEUR A2B DE L'ADÉNOSINE ET DU RÉCEPTEUR A2A DE L'ADÉNOSINE
  申请人：CORVUS PHARMACEUTICALS INC

  公开号：WO2019046784A1

  公开（公告）日：2019-03-07

  Disclosed herein, inter alia, are compositions and methods for modulating Adenosine Receptors. In an aspect is provided a method of inhibiting Adenosine A2B Receptor activity and Adenosine A2A Receptor activity, the method including contacting the Adenosine A2B Receptor and Adenosine A2A Receptor with a compound as described herein, including embodiments.

  在此披露的内容包括调节腺苷受体的组合物和方法。在一个方面，提供了一种抑制腺苷A2B受体活性和腺苷A2A受体活性的方法，该方法包括将腺苷A2B受体和腺苷A2A受体与本文描述的化合物接触，包括各种实施方式。
• THIENOPYRIMIDINE COMPOUNDS AND COMPOSITIONS
  申请人：Jordan Allan

  公开号：US20100298349A1

  公开（公告）日：2010-11-25

  Compounds of formula (I) are A 2B wherein R 1 and R 2 are independently selected from hydrogen, or optionally substituted CrC6 alkyl, C 1 -C 6 alkoxy-(C 1 -C 6 )-alkyl, C 3 -C 8 cycloalkyl, aryl, heteroaryl, aryl-(C 1 -C 6 )-alkyl, or heteroaryl-(C 1 -C 6 ) -alkyl; or R −1 and R 2 taken together with the nitrogen atom to which they are attached form an optionally substituted 5- or 6-membered ring; R 3 and R 4 are independently selected from hydrogen, or optionally substituted C 1 -C 6 alkyl, C 1 -C 6 alkoxy-(C 1 -C 6 )-alkyl, C 3 -C 8 cycloalkyl, aryl, heteroaryl, aryl-(C 1 -C 6 )-alkyl, or heteroaryl-C 1 -C 6 )-alkyl; or R 3 and R 4 taken together with the nitrogen atom to which they are attached form an optionally substituted 5- or 6-membered ring; R 5 and R 6 are independently selected from hydrogen, C 1 -C 6 alkyl, aryl, aryl-(C 1 -C 6 )-alkyl, —NHR 7 —N(—R 8 )—R 9 , —NH—(C═O)—R 10 , —(C═O)—NH—R 11 , —(C═O)—O—R 12 , or halo; and R 7 , R 8 , R 9 , R 10 , R −11 , and R 12 are independently selected from C 1 -C 6 alkyl, aryl, aryl-(C 1 -C 6 )-alkyl and heteroaryl.

  公式（I）的化合物为A2B，其中R1和R2独立地选择氢，或者可选地取代的CrC6烷基，C1-C6氧代烷基，C3-C8环烷基，芳基，杂环芳基，芳基-(C1-C6)-烷基，或杂环芳基-(C1-C6)-烷基；或者R-1和R2与它们附着的氮原子一起形成可选地取代的5-或6-成员环；R3和R4独立地选择氢，或者可选地取代的C1-C6烷基，C1-C6氧代烷基，C3-C8环烷基，芳基，杂环芳基，芳基-(C1-C6)-烷基，或杂环芳基-(C1-C6)-烷基；或者R3和R4与它们附着的氮原子一起形成可选地取代的5-或6-成员环；R5和R6独立地选择氢，C1-C6烷基，芳基，芳基-(C1-C6)-烷基，—NHR7—N(—R8)—R9，—NH—(C═O)—R10，—(C═O)—NH—R11，—(C═O)—O—R12，或卤素；而R7、R8、R9、R10、R-11和R12独立地选择C1-C6烷基，芳基，芳基-(C1-C6)-烷基和杂环芳基。
• Compounds and methods for modulating adenosine A2B receptor and adenosine A2A receptor
  申请人：Corvus Pharmaceuticals, Inc.

  公开号：US11254686B1

  公开（公告）日：2022-02-22

  Disclosed herein, inter alia, are certain substituted thieno[3,2-b]pyrimidine compositions and methods for modulating Adenosine Receptors, for example, having the formula:

  本文特别披露了用于调节腺苷受体的某些取代的噻吩并[3,2-b]嘧啶组合物和方法，例如，具有以下式子的组合物和方法：
• US8354415B2
  申请人：——

  公开号：US8354415B2

  公开（公告）日：2013-01-15
• Discovery and optimization of potent and selective functional antagonists of the human adenosine A2B receptor
  作者：Simon T. Bedford、Karen R. Benwell、Teresa Brooks、Ijen Chen、Mike Comer、Sarah Dugdale、Tim Haymes、Allan M. Jordan、Guy A. Kennett、Anthony R. Knight、Burkhard Klenke、Loic LeStrat、Angela Merrett、Anil Misra、Sean Lightowler、Anthony Padfield、Karine Poullennec、Mark Reece、Heather Simmonite、Melanie Wong、Ian A. Yule

  DOI：10.1016/j.bmcl.2009.08.040

  日期：2009.10

  We herein report the discovery of a novel class of antagonists of the human adenosine A2B receptor. This low molecular weight scaffold has been optimized to offer derivatives with potential utility for the alleviation of conditions associated with this receptor subtype, such as nociception, diabetes, asthma and COPD. Furthermore, preliminary pharmacokinetic analysis has revealed compounds with profiles suitable for either inhaled or systemic routes of administration. (C) 2009 Elsevier Ltd. All rights reserved.