2-[(3-Pyridinylmethyl)amino]thieno[3,2-d]pyrimidine-4-carboxylic acid | 1135299-25-0

• 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-[(3-Pyridinylmethyl)amino]thieno[3,2-d]pyrimidine-4-carboxylic acid
• 英文别名: 2-(pyridin-3-ylmethylamino)thieno[3,2-d]pyrimidine-4-carboxylic acid
• CAS: 1135299-25-0
• 化学式: C₁₃H₁₀N₄O₂S
• 分子量: 286.314
• InChiKey: LKGCKISEGRISGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[(3-Pyridinylmethyl)amino]thieno[3,2-d]pyrimidine-4-carboxylic acid 在 氯化亚砜 作用下， 以 甲醇 为溶剂， 生成 2-[(pyridin-3-ylmethyl)amino]thieno[3,2-d]pyrimidine-4-carboxylic acid methyl ester
  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
• 作为产物：
  描述：

  在 盐酸 作用下， 以 水 为溶剂， 生成 2-[(3-Pyridinylmethyl)amino]thieno[3,2-d]pyrimidine-4-carboxylic acid
  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] THIENOPYRIMIDINE COMPOUNDS AND COMPOSITIONS<br/>[FR] COMPOSÉS DÉTHIÉNOPYRIMIDINE ET COMPOSITIONS
  申请人：VERNALIS R & D LTD

  公开号：WO2009037468A1

  公开（公告）日：2009-03-26

  Compounds of formula (I) are A2B wherein R1 and R2 are independently selected from hydrogen, or optionally substituted CrC6 alkyl, C1-C6 alkoxy-( C1-C6 )-alkyl, C3-C8 cycloalkyl, aryl, heteroaryl, aryl-( C1-C6 )-alkyl, or heteroaryl-( C1-C6 )-alkyl; or R-1 and R2 taken together with the nitrogen atom to which they are attached form an optionally substituted 5- or 6-membered ring; R3 and R4 are independently selected from hydrogen, or optionally substituted C1-C6 alkyl, C1-C6 alkoxy-( C1-C6 )-alkyl, C3- C8 cycloalkyl, aryl, heteroaryl, aryl-( C1-C6 )-alkyl, or heteroaryl- C1-C6 )-alkyl; or R3 and R4 taken together with the nitrogen atom to which they are attached form an optionally substituted 5- or 6-membered ring; R5 and R6 are independently selected from hydrogen, C1-C6 alkyl, aryl, aryl-( C1-C6 )-alkyl, - NHR7 -N(-R8)-R9, -NH-(C=O)-R10, -(C=O)-NH-R11, -(C=O)-O-R12, or halo; and R7, R8, R9, R10, R-11, and R12 are independently selected from C1-C6 alkyl, aryl, aryl-( C1-C6 )-alkyl and heteroaryl.

  式(I)的化合物为A2B，其中R1和R2独立选择氢，或可选取代的CrC6烷基，C1-C6烷氧基-(C1-C6)-烷基，C3-C8环烷基，芳基，杂芳基，芳基-(C1-C6)-烷基，或杂芳基-(C1-C6)-烷基；或R1和R2与它们附着的氮原子一起形成可选取代的5-或6-成员环；R3和R4独立选择氢，或可选取代的C1-C6烷基，C1-C6烷氧基-(C1-C6)-烷基，C3-C8环烷基，芳基，杂芳基，芳基-(C1-C6)-烷基，或杂芳基-(C1-C6)-烷基；或R3和R4与它们附着的氮原子一起形成可选取代的5-或6-成员环；R5和R6独立选择氢，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独立选择C1-C6烷基，芳基，芳基-(C1-C6)-烷基和杂芳基。
• 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。
• US8354415B2
  申请人：——

  公开号：US8354415B2

  公开（公告）日：2013-01-15