{6-chloro-2-[(pyridin-3-ylmethyl)amino]thieno[3,2-d]pyrimidin-4-yl}thiophen-2-yl-methanone | 1131921-11-3

• 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: {6-chloro-2-[(pyridin-3-ylmethyl)amino]thieno[3,2-d]pyrimidin-4-yl}thiophen-2-yl-methanone
• 英文别名: {6-Chloro-2-[(pyridin-3-ylmethyl)-amino]-thieno[3,2-d]pyrimidin-4-yl}-thiophen-2-yl-methanone；[6-chloro-2-(pyridin-3-ylmethylamino)thieno[3,2-d]pyrimidin-4-yl]-thiophen-2-ylmethanone
• CAS: 1131921-11-3
• 化学式: C₁₇H₁₁ClN₄OS₂
• 分子量: 386.886
• InChiKey: HWFLOIWTEDBAFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  {6-chloro-2-[(pyridin-3-ylmethyl)amino]thieno[3,2-d]pyrimidin-4-yl}thiophen-2-yl-methanone 在 3,4-二甲氧基苄胺 、 三氟乙酸 作用下， 以 异丁酰胺 为溶剂， 反应 48.5h， 以10%的产率得到{6-amino-2-[(pyridin-3-ylmethyl)amino]thieno[3,2-d]pyrimidin-4-yl}thiophen-2-yl-methanone
  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：

  3-氨甲基吡啶 、 (2,6-dichlorothieno[3,2-d]pyrimidin-4-yl)thiophen-2-yl-methanone 在 silica gel 、 methanol-dichloromethane 作用下， 以 正丁醇 为溶剂， 反应 2.0h， 以affording the title compound in 38% yield, >95% purity的产率得到{6-chloro-2-[(pyridin-3-ylmethyl)amino]thieno[3,2-d]pyrimidin-4-yl}thiophen-2-yl-methanone
  参考文献：
  名称：

  THIENOPYRIMIDINE COMPOUNDS

  摘要：

  式(I)的化合物是A2B受体拮抗剂，其中R1是可选取代芳基或可选取代的5-或6-成员杂环芳基环；R2和R3独立地选择氢、C1-C6烷基、C3-C8环烷基、C3-C8环烷基-(C1-C6)-烷基、取代环部分的芳基-(C1-C6)-烷基、5-或6-成员单环杂环基，可通过C1-C6亚烷基链连接并可在环部分取代，苯并咪唑-2-基-甲基，吡啶-3-基-羰基或(1-甲基哌啶-4-基)-羰基-甲基；或R2和R3与它们所连接的氮原子一起形成可选取代的5-或6-成员环；R4是C1-C3烷基、C2-C3烯基，-N(-R5)-R6，或可选取代的杂芳基甲基氨基；R5和R6独立地选择氢或C1-C3烷基；或R5和R6与它们所连接的氮原子一起形成可选取代的4-到6-成员饱和环。

  公开号：

  US20110118284A1

文献信息

• [EN] THIENOPYRIMIDINE COMPOUNDS<br/>[FR] COMPOSÉS THIÉNOPYRIMIDINE
  申请人：VERNALIS R & D LTD

  公开号：WO2009037463A1

  公开（公告）日：2009-03-26

  Compounds of formula (I) are A2B receptor antagonists, wherein R1 is optionally substituted aryl or an optionally substituted 5- or 6- membered heteroaryl ring; R2 and R3 are independently selected from hydrogen, C1-C6 alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl-(C1-C6)-alkyl, aryl- (C1-C6)-alkyl optionally substituted in the ring part thereof, a 5- or 6-membered monocyclic heterocyclic group optionally linked via a C1-C6 alkylene chain and optionally substituted in the ring part thereof, benzimidazol-2-yl-methyl, pyrid- 3-yl-carbonyl, or (1-methyl-piperidin-4-yl)-carbonyl-methyl; or R2 and R3 taken together with the nitrogen atom to which they are attached form an optionally substituted 5- or 6-membered ring; R4 is C1-C3 alkyl, C2-C3 alkenyl, -N(-R5)- R6, or optionally substituted heteroarylmethylamino; and R5 and R6 are independently selected from hydrogen or C1-C3 alkyl; or R5 and R6 taken together with the nitrogen atonrto which they are attached form an optionally substituted 4- to 6-membered saturated ring.

  化合物的化学式（I）是A2B受体拮抗剂，其中R1是可选择地取代的芳基或可选择地取代的5-或6-成员杂芳基环；R2和R3分别选自氢、C1-C6烷基、C3-C8环烷基、C3-C8环烷基-(C1-C6)-烷基、芳基-(C1-C6)-烷基，其环部分可选择地取代，一个可选择地经过C1-C6烷基链连接并在其环部分可选择地取代的5-或6-成员单环杂环基团，苯并咪唑-2-基-甲基，吡啶-3-基-酰基，或（1-甲基哌啶-4-基）-酰基-甲基；或R2和R3与它们连接的氮原子一起形成一个可选择地取代的5-或6-成员环；R4是C1-C3烷基，C2-C3烯基，-N(-R5)-R6，或可选择地取代的杂芳基甲基氨基；R5和R6分别选自氢或C1-C3烷基；或R5和R6与它们连接的氮原子一起形成一个可选择地取代的4-至6-成员饱和环。
• Thienopyrimidine compounds
  申请人：Jordan Allan

  公开号：US09120807B2

  公开（公告）日：2015-09-01

  Compounds of formula (I) are A2B receptor antagonists, wherein R1 is optionally substituted aryl or an optionally substituted 5- or 6-membered heteroaryl ring; R2 and R3 are independently selected from hydrogen, C1-C6 alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl-(C1-C6)-alkyl, aryl-(C1-C6)-alkyl optionally substituted in the ring part thereof, a 5- or 6-membered monocyclic heterocyclic group optionally linked via a C1-C6 alkylene chain and optionally substituted in the ring part thereof, benzimidazol-2-yl-methyl, pyrid-3-yl-carbonyl, or (1-methyl-piperidin-4-yl)-carbonyl-methyl; or R2 and R3 taken together with the nitrogen atom to which they are attached form an optionally substituted 5- or 6-membered ring; R4 is C1-C3 alkyl, C2-C3 alkenyl, —N(—R5)—R6, or optionally substituted heteroarylmethylamino; and R5 and R6 are independently selected from hydrogen or C1-C3 alkyl; or R5 and R6 taken together with the nitrogen atom to which they are attached form an optionally substituted 4- to 6-membered saturated ring.

  式(I)的化合物是A2B受体拮抗剂，其中R1是可选取代的芳基或可选取代的5-或6-成员杂环芳基环; R2和R3独立选择自氢，C1-C6烷基，C3-C8环烷基，C3-C8环烷基-(C1-C6)-烷基，芳基-(C1-C6)-烷基，其环部分可选取代，5-或6-成员单环杂环基，其可通过C1-C6亚烷基链连接，其环部分可选取代，苯并咪唑-2-基-甲基，吡啶-3-基-羰基或(1-甲基哌啶-4-基)-羰基-甲基; 或R2和R3与它们所连接的氮原子一起形成可选取代的5-或6-成员环; R4是C1-C3烷基，C2-C3烯基，—N(—R5)—R6或可选取代的杂芳基甲基氨基; R5和R6独立选择自氢或C1-C3烷基; 或R5和R6与它们所连接的氮原子一起形成可选取代的4-至6-成员饱和环。
• Thienopyrimidine Compounds
  申请人：Vernalis (R&D) Ltd.

  公开号：US20150342953A1

  公开（公告）日：2015-12-03

  Compounds of formula (I) are A 2B receptor antagonists: Wherein R 1 is optionally substituted aryl or an optionally substituted 5- or 6-membered heteroaryl ring; R 2 and R 3 are independently selected from hydrogen, C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkyl-(C 1 -C 6 )-alkyl, aryl-(C 1 -C 6 )-alkyl optionally substituted in the ring part thereof, a 5- or 6-membered monocyclic heterocyclic group optionally linked via a C 1 -C 6 alkylene chain and optionally substituted in the ring part thereof, benzimidazol-2-yl-methyl, pyrid-3-yl-carbonyl, or (1-methyl-piperidin-4-yl)-carbonyl-methyl; or R 2 and R 3 taken together with the nitrogen atom to which they are attached form an optionally substituted 5- or 6-membered ring; R 4 is C 1 -C 3 alkyl, C 2 -C 3 alkenyl, —(—R 5 )—R 6 , or optionally substituted heteroarylmethylamino; and R 5 and R 6 are independently selected from hydrogen or C 1 -C 3 alkyl; or R 5 and R 6 taken together with the nitrogen atom to which they are attached form an optionally substituted 4- to 6-membered saturated ring.

  化合物的公式(I)为A2B受体拮抗剂：其中，R1是可选取代的芳基或可选取代的5-或6-成员杂环芳基环；R2和R3独立选择自氢、C1-C6烷基、C3-C8环烷基、C3-C8环烷基-(C1-C6)-烷基、芳基-(C1-C6)-烷基在其环部分上可选取代的、5-或6-成员的单环杂环基，其可以通过C1-C6亚烷基链连接，或苯并咪唑-2-基-甲基、吡啶-3-基-羰基，或(1-甲基哌啶-4-基)-羰基-甲基；或R2和R3结合于它们所连接的氮原子形成可选取代的5-或6-成员环；R4是C1-C3烷基、C2-C3烯基，-(—R5)—R6，或可选取代的杂芳基甲基氨基；R5和R6独立选择自氢或C1-C3烷基；或R5和R6结合于它们所连接的氮原子形成可选取代的4-到6-成员饱和环。
• US9120807B2
  申请人：——

  公开号：US9120807B2

  公开（公告）日：2015-09-01
• US9610290B2
  申请人：——

  公开号：US9610290B2

  公开（公告）日：2017-04-04