4-(piperidin-1-yl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine | 40277-54-1

• 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: 4-(piperidin-1-yl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine
• 英文别名: 4-piperidin-1-yl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidine；4-N-Piperidino-tetrahydro-benzothieno-pyrimidin；4-Piperidin-1-yl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidine
• CAS: 40277-54-1
• 化学式: C₁₅H₁₉N₃S
• 分子量: 273.402
• InChiKey: WUJLSKGQAUVXCX-UHFFFAOYSA-N

物化性质

• 熔点：
  115 °C
• 沸点：
  460.1±40.0 °C(Predicted)
• 密度：
  1.250±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  5,6,7,8-四氢-[1]-苯并噻吩[2,3-d]嘧啶-4(1h)-酮 在 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 0.2h， 生成 4-(piperidin-1-yl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine
  参考文献：
  名称：

  4-取代的噻吩并[2,3-d]嘧啶类作为有效的抗菌剂：合理的设计，微波辅助合成，生物学评估和分子对接研究

  摘要：

  设计，合成4-取代的噻吩并[2,3- d ]嘧啶并评估其抗菌活性。对接研究表明，强效化合物对细菌二氢蝶呤合酶具有抑制活性。因此，还确定了其与DHPS酶的结合亲和力。

  DOI：

  10.1111/cbdd.13028

文献信息

• Thieno[2,3-d]pyrimidines as Potential Chemotherapeutic Agents
  作者：Vishnu Ji Ram

  DOI：10.1002/ardp.19793120105

  日期：——

  A series of new thieno[2,3‐d]pyrimidine derivatives with a carbocyclic ring fused at positions 5 and 6 have been synthesised in order to study their pesticidal activity. Some of the compounds exhibit significant biological activity.

  为了研究其杀虫活性，合成了一系列在 5 和 6 位具有稠合碳环的噻吩并 [2,3-d] 嘧啶衍生物。一些化合物表现出显着的生物活性。
• Identification of 5,6-substituted 4-aminothieno[2,3-d]pyrimidines as LIMK1 inhibitors
  作者：Brad E. Sleebs、George Nikolakopoulos、Ian P. Street、Hendrik Falk、Jonathan B. Baell

  DOI：10.1016/j.bmcl.2011.07.050

  日期：2011.10

  4-Aminobenzothieno[3,2-d]pyrimidines were previously identified in a high throughput screening campaign as LIMK1 inhibitors. Scaffold reversal led to the identification of a series of simple 5,6-substituted 4-aminothieno[2,3-d]pyrimidines with low micromolar inhibition of LIMK1.

  4-氨基苯并噻吩并[3,2- d ]嘧啶先前在高通量筛选活动中被鉴定为LIMK1抑制剂。支架逆转导致鉴定了一系列简单的5,6-取代的4-氨基噻吩并[2,3- d ]嘧啶，对LIMK1的抑制作用很小。
• IRAK INHIBITORS AND USES THEREOF
  申请人：Romero Donna L.

  公开号：US20120283238A1

  公开（公告）日：2012-11-08

  The present invention provides compounds, compositions thereof, and methods of using the same.

  本发明提供了化合物、其组合物以及使用它们的方法。
• 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.
• Robba,M. et al., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1973, vol. 276, p. 93 - 95
  作者：Robba,M. et al.

  DOI：——

  日期：——