2-Cyclopropyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-4-ol | 462066-12-2

• 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-Cyclopropyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-4-ol
• 英文别名: 2-cyclopropyl-5,6.7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-4-ol；2-cyclopropyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-ol；2-cyclopropyl-5,6,7,8-tetrahydro-3H-[1]benzothiolo[2,3-d]pyrimidin-4-one
• CAS: 462066-12-2
• 化学式: C₁₃H₁₄N₂OS
• 分子量: 246.333
• InChiKey: LKRJENMREMBWGQ-UHFFFAOYSA-N

物化性质

• 沸点：
  471.7±55.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  69.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Cyclopropyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-4-ol 、 4-氟苯胺 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 0.75h， 以80%的产率得到2-cyclopropyl-N-(4-fluorophenyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-amine
  参考文献：
  名称：

  Anti-tubercular activities of 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3- d ]pyrimidin-4-amine analogues endowed with high activity toward non-replicative Mycobacterium tuberculosis

  摘要：

  Thirty three derivatives of 2-substituted 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-amine analogues were synthesized by molecular modification of a reported antimycobacterial molecule (GSK163574A). Compounds were evaluated in vitro against actively replicative and nutrient starved non-replicative Mycobacterium tuberculosis (MTB), enzymatic screening and cytotoxicity against RAW 264.7 cell line. Among the compounds, 2-ethyl-N-phenethy1-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d] pyrimidin-4-amine (5c) was found to be the most active compound against non-replicative MTB with 2.7 log reduction of bacteria at 10 mu g/mL and was more potent than isoniazid (1.2 log reduction) and rifampicin (2.0 log reduction) at same dose level. Compound 5c also showed activity against MTB alanine dehydrogenase enzyme with IC50 of 1.82 +/- 0.42 mu M and showed 25% cytotoxicity against RAW 264.7 cell line at 50 mu g/mL. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.09.012
• 作为产物：
  描述：

  2-(Cyclopropanecarbonyl-amino)-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester 在 氨 作用下， 以 水 为溶剂， 反应 24.0h， 以88%的产率得到2-Cyclopropyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-4-ol
  参考文献：
  名称：

  [EN] TRICYCLIC BENZO[4,5]THIENO-[2,3-D]PYRIMIDINE-4-YL-AMIN DERIVATIVES, THEIR SALTS, PROCESS FOR PRODUCING THE COMPOUNDS AND THEIR PHARMACEUTICAL USE
  [FR] DÉRIVÉS TRICYCLIQUES DE BENZO[4,5]THIÉNO-[2,3-D]PYRIMIDIN-4-YLAMINE, LEURS SELS, PROCÉDÉ DE FABRICATION DES COMPOSÉS ET LEUR UTILISATION PHARMACEUTIQUE

  摘要：

  本发明涉及新型三环苯并[4,5]噻吩-[2,3-d]嘧啶-4-基氨基衍生物，以及其药学上可接受的盐。本发明还涉及生产该化合物的方法，以及将其用作药学活性剂和制备用于预防和/或治疗增殖性疾病如癌症的药物组合物。

  公开号：

  WO2009104026A1

文献信息

• TRICYCLIC BENZO[4,5]THIENO-[2,3-D]PYRIMIDINE-4-YL-AMIN DERIVATIVES, THEIR SALTS, PROCESS FOR PRODUCING THE COMPOUNDS AND THEIR PHARMACEUTICAL USE
  申请人：Bánhegyi Pèter

  公开号：US20110015214A1

  公开（公告）日：2011-01-20

  The invention relates to novel tricyclic benzo[4,5]thieno-[2,3-d]pyrimidine-4-yl-amin derivatives, as well as their pharmaceutically acceptable salts. The subject of the invention too the process for producing the compounds and their use as a pharmaceutically active agent and as pharmaceutical compositions for prophylaxis and/or treatment of proliferative diseases such as cancer.

  该发明涉及新颖的三环苯并[4,5]噻吩-[2,3-d]嘧啶-4-基-氨基衍生物，以及它们的药学上可接受的盐。该发明还涉及制备这些化合物的方法，以及它们作为药用活性剂和用于预防和/或治疗增殖性疾病如癌症的药物组合物。
• TRICYCLIC BENZOÝ4,5¨THIENO-Ý2,3-D¨PYRIMIDINE-4-YL-AMIN DERIVATIVES, THEIR SALTS, PROCESS FOR PRODUCING THE COMPOUNDS AND THEIR PHARMACEUTICAL USE
  申请人：Vichem Chemie Kutató KFT

  公开号：EP2257554A1

  公开（公告）日：2010-12-08
• US8802849B2
  申请人：——

  公开号：US8802849B2

  公开（公告）日：2014-08-12
• Anti-tubercular activities of 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3- d ]pyrimidin-4-amine analogues endowed with high activity toward non-replicative Mycobacterium tuberculosis
  作者：Ganesh Samala、Parthiban Brindha Devi、Shalini Saxena、Saritha Gunda、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.bmc.2016.09.012

  日期：2016.11

  Thirty three derivatives of 2-substituted 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-amine analogues were synthesized by molecular modification of a reported antimycobacterial molecule (GSK163574A). Compounds were evaluated in vitro against actively replicative and nutrient starved non-replicative Mycobacterium tuberculosis (MTB), enzymatic screening and cytotoxicity against RAW 264.7 cell line. Among the compounds, 2-ethyl-N-phenethy1-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d] pyrimidin-4-amine (5c) was found to be the most active compound against non-replicative MTB with 2.7 log reduction of bacteria at 10 mu g/mL and was more potent than isoniazid (1.2 log reduction) and rifampicin (2.0 log reduction) at same dose level. Compound 5c also showed activity against MTB alanine dehydrogenase enzyme with IC50 of 1.82 +/- 0.42 mu M and showed 25% cytotoxicity against RAW 264.7 cell line at 50 mu g/mL. (C) 2016 Elsevier Ltd. All rights reserved.
• [EN] TRICYCLIC BENZO[4,5]THIENO-[2,3-D]PYRIMIDINE-4-YL-AMIN DERIVATIVES, THEIR SALTS, PROCESS FOR PRODUCING THE COMPOUNDS AND THEIR PHARMACEUTICAL USE<br/>[FR] DÉRIVÉS TRICYCLIQUES DE BENZO[4,5]THIÉNO-[2,3-D]PYRIMIDIN-4-YLAMINE, LEURS SELS, PROCÉDÉ DE FABRICATION DES COMPOSÉS ET LEUR UTILISATION PHARMACEUTIQUE
  申请人：VICHEM CHEMIE KUTATO KFT

  公开号：WO2009104026A1

  公开（公告）日：2009-08-27

  The invention relates to novel tricyclic benzo[4,5]thieno-[2,3-d]pyrimidine-4-yl-amin derivatives, as well as their pharmaceutically acceptable salts. The subject of the invention too the process for producing the compounds and their use as a pharmaceutically active agent and as pharmaceutical compositions for prophylaxis and/or treatment of proliferative diseases such as cancer.

  本发明涉及新型三环苯并[4,5]噻吩-[2,3-d]嘧啶-4-基氨基衍生物，以及其药学上可接受的盐。本发明还涉及生产该化合物的方法，以及将其用作药学活性剂和制备用于预防和/或治疗增殖性疾病如癌症的药物组合物。