2-氨基-4-(4-硝基苯基)-3-噻吩甲腈 | 86604-41-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-氨基-4-(4-硝基苯基)-3-噻吩甲腈
• 英文名称: 2-amino-4-(4-nitrophenyl)thiophene-3-carbonitrile
• CAS: 86604-41-3
• 化学式: C₁₁H₇N₃O₂S
• 分子量: 245.261
• InChiKey: KXUPJPPYTWTREF-UHFFFAOYSA-N

物化性质

• 熔点：
  202-204 °C(Solv: toluene (108-88-3))
• 沸点：
  477.6±45.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-氨基-4-(4-硝基苯基)-3-噻吩甲腈 在 铁粉 、 氯化铵 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 20.0h， 生成 N-[4-(4-aminothieno[2,3-d]pyrimidin-5-yl)phenyl]-N'-butylurea
  参考文献：
  名称：

  Thienopyrimidine Ureas as Novel and Potent Multitargeted Receptor Tyrosine Kinase Inhibitors

  摘要：

  A series of novel thienopyrimidine-based receptor tyrosine kinase inhibitors has been discovered. Investigation of structure-activity relationships at the 5- and 6-positions of the thienopyrimidine nucleus led to a series of N,N '-diaryl ureas that potently inhibit all of the vascular endothelial growth factor (VEGF) and platelet-derived growth factor (PDGF) receptor tyrosine kinases. A kinase insert domain-containing receptor (KDR) homology model suggests that these compounds bind to the "inactive conformation" of the enzyme with the urea portion extending into the back hydrophobic pocket adjacent to the adenosine 5 '-triphosphate (ATP) binding site. A number of compounds have been identified as displaying excellent in vivo potency. In particular, compounds 28 and 76 possess favorable pharmacokinetic (PK) profiles and demonstrate potent antitumor efficacy against the HT1080 human fibrosarcoma xenograft tumor growth model (tumor growth inhibition (TGI) = 75% at 25 mg/kg-day, per os (po)).

  DOI：

  10.1021/jm050458h
• 作为产物：
  描述：

  对硝基苯乙酮 在 ammonium acetate 、 sulfur 、 溶剂黄146 、 二乙胺 作用下， 以 乙醇 、 苯 为溶剂， 反应 19.5h， 生成 2-氨基-4-(4-硝基苯基)-3-噻吩甲腈
  参考文献：
  名称：

  Thienopyrimidine Ureas as Novel and Potent Multitargeted Receptor Tyrosine Kinase Inhibitors

  摘要：

  A series of novel thienopyrimidine-based receptor tyrosine kinase inhibitors has been discovered. Investigation of structure-activity relationships at the 5- and 6-positions of the thienopyrimidine nucleus led to a series of N,N '-diaryl ureas that potently inhibit all of the vascular endothelial growth factor (VEGF) and platelet-derived growth factor (PDGF) receptor tyrosine kinases. A kinase insert domain-containing receptor (KDR) homology model suggests that these compounds bind to the "inactive conformation" of the enzyme with the urea portion extending into the back hydrophobic pocket adjacent to the adenosine 5 '-triphosphate (ATP) binding site. A number of compounds have been identified as displaying excellent in vivo potency. In particular, compounds 28 and 76 possess favorable pharmacokinetic (PK) profiles and demonstrate potent antitumor efficacy against the HT1080 human fibrosarcoma xenograft tumor growth model (tumor growth inhibition (TGI) = 75% at 25 mg/kg-day, per os (po)).

  DOI：

  10.1021/jm050458h

文献信息

• Thiopyrimidine and isothiazolopyrimidine kinase inhibitors
  申请人：——

  公开号：US20040014756A1

  公开（公告）日：2004-01-22

  Compounds having the formula 1 are useful for inhibiting protein tyrosine kinases. The present invention also discloses methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.

  具有以下化学式的化合物对抑制蛋白酪氨酸激酶具有用处。本发明还公开了制备这些化合物的方法、含有这些化合物的组合物，以及使用这些化合物进行治疗的方法。
• Crystalline N-(4-(4-aminothieno[2,3-d]pyrimidin-5-yl)phenyl)-N'-(2-fluoro-5-(trifluoromethyl)phenyl)urea ethanolate
  申请人：Mellican M. Sean

  公开号：US20070155758A1

  公开（公告）日：2007-07-05

  A crystalline N-(4-(4-aminothieno[2,3-d]pyrimidin-5-yl)phenyl)-N′-[2-fluoro-5-(trifluoromethyl)phenyl)urea ethanolate, ways to make it, compositions comprising it, and methods of treatment using it are disclosed.

  揭示了一种结晶的N-(4-(4-氨基噻吩[2,3-d]嘧啶-5-基)苯基)-N′-[2-氟-5-(三氟甲基)苯基)脲乙醇盐，制备方法，含有该物质的组合物，以及使用它的治疗方法。
• Crystalline N-(4-(4-ammoniumthieno[2,3-d]pyrimidin-5-yl)phenyl)-N'-(2-fluoro-5-(trifluoromethyl)phenyl)urea ethanesulfonate
  申请人：Mellican M. Sean

  公开号：US20070161661A1

  公开（公告）日：2007-07-12

  A crystalline N-(4-(4-ammoniumthieno[2,3-d]pyrimidin-5-yl)phenyl)-N′-(2-fluoro-5-(trifluoromethyl)phenyl)urea ethanesulfonate, ways to make it, compositions comprising it, and methods of treatment using it are disclosed.

  本文披露了一种晶体N-(4-(4-铵基噻吩[2,3-d]嘧啶-5-基)苯基)-N′-(2-氟-5-(三氟甲基)苯基)脲乙烷磺酸盐，以及制备该化合物的方法、含有该化合物的组合物，以及使用该化合物进行治疗的方法。
• Ethylene diamine grafted nanoporous UiO-66 as an efficient basic catalyst in the multi-component synthesis of 2-aminithiophenes
  作者：N. Erfaninia、R. Tayebee、M. Dusek、M.M. Amini

  DOI：10.1002/aoc.4307

  日期：2018.5

  effective solid nanoporous basic catalyst prepared through the amine grafting onto the pores of UiO‐66. The manufactured nanoparticles were identified by FT‐IR, XRD, TGA, FESEM, TEM, CHN and BET and the characterization results certified formation of a single phase nanoporous substance with the medium grain size less than 90 nm. The synthesized material was employed as an efficient catalyst for the preparation

  这项研究表明ED‐UiO‐66是一种通过胺接枝到UiO‐66的孔中而制备的新型有效的固体纳米多孔碱性催化剂。通过FT-IR，XRD，TGA，FESEM，TEM，CHN和BET对制成的纳米颗粒进行鉴定，并且鉴定结果证明形成了中等粒径小于90 nm的单相纳米多孔物质。合成的材料被用作通过Gewald方法制备2-氨基噻吩的有效催化剂。这种热化学稳定的纳米催化剂对环境安全，可重复使用且经济。因此，可以将该方法简单地扩展到工业目标。
• [EN] THIOPYRIMIDINE AND ISOTHIAZOLOPYRIMIDINE KINASE INHIBITORS<br/>[FR] INHIBITEURS DES THIOPYRIMIDINE ET ISOTHIAZOLOPYRIMIDINE KINASES
  申请人：ABBOTT LAB

  公开号：WO2003080625A1

  公开（公告）日：2003-10-02

  Compounds having the formula are useful for inhibiting protein tyrosine kinases. The present invention also discloses methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.

  具有公式的化合物对于抑制蛋白酪氨酸激酶非常有用。本发明还公开了制备该化合物的方法，含有该化合物的组合物以及使用该化合物进行治疗的方法。