3-氨基-N-甲基-2-噻吩甲酰胺 | 147123-48-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 3-氨基-N-甲基-2-噻吩甲酰胺
• 英文名称: 3-amino-N-methylthiophene-2-carboxamide
• CAS: 147123-48-6
• 化学式: C₆H₈N₂OS
• mdl: MFCD12790848
• 分子量: 156.208
• InChiKey: VSTOJEUDQYAUDL-UHFFFAOYSA-N

物化性质

• 沸点：
  411.3±30.0 °C(Predicted)
• 密度：
  1.285±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  83.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-氨基-N-甲基-2-噻吩甲酰胺 在 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 以35%的产率得到3-methylthieno<3,2-d>-1,2,3-triazin-4(3H)-one
  参考文献：
  名称：

  Huddleston, Patrick R.; Barker, John M.; Adamczewska, Yolante Z., Journal of Chemical Research, Miniprint, 1993, # 2, p. 548 - 575

  摘要：

  DOI：
• 作为产物：
  描述：

  BOC-3-氨基噻吩-2-羧酸 在 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.17h， 生成 3-氨基-N-甲基-2-噻吩甲酰胺
  参考文献：
  名称：

  一种含噻吩的嘧啶类化合物其制备方法和应用

  摘要：

  本发明提供一种含噻吩的嘧啶类化合物其制备方法和应用，该类化合物的结构式为R1选自CF3、CH3、Br、Cl、NO2；R2选自本发明含噻吩的嘧啶类化合物结构新颖、具有较好的水溶性、对肿瘤细胞均具有较强的抑制作用，在制备抗肿瘤药物中具有很好的应用前景。

  公开号：

  CN114213400B

文献信息

• FUSED BICYCLIC DERIVATIVES OF 2,4-DIAMINOPYRIMIDINE AS ALK AND c-MET INHIBITORS
  申请人：Ahmed Gulzar

  公开号：US20090221555A1

  公开（公告）日：2009-09-03

  The present invention provides a compound of formula I or II or a pharmaceutically acceptable salt form thereof, wherein R 1 , R 2 , R 3 , R 4 , R 5 , A 1 , A 2 , A 3 , A 4 , and A 5 , are as defined herein. The compounds of formula I or II have ALK and/or c-Met inhibitory activity, and may be used to treat proliferative disorders.

  本发明提供公式I或II化合物或其药学上可接受的盐形式，其中R1、R2、R3、R4、R5、A1、A2、A3、A4和A5如本文所定义。公式I或II化合物具有ALK和/或c-Met抑制活性，可用于治疗增殖性疾病。
• Fused Bicyclic Derivatives of 2,4-Diaminopyrimidine as ALK and c-MET Inhibitors
  申请人：Ahmed Gulzar

  公开号：US20120165519A1

  公开（公告）日：2012-06-28

  The present invention provides a compound of formula I or II or a pharmaceutically acceptable salt form thereof, wherein R 1 , R 2 , R 3 , R 4 , R 5 , A 1 , A 2 , A 3 , A 4 , and A 5 , are as defined herein. The compounds of formula I or II have ALK and/or c-Met inhibitory activity, and may be used to treat proliferative disorders.

  本发明提供了式I或II的化合物或其药学上可接受的盐形式，其中R1、R2、R3、R4、R5、A1、A2、A3、A4和A5如本文所定义。式I或II的化合物具有ALK和/或c-Met抑制活性，并可用于治疗增生性疾病。
• Design, synthesis and antitumor activity of 5-trifluoromethylpyrimidine derivatives as EGFR inhibitors
  作者：Yaqing Zuo、Rongrong Li、Yan Zhang、Guochen Bao、Yi Le、Longjia Yan

  DOI：10.1080/14756366.2022.2128797

  日期：2022.12.31

  Abstract A new series of 5-trifluoromethylpyrimidine derivatives were designed and synthesised as EGFR inhibitors. Three tumour cells A549, MCF-7, PC-3 and EGFR kinase were employed to evaluate their biological activities. The results were shown that most of the target compounds existed excellent antitumor activities. In particular, the IC50 values of compound 9u (E)-3-((2-((4-(3-(3-fluorophenyl)a

  摘要 设计并合成了一系列新的 5-三氟甲基嘧啶衍生物作为 EGFR 抑制剂。三种肿瘤细胞 A549、MCF-7、PC-3 和 EGFR 激酶被用来评估它们的生物活性。结果表明，大部分目标化合物均具有优异的抗肿瘤活性。特别地，化合物9u ( E )-3-((2-((4-(3-(3-氟苯基)丙烯酰胺基)苯基)氨基)-5-(三氟甲基)嘧啶-4-基)的IC 50值氨基) -N-甲基噻吩-2-甲酰胺对 A549、MCF-7、PC-3 细胞和 EGFR 激酶分别达到 0.35 μM、3.24 μM、5.12 μM 和 0.091 μM。此外，进一步的研究表明，化合物9u可诱导A549细胞早期凋亡，使细胞停滞在G2/M期。综上所述，这些发现表明化合物9u具有发展为抗肿瘤试剂的潜力。
• Design, synthesis and biological evaluation of 4-arylamino-pyrimidine derivatives as focal adhesion kinase inhibitors
  作者：Zhiwu Long、Yaqing Zuo、Rongrong Li、Yi Le、Yawen Dong、Longjia Yan

  DOI：10.1016/j.bioorg.2023.106792

  日期：2023.11

  A novel series of 4-arylamino-pyrimidine derivatives were designed and synthesized as focal adhesion kinase (FAK) inhibitors under the strategy of structure-based drug design. Most compounds performed excellent anti-proliferative activity against U87-MG cells. Especially, compounds 8d and 9b revealed the highest activity with IC50 values of 0.975 μM and 1.033 μM, which was much potent than the positive

  在基于结构的药物设计策略下，设计并合成了一系列新型4-芳氨基嘧啶衍生物作为粘着斑激酶（FAK）抑制剂。大多数化合物对 U87-MG 细胞表现出优异的抗增殖活性。特别是，化合物8d和9b显示出最高活性，IC 50值为0.975 μM和1.033 μM，比阳性对照TAE-226（IC 50  = 2.659 μM）更有效。另一方面，总共 27 种化合物对人类正常 2BS 细胞表现出较低的抑制作用。此外，化合物8d和9b对FAK表现出出色的活性，IC 50值为0.2438 nM和0.2691 nM，非常接近TAE-226（IC 50  = 0.1390 nM）。进一步的研究证明化合物8d和9b能够诱导U87-MG细胞早期凋亡并将细胞阻滞在G2/M期。作用机制表明它们可以显着抑制U87-MG细胞克隆形成、细胞迁移和FAK磷酸化。分子对接和分子动力学模拟研究表明，化合物8d和9b可以牢固地占据FAK
• Synthesis and Pharmacological Activity of Triazole Derivatives Inhibiting Eosinophilia
  作者：Youichiro Naito、Fumihiko Akahoshi、Shinji Takeda、Takehiro Okada、Masahiko Kajii、Hiroko Nishimura、Masanori Sugiura、Chikara Fukaya、Yoshio Kagitani

  DOI：10.1021/jm9507993

  日期：1996.1.1

  In order to develop novel antiasthmatic agents based on a new mechanism of action, a series of 3-substituted 5-amino-1-[(methylamino)(thiocarbonyl)]-1H-1,2,4-triazole derivatives were synthesized and evaluated in a model in which eosinophilia was induced in the ah-way through intravenous (iv) injection of Sephadex particles on days 0, 2, and 5. After screening of several hundred derivatives, we finally identified the highly potent eosinophilia inhibitor 5-amino-3-(4-chlorophenyl)-1-[(methylamino)(thiocarbonyl)]-1H-triazole (23c, GCC-AP0341), which had ID50 values of 0.3 and 0.07 mg/kg when administered orally (os) and intraperitoneally tip), respectively. This compound showed complete inhibition of the hypersensitivity induced by ascaris inhalation at an ip dose of 1 mg/kg as well as low toxicity, with an LD(50) value of > 2.0 g/kg in mice. Extensive study of its mechanism of action revealed that 23c inhibited eosinophil survival induced by interleukin-5 (IL-5), but had little or no effect on leukotriene D-4 (LTD(4)) or platelet-activating factor (PAF)-induced responses. Taken together, these results suggest 23e as a novel candidate for the treatment of chronic asthma. Further studies are now underway.