Ethyl 2-amino-5-(2-methoxy-2-oxoethyl)-4-methylthiophene-3-carboxylate | 1029421-22-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: Ethyl 2-amino-5-(2-methoxy-2-oxoethyl)-4-methylthiophene-3-carboxylate
• CAS: 1029421-22-4
• 化学式: C₁₁H₁₅NO₄S
• 分子量: 257.31
• InChiKey: UNRUFMAVCOQZSB-UHFFFAOYSA-N

物化性质

• 沸点：
  373.2±42.0 °C(predicted)
• 密度：
  1.257±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 2-amino-5-(2-methoxy-2-oxoethyl)-4-methylthiophene-3-carboxylate 在 盐酸 、 一水合肼 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 49.0h， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of novel thieno[2,3-d]pyrimidine-based FLT3 inhibitors as anti-leukemic agents

  摘要：

  The most common mutations in acute myeloid leukemia (AML) are those that cause the activation of FMS-like tyrosine kinase 3 (FLT3). Therefore, FLT3 is regarded as a potential target for the treatment of AML A novel series of thieno[2,3-d]pyrimidine-based analogs was designed and synthesized as FLT3 inhibitors. All synthesized compounds were assayed for the tyrosine kinase activity of FLT3 and growth inhibitory activity in four human leukemia cell lines (THP1, MV4-11, K562, and HL-60). Among these compounds, compound 17a, which possesses relatively short and simple substituents at the C-6 position of thieno[2,3-d]pyrimidine, emerged as the most promising anti-leukemic agent. Compound 17a exhibited potent inhibition of FLT3-positive leukemic cell growth and of the FLT3 D835Y kinase; such inhibition is required for the successful treatment of AML. The data supports the further investigation of this class of compounds as potential anti-leukemic agents. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.001
• 作为产物：
  描述：

  乙酰丙酸甲酯 、 氰乙酸乙酯 在 sulfur 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 Ethyl 2-amino-5-(2-methoxy-2-oxoethyl)-4-methylthiophene-3-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of novel thieno[2,3-d]pyrimidine-based FLT3 inhibitors as anti-leukemic agents

  摘要：

  The most common mutations in acute myeloid leukemia (AML) are those that cause the activation of FMS-like tyrosine kinase 3 (FLT3). Therefore, FLT3 is regarded as a potential target for the treatment of AML A novel series of thieno[2,3-d]pyrimidine-based analogs was designed and synthesized as FLT3 inhibitors. All synthesized compounds were assayed for the tyrosine kinase activity of FLT3 and growth inhibitory activity in four human leukemia cell lines (THP1, MV4-11, K562, and HL-60). Among these compounds, compound 17a, which possesses relatively short and simple substituents at the C-6 position of thieno[2,3-d]pyrimidine, emerged as the most promising anti-leukemic agent. Compound 17a exhibited potent inhibition of FLT3-positive leukemic cell growth and of the FLT3 D835Y kinase; such inhibition is required for the successful treatment of AML. The data supports the further investigation of this class of compounds as potential anti-leukemic agents. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.001

文献信息

• Heterobicyclic metalloprotease inhibitors
  申请人：Gege Christian

  公开号：US20080261968A1

  公开（公告）日：2008-10-23

  The present invention relates generally to azabicyclic containing pharmaceutical agents, and in particular, to azabicyclic metalloprotease inhibiting compounds. More particularly, the present invention provides a new class of azabicyclic MMP-3, MMP-8 and/or MMP-13 inhibiting compounds, which exhibit an increased potency and selectivity in relation to currently known MMP-13, MMP-8 and MMP-3 inhibitors.

  本发明涉及含有杂环的药物，特别是含有杂环的金属蛋白酶抑制剂。更具体地说，本发明提供了一种新型的杂环MMP-3、MMP-8和/或MMP-13抑制剂，其在与当前已知的MMP-13、MMP-8和MMP-3抑制剂相比具有更高的效力和选择性。
• US7713966B2
  申请人：——

  公开号：US7713966B2

  公开（公告）日：2010-05-11
• [EN] COMPOUNDS AS SIRT2 INHIBITORS<br/>[FR] COMPOSÉS EN TANT QU'INHIBITEURS DE SIRT2
  申请人：IMP INNOVATIONS LTD

  公开号：WO2016067012A1

  公开（公告）日：2016-05-06

  The invention provides compounds of formula (I) or a salt thereof, wherein R1, R2, R3, R4, R5 and R6 are as defined in the specification. The invention also provides compositions comprising the compounds, and methods of using the compounds for the treatment of a disease in which inhibition of SIRT2 provides a therapeutic or prophylactic effect, for example cancers,metabolic disorders, inflammatory disorders,neurodegenerative disorders and central nervous system disorders.
• Synthesis and biological evaluation of novel thieno[2,3-d]pyrimidine-based FLT3 inhibitors as anti-leukemic agents
  作者：Jee Sun Yang、Chun-Ho Park、Chulho Lee、Hwan Kim、Changmok Oh、Yejoo Choi、Jong Soon Kang、Jieun Yun、Jin-Hyun Jeong、Myung-Hwa Kim、Gyoonhee Han

  DOI：10.1016/j.ejmech.2014.08.001

  日期：2014.10

  The most common mutations in acute myeloid leukemia (AML) are those that cause the activation of FMS-like tyrosine kinase 3 (FLT3). Therefore, FLT3 is regarded as a potential target for the treatment of AML A novel series of thieno[2,3-d]pyrimidine-based analogs was designed and synthesized as FLT3 inhibitors. All synthesized compounds were assayed for the tyrosine kinase activity of FLT3 and growth inhibitory activity in four human leukemia cell lines (THP1, MV4-11, K562, and HL-60). Among these compounds, compound 17a, which possesses relatively short and simple substituents at the C-6 position of thieno[2,3-d]pyrimidine, emerged as the most promising anti-leukemic agent. Compound 17a exhibited potent inhibition of FLT3-positive leukemic cell growth and of the FLT3 D835Y kinase; such inhibition is required for the successful treatment of AML. The data supports the further investigation of this class of compounds as potential anti-leukemic agents. (C) 2014 Elsevier Masson SAS. All rights reserved.