Methyl 4-((ethoxycarbonyl)methyl)-2-aminothiophene-3-carboxylate | 80690-18-2

• 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: Methyl 4-((ethoxycarbonyl)methyl)-2-aminothiophene-3-carboxylate
• 英文别名: methyl 2-amino-4-(2-ethoxy-2-oxoethyl)thiophene-3-carboxylate
• CAS: 80690-18-2
• 化学式: C₁₀H₁₃NO₄S
• 分子量: 243.284
• InChiKey: HQAVDPFNXUNLND-UHFFFAOYSA-N

物化性质

• 沸点：
  376.0±42.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  Methyl 4-((ethoxycarbonyl)methyl)-2-aminothiophene-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 、 氯仿 、 水 为溶剂， 生成 Ethyl 2-[4-[(3-methyl-2,5-dioxopyrrol-1-yl)amino]-2-thiophen-2-ylthieno[2,3-d]pyrimidin-5-yl]acetate
  参考文献：
  名称：

  Discovery of thienopyrimidine-based FLT3 inhibitors from the structural modification of known IKKβ inhibitors

  摘要：

  Inactivation of the NF-kappa B signaling pathway by inhibition of IKK beta is a well-known approach to treat inflammatory diseases such as rheumatoid arthritis and cancer. Thienopyrimidine-based analogues were designed through modification of the known IKKb inhibitor, SPC-839, and then biologically evaluated. The resulting analogues had good inhibitory activity against both nitric oxide and TNF-alpha, which are well-known inflammatory responses generated by activated NF-kappa B. However, no inhibitory activity against IKK beta was observed with these compounds. The thienopyrimidine-based analogues were subsequently screened for a target kinase, and FLT3, which is a potential target for acute myeloid leukemia (AML), was identified. Thienopyrimidine-based FLT3 inhibitors showed good inhibition profiles against FLT3 under 1 mu M. Overall, these compounds represent a promising family of inhibitors for future development of a treatment for AML. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.058
• 作为产物：
  描述：

  在 哌啶 、 sulfur 作用下， 以 乙醇 为溶剂， 生成 Methyl 4-((ethoxycarbonyl)methyl)-2-aminothiophene-3-carboxylate
  参考文献：
  名称：

  Discovery of thienopyrimidine-based FLT3 inhibitors from the structural modification of known IKKβ inhibitors

  摘要：

  Inactivation of the NF-kappa B signaling pathway by inhibition of IKK beta is a well-known approach to treat inflammatory diseases such as rheumatoid arthritis and cancer. Thienopyrimidine-based analogues were designed through modification of the known IKKb inhibitor, SPC-839, and then biologically evaluated. The resulting analogues had good inhibitory activity against both nitric oxide and TNF-alpha, which are well-known inflammatory responses generated by activated NF-kappa B. However, no inhibitory activity against IKK beta was observed with these compounds. The thienopyrimidine-based analogues were subsequently screened for a target kinase, and FLT3, which is a potential target for acute myeloid leukemia (AML), was identified. Thienopyrimidine-based FLT3 inhibitors showed good inhibition profiles against FLT3 under 1 mu M. Overall, these compounds represent a promising family of inhibitors for future development of a treatment for AML. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.058

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。
• METALLOPROTEASE INHIBITORS CONTAINING A HETEROCYCLIC MOIETY
  申请人：Alantos Pharmaceuticals Holding, Inc.

  公开号：EP2139887A2

  公开（公告）日：2010-01-06
• Metalloprotease inhibitors containing a heterocyclic moiety
  申请人：Gege Christian

  公开号：US20080221093A1

  公开（公告）日：2008-09-11

  The present invention relates generally to pharmaceutical agents containing a heterocyclic moiety, and in particular, to heterocyclic metalloprotease inhibiting compounds. More particularly, the present invention provides a new class of heterocyclic MMP-13 inhibiting compounds with a benzoxazinone moiety, that exhibit an increased potency and selectivity in relation to currently known MMP-13 inhibitors.
• US7713966B2
  申请人：——

  公开号：US7713966B2

  公开（公告）日：2010-05-11
• [EN] METALLOPROTEASE INHIBITORS CONTAINING A HETEROCYCLIC MOIETY<br/>[FR] INHIBITEURS DE MÉTALLOPROTÉASE CONTENANT UNE FRACTION HÉTÉROCYCLIQUE
  申请人：ALANTOS PHARMACEUTICALS HOLDING

  公开号：WO2008109180A2

  公开（公告）日：2008-09-12

  [EN] The present invention relates generally to pharmaceutical agents containing a heterocyclic moiety, and in particular, to heterocyclic metalloprotease inhibiting compounds. More particularly, the present invention provides a new class of heterocyclic MMP-13 inhibiting compounds with a benzoxazinone moiety, that exhibit an increased potency and selectivity in relation to currently known MMP-13 inhibitors.
  [FR] De manière générale, l'invention concerne des agents pharmaceutiques contenant une fraction hétérocyclique, et en particulier, des composés inhibiteurs de métalloprotéase hétérocycliques. Plus particulièrement, la présente invention fournit une nouvelle catégorie de composés inhibiteurs de MMP-13 hétérocycliques pourvus d'une fraction de benzoxazinone, qui présentent une efficacité et une sélectivité accrues par rapport aux inhibiteurs de MMP-13 actuellement connus.