5-(2-Methylamino-pyrimidin-4-yl)-thiophene-2-carboxylic acid ethyl ester | 866523-74-2

• 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: 5-(2-Methylamino-pyrimidin-4-yl)-thiophene-2-carboxylic acid ethyl ester
• 英文别名: Ethyl 5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxylate
• CAS: 866523-74-2
• 化学式: C₁₂H₁₃N₃O₂S
• 分子量: 263.32
• InChiKey: UIMVQRCUBFRYGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(2-Methylamino-pyrimidin-4-yl)-thiophene-2-carboxylic acid ethyl ester 在 盐酸 、 肼 、 sodium nitrite 作用下， 以 甲醇 、 溶剂黄146 、 xylene 为溶剂， 反应 17.67h， 生成 4-fluorobenzyl 5-[2-(methylamino)pyrimidin-4-yl]thien-2-ylcarbamate
  参考文献：
  名称：

  Discovery of 2-pyrimidyl-5-amidothiophenes as potent inhibitors for AKT: Synthesis and SAR studies

  摘要：

  A series of 2-pyrimidyl-5-amidothiophenes has been synthesized and evaluated for AKT inhibition. SAR studies resulted in potent inhibitors of AKT with IC(50) values as low as single digit nanomolar as represented by compound 2aa. Compound 2aa showed cellular activity including antiproliferation and downstream target modulation. Selectivity profile is described. A co-crystal of 2aa with PKA is determined and discussed.

  DOI：

  10.1016/j.bmcl.2006.05.092
• 作为产物：
  描述：

  5-乙酰基噻吩-2-甲酸 在 sodium ethanolate 作用下， 以 甲苯 为溶剂， 反应 56.0h， 生成 5-(2-Methylamino-pyrimidin-4-yl)-thiophene-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Discovery of 2-pyrimidyl-5-amidothiophenes as potent inhibitors for AKT: Synthesis and SAR studies

  摘要：

  A series of 2-pyrimidyl-5-amidothiophenes has been synthesized and evaluated for AKT inhibition. SAR studies resulted in potent inhibitors of AKT with IC(50) values as low as single digit nanomolar as represented by compound 2aa. Compound 2aa showed cellular activity including antiproliferation and downstream target modulation. Selectivity profile is described. A co-crystal of 2aa with PKA is determined and discussed.

  DOI：

  10.1016/j.bmcl.2006.05.092

文献信息

• [EN] SUBSTITUTED THIOPHENE DERIVATIVES AS ANTI-CANCER AGENTS<br/>[FR] DERIVES DU THIOPHENE SUBSTITUES EN TANT QU'AGENTS ANTICANCEREUX
  申请人：CHIRON CORP

  公开号：WO2005095386A1

  公开（公告）日：2005-10-13

  The present invention relates to new substituted five-membered compounds and pharmaceutically acceptable salts, esters or prodrugs thereof, compositions of the new compounds together with pharmaceutically acceptable carriers, and uses of the new compounds. The compounds of the invention have the following general formula (I).

  本发明涉及新的取代五元化合物及其药用盐、酯或前药，新化合物与药用载体的组合物，以及新化合物的用途。本发明的化合物具有以下一般式（I）。
• SUBSTITUTED 2,5-HETEROCYCLIC DERIVATIVES
  申请人：Lin Xiaodong

  公开号：US20080255120A1

  公开（公告）日：2008-10-16

  The present invention relates to new substituted five-membered compounds and pharmaceutically acceptable salts, esters or prodrugs thereof, compositions of the new compounds together with pharmaceutically acceptable carriers, and uses of the new compounds. The compounds of the invention have the following general formula:

  本发明涉及新的取代五元化合物及其药学上可接受的盐、酯或前药，新化合物与药学上可接受的载体的组合物，以及新化合物的用途。本发明的化合物具有以下一般式：
• US7470701B2
  申请人：——

  公开号：US7470701B2

  公开（公告）日：2008-12-30
• [EN] AKT3 COMPOSITIONS AND METHODS OF USE<br/>[FR] COMPOSITIONS D'AKT3 ET PROCÉDÉS D'UTILISATION ASSOCIÉS
  申请人：CHIRON CORP

  公开号：WO2006022718A1

  公开（公告）日：2006-03-02

  The present invention relates to the compositions, crystals, and the three dimensional structures of Akt3 and its mutants, to methods for forming the crystals, and to methods for using the three dimensional structures to design and identify therapeutic compounds for the treatment of Akt3 mediated diseases.
• Discovery of 2-pyrimidyl-5-amidothiophenes as potent inhibitors for AKT: Synthesis and SAR studies
  作者：Xiaodong Lin、Jeremy M. Murray、Alice C. Rico、Michael X. Wang、Daniel T. Chu、Yasheen Zhou、Merci Del Rosario、Susan Kaufman、Sylvia Ma、Eric Fang、Kenneth Crawford、A.B. Jefferson

  DOI：10.1016/j.bmcl.2006.05.092

  日期：2006.8

  A series of 2-pyrimidyl-5-amidothiophenes has been synthesized and evaluated for AKT inhibition. SAR studies resulted in potent inhibitors of AKT with IC(50) values as low as single digit nanomolar as represented by compound 2aa. Compound 2aa showed cellular activity including antiproliferation and downstream target modulation. Selectivity profile is described. A co-crystal of 2aa with PKA is determined and discussed.