ethyl 3-(4-chloro-2-methylthiopyrimidin-5-yl)-3-oxopropionate | 174726-99-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: ethyl 3-(4-chloro-2-methylthiopyrimidin-5-yl)-3-oxopropionate
• 英文别名: 3-(2-methylthio-4-chloropyrimidin-5-yl)-3-oxopropionic acid ethyl ester；ethyl 3-(4-chloro-2-methylsulfanylpyrimidin-5-yl)-3-oxopropanoate
• CAS: 174726-99-9
• 化学式: C₁₀H₁₁ClN₂O₃S
• 分子量: 274.728
• InChiKey: LAFAOBQCPXEUBK-UHFFFAOYSA-N

物化性质

• 沸点：
  363.0±27.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  94.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 3-(4-chloro-2-methylthiopyrimidin-5-yl)-3-oxopropionate 在 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 异丙醚 为溶剂， 反应 21.0h， 生成 ethyl 5,8-dihydro-2-methanesulfonyl-5-oxo-8-(2-thiazolyl)pyrido[2,3-d]pyrimidine-6-carboxylate
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Novel 7-Substituted 1,4-Dihydro-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic Acids as Antitumor Agents. Part 1

  摘要：

  In an attempt to search for clinically useful antitumor agents, we have discovered that a series of 1,1-disubstituted-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids possessed moderate cytotoxic activity.,We investigated the structure-activity relationships in this series of compounds by changing N-1 and C-7 positions and the core ring structure itself and evaluated the synthesized compounds against several murine and human tumor cell lines. These modifications led us to the following findings. (1) The 2-thiazolyl group at the N-1 position of the naphthyridine structure is the best substituent for antitumor activity. (2) Regarding core ring structure, the naphthyridine derivative is the most active followed by pyridopyrimidine analogue. (3) At the C-7 position, -aminopyrrolidine derivatives are more effective than other amines or thioether derivatives. Finally, the trans-3-amino-4-methoxypyrrolidinyl derivative (43j), and the 3-amino-3-methylpyrrolidinyl derivative (43f) as well as 3-aminopyrrolidinyl derivative (AT-3639, 1) were determined to be effective in in vitro and in vivo antitumor assays, and their activity was comparable to that of etoposide.

  DOI：

  10.1021/jm010057b
• 作为产物：
  描述：

  丙二酸单乙酯 、 4-氯-2-甲巯基嘧啶-5-甲酰氯 在 甲基溴化镁 作用下， 以 四氢呋喃 为溶剂， 生成 ethyl 3-(4-chloro-2-methylthiopyrimidin-5-yl)-3-oxopropionate
  参考文献：
  名称：

  Compounds, processes for the preparation thereof and anti-tumor agents

  摘要：

  本发明涉及具有以下通式的吡啶酮羧酸衍生物或其盐：##STR1##其中R1为氢原子、卤素原子等，R2为羧基等，R3为氢原子等，A为氮原子或CH，m为1或2，Y为可消除基团或具有以下通式的基团：##STR2##其中R4为氢原子或低级烷基，Z为氢原子、低级烷基等，R5为氢原子、低级烷基等，n为0或1，p为1、2、3或4，以及制备这些化合物的方法，并且进一步涉及含有上述化合物作为有效成分的抗肿瘤药物。

  公开号：

  US05817669A1

文献信息

• NOVEL COMPOUND, PROCESS FOR PRODUCING THE SAME, AND ANTITUMOR AGENT
  申请人：DAINIPPON PHARMACEUTICAL CO., LTD.

  公开号：EP0787726A1

  公开（公告）日：1997-08-06

  This invention relates to pyridone-carboxylic acid derivatives of the following formula or salts thereof:    wherein R1 is a hydrogen atom, a halogen atom, etc., R2 is a carboxyl group etc., R3 is a hydrogen atom etc., A is a nitrogen atom or CH, m is 1 or 2, and Y is an eliminable group or a group having the following formula:    wherein R4 is a hydrogen atom or a lower alkyl group, Z is a hydrogen atom, a lower alkyl group, etc., R5 is a hydrogen atom, a lower alkyl group, etc., n is 0 or 1, and p is 1, 2, 3 or 4 and to processes for the preparation of these compounds, and further to anti-tumor agents which contain the above compounds as effective ingredients.

  本发明涉及下式的吡啶酮-羧酸衍生物或其盐类： 其中 R1 是氢原子、卤素原子等 R2 是羧基等 R3 是氢原子等 A 是氮原子或 CH、 m 是 1 或 2，以及 Y 是可消除基团或具有下式的基团： 其中 R4 是氢原子或低级烷基、 Z 是氢原子、低级烷基等、 R5 是氢原子、低级烷基等、 n 是 0 或 1，以及 p 是 1、2、3 或 4 以及制备这些化合物的工艺，以及含有上述化合物作为有效成分的抗肿瘤制剂。
• US20140275023A1
  申请人：——

  公开号：US20140275023A1

  公开（公告）日：2014-09-18
• US5817669A
  申请人：——

  公开号：US5817669A

  公开（公告）日：1998-10-06
• US9012466B2
  申请人：——

  公开号：US9012466B2

  公开（公告）日：2015-04-21
• [EN] SUBSTITUTED TRICYCLIC PYRAZOLO-PYRIMIDINE COMPOUNDS<br/>[FR] COMPOSÉS TRICYCLIQUES SUBSTITUÉS DE PYRAZOLO-PYRIMIDINE
  申请人：ARQULE INC

  公开号：WO2014164729A1

  公开（公告）日：2014-10-09

  The present invention relates to substituted tricyclic pyrazolo-pyrimidine compounds and methods of synthesizing these compounds. The present invention also relates to pharmaceutical compositions containing substituted tricyclic pyrazolo-pyrimidine compounds and methods of treating cell proliferative disorders, such as cancer, by administering these compounds and pharmaceutical compositions to subjects in need thereof.