2-((thiophen-2-ylmethylene)amino)acetic acid | 1379420-20-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-((thiophen-2-ylmethylene)amino)acetic acid
• CAS: 1379420-20-8
• 化学式: C₇H₇NO₂S
• 分子量: 169.204
• InChiKey: KSNOTYMJTWFPJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.25
• 重原子数：
  11.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  49.66
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-((thiophen-2-ylmethylene)amino)acetic acid 、 亚磷酸二乙酯 以 甲醇 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  A Convenient Synthesis of ω-[(Arylphosphonomethyl)Amino] Alkylphosphonic and Carboxylic Acids via in Situ–Generated Arylideneaminoalkyl- Phosphonic or Carboxylic Acids

  摘要：

  -[(Arylphosphonomethyl)amino]alkylphosphonic and carboxylic acids are prepared in an easy work-up procedure, by addition of diethyl phosphite to in situ-generated arylideneaminoalkylphosphonic or carboxylic acids followed by hydrolysis with hydrochloric acid.

  DOI：

  10.1080/10426500902994338
• 作为产物：
  描述：

  2-噻吩甲醛 、 聚甘氨酸 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 2-((thiophen-2-ylmethylene)amino)acetic acid
  参考文献：
  名称：

  A Convenient Synthesis of ω-[(Arylphosphonomethyl)Amino] Alkylphosphonic and Carboxylic Acids via in Situ–Generated Arylideneaminoalkyl- Phosphonic or Carboxylic Acids

  摘要：

  -[(Arylphosphonomethyl)amino]alkylphosphonic and carboxylic acids are prepared in an easy work-up procedure, by addition of diethyl phosphite to in situ-generated arylideneaminoalkylphosphonic or carboxylic acids followed by hydrolysis with hydrochloric acid.

  DOI：

  10.1080/10426500902994338

文献信息

• Hit-to-Lead Studies for the Antimalarial Tetrahydroisoquinolone Carboxanilides
  作者：David M. Floyd、Philip Stein、Zheng Wang、Jian Liu、Steve Castro、Julie A. Clark、Michele Connelly、Fangyi Zhu、Gloria Holbrook、Amy Matheny、Martina S. Sigal、Jaeki Min、Rajkumar Dhinakaran、Senthil Krishnan、Sridevi Bashyum、Spencer Knapp、R. Kiplin Guy

  DOI：10.1021/acs.jmedchem.6b00752

  日期：2016.9.8

  Phenotypic whole-cell screening in erythrocytic cocultures of Plasmodium falciparum identified a series of dihydroisoquinolones that possessed potent antimalarial activity against multiple resistant strains of P. falciparum in vitro and show no cytotoxicity to mammalian cells. Systematic structure activity studies revealed relationships between potency and modifications at N-2, C-3, and C-4. Careful structure property relationship studies, coupled with studies of metabolism, addressed the poor aqueous solubility and metabolic vulnerability, as well as potential toxicological effects, inherent in the more potent primary screening hits such as 10b. Analogues 13h and 13i, with structural modifications at each site, were shown to possess excellent antimalarial activity in vivo. The (+)-(35,4S) enantiomer of 13i and similar analogues were identified as the more potent. On the basis of these studies, we have selected (+)-13i for further study as a preclinical candidate.