Methyl 4-(2-hydroxyethyl)thiophene-2-carboxylate | 272130-60-6

• 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-(2-hydroxyethyl)thiophene-2-carboxylate
• CAS: 272130-60-6
• 化学式: C₈H₁₀O₃S
• 分子量: 186.232
• InChiKey: CZULKROWRXVUNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 4-(2-hydroxyethyl)thiophene-2-carboxylate 在 四溴化碳 、 sodium hydride 、 三苯基膦 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 Methyl 4-[2-(8-oxo-4,7-dihydroimidazo[4,5-d][1,3]diazepin-3-yl)ethyl]thiophene-2-carboxylate
  参考文献：
  名称：

  AMP Deaminase Inhibitors. 3. SAR of 3-(Carboxyarylalkyl)coformycin Aglycon Analogues

  摘要：

  N3-Substituted coformycin aglycon analogues with improved AMP deaminase (AMPDA) inhibitory potency are described. Replacement of the 5-carboxypentyl substituent in the lead AMPDA inhibitor 3-(5-carboxypentyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol (2) described in the previous article with various carboxyarylalkyl groups resulted in compounds with 10-100-fold improved AMPDA inhibitory potencies. The optimal N3 substituent had m-carboxyphenyl with a two-carbon alkyl tether. For example, 3-[2-(3-carboxy-5-ethylphenyl)-ethyl]-3,6,7,8-tetrahydroimidazo[4,5-d] [1,3]diazepin-8-ol (43g) inhibited human AMPDA with a K-i = 0.06 mu M. The compounds within the series also exhibited >1000-fold specificity for AMPDA relative to adenosine deaminase.

  DOI：

  10.1021/jm990448e
• 作为产物：
  描述：

  methyl 4-(tert-butyldimethylsilyloxyethyl)-2-thiophenecarboxylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 Methyl 4-(2-hydroxyethyl)thiophene-2-carboxylate
  参考文献：
  名称：

  AMP Deaminase Inhibitors. 3. SAR of 3-(Carboxyarylalkyl)coformycin Aglycon Analogues

  摘要：

  N3-Substituted coformycin aglycon analogues with improved AMP deaminase (AMPDA) inhibitory potency are described. Replacement of the 5-carboxypentyl substituent in the lead AMPDA inhibitor 3-(5-carboxypentyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol (2) described in the previous article with various carboxyarylalkyl groups resulted in compounds with 10-100-fold improved AMPDA inhibitory potencies. The optimal N3 substituent had m-carboxyphenyl with a two-carbon alkyl tether. For example, 3-[2-(3-carboxy-5-ethylphenyl)-ethyl]-3,6,7,8-tetrahydroimidazo[4,5-d] [1,3]diazepin-8-ol (43g) inhibited human AMPDA with a K-i = 0.06 mu M. The compounds within the series also exhibited >1000-fold specificity for AMPDA relative to adenosine deaminase.

  DOI：

  10.1021/jm990448e

文献信息

• L-glutamic acid derivatives
  申请人：THE TRUSTEES OF PRINCETON UNIVERSITY

  公开号：EP0415510A2

  公开（公告）日：1991-03-06

  Pyrimidin-5-yl derivatives of L-glutamic acid are anti-neoplastic agents. A typical embodiment is N-(4-[5-(2,6-diamino-4-hydroxypyrimidin-5-yl)-butyl]­thien-2-ylcarboxy)-L-glutamic acid.

  L-谷氨酸的嘧啶-5-基衍生物是一种抗肿瘤药物。一个典型的例子是 N-(4-[5-(2,6-二氨基-4-羟基嘧啶-5-基)-丁基]噻吩-2-基羧基)-L-谷氨酸。
• US4920125A
  申请人：——

  公开号：US4920125A

  公开（公告）日：1990-04-24
• AMP Deaminase Inhibitors. 3. SAR of 3-(Carboxyarylalkyl)coformycin Aglycon Analogues
  作者：Srinivas Rao Kasibhatla、Brett C. Bookser、Gary Probst、James R. Appleman、Mark D. Erion

  DOI：10.1021/jm990448e

  日期：2000.4.1

  N3-Substituted coformycin aglycon analogues with improved AMP deaminase (AMPDA) inhibitory potency are described. Replacement of the 5-carboxypentyl substituent in the lead AMPDA inhibitor 3-(5-carboxypentyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol (2) described in the previous article with various carboxyarylalkyl groups resulted in compounds with 10-100-fold improved AMPDA inhibitory potencies. The optimal N3 substituent had m-carboxyphenyl with a two-carbon alkyl tether. For example, 3-[2-(3-carboxy-5-ethylphenyl)-ethyl]-3,6,7,8-tetrahydroimidazo[4,5-d] [1,3]diazepin-8-ol (43g) inhibited human AMPDA with a K-i = 0.06 mu M. The compounds within the series also exhibited >1000-fold specificity for AMPDA relative to adenosine deaminase.