3-{[(噻吩-2-基)甲基]氨基}丙酸乙酯 | 131436-68-5

• 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
• 中文名称: 3-{[(噻吩-2-基)甲基]氨基}丙酸乙酯
• 英文名称: ethyl 3-<(2-thienylmethyl)amino>propionate
• 英文别名: ethyl 3-((thiophen-2-ylmethyl)amino)propanoate；ethyl β-(thien-2-ylmethylamino)-propionate；Ethyl 3-[(2-thienylmethyl)amino]propanoate；ethyl 3-(thiophen-2-ylmethylamino)propanoate
• CAS: 131436-68-5
• 化学式: C₁₀H₁₅NO₂S
• mdl: MFCD03450395
• 分子量: 213.301
• InChiKey: RVUKMQHTMQHBPR-UHFFFAOYSA-N

物化性质

• 沸点：
  118-126 °C(Press: 3.0 Torr)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  3-{[(噻吩-2-基)甲基]氨基}丙酸乙酯 在 盐酸 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 ethyl (R)-3-(2-(2-methoxyphenyl)-2-((2-oxo-2,3-dihydrobenzo[d]thiazole)-6-sulfonamido)-N-(thiophen-2-ylmethyl)acetamido)propanoate
  参考文献：
  名称：

  使用支架跳跃设计 OSMI-4 类似物：研究尿苷模拟物在 OGT 抑制剂结合中的重要性

  摘要：

  β- N-乙酰氨基葡萄糖转移酶(OGT) 是一个很有前途的治疗靶点。第一个纳摩尔 OGT 抑制剂 OSMI-4 仍然是迄今为止报道的最有效的抑制剂，但其物理化学性质限制了其作为潜在候选药物和生物工具的实用性。为了解决这个问题，我们进行了支架跳跃，产生了新的 OSMI-4 衍生物，从而提供了对氢键角和去溶剂化惩罚等识别特征的深入了解。

  DOI：

  10.1002/cmdc.202300001
• 作为产物：
  描述：

  2-噻吩甲醛 、 beta-丙氨酸乙酯盐酸盐 在 三乙胺 、 甲醇 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 3-{[(噻吩-2-基)甲基]氨基}丙酸乙酯
  参考文献：
  名称：

  EP2141168

  摘要：

  公开号：

文献信息

• Synthesis and structure-activity relationship study of arylsulfonamides as novel potent H5N1 inhibitors
  作者：Yongshi Yu、Qi Tang、Zhichao Xu、Siliang Li、Mengyu Jin、Zixuan Zhao、Chune Dong、Shuwen Wu、Hai-Bing Zhou

  DOI：10.1016/j.ejmech.2018.09.065

  日期：2018.11

  H5N1 virus, one subtype of highly pathogenic influenza A virus in human infection, has recently received attention due to its unpredictable and high mortality. In this study, a series of arylsulfonamide derivatives were identified as improved H5N1 inhibitors for the influenza treatment by systematic structure-activity relationship investigation. Among them, the most potent H5N1 inhibitor 3h exhibited

  H5N1病毒是人类感染中高致病性甲型流感病毒的一种亚型，最近由于其不可预测的高死亡率而受到关注。在这项研究中，通过系统的结构-活性关系研究，一系列芳基磺酰胺衍生物被确定为用于流感治疗的改良H5N1抑制剂。其中，最有效的H5N1抑制剂3h对H5N1病毒表现出优异的抗病毒活性，EC 50值为0.006μM，选择性指数为33543.3。此外，3h与M2质子通道蛋白的分子对接为理解这类化合物对H5N1的抑制提供了实用的方法。
• HETEROARYL DERIVATIVES
  申请人：Matsuoka Masato

  公开号：US20100048537A1

  公开（公告）日：2010-02-25

  The present invention relates to a compound represented by formula [1] or a pharmaceutically acceptable salt thereof: In formula [1], one of X and Y is CH and the other is oxygen or sulfur; R is hydrogen, etc.; Z is hydrogen, etc.; Ar is phenyl, etc.; and n is 1 or 2 and or m is 1 or 2, excluding compounds where n is 2 and m is 2 simultaneously. Also provided is a pharmaceutical composition comprising a compound of formula [1] or a pharmaceutically acceptable salt thereof as an active ingredient. The composition is usable as an agent for the prevention or treatment of depression, panic disorder, anxiety, obsessive-compulsive disorder, chronic pain, fibromyalgia, obesity, stress urinary incontinence, and overactive bladder.

  本发明涉及一种由公式[1]表示的化合物或其药学上可接受的盐： 在公式[1]中，X和Y中的一个是CH，另一个是氧或硫；R是氢等；Z是氢等；Ar是苯等；n为1或2，m为1或2，不包括n为2且m为2的化合物。还提供了一种药物组合物，其包括公式[1]的化合物或其药学上可接受的盐作为活性成分。该组合物可作为预防或治疗抑郁症、惊恐障碍、焦虑症、强迫症、慢性疼痛、纤维肌痛、肥胖症、压力性尿失禁和过度活动膀胱的药物。
• Heteroaryl derivatives
  申请人：Nippon Shinyaku Co., Ltd.

  公开号：US08217031B2

  公开（公告）日：2012-07-10

  The present invention relates to a compound represented by formula [1] or a pharmaceutically acceptable salt thereof: In formula [1], one of X and Y is CH and the other is oxygen or sulfur; R is hydrogen, etc.; Z is hydrogen, etc.; Ar is phenyl, etc.; and n is 1 or 2 and or m is 1 or 2, excluding compounds where n is 2 and m is 2 simultaneously. Also provided is a pharmaceutical composition comprising a compound of formula [1] or a pharmaceutically acceptable salt thereof as an active ingredient. The composition is usable as an agent for the prevention or treatment of depression, panic disorder, anxiety, obsessive-compulsive disorder, chronic pain, fibromyalgia, obesity, stress urinary incontinence, and overactive bladder.

  本发明涉及一种由公式[1]表示的化合物或其药学上可接受的盐： 在公式[1]中，X和Y中的一个是CH，另一个是氧或硫；R是氢等；Z是氢等；Ar是苯等；n为1或2，m为1或2，但不包括n和m同时为2的化合物。还提供了一种药物组合物，其包含公式[1]的化合物或其药学上可接受的盐作为活性成分。该组合物可用作预防或治疗抑郁症、惊恐障碍、焦虑症、强迫症、慢性疼痛、纤维肌痛、肥胖症、压力性尿失禁和过度活动膀胱的药剂。
• PYRROLIDINE DIONE DERIVATIVES
  申请人：PFIZER INC.

  公开号：EP0553130B1

  公开（公告）日：1996-01-03
• A highly specific aldose reductase inhibitor, ethyl 1-benzyl-3-hydroxy-2(5H)-oxopyrrole-4-carboxylate and its congeners
  作者：Banavara L. Mylari、Thomas A. Beyer、Todd W. Siegel

  DOI：10.1021/jm00107a020

  日期：1991.3

  Ethyl 1-benzyl-3-hydroxy-2(5H)-oxopyrrole-4-carboxylate (1, EBPC) is a potent and specific inhibitor of aldose reductase. It was > 4000 x more potent in its inhibition of rat lens aldose reductase than the closely related rat or pig kidney aldehyde reductase, thus making it the most selective inhibitor of a NADPH-dependent carbonyl reductase identified to date. In agreement with this observation, it was found to be a highly potent inhibitor of aldose reductase from rat sciatic nerve with > 98% inhibition at 1-mu-M, but it was practically devoid of activity against aldehyde reductases from rat liver and brain. Inhibition of aldose reductase was mixed type for glyceraldehyde (K(i) = 8.0 x 10(-8) M) and noncompetitive for NADPH (K(i) = 1.70 x 10(-8) M). Its potential as an in vitro tool to quantitate monomeric aldo/keto reductase activities in crude tissue extracts is presented. Structure-activity relationships emerging from synthetic modifications of EBPC are discussed. Several modifications were found to be active in vitro against aldose reductase from human placenta and in vivo in a rat model of diabetic complications, but none was more potent than EBPC.