N-Cyanomethyl-β-alanin-ethylester | 1438-39-7

• 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: N-Cyanomethyl-β-alanin-ethylester
• 英文别名: N-cyanomethyl-β-alanine ethyl ester；N-Cyanmethyl-β-alanin-aethylester；Ethyl 3-[(cyanomethyl)amino]propanoate；ethyl 3-(cyanomethylamino)propanoate
• CAS: 1438-39-7
• 化学式: C₇H₁₂N₂O₂
• 分子量: 156.184
• InChiKey: VREBIGCURGKCDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-Cyanomethyl-β-alanin-ethylester 在 4-二甲氨基吡啶 、 sodium hydroxide 、 盐酸羟胺 、 碳酸氢钠 、 三乙胺 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 26.0h， 生成 N-[2-amino-2-(hydroxyimino)ethyl](tert-butoxycarbonyl)-beta-alanine
  参考文献：
  名称：

  Synthesis and Biological Activity of Aminoguanidine and Diaminoguanidine Analogues of the Antidiabetic/Antiobesity Agent 3-Guanidinopropionic Acid

  摘要：

  3-Guanidinopropionic acid (1) has been demonstrated both to improve insulin sensitivity and to promote weight loss selectively from adipose tissue in animal models of non-insulin-dependent diabetes mellitus (NIDDM). However, 1 has also been shown to be a substrate for both the creatine transporter and creatine kinase, leading to marked accumulation in muscle tissue as the corresponding N-phosphate. The corresponding aminoguanidine analogue 2 was recently discovered to retain the antidiabetic activity of 1 while being markedly less susceptible to creatine-like metabolism, suggesting that it should have less potential to accumulate in muscle. Further structural modification of 2 was undertaken to investigate whether the antidiabetic potency could be augmented while maintaining resistance to creatine-like metabolism. Modifications such as a-alkylation, homologation, and bioisosteric replacement of the aminoguanidine all were detrimental to antidiabetic activity. However, the simple regioisomeric aminoguanidinoacetic acid 9 and diaminoguanidinoacetic acid-analogue 7 were found to be equipotent to 2, leading eventually to the discovery of the significantly more potent diaminoguanidinoacetic acid regioisomers 52 and 53. Further attempts to modify the more active template represented by 52 led only to reductions in; antidiabetic activity. Each of the new active analogues displayed the same resistance to creatine-like metabolism as 2. Further testing of 7, 9, and 53 in obese diabetic ob;lob mice confirmed that weight loss is induced selectively from adipose tissue, similar to the lead 1. Administration of 53 to insulin-resistant rhesus monkeys led to reductions in both fasting and post-prandial plasma glucose levels with concomitant reductions in plasma insulin levels, suggesting that the compound improved the action of endogenous insulin. Compounds 7 and 53 were selected for further preclinical development.

  DOI：

  10.1021/jm000094n
• 作为产物：
  描述：

  3-氨基丙酸乙酯 、 碘乙腈 在 苯 作用下， 生成 N-Cyanomethyl-β-alanin-ethylester
  参考文献：
  名称：

  Uchibayashi, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1958, vol. 78, p. 845,848

  摘要：

  DOI：

文献信息

• Condensed pyrimidine derivative
  申请人：Eisai Co., Ltd.

  公开号：US05554615A1

  公开（公告）日：1996-09-10

  A novel pyrimidine derivative having an excellent antitumor activity, which is represented by the following general formula (I) or a pharmacologically acceptable salt thereof: ##STR1## wherein R.sup.1 represents a hydroxyl or amino group; R.sup.2 represents a phenylene, pyridinediyl, thiendiyl, furandiyl or thiazoldiyl group, --CO.sub.2 R.sup.5 and --CO.sub.2 R.sup.6 may be the same or different from each other and each represents a carboxyl group or a carboxylic acid ester, the part ##STR2## A represents an oxygen atom, a group represented by the formula: ##STR3## (wherein R.sup.3 and R.sup.4 may be the same or different from each other and each represents a hydrogen or halogen atom or a hydrocarbon group which may be substituted, or alternatively R.sup.3 and R.sup.4 may be united to form an alkylidene group which may be substituted) or a group represented by the formula: ##STR4## (wherein R.sup.70 represents a hydrogen atom or a hydrocarbon group), and n is an integer of 1 to 3, provided that the compound in which R.sup.1 represents oxygen, and hydrogen is attached to nitrogen at 3-position is included in the above shown definition, a process for preparation the same, and an antitumor drug containing the same.

  一种具有优异抗肿瘤活性的新型嘧啶衍生物，其由以下一般式（I）或其药理学上可接受的盐所代表：##STR1## 其中R.sup.1代表一个羟基或氨基团；R.sup.2代表苯基、吡啶基、噻吩基、呋喃基或噻唑基团，--CO.sub.2R.sup.5和--CO.sub.2R.sup.6可以相同也可以不同，每个代表一个羧基或羧酸酯，部分##STR2## A代表氧原子，一个由式表示的基团：##STR3## （其中R.sup.3和R.sup.4可以相同也可以不同，每个代表氢或卤素原子或一个可被取代的碳氢基团，或者R.sup.3和R.sup.4可以结合形成一个可被取代的烷基亚甲基）或一个由式表示的基团：##STR4## （其中R.sup.70代表氢原子或一个碳氢基团），n是1到3的整数，前提是在上述定义中包括R.sup.1代表氧，氢附着在3-位置的氮化合物，一种制备该化合物的方法，以及含有该化合物的抗肿瘤药物。
• Condensed pyrimidine derivatives antitumor agents
  申请人：Eisai Co., Ltd.

  公开号：EP0530579A1

  公开（公告）日：1993-03-10

  A novel pyrimidine derivative having an excellent antitumor activity, which is represented by the following general formula (I) or a pharmacologically acceptable salt thereof:    wherein R¹ represents a hydroxyl or amino group; R² represents a phenylene, pyridinediyl, thiendiyl, furandiyl or thiazoldiyl group, -CO₂R⁵ and -CO₂R⁶ may be the same or different from each other and each represents a carboxyl group or a carboxylic acid ester, the part 〉X-Y-Z- represents 〉N-CH₂-CH₂-, 〉N-CH=CH- or 〉CH-CH₂-CH₂-, A represents an oxygen atom, a group represented by the formula: (wherein R³ and R⁴ may be the same or different from each other and each represents a hydrogen or halogen atom or a hydrocarbon group which may be substituted, or alternatively R³ and R⁴ may be united to form an alkylidene group which may be substituted) or a group represented by the formula: (wherein R⁷⁰ represents a hydrogen atom or a hydrocarbon group), and n is an integer of 1 to 3, provided that the compound in which R¹ represents oxygen, and hydrogen is attached to nitrogen at 3-position is included in the above shown definition, a process for preparation the same, and an antitumor drug containing the same.

  一种具有优异抗肿瘤活性的新型嘧啶衍生物，由以下通式（I）或其药理上可接受的盐表示： 其中 R¹ 代表羟基或氨基；R²代表苯基、吡啶二基、噻吩二基、呋喃二基或噻唑二基，-CO₂R⁵和-CO₂R⁶可以相同或不同，且各自代表羧基或羧酸酯、X-Y-Z-代表〉N-CH₂-CH₂-、〉N-CH=CH-或〉CH-CH₂-CH₂-，A代表氧原子、由式： (其中 R³ 和 R⁴ 可以相同或不同，各自代表氢原子、卤素原子或可被取代的烃基，或者 R³ 和 R⁴ 可以结合形成可被取代的亚烷基）或由式表示的基团： (其中，R⁷⁰ 代表氢原子或烃基，且 n 为 1 至 3 的整数）的化合物、其制备方法以及含有该化合物的抗肿瘤药物均包括在上述定义中。
• US4421693A
  申请人：——

  公开号：US4421693A

  公开（公告）日：1983-12-20
• US4413005A
  申请人：——

  公开号：US4413005A

  公开（公告）日：1983-11-01
• US5554615A
  申请人：——

  公开号：US5554615A

  公开（公告）日：1996-09-10