ethyl α-(cyanomethylamino)acetate | 76753-44-1

• 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: ethyl α-(cyanomethylamino)acetate
• 英文别名: N-cyanomethyl glycine ethyl ester；Iminodiessigsaeure-aethylester-nitril；N-Cyanmethyl-glycin-aethylester；Ethyl (cyanomethyl)glycinate；ethyl 2-(cyanomethylamino)acetate
• CAS: 76753-44-1
• 化学式: C₆H₁₀N₂O₂
• 分子量: 142.158
• InChiKey: HJHAOMCORINKOB-UHFFFAOYSA-N

物化性质

• 沸点：
  263.0±20.0 °C(Predicted)
• 密度：
  1.066±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  ethyl α-(cyanomethylamino)acetate 在 4-二甲氨基吡啶 、 盐酸羟胺 、 碳酸氢钠 、 三乙胺 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 24.0h， 生成 [tert-Butoxycarbonyl-(N-hydroxycarbamimidoylmethyl)-amino]-acetic acid ethyl ester
  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：

  三甲基氰硅烷 、 1,3,5-tri-(ethoxycarbonylmethyl)hexahydro-1,3,5-triazine 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以65%的产率得到ethyl α-(cyanomethylamino)acetate
  参考文献：
  名称：

  TiCl₄induced N-Methyleneamine Equivalents: A New Route to Aminoacetonitriles

  摘要：

  TiCl4 induced N-methyleneamine equivalents from hexahydro-1,3,5-triazines or N-(methoxymethyl)amines were reacted with trimethylsilyl cyanide to give aminoacetonitriles in 40-90% yield.

  DOI：

  10.1080/00397919108020806

文献信息

• The Ion-exchange Chromatography of Imino Derivatives of Glycine
  作者：Katsuhiro Kawashiro、Shiro Morimoto、Hideyuki Yoshida

  DOI：10.1246/bcsj.56.792

  日期：1983.3

  The resolution of the six imino derivatives of glycine (Gly) by ion-exchange chromatography is described. The imino compounds included iminodiacetonitrile (1), iminodiacetamide (2), iminodiacetic acid (3), α-(cyanomethylamino)acetamide (4), α-(cyanomethylamino)acetic acid (5), and α-(carbamoylmethylamino)acetic acid (6). A mixture of 1–6 was chromatographed along with Gly, glycinamide, aminoacetonitrile, and NH3 with an automatic amino acid analyzer using Aminex A-4 resin column (0.25φ×50 cm) and sodium citrate buffers. When the initial buffer of pH 3.25 was changed to pH 6.50 15 min after beginning the analysis, these ten components were completely resolved. The analysis was completed in about 4.5 h. The stability of 1, 4, and 5 in aqueous media at room temperature was also studied.

  离子交换色谱法对甘氨酸（Gly）的六种亚氨基衍生物的分离进行了描述。这些亚氨基化合物包括亚氨基二乙腈（1）、亚氨基二乙酰胺（2）、亚氨基二乙酸（3）、α-（氰甲基氨基）乙酰胺（4）、α-（氰甲基氨基）乙酸（5）和α-（碳酰甲基氨基）乙酸（6）。混合物1-6与甘氨酸、甘氨酰胺、氨基乙腈和NH3一起，在自动氨基酸分析仪上使用Aminex A-4树脂柱（0.25φ×50 cm）和柠檬酸钠缓冲液进行色谱分析。当分析开始15分钟后，初始的pH 3.25缓冲液改为pH 6.50时，这十种成分完全分离。分析过程大约需要4.5小时。还研究了1、4和5在水溶液中室温下的稳定性。
• Hydantoin derivative as metalloprotease inhibitor
  申请人：FUJIREBIO INC.

  公开号：EP0640594A1

  公开（公告）日：1995-03-01

  A hydantoin derivative represented by formula (I): wherein the all symbols are defined in the disclosure. The hydantoin derivative has an inhibitory activity on metalloprotease and hence is useful as analgesic and cardiovascular drug.

  一种以化学式(I)表示的噻唑烷酮衍生物：其中所有符号均在披露中定义。该噻唑烷酮衍生物具有对金属蛋白酶的抑制活性，因此可用作镇痛和心血管药物。
• Scheibler; Neef, Chemische Berichte, 1926, vol. 59, p. 1503
  作者：Scheibler、Neef

  DOI：——

  日期：——
• Radical Scavenging Activity of Ascorbic Acid Analogs Containing a Carbonyl Conjugated Ene-Diol Structure
  作者：Masataka Mochizuki、Shogo Nomura、Keiko Inami

  DOI：10.3987/com-15-13366

  日期：——

  Small molecule antioxidants such as ascorbic acid (AscH(2)) prevent the oxidative damage of biological molecules by scavenging reactive oxygen species. A carbonyl-conjugated ene-diol structure is essential for the antioxidant activity of AscH(2). As such, we synthesized novel AscH(2) analogs containing a carbonyl conjugated ene-diol structure and evaluated their radical scavenging activities. When the 1,2-dihydroxyethyl group was removed, radical scavenging activity equal to AscH(2) was observed. Analogs containing an endocyclic nitrogen atom instead of a ring oxygen displayed higher radical scavenging activities than AscH(2). Therefore, the electron donating effect of the carbonyl conjugated ene-diol structure greatly increased the radical scavenging activity of AscH(2) analogs.
• HA, HYUN-JOON;NAM, GONG-SIL;PARK, KYONG PAE, SYNTH. COMMUN., 21,(1991) N, C. 155-160
  作者：HA, HYUN-JOON、NAM, GONG-SIL、PARK, KYONG PAE

  DOI：——

  日期：——