benzyl 2-(2-ethoxy-2-ethoxyethyl)-1-hydrazinecarboxylate | 4503-58-6

• 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: benzyl 2-(2-ethoxy-2-ethoxyethyl)-1-hydrazinecarboxylate
• 英文别名: Ethyl 2-(2-phenylmethoxycarbonylhydrazinyl)acetate
• CAS: 4503-58-6
• 化学式: C₁₂H₁₆N₂O₄
• 分子量: 252.27
• InChiKey: DGDYVJAABABJNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl 2-(2-ethoxy-2-ethoxyethyl)-1-hydrazinecarboxylate 在 sodium hydroxide 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 1.0h， 生成 2-{1-(aminocarbothioyl)-2-[(benzyloxy)carbonyl]hydrazino}acetic acid
  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：

  苯甲氧羰酰琥珀酰亚胺 、 肼基乙酸乙酯盐酸盐 在 N-甲基吗啉 作用下， 生成 benzyl 2-(2-ethoxy-2-ethoxyethyl)-1-hydrazinecarboxylate
  参考文献：
  名称：

  含AzAsx-Pro的Aza肽的合成与结构

  摘要：

  肽中的一种可能的α-修饰是用氮取代CαH基团。我们建议使用三光气作为羰基化剂，以将适当取代的酰肼偶联至脯氨酸氮上，从而获得AzAsx-Pro或AzAla-Pro氮杂序列（Az表示取代，而Asx代表Asn或Asp）。通过1 H-NMR和IR光谱研究了三种Z-AzAsx-Pro-NH i Pr和Boc-AzAla-Pro-NH i Pr氮杂二肽的结构，并在其中研究了其中的三种。通过X射线衍射得到结晶态。

  DOI：

  10.1016/0040-4039(95)02124-8

文献信息

• Synthese eines Azaanalogen des Antibiotikums Negamycin
  作者：Wolfgang Streicher、Hellmuth Reinshagen

  DOI：10.1002/cber.19751080314

  日期：1975.3

  Die Synthese des 3-Azaanalogen (2) des Antibiotikums Negamycin wird mitgeteilt. Das neue Derivat besitzt keine antibakterielle Aktivität.

  据报道，抗生素尼古霉素的3-氮杂类似物（2）的合成。新衍生物没有抗菌活性。
• Hydrazino and N-Amino peptides. Chemical and structural aspects
  作者：Alain Lecoq、Michel Marraud、André Aubry

  DOI：10.1016/0040-4039(91)85080-o

  日期：1991.6

  The regioselective acylation of the nitrogens in hydrazino acetic acid has been studied to obtain the hydrazide and N-amino amide peptidomimetic groups Their conformational influence on the β-turn structure has also been considered.

  为了研究酰肼和N-氨基酰胺的拟肽基团，研究了肼基乙酸中氮的区域选择性酰化，还考虑了它们对β-turn结构的构象影响。
• Synthesis of aza-β-lactams by rhodium carbenoid mediated cyclisation
  作者：Christopher J. Moody、Christopher J. Pearson、Geoffrey Lawton

  DOI：10.1016/s0040-4039(00)98648-9

  日期：1985.1

  Treatment of the diazo-compounds (3), obtained in two steps from readily available hydrazine derivatives (1), with a catalytic amount of rhodium (II) acetate in benzene gives the aza-β-lactams (4) in high yield.

  分两步从易得的肼衍生物（1）中获得的重氮化合物（3），经催化量的乙酸铑（II）在苯中的处理，可以高收率得到氮杂-β-内酰胺（4）。
• Synthesis and activity of HIV protease inhibitors
  作者：Patrick Garrouste、Macek Pawlowski、Thierry Tonnaire、Sames Sicsic、Pascal Dumy、Eve de Rosny、Michèle Reboud-Ravaux、Pierre Fulcrand、Jean Martinez

  DOI：10.1016/s0223-5234(98)80043-3

  日期：1998.6

  We report here the synthesis and activity of HIV protease inhibitors. Ln the first stage hydrophobic compounds incorporating a 'carba' bond surrogate or a beta-homologated residue were synthesized. Secondly, we synthesized cyclic compounds in which we incorporated 2-quinoline carboxylic acid in the P3 position and the amino-hydroxyindane moiety in the P'3. The last part of this work was dedicated to a structure/activity study of a peptide substrate. These modifications allowed us to work up the synthesis of new pseudopeptide bonds: amino-amide and hydroxy-amide, Compounds with activity in the micromolar range were actually a starting point for the synthesis of new protease inhibitors. (C) Elsevier, Paris.
• Niedrich,H.; Pirrwitz,J., Journal fur praktische Chemie (Leipzig 1954), 1972, vol. 314, p. 735 - 750
  作者：Niedrich,H.、Pirrwitz,J.

  DOI：——

  日期：——