2-hydrazinobutyric acid | 19866-33-2

• 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: 2-hydrazinobutyric acid
• 英文别名: α-hydrazinobutyric acid；2-Hydrazino-buttersaeure；α-Hydrazino-buttersaeure；α-Hydrazino-propan-α-carbonsaeure；2-Hydrazino-butansaeure-(1)；2-Hydrazinylbutanoic acid
• CAS: 19866-33-2
• 化学式: C₄H₁₀N₂O₂
• mdl: MFCD18432035
• 分子量: 118.136
• InChiKey: AJYLWDRNNNHBEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  75.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydrazinobutyric acid 、 间硝基苯甲醛 生成 2-<3-Nitro-phenyl-methylen-hydrazino>-buttersaeure
  参考文献：
  名称：

  α-肼基羧酸与茚三酮反应

  摘要：

  已经制备并表征了几种α-肼基羧酸及其间硝基苯甲腙。后者和前者中的两个以前没有报道过。发现α-肼酸与茚三酮反应产生鲁赫曼紫，但其产率远低于相应的氨基酸。然而，肼本身会产生不同颜色的产品。研究了茚三酮与 α-肼基酸之间反应的各个方面，并提出了鲁赫曼紫的形成机制。加拿大化学杂志, 46, 3013 (1968)

  DOI：

  10.1139/v68-501
• 作为产物：
  描述：

  2-(hydroxy-nitroso-amino)-butyric acid 在 sodium amalgam 作用下， 生成 2-hydrazinobutyric acid
  参考文献：
  名称：

  Gender difference in the mean age at the induction of hemodialysis in patients with autosomal dominant polycystic kidney disease

  摘要：

  Male patients with autosomal dominant polycystic kidney disease (ADPKD) begin hemodialysis earlier than female patients, The rate of progression of many other renal diseases is also faster in men than women. In this study, gender difference in ADPKD was compared with that in other diseases, such as chronic glomerulonephritis, diabetic nephropathy, and nephrosclerosis, using the data obtained from an annual statistical survey of the Japanese Society for Dialysis Therapy, The male-female ratio in ADPKD (n = 8,176) was 1.17:1 and closer to 1.0:1 than the other diseases. Men with ADPKD started hemodialysis therapy 1.3 years earlier than women (male age, 55.9 +/- 12.4 years versus female age, 57.2 +/- 11.5 years), and the age difference was less than that in other diseases. These results suggest that the prognosis in women with ADPKD is relatively worse than that in men with ADPKD or that women are not well protected against the progression of this disease compared with other renal diseases. In conclusion, men with ADPKD are introduced to hemodialysis therapy earlier than women; however, the age difference was small compared with other common renal diseases. (C) 2000 by the National Kidney Foundation, Inc.

  DOI：

  10.1016/s0272-6386(00)70042-4

文献信息

• Synthesis and Biological Activity of Aminoguanidine and Diaminoguanidine Analogues of the Antidiabetic/Antiobesity Agent 3-Guanidinopropionic Acid
  作者：Valerie A. Vaillancourt、Scott D. Larsen、Steven P. Tanis、Jeffery E. Burr、Mark A. Connell、Michele M. Cudahy、Bruce R. Evans、Peter V. Fisher、Paul D. May、Martin D. Meglasson、Deborah D. Robinson、F. Craig Stevens、John A. Tucker、Thomas J. Vidmar、Jen H. Yu

  DOI：10.1021/jm000094n

  日期：2001.4.1

  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.
• Reaction of α-bromocarboxylic acids with hydrazine and dimethylhydrazine
  作者：S. A. Malin、B. M. Laskin、A. S. Malin

  DOI：10.1134/s1070427207120348

  日期：2007.12

  Nucleofilic reaction of a series of alpha-bromocarboxylic acids with hydrazine and dimethylhydrazine is studied. High reactivity of a-bromocarboxylic acids is revealed and a series of alpha-hydrazinoarboxylic acids and N-(1-carboxyalkyl)-N,N-dimethylhydrazinium bromides are synthesized.
• Reaction of α-hydrazino carboxylic acids with ninhydrin
  作者：Edward Ronwin、Jerry V. Roach、Burrell L. Tucker

  DOI：10.1139/v68-501

  日期：1968.10.1

  were found to react with ninhydrin to yield Ruhemann's purple, but in much lower yield than the corresponding amino acids. However, hydrazine itself yields a different colored product. Various aspects of the reaction between ninhydrin and the a-hydrazino acids were investigated and a mechanism for the formation of Ruhemann's purple is suggested. Canadian Journal of Chemistry, 46, 3013 (1968)

  已经制备并表征了几种α-肼基羧酸及其间硝基苯甲腙。后者和前者中的两个以前没有报道过。发现α-肼酸与茚三酮反应产生鲁赫曼紫，但其产率远低于相应的氨基酸。然而，肼本身会产生不同颜色的产品。研究了茚三酮与 α-肼基酸之间反应的各个方面，并提出了鲁赫曼紫的形成机制。加拿大化学杂志, 46, 3013 (1968)
• Gender difference in the mean age at the induction of hemodialysis in patients with autosomal dominant polycystic kidney disease
  作者：Isao Ishikawa、Kenji Maeda、Shigeru Nakai、Yoshindo Kawaguchi

  DOI：10.1016/s0272-6386(00)70042-4

  日期：2000.6

  Male patients with autosomal dominant polycystic kidney disease (ADPKD) begin hemodialysis earlier than female patients, The rate of progression of many other renal diseases is also faster in men than women. In this study, gender difference in ADPKD was compared with that in other diseases, such as chronic glomerulonephritis, diabetic nephropathy, and nephrosclerosis, using the data obtained from an annual statistical survey of the Japanese Society for Dialysis Therapy, The male-female ratio in ADPKD (n = 8,176) was 1.17:1 and closer to 1.0:1 than the other diseases. Men with ADPKD started hemodialysis therapy 1.3 years earlier than women (male age, 55.9 +/- 12.4 years versus female age, 57.2 +/- 11.5 years), and the age difference was less than that in other diseases. These results suggest that the prognosis in women with ADPKD is relatively worse than that in men with ADPKD or that women are not well protected against the progression of this disease compared with other renal diseases. In conclusion, men with ADPKD are introduced to hemodialysis therapy earlier than women; however, the age difference was small compared with other common renal diseases. (C) 2000 by the National Kidney Foundation, Inc.