α-hydrazinophenylacetic acid | 19866-39-8

• 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: α-hydrazinophenylacetic acid
• 英文别名: 2-hydrazino-2-phenylacetic acid；2-hydrazinophenylacetic acid；(+/-)-hydrazino-phenyl-acetic acid；hydrazino-phenyl-acetic acid；(+/-)-Hydrazino-phenyl-essigsaeure；Inakt. α-Hydrazino-phenylessigsaeure；alpha-Hydrazinophenyl-acetic acid；2-hydrazinyl-2-phenylacetic acid
• CAS: 19866-39-8
• 化学式: C₈H₁₀N₂O₂
• mdl: MFCD19201326
• 分子量: 166.18
• InChiKey: FZOOXGZQJUAYHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 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：

  α-hydrazinophenylacetic acid 在 溶剂黄146 、 sodium nitrite 作用下， 生成 α-(1-Nitrosohydrazino)-phenylessigsaeure
  参考文献：
  名称：

  LiBassi,G. et al., Gazzetta Chimica Italiana, 1977, vol. 107, p. 253 - 255

  摘要：

  DOI：
• 作为产物：
  描述：

  2-溴-2-苯基丙二酸 在 乙醇 、 一水合肼 作用下， 生成 α-hydrazinophenylacetic acid
  参考文献：
  名称：

  Berger, Journal fur praktische Chemie (Leipzig 1954), 1939, vol. <2> 152, p. 267,314

  摘要：

  DOI：

文献信息

• [EN] THIOSEMICARBAZATES AND USES THEREOF<br/>[FR] THIOSEMICARBAZATES ET LEURS UTILISATIONS
  申请人：FEINSTEIN INSTITUTES FOR MEDICAL RESEARCH

  公开号：WO2020227592A1

  公开（公告）日：2020-11-12

  Thioesters, thiocarbamates, thiocarbazates, semithiocarbazates, peptides, aza-amino acid conjugates, and azapeptides; and a chemoselective and site-specific functionalization protocol of protected thiocarbazates and semithiocarbazates are described. The protocol features the use of Mitsunobu reaction to alkylate specifically the nitrogen atom close to the acylthiol moiety with alcohols to produce protected mono-substituted thiocarbazates that can be stored for months, activated under mild conditions at low temperature using halonium reagents and integrated orthogonally to make substituted semicarbazides that can be used, e.g., as synthons in synthesis of aza-amino acid conjugates, azapeptides and other peptidomimetics. Methods for preparing and using ureases, carbazides, semicarbazides, beta-peptides, azapeptides, and other peptidomimetics and azapeptide conjugates, and uses of ureases, carbazides, semicarbazides, beta-peptides, azapeptides in drug discovery, diagnosis, inhibition, prevention and treatment of diseases are also described.

  巯酯，硫代氨基甲酸酯，硫代氨基甲酸酯，半硫代氨基甲酸酯，肽，氮代氨基酸共轭物和氮代肽；以及一种对受保护的硫代氨基甲酸酯和半硫代氨基甲酸酯进行化学选择性和位点特异性功能化的方法被描述。该方法采用三甲基脲反应特异性烷基化靠近酰硫醇基团的氮原子，使用醇生成可储存数月的受保护的单取代硫代氨基甲酸酯，在低温下使用卤化物试剂轻微条件下激活，并与其他基团正交集成以制备取代半氨基甲酸酰胺，例如，可用作氮代氨基酸共轭物，氮代肽和其他肽类模拟物的合成中间体。还描述了制备和使用尿酶，卡巴酰胺，半氨基甲酸酰胺，β-肽，氮代肽和其他肽类模拟物以及氮代肽共轭物的方法，以及尿酶，卡巴酰胺，半氨基甲酸酰胺，β-肽，氮代肽在药物发现，诊断，抑制，预防和治疗疾病中的用途。
• 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)
• Acid Hydrolysis of 1,6-Dihydro-4-amino-3-methyl-6-phenyl-1,2,4-triazin-5(4<i>H</i>)-one (1,6-Dihydrometamitron)
  作者：Jiří Ludvík、Jaromír Jirkovský、Jiří Urban、Petr Zuman

  DOI：10.1021/jf9902346

  日期：1999.9.1

  Metamitron (1) does not undergo hydrolysis at pH 1-8 and up to 5 M H(2)SO(4). The product of its two-electron reduction, 1, 6-dihydrometamitron (2), on the other hand, undergoes at pH <3 relatively fast hydrolysis. The dependence of the measured rate constant on acidity indicates that the completely protonated form (AH(2)(2+)) predominating in strongly acidic media undergoes hydrolysis slower than the species

  Metamitron（1）在pH 1-8和不超过5 MH（2）SO（4）时不会水解。另一方面，其双电子还原的产物1、6-二氢亚甲基同孕酮（2）在pH <3时经历相对较快的水解。测得的速率常数对酸度的依赖性表明，在强酸性介质中占优势的完全质子化形式（AH（2）（2+））的水解速度比质子少（AH（+））的物质慢。后一种活性最高的物质在pH介于0和2之间的溶液中浓度最高。该物质在2,3-偶氮甲亚胺键上质子化，并最终生成2-肼基-2-苯基乙酸（4）和乙酰肼（ 5）。动力学，极谱法和分光光度法测量表明，第一次解离的平均值pK（a）= -0.8，第二次解离的pK（a）= 0.95。这些观察结果以及易分解的间位子（1）中的1,6-键表明，在本质上，间位子的裂解可先将其还原为1，6-二氢金属亚甲基（2），然后再进行水解。因此，厌氧的还原条件可能对于metamitron的总微生物降解是更可取的。
• [EN] PYRROLIDINE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY<br/>[FR] PYRROLIDINES MODULATEURS DE L'ACTIVITE DU RECEPTEUR DE CHIMIOKINE
  申请人：MERCK & CO INC

  公开号：WO2000059502A1

  公开（公告）日：2000-10-12

  The present invention is directed to pyrrolidine compounds of formula (I) (wherein R?1, R2, R3, R4, R5, R6, R14¿ and n are defined herein) which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptors CCR-5 and/or CCR-3.

  本发明涉及式(I)的吡咯烷化合物（其中R1，R2，R3，R4，R5，R6，R14和n在此定义），其作为趋化因子受体活性调节剂具有用途。特别地，这些化合物作为趋化因子受体CCR-5和/或CCR-3的调节剂具有用途。
• 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.