<<(benzyloxycarbonyl)glycyl>amino>acetonitrile | 20855-76-9

• 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: <<(benzyloxycarbonyl)glycyl>amino>acetonitrile
• 英文别名: (Z-glycylamino)acetonitrile；Z-Gly-NHCH2CN；N--aminoacetonitril；N-(N-Benzyloxycarbonyl-glycyl)-aminoacetonitril；benzyl N-{[(cyanomethyl)carbamoyl]methyl}carbamate；benzyl N-[2-(cyanomethylamino)-2-oxoethyl]carbamate
• CAS: 20855-76-9
• 化学式: C₁₂H₁₃N₃O₃
• 分子量: 247.254
• InChiKey: STYZMWDBHMMOCR-UHFFFAOYSA-N

物化性质

• 熔点：
  144-146 °C(Solv: cyclohexane (110-82-7); ethyl acetate (141-78-6))
• 沸点：
  542.5±45.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  91.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  <<(benzyloxycarbonyl)glycyl>amino>acetonitrile 在 盐酸 、 六甲基磷酰三胺 、 正丁基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 28.0h， 生成 methyl 1-[[2-(phenylmethoxycarbonylamino)acetyl]amino]cyclopropane-1-carboxylate
  参考文献：
  名称：

  McMath, Andrew R.; Guillaume, Dominique; Aitken, David J., Bulletin de la Societe Chimique de France, 1997, vol. 134, # 1, p. 105 - 110

  摘要：

  DOI：
• 作为产物：
  描述：

  N-苄氧羰基甘氨酸 在 氯化亚砜 作用下， 以 六甲基磷酰三胺 、 乙腈 为溶剂， 反应 1.0h， 生成 <<(benzyloxycarbonyl)glycyl>amino>acetonitrile
  参考文献：
  名称：

  Amino acid amide derivatives of 2-[3-(aminomethyl)-4H-1,2,4-triazol-4-yl]benzophenones, a novel class of annulated peptidoaminobenzophenones

  摘要：

  A series of the title compounds was prepared via condensation of the 3-(aminomethyl)triazolylbenzophenone (5) with N-protected amino acids, followed by deprotection, amination of the 3-[(chloroacetamido)methyl]triazolylbenzophenone (6a,b), or reduction of the relevant azide derivative (6c). Some of the title compounds were also derived directly from the quinazolines 3 or 4 by acid-induced rearrangement, followed by deprotection. These new amino acid amide derivatives of the triazolylbenzophenones (2) were evaluated for central nervous system (CNS) activity. Members of this class of compounds exhibited a high level of CNS activities. For example, 2',5-dichloro-2-[3-[(glycylamino)methyl]-5-methyl-4H-1,2,4-triazol-4-yl] benzophenone (2c) was as active as triazolam, with an ED50 of 0.58 mg/kg (mice, po), against antifighting activity in the foot shock-induced fighting test. Other triazolylbenzophenone derivatives (2a-f) showed similar pharmacological activities.

  DOI：

  10.1021/jm00354a015

文献信息

• Interaction of Papain-like Cysteine Proteases with Dipeptide-Derived Nitriles
  作者：Reik Löser、Klaus Schilling、Elke Dimmig、Michael Gütschow

  DOI：10.1021/jm050686b

  日期：2005.12.1

  were introduced, and systematic fluorine, bromine, and phenyl scans for phenylalanine in the P2 position were performed. Moreover, the N-terminal protection was varied. Kinetic investigations were carried out with cathepsin L, S, and K as well as papain. Changes in the backbone structure of the parent N-(tert-butoxycarbonyl)-phenylalanyl-glycine-nitrile (16), such as the introduction of an R-configured

  制备一系列44个在P2位具有各种氨基酸和在P1位具有甘氨酸的二肽腈，并将其评估为半胱氨酸蛋白酶的抑制剂。关于P2-S2相互作用对酶抑制剂复合物形成的重要贡献，重点是将结构多样性引入P2侧链。引入了非蛋白氨基酸，并进行了系统的氟，溴和苯基扫描，以检测P2位置的苯丙氨酸。而且，N-末端保护是多种多样的。使用组织蛋白酶L，S和K以及木瓜蛋白酶进行动力学研究。母体N-（叔丁氧羰基）-苯丙氨酰基-甘氨酸-腈的骨架结构变化（16），例如将R构型的氨基酸或氮杂氨基酸引入P2以及P1氮的甲基化，会导致亲和力的急剧下降。示例性地，16的氰基被醛或甲基酮官能团取代。关于靶酶的底物特异性，讨论了构效关系。
• Studies on Hepatic Agents. I. Synthesis of Aminoacyl (and Hydroxyacyl) Aminoacetonitriles
  作者：SEIGO SUZUE、TUTOMU IRIKURA

  DOI：10.1248/cpb.16.1417

  日期：——

  For the purpose of elucidating the structural relationship between lathyrism and inhibition of necrosis induced by CCl4 in the liver of the rat, many compounds related to aminoacetonitrile were synthesized. N-Aminoacylaminoacetonitriles (VIII, XIV) were synthesized from phthaloylaminoacylaminoacetonitriles. VIII were converted to 2-hydroxyimino-5-oxopiperazine derivatives (XV) and 5-oxo-2-thio-piperazines (XX). Preparations of N-(N-acylaminoacyl) aminoacetonitriles were also described. Further, N-α-hydroxyacylaminoacetonitriles were prepared from chloralides of α-hydroxyacids with aminoacetonitrile. In addition, XV (R=H) was converted to 2-acetamino-5-acetoxypyrazine by treatment with acetic anhydride.

  为了阐明贻贝症与四氯化碳诱导的大鼠肝脏坏死抑制之间的结构关系，合成了许多与氨基乙腈相关的化合物。N-氨基酰氨基乙腈（VIII，XIV）是从邻苯二甲酰氨基酰氨基乙腈合成的。VIII被转化为2-羟基亚胺-5-氧杂哌嗪衍生物（XV）和5-氧-2-硫杂哌嗪（XX）。还描述了N-(N-酰氨基酰)氨基乙腈的制备。此外，N-α-羟基酰氨基乙腈是由α-羟基酸的氯化物与氨基乙腈反应制备的。此外，通过用醋酸无水物处理，XV（R=H）被转化为2-乙酰氨基-5-乙酰氧基吡唑。
• Tetrazole analogues of amino acids and peptides— V
  作者：Z. Grzonka、E. Rekowska、B. Liberek

  DOI：10.1016/s0040-4020(01)91629-1

  日期：1971.1

  coupling of N-protected amino acids with triethylammonium salts of tetrazole analogues of amino acids followed by removal of amino protection. Alternatively the products were prepared from amides of N-protected peptides by dehydration to the corresponding nitriles, formation of the tetrazole nucleus by the reaction of the cyano group with ammonium azide, and removal of amino protection.

  通过将N-保护的氨基酸与氨基酸的四唑类似物的三乙基铵盐偶联，然后除去氨基保护基，来制备标题化合物。或者，由N-保护的肽的酰胺通过脱水成相应的腈，通过氰基与叠氮化铵的反应形成四唑核，并除去氨基保护来制备产物。
• Elmore, Donald T.; Guthrie, David J. S.; Kay, Gillian, Journal of the Chemical Society. Perkin transactions I, 1988, p. 1051 - 1056
  作者：Elmore, Donald T.、Guthrie, David J. S.、Kay, Gillian、Williams, Carrell H.

  DOI：——

  日期：——
• HIRAI, KENTARO;FUJISHITA, TOSHIO;ISHIBA, TERUYUKI;SUGIMOTO, HIROHIKO;MATS+, J. MED. CHEM., 1982, 25, N 12, 1466-1473
  作者：HIRAI, KENTARO、FUJISHITA, TOSHIO、ISHIBA, TERUYUKI、SUGIMOTO, HIROHIKO、MATS+

  DOI：——

  日期：——