N-(tert-butyloxycarbonyl)glycine isopentylamide | 84851-16-1

• 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: N-(tert-butyloxycarbonyl)glycine isopentylamide
• 英文别名: N-(tert-butyloxycarbonyl)glycyl isoamylamide；tert-butyl N-[2-(3-methylbutylamino)-2-oxoethyl]carbamate
• CAS: 84851-16-1
• 化学式: C₁₂H₂₄N₂O₃
• mdl: MFCD24391791
• 分子量: 244.334
• InChiKey: CDKCNWKCXPKVPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(tert-butyloxycarbonyl)glycine isopentylamide 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 glycine isopentylamide
  参考文献：
  名称：

  设计，合成和评价3-亚甲基取代的吲哚啉酮类抗疟药

  摘要：

  描述，设计和合成的3-亚甲基取代的吲哚啉酮作为falcipain抑制剂和抗疟原虫剂。这些化合物通过加成消除机制容易与硫醇反应，表明它们作为半胱氨酸蛋白酶抑制剂的潜力。含有具有Leu-几个吲哚满酮我发现戊识别部分是适度抑制剂的恶性疟原虫半胱氨酸蛋白酶falcipain-2，但不相关的蛋白酶falcipain-3，和针对抗氯喹显示抗疟原虫活性恶性疟原虫W2在低微摩尔范围内的应变。将7-氯喹啉部分偶联至3-亚甲基取代的吲哚酮骨架上导致抗血浆活性的显着改善。

  DOI：

  10.1016/j.ejmech.2011.01.008
• 作为产物：
  描述：

  BOC-甘氨酸 、 异戊胺 在 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以90%的产率得到N-(tert-butyloxycarbonyl)glycine isopentylamide
  参考文献：
  名称：

  胃抑素类似物的合成。P1'，P2'和P2子位点的结构对猪胃蛋白酶抑制作用的影响。

  摘要：

  已经合成了一系列在P2′，P1′和P2位置具有结构变化的胃抑素类似物，并测试了其对猪胃蛋白酶的抑制作用。这项研究的标准肽是Iva-Sta-Val-Ala-Iaa。P2'和P1'位置的结构变化对Ki的影响相对较小；然而，P2位置的微小变化对Ki和时间依赖性抑制具有更显着的影响。还合成了一系列胃抑素片段，并测试了其对猪胃蛋白酶的抑制作用。

  DOI：

  10.1021/jm00360a022

文献信息

• Synthesis of analogs of pepstatin. Effect of structure in subsites P1', P2', and P2 on inhibition of porcine pepsin
  作者：Daniel H. Rich、Francesco G. Salituro

  DOI：10.1021/jm00360a022

  日期：1983.6

  A series of pepstatin analogues having structural variations in the P2', P1', and P2 positions have been synthesized and tested for inhibition of porcine pepsin. The standard peptide for this study was Iva-Sta-Val-Ala-Iaa. Structural variations in the P2' and P1' positions have relatively little effect on Ki; however, small variations in the P2 position have a more dramatic effect on Ki and time-dependent

  已经合成了一系列在P2′，P1′和P2位置具有结构变化的胃抑素类似物，并测试了其对猪胃蛋白酶的抑制作用。这项研究的标准肽是Iva-Sta-Val-Ala-Iaa。P2'和P1'位置的结构变化对Ki的影响相对较小；然而，P2位置的微小变化对Ki和时间依赖性抑制具有更显着的影响。还合成了一系列胃抑素片段，并测试了其对猪胃蛋白酶的抑制作用。
• New bidentates as full inhibitors of enkephalin-degrading enzymes: synthesis and analgesic properties
  作者：Marie Claude Fournie-Zaluski、Annie Coulaud、Romaine Bouboutou、Pierre Chaillet、Jocelyne Devin、Gilles Waksman、Jean Costentin、Bernard P. Roques

  DOI：10.1021/jm00147a007

  日期：1985.9

  New compounds were designed to fully inhibit the in vitro metabolism of enkephalins, ensured by three different metallopeptidases. For this purpose, bidentate ligands as hydroxamate and N-hydroxy-N-formylamino groups were selected as highly potent metal coordinating agents and introduced on Phe-Gly and Phe-Ala related structures. Compounds corresponding to the general formula HC(O)N(OH)CH2CH(CH2Ph)CONHCH2COOH (compound 7) and HN(OH)C(O)CH2CH(CH2Ph)CONHCH(R)COOH (compound 11, R = H; compound 13, R = CH3) behave as full inhibitors of the three enzymes, with IC50's in the nanomolar range for enkephalinase, from 0.3 microM to 1 nM for dipeptidylaminopeptidase, and in the micromolar range for a biologically relevant aminopeptidase. Two diastereoisomers of the most active inhibitor 13 were separated by HPLC and their stereochemistry was assigned by 1H NMR spectroscopy. Both isomers were efficient as enkephalinase blockers, but only the RS isomer, designated kelatorphan, was able to strongly inhibit aminopeptidase and dipeptidylaminopeptidase. Intracerebroventricular injection in mice of these mixed inhibitors, especially kelatorphan, led to naloxone reversible analgesic responses (hot-plate test) that were slightly better than those produced by a mixture of thiorphan and bestatin, two potent inhibitors of enkephalinase and aminopeptidase, respectively. Kelatorphan was also more efficient in potentiating the analgesia induced by a subanalgesic dose of Met-enkephalin. All these results support a physiological role in pain transmission for enkephalinase and a probably synaptic aminopeptidase M.
• Design, synthesis and evaluation of 3-methylene-substituted indolinones as antimalarials
  作者：S. Praveen Kumar、Jiri Gut、Rita C. Guedes、Philip J. Rosenthal、Maria M.M. Santos、Rui Moreira

  DOI：10.1016/j.ejmech.2011.01.008

  日期：2011.3

  The design, synthesis and evaluation of 3-methylene-substituted indolinones as falcipain inhibitors and antiplasmodial agents are described. These compounds react readily with thiols via an addition-elimination mechanism, indicating their potential as cysteine protease inhibitors. Several indolinones containing a Leu-i-amyl recognition moiety were found to be moderate inhibitors of the Plasmodium falciparum

  描述，设计和合成的3-亚甲基取代的吲哚啉酮作为falcipain抑制剂和抗疟原虫剂。这些化合物通过加成消除机制容易与硫醇反应，表明它们作为半胱氨酸蛋白酶抑制剂的潜力。含有具有Leu-几个吲哚满酮我发现戊识别部分是适度抑制剂的恶性疟原虫半胱氨酸蛋白酶falcipain-2，但不相关的蛋白酶falcipain-3，和针对抗氯喹显示抗疟原虫活性恶性疟原虫W2在低微摩尔范围内的应变。将7-氯喹啉部分偶联至3-亚甲基取代的吲哚酮骨架上导致抗血浆活性的显着改善。