glycine benzylamide trifluoroacetate | 81110-67-0

• 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: glycine benzylamide trifluoroacetate
• 英文别名: glycine benzylamide hydrotrifluoroacetate；2-amino-N-benzylacetamide;2,2,2-trifluoroacetic acid
• CAS: 81110-67-0
• 化学式: C₂HF₃O₂*C₉H₁₂N₂O
• 分子量: 278.231
• InChiKey: OZJCENJVADROOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.89
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  92.4
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-叔丁氧羰基-(S)-1,2,3,4-四氢异喹啉-3-羧酸 、 glycine benzylamide trifluoroacetate 在 N-甲基吗啉 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 以88%的产率得到Boc-Tic-Gly-NH-Bzl
  参考文献：
  名称：

  Evaluation of the Dmt−Tic Pharmacophore:  Conversion of a Potent δ-Opioid Receptor Antagonist into a Potent δ Agonist and Ligands with Mixed Properties

  摘要：

  Analogues of the 2',6'-dimethyl-L-tyrosine (Dmt)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) pharmacophore were prepared to test the hypothesis that a "spacer" and a third aromatic center in opioid peptides are required to convert a delta-antagonist into ligands with delta-agonist or with mixed delta-antagonist/mu-agonist properties. Potent delta-agonists and bifunctional compounds with high delta- and mu-opioid receptor affinities were obtained by varying the spacer length [none, NH-CH2, NH-CH2-CH2, Gly-NH-CH2] and C-terminal aromatic nucleus [1H-benzimidazole-2-yl, phenyl (Ph) and benzyl groups]: C-terminal modification primarily affected,mu-opioid receptor affinities, which increased maximally 1700-fold relative to the prototype delta-antagonist H-Dmt-Tic-NH2 and differentially modified bioactivity. In the absence of a spacer (1), the analogue exhibited dual delta-agonism (pEC(50), 7.28) and delta-antagonism (pA(2), 7.90). H-Dmt-Tic-NH-CH2-1H-benzimidazol-2-yl (Bid) (2) became a highly potent delta-agonist (pEC(50), 9.90), slightly greater than deltorphin C (pEC(50), 9.56), with mu-agonism (pE(50), 7.57), while H-Dmt-Tic-Gly-NH-CH2-Bid (4) retained potent delta-antagonism, (pA2, 9.0) but with an order of magnitude less mu-agonism. Similarly, H-Dmt-Tic-Gly-NH-Ph (5) had nearly equivalent high mu-agonism (pEC(50), 8.52) and mu-agonism (pEC(50), -8.59), while H-Dmt-TicGly-NH-CH2-Ph (6) whose spacer was longer by a single methylene group exhibited potent delta-antagonism. (pA2, 9.25) and very high mu-agonism (pEC(50), 8.57). These data confirm that the distance between the Dmt-Tic pharmacophore and a third aromatic nucleus is an important criterion in converting Dint-Tic from a highly potent delta-antagonist into a potent delta-agonist or into ligands with mixed delta- and,mu-opioid properties.

  DOI：

  10.1021/jm010449i
• 作为产物：
  描述：

  苄胺 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 glycine benzylamide trifluoroacetate
  参考文献：
  名称：

  N-transfer reagent and method for preparing the same and its application

  摘要：

  提供了一种新颖的N-转移试剂及其制备方法和应用。N-转移试剂由以下式（I）表示：本发明的各种新颖N-转移试剂可以通过采用不同的硝基苯前体快速制备。在温和条件下，N-转移试剂可以直接将各种氨基化合物转化为重氮化合物。特别地，N-转移试剂可以促进重氮化合物的合成。本发明用于合成重氮化合物的应用可以大大降低操作难度，增加实验安全性，减少生产成本和环境污染，提高重氮化合物的工业价值。

  公开号：

  US11040939B1

文献信息

• Pesticidal cyclopropanoylamino acid amide derivatives
  申请人：Bayer Aktiengesellschaft

  公开号：US05034408A1

  公开（公告）日：1991-07-23

  Fungicidal cyclopropanoylamino acid amide derivative of the formula ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and represent hydrogen or alkyl; Q represents an unsubstituted or substituted straight-chain or branched alkylene chain, or together with the radical R.sup.4 and the nitrogen atom forms a pyrrolidine ring; A represents a straight-chain or branched alkylene chain; n represents the number 0 or 1 and Ar represents unsubstituted or substituted aryl.

  公式为##STR1##的杀真菌环丙酰氨酸酰胺衍生物，其中R.sup.1，R.sup.2，R.sup.3，R.sup.4和R.sup.5相同或不同，代表氢或烷基; Q代表未取代或取代的直链或支链烷基链，或与基团R.sup.4和氮原子一起形成吡咯烷环; A代表直链或支链烷基链; n代表数字0或1，Ar代表未取代或取代的芳基。
• New peptide, process for preparation thereof and use thereof
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0057419A1

  公开（公告）日：1982-08-11

  A compound of the following formula or its pharmaceutically acceptable salt: and processes for their preparation, and also a pharmaceutical composition comprising, as an active ingrediant, the above compound or its pharmaceutically acceptable salt.

  下式化合物或其药学上可接受的盐： 及其制备方法，以及包含上述化合物或其药学上可接受的盐作为活性成分的药物组合物。
• Derivatized Amino Acids Relevant to Native Peptide Synthesis by Chemical Ligation and Acyl Transfer
  作者：Derrick L. J. Clive、Soleiman Hisaindee、Don M. Coltart

  DOI：10.1021/jo030192r

  日期：2003.11.1

  Three amino acids were converted into the derivatives 5.2 (from glycine), 6.4a and 6.4b (from alanine), and 8.3a and 8.3b (from O-benzyl serine). These N-alkylated amino acids, which can be deprotected after conversion of the carboxyl into an amide, correspond to the general structure 2.1, a compound class of use in the study of peptide segment coupling by the ligation-acyl transfer method.
• 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.
• Cyclopropanoylaminosäureamid-Derivate
  申请人：BAYER AG

  公开号：EP0398059B1

  公开（公告）日：1993-08-25