N-(tert-butyloxycarbonyl)-L-tyrosyl-D-alanylglycine methyl ester | 78537-07-2

• 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: N-(tert-butyloxycarbonyl)-L-tyrosyl-D-alanylglycine methyl ester
• 英文别名: N-Boc-L-tyrosyl-D-alanyl-glycine methyl ester；Boc Tyr D.Ala Gly OMe；Boc-Tyr-ala-Gly-OMe；methyl Boc-L-tyrosyl-D-alanylglycinate；methyl 2-[[(2R)-2-[[(2S)-3-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]propanoyl]amino]acetate
• CAS: 78537-07-2
• 化学式: C₂₀H₂₉N₃O₇
• 分子量: 423.466
• InChiKey: UOEHSBGEYDRCPT-DOMZBBRYSA-N

物化性质

• 沸点：
  696.7±55.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  143
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(tert-butyloxycarbonyl)-L-tyrosyl-D-alanylglycine methyl ester 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 0.2h， 以76%的产率得到Boc-酪氨酸-D-丙氨酸-甘氨酸
  参考文献：
  名称：

  的类似脑啡肽的苯丙氨酸代替含有Carboranylalanine肽合成及生物属性†

  摘要：

  详细描述[D-Ala 2，Car 4，Leu 5 ]-脑啡肽的酰胺和[D-Ala 2，Car 4，Met 5 ]-脑啡肽酰胺的合成。这三种化合物在某些生物测定中显示出明显的吗啡样效力，并用于研究4号和5号氨基酸侧链的电子，空间和疏水性质对阿片类药物活性的影响（参见[13] ）。

  DOI：

  10.1002/hlca.19810640712
• 作为产物：
  描述：

  Boc tyrosine 在 sodium hydroxide 、 水 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 formamide 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-(tert-butyloxycarbonyl)-L-tyrosyl-D-alanylglycine methyl ester
  参考文献：
  名称：

  Audigier; Mazarguil; Gout, European Journal of Medicinal Chemistry, 1980, vol. 15, # 2, p. 173 - 177

  摘要：

  DOI：

文献信息

• Synthesis and Biological Properties of Enkephalin-like Peptides Containing Carboranylalanine in Place of Phenylalanine
  作者：Robert Schwyzer、Kim Quang Do、Alex N. Eberle、Jean-Luc Fauchére

  DOI：10.1002/hlca.19810640712

  日期：1981.11.4

  amide are described in detail. The three compounds show pronounced morphine-like potencies in certain bio-assays, and were used to investigate the influence of electronic, steric and hydrophobic properties of the side-chains of amino acids no. 4 and 5 on opioid activity (see [13]).

  详细描述[D-Ala 2，Car 4，Leu 5 ]-脑啡肽的酰胺和[D-Ala 2，Car 4，Met 5 ]-脑啡肽酰胺的合成。这三种化合物在某些生物测定中显示出明显的吗啡样效力，并用于研究4号和5号氨基酸侧链的电子，空间和疏水性质对阿片类药物活性的影响（参见[13] ）。
• N-Adamantane-substituted tetrapeptide amides
  申请人：G. D. Searle & Co.

  公开号：US04273704A1

  公开（公告）日：1981-06-16

  N-Adamantane-substituted tetrapeptide amides and the pharmacologically acceptable salts thereof are disclosed herein. These compounds are analogs of enkephalin wherein the methionine or leucine of position 5 has been substituted by an adamantyl amide and the glycine of position 2 has been substituted by various amino acid residues. Optionally the tyrosine of position 1 and the phenylalanine of position 4 may be substituted by various amino acid residues. These compounds exhibit agonist activity at opiate receptor sites and are useful as analgesics.

  本文披露了N-金刚烷取代的四肽酰胺及其药理学上可接受的盐。这些化合物是脑啡肽的类似物，其中第5位的蛋氨酸或亮氨酸被金刚烷酰胺替代，第2位的甘氨酸被各种氨基酸残基替代。选项地，第1位的酪氨酸和第4位的苯丙氨酸可以被各种氨基酸残基替代。这些化合物在鸦片受体位点表现出激动剂活性，并可用作镇痛剂。
• Evidence of the preferential involvement of .mu.-receptors in analgesia using enkephalins highly selective for peripheral .mu. or .delta. receptors
  作者：Gilles Gacel、Marie Claude Fournie-Zaluski、Etienne Fellion、Bernard P. Roques

  DOI：10.1021/jm00142a002

  日期：1981.10

  In order to study the preferential involvement of mu or delta receptors in the analgesic effects of enkephalins, several peptides which selectively interact with these two kinds of receptors in peripheral organs were synthesized. The inhibitory potency on the electrically stimulated mouse vas deferens (delta receptors) of the short peptide Tyr-D-Ala-Gly-NH-CH(CH3)CH2CH(CH3)2 (6) is 2100 times lower (IC50 = 1220 nM) than that of the longer and more hydrophilic peptide Tyr-D-Ser-Gly-Phe-Leu-Thr (10) (IC50 = 0.58 nM). In contrast, the IC50 values of all the synthesized compounds on the guinea pig ileum assay (mu receptors) are in the same range (100-360 nM). Likewise, their analgesic activities in mice, measured on the hot-plate test after intracerebroventricular injection, are similar. Therefore, the dissociation between antinociceptive properties in mice and potencies on the mouse vas deferens unambiguously reflects a preferential implication of mu receptors in analgesia. The possible involvement of brain delta receptors in behavioral effects is discussed.
• Korshunova, G. A.; Dobkina, I. M.; Ryabtseva, O. N., Journal of general chemistry of the USSR, 1987, vol. 57, p. 1469 - 1476
  作者：Korshunova, G. A.、Dobkina, I. M.、Ryabtseva, O. N.、Shvachkin, Yu. P.

  DOI：——

  日期：——
• GACEL, G.;ZAJAC, J. M.;DELAY-GOYET, P.;DAUGE, V.;ROQUES, B. P., J. MED. CHEM., 31,(1988) N 2, 374-383
  作者：GACEL, G.、ZAJAC, J. M.、DELAY-GOYET, P.、DAUGE, V.、ROQUES, B. P.

  DOI：——

  日期：——