N²-tert-butyloxycarbonyl-N¹-benzyl-L-aspartamide 4-benzyl ester | 92235-71-7

• 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: N²-tert-butyloxycarbonyl-N¹-benzyl-L-aspartamide 4-benzyl ester
• 英文别名: Boc-Asp(OBzl)-NH-Bzl；Boc-Asp(OBzl)-NHCH₂C₆H₅；benzyl (S)-3-(1,1-dimethylethoxycarbonylamino)-4-benzylamino-4-oxo-butyrate；benzyl (3S)-4-(benzylamino)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoate
• CAS: 92235-71-7
• 化学式: C₂₃H₂₈N₂O₅
• 分子量: 412.486
• InChiKey: HQBUDUANZXXEBD-IBGZPJMESA-N

物化性质

• 熔点：
  91 °C
• 沸点：
  623.8±55.0 °C(Predicted)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N²-tert-butyloxycarbonyl-N¹-benzyl-L-aspartamide 4-benzyl ester 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 7.0h， 以93%的产率得到N¹-benzyl-L-aspartamide 4-benzyl ester hydrochloride
  参考文献：
  名称：

  Design and photophysical properties of new RGD targeted tetraphenylchlorins and porphyrins

  摘要：

  The synthesis, characterization, fluorescence, and singlet oxygen quantum yields of tetraphenylporphyrin and tetraphenylchlorin coupled to RGD type peptide are reported. C-terminus protected RGD derivatives were synthesized in liquid phase at the gram scale via an efficient convergent process. C-terminus unprotected RGD derivatives were synthesized on solid support. The UV-vis, fluorescence, and singlet emission spectra showed that the photophysical properties of the photosensitizers were retained in all compounds and some of them are very promising for potential PDT applications. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.142
• 作为产物：
  描述：

  Boc-L-天冬氨酸 4-苄酯 、 苄胺 在 1-羟基苯并三唑一水物 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.25h， 以93%的产率得到N²-tert-butyloxycarbonyl-N¹-benzyl-L-aspartamide 4-benzyl ester
  参考文献：
  名称：

  Design and photophysical properties of new RGD targeted tetraphenylchlorins and porphyrins

  摘要：

  The synthesis, characterization, fluorescence, and singlet oxygen quantum yields of tetraphenylporphyrin and tetraphenylchlorin coupled to RGD type peptide are reported. C-terminus protected RGD derivatives were synthesized in liquid phase at the gram scale via an efficient convergent process. C-terminus unprotected RGD derivatives were synthesized on solid support. The UV-vis, fluorescence, and singlet emission spectra showed that the photophysical properties of the photosensitizers were retained in all compounds and some of them are very promising for potential PDT applications. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.142

文献信息

• Guanidine derivatives compositions and use
  申请人：Hofmann-La Roche Inc.

  公开号：US05260307A1

  公开（公告）日：1993-11-09

  Compounds of the formula ##STR1## wherein L, M, R, T and X are set forth in the description, as well as hydrates or solvates thereof, which inhibit thrombin-induced platelet aggregation and clotting of fibrinogen in plasma, are described. The compounds of formula I are prepared by amidination or, depending on whether L is NH or O, by amide formation or esterification.

  式中L、M、R、T和X在描述中阐述的化合物I，以及其水合物或溶剂化物，可以抑制血浆中凝血酶诱导的血小板聚集和纤维蛋白原的凝结。化合物I可以通过酰胺化或酯化反应来制备，具体取决于L是NH还是O。
• Further Studies on Lead Compounds Containing the Opioid Pharmacophore Dmt-Tic
  作者：Gianfranco Balboni、Stella Fiorini、Anna Baldisserotto、Claudio Trapella、Yusuke Sasaki、Akihiro Ambo、Ewa D. Marczak、Lawrence H. Lazarus、Severo Salvadori

  DOI：10.1021/jm800587e

  日期：2008.8.1

  Some reference opioids containing the Dmt-Tic pharmacophore, especially the delta agonists H-Dmt-Tic-Gly-NH-Ph (1) and H-Dmt-Tic-NH-(S)CH(CH2-COOH)-Bid (4) (UFP-512) were evaluated for the influence of the substitution of Gly with aspartic acid, its chirality, and the importance of the -NH-Ph and N(1)H-Bid hydrogens in the inductions of delta agonism. The results provide the following conclusions:

  一些含有 Dmt-Tic 药效团的参考阿片类药物，尤其是 δ 激动剂 H-Dmt-Tic-Gly-NH-Ph (1) 和 H-Dmt-Tic-NH-(S)CH(CH2-COOH)-Bid (4) ) (UFP-512) 评估了用天冬氨酸取代 Gly 的影响、其手性，以及 -NH-Ph 和 N(1)H-Bid 氢在 δ 激动诱导中的重要性。结果提供以下结论： (i) Asp 通过降低 mu 亲和力增加 delta 选择性；(ii) -NH-Ph 和 N(1)H-Bid 氮甲基化将 delta 激动剂转化为 delta 拮抗剂；(iii)在δ激动剂H-Dmt-Tic-Gly-NH-Ph中用L-Asp/D-Asp取代Gly得到δ拮抗剂；δ 激动剂 H-Dmt-Tic-NH-CH2-Bid 中的相同取代产生更具选择性的激动剂 H-Dmt-Tic-NH-(S)CH(CH2-COOH)-Bid 和 H-Dmt-Tic-NH
• Studies on Inhibition of Enzymatic Arginyltransfer Reaction.
  作者：Koichi TAKAO、Toshihisa IGARASHI、Hironao OGISO、Kazuya UGATA、Akira SHIRAHATA、Keijiro SAMEJIMA

  DOI：10.1248/cpb.46.1169

  日期：——

  Synthetic polyamines and various derivatives of aspartic acid and glutamic acid were examined in vitro for their inhibitory activity on arginyl-tRNA-protein transferase. All the polyamines tested showed non-specific activation or inhibition at 0.1 or 10 mM, respectively, suggesting an interaction of polyamines with tRNA. Of the newly prepared active site directed compounds including the inhibitory peptides so far reported, L-aspartic acid α-[(S)-(-)-naphthylethylamide] was found to inhibit the enzyme activity most potently with a slight substrate activity, whereas the R-isomer showed very weak inhibition, giving information on the active site of the enzyme.

  体外研究了合成多胺以及天冬氨酸和谷氨酸的各种衍生物对精氨酰-tRNA-蛋白转移酶的抑制活性。所有测试的多胺在 0.1 或 10 mM 的浓度下分别显示出非特异性的激活或抑制作用，这表明多胺与 tRNA 之间存在相互作用。在新制备的活性位点定向化合物（包括迄今报道的抑制肽）中，发现 L-天冬氨酸 α-[(S)-(-)-萘乙基酰胺]对酶活性的抑制作用最强，且有轻微的底物活性，而 R-异构体的抑制作用很弱，从而提供了有关酶活性位点的信息。
• Synthesis of gastrin antagonists, analogs of the C-terminal tetrapeptide of gastrin, by introduction of a .beta.-homo residue
  作者：M. Rodriguez、P. Fulcrand、J. Laur、A. Aumelas、J. P. Bali、Jean Martinez

  DOI：10.1021/jm00123a003

  日期：1989.3

  A series of analogues of Boc-Trp-Leu-Asp-Phe-NH2, a potent gastrin agonist, were synthesized by introducing a beta-homo residue in the sequence. These compounds were tested in vivo on acid secretion, in the anesthetized rat, and for their ability to inhibit binding of labeled gastrin to its receptors on gastric mucosal cells. These analogues behaved as gastrin antagonists. The most potent compounds in this series were Boc-Trp-Leu-beta-homo-Asp-NHCH2C6H5 (10) (IC50 = 1 microM, ED50 = 0.2 mg/kg), Boc-Trp-Leu-beta-homo-Asp-NHCH2CH2C6H5 (11) (IC50 = 0.75 microM, ED50 = 0.5 mg/kg), Boc-Trp-Leu-beta-homo-Asp-Phe-NH2 (12) (IC50 = 1.5 microM, ED50 = 0.1 mg/kg), and Boc-Trp-Leu-beta-homo-Asp-D-Phe-NH2 (13) (IC50 = 2 microM, ED50 = 0.1 mg/kg). We could demonstrate the importance of the region of the peptide bond between leucine and aspartic acid and of the structure of the C-terminal dipeptide Asp-Phe-NH2, for exhibiting biological activity on acid secretion.
• Pd-catalyzed one-pot chemoselective hydrogenation protocol for the preparation of carboxamides directly from azides
  作者：Sudhir N. Bavikar、Deepak B. Salunke、Braja G. Hazra、Vandana S. Pore、Josiane Thierry、Robert H. Dodd

  DOI：10.1016/j.tetlet.2010.05.066

  日期：2010.7

  Carboxamides were obtained efficiently in high yields from azides on reaction with the corresponding pre-formed activated carboxylic acids in a single-step reductive transformation using hydrogen atmosphere (balloon) under Pd/BaSO4 or Pd/CaCO3 catalysis. The method is highly chemoselective and compatible with extremely labile functional groups such as benzyl carbamates, benzyl ethers, benzyl esters, and olefins. (C) 2010 Elsevier Ltd. All rights reserved.