Boc-Asn-Phe-OMe | 56439-61-3

• 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: Boc-Asn-Phe-OMe
• 英文别名: (S)-2-((S)-2-tert-butoxycarbonylamino-3-carbamoylpropionylamino)-3-phenylpropionic acid methyl ester；N^α-t-butyloxycarbonyl-L-asparginyl-L-phenylalanyl methyl ester；Boc-Asp(NH2)-Phe-OCH3；methyl (2S)-2-[[(2S)-4-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoyl]amino]-3-phenylpropanoate
• CAS: 56439-61-3
• 化学式: C₁₉H₂₇N₃O₆
• 分子量: 393.44
• InChiKey: WWFFASUPFPBYQT-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.66
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  136.82
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Boc-Asn-Phe-OMe 在 palladium on activated charcoal 盐酸 、 亚硝酸正戊酯 、 氢气 、 一水合肼 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 氯仿 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 94.0h， 生成 谷氨酰-缬氨酰-天冬氨酰胺酰-苯基甘氨酰-丝氨酰-脯氨酰-天冬氨酰胺酰-色氨酰胺
  参考文献：
  名称：

  Konopinska, Danuta; Rosinski, Grzegorz; Sobotka, Wieslaw, Bulletin of the Polish Academy of Sciences: Chemistry, 1989, vol. 37, # 7-8, p. 331 - 338

  摘要：

  DOI：
• 作为产物：
  描述：

  BOC-L-天冬酰胺 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 20.17h， 生成 Boc-Asn-Phe-OMe
  参考文献：
  名称：

  Konopinska, Danuta; Rosinski, Grzegorz; Sobotka, Wieslaw, Bulletin of the Polish Academy of Sciences: Chemistry, 1989, vol. 37, # 7-8, p. 331 - 338

  摘要：

  DOI：

文献信息

• C-Glycoside Analogues ofN4-(2-Acetamido-2-deoxy-?-D-glucopyranosyl)-L-asparagine: Synthesis and conformational analysis of a cyclicC-glycopeptide
  作者：Matthias Hoffmann、Fred Burkhart、Gerhard Hessler、Horst Kessler

  DOI：10.1002/hlca.19960790602

  日期：1996.9.18

  propanoic acid (22) can be used in solid-phase peptide synthesis. The conformation of 24 was determined by NMR and molecular-dynamics (MD) techniques. Evidence is provided that the CGaa side chain interacts with the peptide backbone. The different C-glycosylated amino acids 15–21 were prepared by coupling 3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-β-D-glycero-D-gulo-heptonic acid (4) with diamino-acid

  的合成Ç糖苷类似物15-22的ñ 4 - （2-乙酰氨基-2-脱氧- β-d-D-吡喃葡萄糖基）-L-天冬酰胺（ASN（Ñ 4的GlcNAc））具有相反的酰胺键为电子等排取代给出了N-糖苷键的结构。制备了肽环（-D-Pro-Phe-Ala-CGaa-Phe-Phe-）（CGaa = C-糖基化氨基酸；24），以证明3-[（3-acetamido-2,6-anhydro- 4,5,7-三-O-苄基-3-脱氧-β-D-甘油-D-邻庚基庚酰基）氨基] -2-[（9 H-氟-9-酰氧基羰基）氨基]丙酸（22）可以用于固相肽合成。的构象通过NMR和分子动力学（MD）技术确定24。提供的证据表明，CGaa侧链与肽主链相互作用。不同Ç -glycosylated氨基酸15-21被偶合制备3-乙酰氨基-2,6-脱水-4,5,7-三ö苄基-3-脱氧β-D-甘油基-D-庚-带有二氨基酸衍生物8-14的庚酸（4
• Hartrodt; Neubert; Jakubke, Pharmazie, 1982, vol. 37, # 6, p. 403 - 407
  作者：Hartrodt、Neubert、Jakubke、Balaspiri、Telegdy

  DOI：——

  日期：——
• The 5-substituted piperazine as a novel secondary pharmacophore greatly improving the physical properties of urea-based inhibitors of soluble epoxide hydrolase
  作者：Hui-Yuan Li、Yi Jin、Christophe Morisseau、Bruce D. Hammock、Ya-Qiu Long

  DOI：10.1016/j.bmc.2006.06.005

  日期：2006.10

  The inhibition of the mammalian soluble epoxide hydrolase (sEH) is a promising new therapy in the treatment of hypertention and inflammation. The problems of limited water solubility and high melting points commonly displayed by the active 1,3-disubstituted ureas prevent the further development of potent urea-based sEH inhibitors. Therefore, a new class of potent inhibitors of sEH were designed and synthesized by the introduction of a polar constrained piperazino group in the right side of adasmantyl urea to increase the water solubility. A facile and general synthesis was established to prepare a series of 1-adamantan-1-yl-3-(2-piperazin-2-yl-ethyl)-ureas (1a-d) with various 5-substitutions on the 2-piperazino ring, which will advance the SAR study by the efficient making of structurally diverse analogs. The effect of the 5-substitution on the activity and the water solubility was examined. The best potency was exhibited by the 5-benzyl-substituted-piperazine-containing urea with an IC50 value of 1.37 mu M against human sEH and good water solubility (S = 7.46 mg/mL) and low melting point, in which the 5-substituted piperazine serves as a favorable secondary pharmacophore and a water-solubility enhancing group. Our present work provides a promising new template for the design of orally available therapeutic agents for the disorders that can be addressed by changing the in vivo concentration of the chemical mediators that contain an epoxide. (c) 2006 Elsevier Ltd. All rights reserved.
• KONOPINSKA, DANUTA;ROSINSKI, GRZEGORZ;SOBOTKA, WIESLAW, BULL. POL. ACAD. SCI. CHEM., 37,(1989) N-8, C. 331-338
  作者：KONOPINSKA, DANUTA、ROSINSKI, GRZEGORZ、SOBOTKA, WIESLAW

  DOI：——

  日期：——