4-(氨基磺酰基)-N-叔丁氧羰基-L-苯丙氨酸 | 84053-14-5

• 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
• 中文名称: 4-(氨基磺酰基)-N-叔丁氧羰基-L-苯丙氨酸
• 英文名称: L-4'-(aminosulfonyl)-N^α-t-butoxycarbonylphenylalanine
• 英文别名: 4-(Aminosulfonyl)-N-Boc-L-phenylalanine；(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(4-sulfamoylphenyl)propanoic acid
• CAS: 84053-14-5
• 化学式: C₁₄H₂₀N₂O₆S
• 分子量: 344.389
• InChiKey: COMNQBHSVKJFIQ-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  144
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(氨基磺酰基)-N-叔丁氧羰基-L-苯丙氨酸 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸 作用下， 生成 4-{(S)-2-Amino-3-oxo-3-[(S)-3-(4-phenyl-1H-imidazol-2-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-propyl}-benzenesulfonamide
  参考文献：
  名称：

  Identification of potent phenyl imidazoles as opioid receptor agonists

  摘要：

  Using previously reported opioid receptor (OR) agonist analogs 4a-c as starting points, the structure-activity relationship (SAR) for their related series has been further refined. This SAR Study has led to the identification of 2,6-di-Me-Tyr (DMT) analogs 4h and 4j as the most potent OR agonist within the series. in addition, it was discovered that 4-(aminocarbonyl)-2,6-dimethyl-Phe is a reasonable bioisostere surrogate for the DMT moiety, as supported by the OR activities Of Compounds 4x and 4y. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.082
• 作为产物：
  描述：

  L-苯丙氨酸 在 氯磺酸 、 ammonium hydroxide 、 sodium hydroxide 作用下， 以 水 、 叔丁醇 为溶剂， 反应 26.0h， 生成 4-(氨基磺酰基)-N-叔丁氧羰基-L-苯丙氨酸
  参考文献：
  名称：

  血管紧张素II类似物。第二部分 含硫芳族氨基酸：L-（4'-SH）Phe，L-（4'-SO 2 NH 2）Phe，L-（4'-SO）Phe和L-（4' -S-CH 3）Phe † ‡

  摘要：

  L-苯丙氨酸已用氯磺酸处理过，产物被水解，氨解或还原。将得到的磺酸和氨基磺酰基衍生物已被用于肽合成与N的将Boc-保护α仅位上。还原产物L-（4'-SH）Phe通过形成不对称的二硫键或各种硫醇保护基（苄基，甲基和乙酰氨基甲基，后者最适合于肽合成）来保护。

  DOI：

  10.1002/hlca.19830660504

文献信息

• Angiotensin II Analogues. Part II. Synthesis and incorporation of the sulfur-containing aromatic amino acids:L-(4?-SH)Phe,L-(4?-SO2NH2)Phe,L-(4?-SO3?)Phe andL-(4?-S-CH3)Phe
  作者：Emanuel Escher、Michel Bernier、Paul Parent

  DOI：10.1002/hlca.19830660504

  日期：1983.7.27

  L-Phenylalanine has been treated with chlorosulfonic acid and the product was either hydrolyzed, ammonolyzed or reduced. The resulting sulfonic-acid and aminosulfonyl derivatives have been employed for peptide synthesis with Boc-protection of the Nα-position only. The reduction product L-(4′-SH)Phe has been protected by formation of asymmetric disulfides or with various thiol protecting groups (benzyl-

  L-苯丙氨酸已用氯磺酸处理过，产物被水解，氨解或还原。将得到的磺酸和氨基磺酰基衍生物已被用于肽合成与N的将Boc-保护α仅位上。还原产物L-（4'-SH）Phe通过形成不对称的二硫键或各种硫醇保护基（苄基，甲基和乙酰氨基甲基，后者最适合于肽合成）来保护。
• Identification of potent phenyl imidazoles as opioid receptor agonists
  作者：Henry J. Breslin、Chaozhong Cai、Tamara A. Miskowski、Santosh V. Coutinho、Sui-Po Zhang、Pamela Hornby、Wei He

  DOI：10.1016/j.bmcl.2006.01.082

  日期：2006.5

  Using previously reported opioid receptor (OR) agonist analogs 4a-c as starting points, the structure-activity relationship (SAR) for their related series has been further refined. This SAR Study has led to the identification of 2,6-di-Me-Tyr (DMT) analogs 4h and 4j as the most potent OR agonist within the series. in addition, it was discovered that 4-(aminocarbonyl)-2,6-dimethyl-Phe is a reasonable bioisostere surrogate for the DMT moiety, as supported by the OR activities Of Compounds 4x and 4y. (C) 2006 Elsevier Ltd. All rights reserved.