(S)-N-tert-butoxycarbonyl-4-iodophenylalaninol | 210962-68-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-N-tert-butoxycarbonyl-4-iodophenylalaninol
• 英文别名: Boc-p(I)-Phe-ol；t-butyl [(1S)-2-hydroxy-1-(4-iodobenzyl)ethyl]carbamate；tert-butyl N-[(2S)-1-hydroxy-3-(4-iodophenyl)propan-2-yl]carbamate
• CAS: 210962-68-8
• 化学式: C₁₄H₂₀INO₃
• 分子量: 377.222
• InChiKey: IHPVVBDNLUZOLT-LBPRGKRZSA-N

物化性质

• 熔点：
  143-145 °C
• 沸点：
  460.6±40.0 °C(Predicted)
• 密度：
  1.487±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-N-tert-butoxycarbonyl-4-iodophenylalaninol 在 盐酸 、 palladium diacetate 、 lithium hydroxide 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.25h， 生成
  参考文献：
  名称：

  Development of the First Potential Covalent Inhibitors of Anandamide Cellular Uptake

  摘要：

  On the basis of the chemical structures of two previously developed metabolically stable and relatively potent inhibitors of anandamide uptake, OMDM-1,2, two series of potential covalent inhibitors of anandamide cellular reuptake, which might be used for the molecular characterization of the protein(s) involved in the membrane transport of endocannabinoids, have been designed and synthesized. Most of the compounds inhibited uptake to a varied extent and in a generally enantio-sensitive manner when co-incubated with [C-14]anandamide, but only three of them, the photoactivatable 1a (OMDM-37), 1b (OMDM-39), and 8 (Lo395), also produced a significant inhibition of uptake following the preincubation only of the cells, and this effect was significantly enhanced following UV exposure only in the case of 8. None of the new compounds inhibited [C-14]anandamide hydrolysis with IC50 < 50 mu M, except for 1b.

  DOI：

  10.1021/jm051226l
• 作为产物：
  描述：

  Boc-4-碘-L-苯丙氨酸 在 N-甲基吗啉 、 氯甲酸异丁酯 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以89%的产率得到(S)-N-tert-butoxycarbonyl-4-iodophenylalaninol
  参考文献：
  名称：

  Development of the First Potential Covalent Inhibitors of Anandamide Cellular Uptake

  摘要：

  On the basis of the chemical structures of two previously developed metabolically stable and relatively potent inhibitors of anandamide uptake, OMDM-1,2, two series of potential covalent inhibitors of anandamide cellular reuptake, which might be used for the molecular characterization of the protein(s) involved in the membrane transport of endocannabinoids, have been designed and synthesized. Most of the compounds inhibited uptake to a varied extent and in a generally enantio-sensitive manner when co-incubated with [C-14]anandamide, but only three of them, the photoactivatable 1a (OMDM-37), 1b (OMDM-39), and 8 (Lo395), also produced a significant inhibition of uptake following the preincubation only of the cells, and this effect was significantly enhanced following UV exposure only in the case of 8. None of the new compounds inhibited [C-14]anandamide hydrolysis with IC50 < 50 mu M, except for 1b.

  DOI：

  10.1021/jm051226l

文献信息

• Kinase inhibitors
  申请人：——

  公开号：US20030187026A1

  公开（公告）日：2003-10-02

  Compounds having the formula 1 are useful for inhibiting protein kinases. Also disclosed are compositions which inhibit protein kinases and methods of inhibiting protein kinases in a patient.

  具有以下化学式的化合物对抑制蛋白激酶很有用。还公开了抑制蛋白激酶的组合物以及在患者中抑制蛋白激酶的方法。
• Design and Synthesis of Unsymmetrical Peptidyl Urea Inhibitors of Aspartic Peptidases
  作者：Natalie A. Dales、Regine S. Bohacek、Kenneth A. Satyshur、Daniel H. Rich

  DOI：10.1021/ol0160912

  日期：2001.7.1

  synthesis, and enzyme inhibition of a new class of aspartic peptidase inhibitors is described. Unsymmetrical ureas were designed from computer-generated structures. Using mechanism-based and substrate-based design techniques, potent pepsin inhibitors were developed and the binding mode was established. Two X-ray crystal structures of enzyme-bound inhibitors revealed a new binding mode that is closely related

  [结构：见正文]描述了新型天冬氨酸肽酶抑制剂的设计，合成和酶抑制作用。从计算机生成的结构设计不对称脲。使用基于机制和基于底物的设计技术，开发了有效的胃蛋白酶抑制剂并建立了结合模式。酶结合抑制剂的两个X射线晶体结构揭示了一种新的结合模式，该模式与计算机生成的结合模式密切相关。
• Benzamidine derivatives
  申请人：Ajinomoto Co., Inc.

  公开号：US07396844B1

  公开（公告）日：2008-07-08

  Benzamidine derivatives of the following formulae or analogs thereof, i.e., pharmaceutically acceptable salts thereof, are provided. These compounds or salts thereof have a blood-coagulation inhibiting effect based on an excellent effect of inhibiting the action of activated blood coagulation factor X, and they are useful as anticoagulants

  以下化学式或其类似物的苯甲酰胺衍生物，即其药学上可接受的盐，被提供。这些化合物或其盐具有抗血凝作用，基于抑制活化的血凝因子X的作用具有优异的效果，它们可用作抗凝剂。
• BENZAMIDINE DERIVATIVES
  申请人：Ajinomoto Co., Inc.

  公开号：EP0976722B1

  公开（公告）日：2009-03-11
• Mild and facile procedure for clay-catalyzed acetonide protection and deprotection of N (Boc)-amino alcohols and protection of 1,2-diols
  作者：Nadim S Shaikh、Santosh S Bhor、Anil S Gajare、Vishnu H Deshpande、Radhika D Wakharkar

  DOI：10.1016/j.tetlet.2004.05.079

  日期：2004.7

  The application of clay as a catalyst for acetonide protection of N(Boc)-amino alcohols and 1,2-diols to obtain good to excellent yields of the acetonide derivatives is described. Acetonide deprotection to obtain the parent amino alcohol was carried Out using a similar catalyst in the presence of methanol as solvent. The reaction takes place at room temperature within 2 h to give the parent amino alcohol in quantitative yield keeping the N(Boc) group intact. (C) 2004 Elsevier Ltd. All rights reserved.