N,4-bis[(1,1-dimethylethoxy)carbonyl]-L-Phe | 214750-69-3

• 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: N,4-bis[(1,1-dimethylethoxy)carbonyl]-L-Phe
• 英文别名: 4-(2-tert-butoxycarbonylamino-2-carboxyethyl)benzoic acid tert-butyl ester；(2S)-2-(N-Boc)amino-3-[4-t-butyloxycarbonylphenyl]propanoic acid；tert-butyl 4-((S)-2-tert-butoxycarbonylamino-2-carboxy-ethyl)-benzoate；Boc-(4-tert-butyloxycarbonyl)-L-phenylalanine；(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[4-[(2-methylpropan-2-yl)oxycarbonyl]phenyl]propanoic acid
• CAS: 214750-69-3
• 化学式: C₁₉H₂₇NO₆
• 分子量: 365.426
• InChiKey: JQJBYNUASUPTSZ-AWEZNQCLSA-N

物化性质

• 沸点：
  515.1±50.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,4-bis[(1,1-dimethylethoxy)carbonyl]-L-Phe 在 N-甲基吗啉 、 正丁基锂 、 六甲基二硅氮烷 、 三丁基氧化锡 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 乙腈 为溶剂， 反应 126.5h， 生成 4-[2-tert-butoxycarbonylamino-3-carboxy-3-(4-methoxybenzylsulfanyl)propyl]benzoic acid tert-butyl ester
  参考文献：
  名称：

  Development of Potent Inhibitors of Botulinum Neurotoxin Type B

  摘要：

  Botulinum neurotoxins are the most potent toxins known to date. They are zinc-metalloproteases able to cleave selectively an essential component of neurotransmitter exocytosis, causing the syndrome of botulism characterized by a flaccid paralysis. There is a great interest in designing antagonists of the action of these toxins. One way is to inhibit their catalytic activity. In this study, we report the design of such inhibitors directed toward BoNT/B. A study of the S-1 subsite specificity, using several beta-amino thiols, has shown that this subsite prefers a p-carboxybenzyl moiety. The specificity of the S-1' and S-2' subsites was studied using two libraries of pseudotripeptides containing the S-1 synthon derived from the best beta-amino thiol tested. Finally, a selection of various non natural amino acids for the recognition of the "prime" domain led to the most potent inhibitor of BoNT/B described to date with a K-i value of 20 nM.

  DOI：

  10.1021/jm0300680
• 作为产物：
  描述：

  4-溴甲基苯甲酸叔丁酯 在 lithium hydroxide 、 正丁基锂 、 四丁基溴化铵 、 三乙胺 、 柠檬酸 、 lithium bromide 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 53.25h， 生成 N,4-bis[(1,1-dimethylethoxy)carbonyl]-L-Phe
  参考文献：
  名称：

  Development of Potent Inhibitors of Botulinum Neurotoxin Type B

  摘要：

  Botulinum neurotoxins are the most potent toxins known to date. They are zinc-metalloproteases able to cleave selectively an essential component of neurotransmitter exocytosis, causing the syndrome of botulism characterized by a flaccid paralysis. There is a great interest in designing antagonists of the action of these toxins. One way is to inhibit their catalytic activity. In this study, we report the design of such inhibitors directed toward BoNT/B. A study of the S-1 subsite specificity, using several beta-amino thiols, has shown that this subsite prefers a p-carboxybenzyl moiety. The specificity of the S-1' and S-2' subsites was studied using two libraries of pseudotripeptides containing the S-1 synthon derived from the best beta-amino thiol tested. Finally, a selection of various non natural amino acids for the recognition of the "prime" domain led to the most potent inhibitor of BoNT/B described to date with a K-i value of 20 nM.

  DOI：

  10.1021/jm0300680

文献信息

• Alpha4beta1 and alpha4beta7 integrin inhibitors
  申请人：——

  公开号：US20020091142A1

  公开（公告）日：2002-07-11

  Compounds of the formula I 1 as defined and their pharmaceutically acceptable salts are inhibitors of &agr; 4 &bgr; 1 and/or &agr; 4 &bgr; 7 integrins, and are useful in inhibiting cell adhesion and in the therapeutic or prophylactic treatment of transplant rejection and inflammatory and autoimmune diseases.

  公式I1所定义的化合物及其药用盐是α4β1和/或α4β7整合素的抑制剂，并且在抑制细胞粘附以及治疗或预防移植排斥和炎症性和自身免疫疾病方面是有用的。
• Type b botulism toxin inhibitors
  申请人：——

  公开号：US20040176333A1

  公开（公告）日：2004-09-09

  The invention relates to novel compounds of genera formula (I), with inhibitory properties for the type B botulism toxin activity, the methods for preparation thereof and corresponding pharmaceutical compositions. The invention further relates to corresponding pharmaceutical compositions. 1

  该发明涉及一般式（I）的新化合物，具有对B型肉毒杆菌毒素活性的抑制性能，以及其制备方法和相应的药物组成。该发明还涉及相应的药物组成。
• 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.
• US7205435B2
  申请人：——

  公开号：US7205435B2

  公开（公告）日：2007-04-17
• [EN] alpha 4 beta 1 AND alpha 4 beta 7 INTEGRIN INHIBITORS<br/>[FR] INHIBITEURS D'INTEGRINES alpha 4 beta 1 ET alpha 4 beta 7
  申请人：NOVARTIS AG

  公开号：WO2001068586A2

  公开（公告）日：2001-09-20

  Compounds of formula (I) as defined and their pharmaceutically acceptable salts are inhibitors of α4β1 and/or α4β7 integrins, and are useful in inhibiting cell adhesion and in the therapeutic or prophylactic treatment of transplant rejection and inflammatory and autoimmune diseases.