N,N'-双-BOC-D-组氨酸 | 75498-93-0

• 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: N,N'-双-BOC-D-组氨酸
• 英文名称: (1R)-4-(2-tert-butoxycarbonylamino-2-carboxyethyl)imidazole-1-carboxylic acid tert-butyl ester
• 英文别名: N-α-tert.-butoxycarbonyl-N-im-tert.-butoxycarbonyl-D-histidine；(R)-3-(1-(tert-Butoxycarbonyl)-1H-imidazol-4-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid；(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[1-[(2-methylpropan-2-yl)oxycarbonyl]imidazol-4-yl]propanoic acid
• CAS: 75498-93-0
• 化学式: C₁₆H₂₅N₃O₆
• 分子量: 355.391
• InChiKey: IXHPIPUIOSSAIS-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  7

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  N,N'-双-BOC-D-组氨酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 46.0h， 生成
  参考文献：
  名称：

  通过手性C60结合的组氨酸在氢键驱动的锌卟啉折叠剂中的螺旋诱导作用。

  摘要：

  DOI：

  10.1002/anie.200502465

文献信息

• Heterodimers of Histidine and Amantadine as Inhibitors for Wild Type and Mutant M2 Channels of Influenza A
  作者：Wenjuan Zhang、Jing Xu、Fang Liu、Chufang Li、Yanling Jie、Shaopeng Chen、Zhiyuan Li、Jinsong Liu、Ling Chen、Guochun Zhou

  DOI：10.1002/cjoc.201090242

  日期：——

  Inhibitors bearing the imidazole, adamantane and related structures were synthesized and tested against WT, S31N and S31N‐L26I mutant M2 channels. Although amantadine (1) only inhibited WT M2 channel, compound 6 containing the imidazole and adamantane groups showed good inhibitory activity to WT and mutant M2 channels. The stereochemistry and basic pKa of α‐amine are important for the activity of inhibitors

  合成了带有咪唑，金刚烷和相关结构的抑制剂，并针对WT，S31N和S31N-L26I突变M2通道进行了测试。尽管金刚烷胺（1）仅抑制WT M2通道，但含有咪唑和金刚烷基团的化合物6对WT和突变M2通道显示出良好的抑制活性。α-胺的立体化学和碱性p K a对抑制剂的活性很重要，我们的数据表明，天然组氨酸的衍生物对M2通道的活性比非天然组氨酸的衍生物高。我们当前结果的意义在于，我们已经建立了一种针对WT和突变型M2通道针对甲型流感的药物发现的前瞻性策略。
• CHOLINERGIC ENHANCERS WITH IMPROVED BLOOD-BRAIN BARRIER PERMEABILITY FOR THE TREATMENT OF DISEASES ACCOMPANIED BY COGNITIVE IMPAIRMENT
  申请人：Maelicke Alfred

  公开号：US20090253654A1

  公开（公告）日：2009-10-08

  The present invention refers to compounds that, in addition to enhancing the sensitivity to acetylcholine and choline, and their exogenous agonists, of neuronal cholinergic receptors and/or acting as cholinesterase inhibitors and/or neuroprotective agents, have enhanced blood-brain barrier permeability in comparison to their parent compounds. The compounds are derived (either formally by their chemical structure or directly by chemical synthesis) from natural compounds belonging to the class of amaryllidaceae alkaloids e.g., galantamine, narwedine and lycoramine, or from metabolites of said compounds. The compounds of the present invention can either interact as such with their target molecules, or they can act as “pro-drugs”, in the sense that after reaching their target regions in the body they are converted by hydrolysis or enzymatic attack to the original parent compound and react as such with their target molecules, or both. The compounds of this invention may be used as medicaments.

  本发明涉及化合物，除了增强神经元胆碱能受体及/或作为胆碱酯酶抑制剂和/或神经保护剂的敏感性，还具有与其母体化合物相比增强的血脑屏障通透性。这些化合物是从天仙子科生物碱类天仙子碱、纳尔韦丁和丝兰碱或其代谢物中衍生出来的（无论是通过其化学结构或直接通过化学合成）。本发明的化合物可以直接与其靶分子相互作用，也可以作为“前药”，在到达体内的目标区域后，通过水解或酶攻击被转化为原始母体化合物，并与其靶分子反应，或两者兼有。本发明的化合物可用作药物。
• Cholinergic enhancers with improved blood-brain barrier permeability for the treatment of diseases accompanied by cognitive impairment
  申请人：NEURODYN LIFE SCIENCES INC.

  公开号：US10265325B2

  公开（公告）日：2019-04-23

  A method for the treatment of a neurodegenerative, psychiatric or neurological disease associated with a cholinergic deficit comprising administering GLN-1062 or a pharmaceutically acceptable salt thereof by nasal administration to a patient in need thereof.

  一种治疗与胆碱能不足有关的神经退行性疾病、精神疾病或神经系统疾病的方法，包括通过鼻腔给药给有需要的患者施用 GLN-1062 或其药学上可接受的盐。
• [EN] 2,5-DIKETOPIPERAZINES FOR THE TREATMENT OF OBESITY<br/>[FR] COMPOSES DESTINES AU TRAITEMENT DE L'OBESITE
  申请人：NOVO NORDISK AS

  公开号：WO2004048345A3

  公开（公告）日：2004-07-15
• US9763953B2
  申请人：——

  公开号：US9763953B2

  公开（公告）日：2017-09-19