(S)-3-(9-Fluorenylmethyloxycarbonyl)amino-4-azido-butanoic acid | 934502-72-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (S)-3-(9-Fluorenylmethyloxycarbonyl)amino-4-azido-butanoic acid
• 英文别名: (3S)-4-azido-3-(9H-fluoren-9-ylmethoxycarbonylamino)butanoic acid
• CAS: 934502-72-4
• 化学式: C₁₉H₁₈N₄O₄
• 分子量: 366.376
• InChiKey: PNIMZMLVZIUHAV-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  90
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-3-(9-Fluorenylmethyloxycarbonyl)amino-4-azido-butanoic acid 、 2-chlorotrityl chloride polystyrene resin 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  WO2007/41775

  摘要：

  公开号：
• 作为产物：
  描述：

  tert-butyl (S)-4-azido-3-fluoromethyloxycarbamidobutyrate 在 三异丙基硅烷 、 水 、 三氟乙酸 作用下， 反应 2.0h， 生成 (S)-3-(9-Fluorenylmethyloxycarbonyl)amino-4-azido-butanoic acid
  参考文献：
  名称：

  WO2007/41775

  摘要：

  公开号：

文献信息

• CONOTOXIN PEPTIDE ANALOGS AND USES FOR THE TREATMENT OF PAIN AND INFLAMMATORY CONDITIONS
  申请人：Kineta Chronic Pain, LLC

  公开号：US20200237924A1

  公开（公告）日：2020-07-30

  Provided herein are alpha-conotoxin peptide analogs, including alpha-conotoxin peptide analogs that are covalently attached to polyethylene glycol (PEG), and pharmaceutical compositions of such alpha-conotoxin peptide analogs. Also provided herein are methods of treating or preventing a condition conducive to treatment or prevention by inhibition of an α9-containing nicotinic acetylcholine receptor (nAChR) (e.g., the α9α10 subtype of the nAChR) in a subject.

  本文提供了α-鼠尾草毒素肽类似物，包括与聚乙二醇（PEG）共价连接的α-鼠尾草毒素肽类似物，以及这些α-鼠尾草毒素肽类似物的药物组合物。本文还提供了一种通过抑制受体中含有α9的尼古丁酸乙酰胆碱受体（nAChR）（例如nAChR的α9α10亚型）来治疗或预防适合治疗或预防的疾病的方法。
• Organic Azide Inhibitors of Cysteine Proteases
  作者：Giang Thanh Le、Giovanni Abbenante、Praveen K. Madala、Huy N. Hoang、David P. Fairlie

  DOI：10.1021/ja0637649

  日期：2006.9.1

  Cysteine proteases are crucial regulatory enzymes in human physiology and disease. Inhibitors are usually designed with reactive electrophiles to covalently bond to the catalytic cysteinyl sulfur, and consequently they also indiscriminately interact with biological thiolates and other nucleophiles, leading to toxic side effects in vivo. Here we describe an alternative to using reactive electrophiles, demonstrating the use of a much less reactive azidomethylene substituent (-CH2-N3) that confers potent inhibition of cysteine proteases. This new approach resulted in potent, reversible, competitive inhibitors of caspase-1 (IC50 < 10 nM), with significant advantages over aldehydes such as high stability in vitro to thiols (10 mM dithiothreitol (pH 7.2), 20 mM glutathione (pH 7.2, 9, 11)) and aqueous media, as well as some highly desirable druglike features. It was also demonstrated that azides can be incorporated into inhibitors of other caspases (e.g. 3, 8) and cathepsins (e.g. K, S, B), indicating the versatility of this valuable new approach to cysteine protease inhibition.