t-butoxycarbonylglicyne N-succinimidyl ester | 56406-63-4

• 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: t-butoxycarbonylglicyne N-succinimidyl ester
• 英文别名: N-(tert-butoxycarbonyl)glycine succinimide ester；N-[2-(tert-butoxycarbonylamino)acetoxy]succinimide；N-t-butyloxycarbonyl-glycine succinimide；N-[2-(2,5-dioxo-1-pyrrolidinyl)-2-oxoethyl]carbamic acid 1,1-dimethylethyl ester；tert-butyl N-[2-(2,5-dioxopyrrolidin-1-yl)-2-oxoethyl]carbamate
• CAS: 56406-63-4
• 化学式: C₁₁H₁₆N₂O₅
• 分子量: 256.258
• InChiKey: XMFMOIYMZHJHOO-UHFFFAOYSA-N

物化性质

• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.19
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  92.78
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-氨基苯甲醇 、 t-butoxycarbonylglicyne N-succinimidyl ester 在 偶氮二甲酸二异丙酯 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 DMF' (N,N-dimethylformamide) 为溶剂， 生成 2-(tert-butoxycarbonyl)amino-N-(3-(1,2-bis(tert-butoxycarbonyl)guanidino)methylphenyl)acetamide
  参考文献：
  名称：

  [EN] NON-RADIOACTIVE AGENTS FOR NEUROBLASTOMA IMAGING
  [FR] AGENTS NON RADIOACTIFS POUR L'IMAGERIE DE NEUROBLASTOMES

  摘要：

  神经母细胞瘤的多模态肿瘤成像对于肿瘤分期、反应评估和复发疾病的检测至关重要。本发明提供了一种含有近红外（近红外）染料W765-BG的去甲肾上腺素类似物，可通过近红外光学成像在体内高效稳定地检测神经母细胞瘤。神经母细胞瘤异种移植物的共聚焦显微镜和光学成像显示细胞特异性摄取，并揭示出在注射W765-BG后高达7天的异常肿瘤保留率和高肿瘤/组织比率。

  公开号：

  WO2011123742A1
• 作为产物：
  描述：

  2-(叔丁氧羰基氧亚氨基)-2-苯乙腈 在 N,N'-二环己基碳二亚胺 作用下， 生成 t-butoxycarbonylglicyne N-succinimidyl ester
  参考文献：
  名称：

  Elsworth, John F.; Msimang, Lorenzo N.; Jackson, Graham E., South African Journal of Chemistry, 1999, vol. 52, # 1, p. 44 - 48

  摘要：

  DOI：

文献信息

• [EN] CEPHEM COMPOUNDS<br/>[FR] CEPHEMES
  申请人：FUJISAWA PHARMACEUTICAL CO

  公开号：WO2005027909A1

  公开（公告）日：2005-03-31

  The present invention relates to a compound of the formula [I]: wherein R1 is lower alkyl or hydroxy (lower) alkyl, and R2 is hydrogen or amino protecting group, or R1 and R2 are bonded together and form lower alkylene ; R3 is -A-R6 wherein A is bond, -NHCO-(CH2CO)n-, lower alkylene, -NH-CO-CO- or the like, and R6 is (a) ou (b) wherein R7, R8, R9 and R10 are independently amino, guanidino, amidino or the like ; R4 is carboxy or protected carboxy; and R5 is amino or protected amino, or a pharmaceutically acceptable salt thereof, a process for preparing a compound of the formula [I], and a pharmaceutical composition comprising a compound of the formula [I] in admixture with a pharmaceutically acceptable carrier.

  本发明涉及一种公式的化合物[I]：其中R1是低级烷基或羟基（低级）烷基，R2是氢或氨基保护基团，或者R1和R2连接并形成低级亚烷基；R3是-A-R6，其中A是键，-NHCO-(CH2CO)n-，低级亚烷基，-NH-CO-CO-或类似物质，R6是(a)或(b)其中R7，R8，R9和R10是独立的氨基，胍基，脒基或类似物质；R4是羧基或受保护的羧基；R5是氨基或受保护的氨基，或药用可接受的盐，一种制备公式化合物[I]的方法，以及一种包括与药用可接受载体混合的公式化合物[I]的药物组合物。
• Discovery of an l-alanine ester prodrug of the Hsp90 inhibitor, MPC-3100
  作者：Se-Ho Kim、Rajendra Tangallapally、In Chul Kim、Richard Trovato、Daniel Parker、J. Scott Patton、Leslie Reeves、Chad Bradford、Daniel Wettstein、Vijay Baichwal、Damon Papac、Ashok Bajji、Robert Carlson、Kraig M. Yager

  DOI：10.1016/j.bmcl.2015.09.053

  日期：2015.11

  Various types of Hsp90 inhibitors have been and continue to undergo clinical investigation. One development candidate is the purine-based, synthetic Hsp90 inhibitor 1 (MPC-3100), which successfully completed a phase I clinical study. However, further clinical development of 1 was hindered by poor solubility and consequent formulation issues and promoted development of a more water soluble prodrug. Towards this end, numerous pro-moieties were explored in vitro and in vivo. These studies resulted in identification of L-alanine ester mesylate, 2i (MPC-0767), which exhibited improved aqueous solubility, adequate chemical stability, and rapid bioconversion without the need for solubilizing excipients. Based on improved physical characteristics and favorable PK and PD profiles, 2i mesylate was selected for further development. A convergent, scalable, chromatography-free synthesis for 2i mesylate was developed to support further clinical evaluation. (C) 2015 Elsevier Ltd. All rights reserved.
• Stewart, Frederick H.C., Australian Journal of Chemistry, 1980, vol. 33, # 1, p. 121 - 129
  作者：Stewart, Frederick H.C.

  DOI：——

  日期：——
• [EN] MEXILETINE AMINO ACID AND PEPTIDE PRODRUGS AND USES THEREOF<br/>[FR] PROMÉDICAMENTS D'ACIDE AMINÉ DE MEXILITINE ET DE PEPTIDE, ET LEURS UTILISATIONS
  申请人：SHIRE LLC

  公开号：WO2010149760A3

  公开（公告）日：2011-09-29