N-(tert-butoxycarbonyl)-N,O-dimethyltyrosine

• 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-(tert-butoxycarbonyl)-N,O-dimethyltyrosine
• 英文别名: N-tert-Butoxycarbonyl-N,O-dimethyltyrosine；3-(4-Methoxyphenyl)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]propanoic acid
• 化学式: C₁₆H₂₃NO₅
• 分子量: 309.362
• InChiKey: GVPXAJMOULURAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)-N,O-dimethyltyrosine 在 盐酸 、 三乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 反应 28.0h， 生成 N-(4-tert-butylphenyl)-N^α,O-dimethyltyrosinamide
  参考文献：
  名称：

  Discovery of orally efficacious RORγt inverse agonists, part 1: Identification of novel phenylglycinamides as lead scaffolds

  摘要：

  A series of novel phenylglycinamides as retinoic acid receptor-related orphan receptor-gamma t (ROR gamma t) inverse agonists were discovered through optimization of a high-throughput screen hit 1. (R)-N-(2-((3,5-Difluoro-4-(trimethylsilyl)phenyl) amino)-1-(4-methoxyphenyl)-2-oxoethyl)-3-hydroxy-N-methylisoxazole-5-carboxamide (22) was identified as one of the best of these compounds. It displayed higher subtype selectivity and specificity over other nuclear receptors and demonstrated in vivo potency to suppress the transcriptional activity of ROR gamma t in a mouse PD (pharmacodynamic) model upon oral administration. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.12.006
• 作为产物：
  描述：

  N-(叔丁氧羰基)-DL-酪氨酸 、 碘甲烷 以 四氢呋喃 、 tetrahydrofuran-water 、 水 为溶剂， 以90%的产率得到N-(tert-butoxycarbonyl)-N,O-dimethyltyrosine
  参考文献：
  名称：

  Total synthesis of the amino hip analogue of didemnin A

  摘要：

  揭示了一种合成方法，用于制备Didemnin A（1）的类似物，特别是Didemnin A的Amino-Hip类似物，也称为“AipDidemnin A”（8）。这些化合物具有以下结构：

  公开号：

  US06380156B1

文献信息

• TOTAL SYNTHESIS OF THE AMINO HIP ANALOGUE OF DIDEMNIN A
  申请人：THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS

  公开号：EP0956033B1

  公开（公告）日：2003-07-23
• US6380156B1
  申请人：——

  公开号：US6380156B1

  公开（公告）日：2002-04-30
• Total synthesis of the amino hip analogue of didemnin A
  申请人：The Board of Trustees of the University of Illnois

  公开号：US06380156B1

  公开（公告）日：2002-04-30

  Disclosed is a synthetic method for the preparation of analogs of Didemnin A (1), particularly the Amino-Hip analog of Didemnin A, also known as “AipDidemnin A” (8). These compounds have the following structures:

  揭示了一种合成方法，用于制备Didemnin A（1）的类似物，特别是Didemnin A的Amino-Hip类似物，也称为“AipDidemnin A”（8）。这些化合物具有以下结构：
• Discovery of orally efficacious RORγt inverse agonists, part 1: Identification of novel phenylglycinamides as lead scaffolds
  作者：Junya Shirai、Yoshihide Tomata、Mitsunori Kono、Atsuko Ochida、Yoshiyuki Fukase、Ayumu Sato、Shinichi Masada、Tetsuji Kawamoto、Kazuko Yonemori、Ryoukichi Koyama、Hideyuki Nakagawa、Masaharu Nakayama、Keiko Uga、Akira Shibata、Keiko Koga、Toshitake Okui、Mikio Shirasaki、Robert Skene、BiChing Sang、Isaac Hoffman、Wes Lane、Yasushi Fujitani、Masashi Yamasaki、Satoshi Yamamoto

  DOI：10.1016/j.bmc.2017.12.006

  日期：2018.1

  A series of novel phenylglycinamides as retinoic acid receptor-related orphan receptor-gamma t (ROR gamma t) inverse agonists were discovered through optimization of a high-throughput screen hit 1. (R)-N-(2-((3,5-Difluoro-4-(trimethylsilyl)phenyl) amino)-1-(4-methoxyphenyl)-2-oxoethyl)-3-hydroxy-N-methylisoxazole-5-carboxamide (22) was identified as one of the best of these compounds. It displayed higher subtype selectivity and specificity over other nuclear receptors and demonstrated in vivo potency to suppress the transcriptional activity of ROR gamma t in a mouse PD (pharmacodynamic) model upon oral administration. (C) 2017 Elsevier Ltd. All rights reserved.