2'-(2-hydroxyphenyl)-2'-thiazoline-4'-(N-methoxy,N-methyl) carboxamide | 262419-96-5

• 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: 2'-(2-hydroxyphenyl)-2'-thiazoline-4'-(N-methoxy,N-methyl) carboxamide
• 英文别名: (4R)-2-(2-hydroxyphenyl)-4,5-dihydrothiazole-4-carboxylic acid N-methoxy-N-methylamide；(R)-2-(2-hydroxyphenyl)-N-methoxy-N-methyl-4,5-dihydrothiazole-4-carboxamide；(4R)-2-(2-hydroxyphenyl)-N-methoxy-N-methyl-4,5-dihydro-1,3-thiazole-4-carboxamide
• CAS: 262419-96-5
• 化学式: C₁₂H₁₄N₂O₃S
• 分子量: 266.321
• InChiKey: LNDAMQPSKUBGQY-VIFPVBQESA-N

物化性质

• 沸点：
  415.1±55.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.27
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  62.13
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2'-(2-hydroxyphenyl)-2'-thiazoline-4'-(N-methoxy,N-methyl) carboxamide 在 lithium aluminium tetrahydride 、 potassium acetate 、 N,N-二异丙基乙胺 、 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 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成
  参考文献：
  名称：

  [EN] COMPOUNDS, PHARMACEUTICAL COMPOSITIONS AND METHODS FOR TREATING INFLAMMATORY BOWEL DISEASE
  [FR] COMPOSÉS, COMPOSITIONS PHARMACEUTIQUES ET MÉTHODES DE TRAITEMENT D'UNE MALADIE INTESTINALE INFLAMMATOIRE

  摘要：

  The disclosure provides pharmaceutical compositions comprising a therapeutically effective amount of compound (A), compound (B), compound (C), compound (D), compound (E), compound (F), compound (G), compound (H), compound (J), compound (K), compound (L), compound (M), compound (N), compound (O), compound (P), or compound (Q)or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient: Also provided are dosage units comprising one or more of compound (A), compound (B), compound (C), compound (D), compound (E), compound (F), compound (G), compound (H), compound (J), compound (K), compound (L), compound (M), compound (N), compound (O), compound (P), or compound (Q) or the pharmaceutical compositions described herein, methods of treating an inflammatory bowel disease in a subject in need thereof, or methods of modulating an inflammatory bowel disease marker in a subject in need thereof.

  公开号：

  WO2023192388A1
• 作为产物：
  描述：

  邻羟基苯甲腈 在 phosphate buffer 、 氰基磷酸二乙酯 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 生成 2'-(2-hydroxyphenyl)-2'-thiazoline-4'-(N-methoxy,N-methyl) carboxamide
  参考文献：
  名称：

  改进的立体控制合成的秋葵素，铜绿假单胞菌和洋葱伯克霍尔德菌的铁载体

  摘要：

  描述了铜绿假单胞菌和洋葱伯克霍尔德氏菌大多数菌株常见的pyochelin（一种羟基苯基噻唑啉基噻唑烷型铁载体）的立体控制合成得到了显着改善。通过还原2'-（2-羟基苯基）-2'-噻唑啉-4'-（2'-（2-羟基苯基）-2'-噻唑啉-4'-甲醛，该合成涉及的关键分子。N-甲氧基，N-甲基）羧酰胺与氢化铝锂。将该醛进一步与（R）-N-甲基半胱氨酸偶联以产生秋水仙素。在报道的条件下，C-4'中心的差向异构化大大减少。

  DOI：

  10.1016/s0040-4020(99)00946-1

文献信息

• Synthetic studies of thiazoline and thiazolidine-containing natural products. Part 3: Total synthesis and absolute configuration of the siderophore yersiniabactin
  作者：Akira Ino、Akira Murabayashi

  DOI：10.1016/s0040-4020(01)00012-6

  日期：2001.3

  Total synthesis of yersiniabactin, a siderophore from cultures of the bacterium Yersinia enterocolitica, was accomplished. Chirality at the readily racemizable C-9 carbon was preserved during cyclization of β-hydroxythioamide by means of Burgess reagent leading to thiazoline. Based on its synthesis, the absolute configuration of natural yersiniabactin has been determined as 9R, 10RS, 12R, 13S and 19S

  完成了耶尔西菌素的全合成，这是一种来自小肠结肠炎耶尔森氏菌培养物的铁载体。在β-羟基硫酰胺的环化过程中，通过伯硫试剂生成噻唑啉，可以保持易于消旋的C-9碳的手性。根据它的合成，天然耶尔森杆菌的绝对构型已被确定为9 - [R，10个RS，12 - [R，13小号和19小号。
• Synthesis and biological properties of thiazole-analogues of pyochelin, a siderophore of Pseudomonas aeruginosa
  作者：Sabrina Noël、Françoise Hoegy、Freddy Rivault、Didier Rognan、Isabelle J. Schalk、Gaëtan L.A. Mislin

  DOI：10.1016/j.bmcl.2013.11.054

  日期：2014.1

  Pyochelin is a siderophore common to all strains of Pseudomonas aeruginosa utilized by this Gram-negative bacterium to acquire iron(III). FptA is the outer membrane transporter responsible of ferric-pyochelin uptake in P. aeruginosa. We describe in this Letter the synthesis and the biological properties (Fe-55 uptake, binding to FptA) of several thiazole analogues of pyochelin. Among them we report in this Letter the two first pyochelin analogues able to bind FptA without promoting any iron uptake in P. aeruginosa. (C) 2013 Elsevier Ltd. All rights reserved.
• Bacterial siderophores: synthesis and biological activities of novel pyochelin analogues
  作者：A Zamri、I.J Schalk、F Pattus、M.A Abdallah

  DOI：10.1016/s0960-894x(03)00010-6

  日期：2003.3

  The synthesis and biological activities of four pyochelin analogues substituted in different parts of the molecule are reported: 5-NHBoc-pyochelin, 3"N-Boc-pyochelin, 3"-nor-NH-pyochelin and neopyochelin II, the enantiomer of natural pyochelin. All these compounds complex iron(III) and transport it at different rates into the cells of Pseudomonas aeruginosa. (C) 2003 Elsevier Science Ltd. All rights reserved.