aerugine | 112515-23-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: aerugine
• 英文别名: (R)-2-(2-hydroxyphenyl)-4-hydroxymethyl-4,5-dihydrothiazole；(R)-2-(4-(hydroxymethyl)-4,5-dihydrothiazol-2-yl)phenol；Aerugine；2-[(4R)-4-(hydroxymethyl)-4,5-dihydro-1,3-thiazol-2-yl]phenol
• CAS: 112515-23-8
• 化学式: C₁₀H₁₁NO₂S
• 分子量: 209.269
• InChiKey: CQCVSXXDUMTFCR-SSDOTTSWSA-N

物化性质

• 沸点：
  402.0±51.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  78.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  aerugine 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以39%的产率得到aeruginaldehyde
  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
• 作为产物：
  描述：

  邻羟基苯甲腈 在 甲醇 、 sodium tetrahydroborate 、 phosphate buffer 、 乙酰氯 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 120.0h， 生成 aerugine
  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

• Synthesis and Antibacterial Activities of Yanglingmycin Analogues
  作者：Long-Bo Li、Wen-Jia Dan、Fang-Fang Tan、Li-Hui Cui、Zhi-Peng Yuan、Wen-Jun Wu、Ji-Wen Zhang

  DOI：10.1248/cpb.c14-00578

  日期：——

  The synthesis of Yanglingmycin and its enantiomer, along with eighteen Yanglingmycin analogues is reported. The structures were confirmed mainly by analyses of NMR spectral data. Antibacterial activity assays showed that Yanglingmycin and some of its analogues exhibited significant antibacterial activities against two important agricultural pathogenic bacteria, Ralstonia solanacearum and Pseudomonas syringae pv. actinidiae, with minimum inhibitory concentration (MIC) values ranging from 3.91 to 15.62 µg/mL. The antibacterial activities exhibited by Yanglingmycin and its analogues are promising, suggesting potential in the development of compounds for novel bactericides.

  报告了阳灵霉素及其对映体，以及十八种阳灵霉素类药物的合成。其结构主要通过核磁共振(NMR)光谱数据的分析得以确认。抗菌活性测定表明，阳灵霉素及其部分类药物对两种重要的农业病原菌——苏云金芽孢杆菌（Ralstonia solanacearum）和青枯病细菌（Pseudomonas syringae pv. actinidiae）具有显著的抗菌活性，最低抑菌浓度（MIC）值范围为3.91至15.62 µg/mL。阳灵霉素及其类药物表现出的抗菌活性具有潜力，建议在新型杀菌剂的化合物开发中具有应用前景。
• Design and Synthesis of New 2-Aryl-4,5-Dihydro-thiazole Analogues: In Vitro Antibacterial Activities and Preliminary Mechanism of Action
  作者：Fangfang Tan、Baojun Shi、Jian Li、Wenjun Wu、Jiwen Zhang

  DOI：10.3390/molecules201119680

  日期：——

  Sixty 2-aryl-4,5-dihydrothiazoles were designed and synthesized in yields ranging from 64% to 89% from cysteine and substituted-benzonitriles via a novel metal- and catalyst-free method. The structures of the title compounds were confirmed mainly by NMR spectral data analysis. Antibacterial activity assays showed that the compounds (S)-2-(2′-hydroxyphenyl)-4-hydroxy-methyl- 4,5-dihydrothiazole (7h) and (R)-2-(2′-hydroxyphenyl)-4-hydroxymethyl-4,5-dihydro-thiazole (7h′) exhibited significant inhibition against Ralstonia solanacearum, Pseudomonas syringae pv. actinidiae, Bacillus subtilis and Bacillus cereus, with minimum inhibitory concentrations (MICs) ranging from 3.91 to 31.24 μg·mL−1. The effect of substituents showed that not only electron-withdrawing groups, but also electron-donating groups could abolish the antibacterial activities unless a 2′-hydroxy group was introduced on the 2-aryl substituent of the 4,5-dihydrothiazole analogues. The results of scanning electron microscope (SEM) and fatty acid exposure experiments indicated that these antibacterial compounds influence fatty acid synthesis in the tested bacteria.

  通过一种新型的无金属和催化剂方法，设计并合成了 60 个 2-芳基-4,5-二氢噻唑类化合物，其中半胱氨酸和取代苯腈类化合物的产率为 64% 至 89%。标题化合物的结构主要通过核磁共振光谱数据分析得到了证实。抗菌活性测定结果表明，(S)-2-(2′-羟基苯基)-4-羟甲基-4,5-二氢噻唑（7h）和(R)-2-(2′-羟基苯基)-4-羟甲基-4,5-二氢噻唑（7h′）化合物对茄属拉氏菌（Ralstonia solanacearum）、丁香假单胞菌（PSEudomonas syringae pv.最低抑菌浓度为 3.91 μg-mL-1 至 31.24 μg-mL-1。取代基的影响表明，不仅取电子基团会削弱抗菌活性，而且供电子基团也会削弱抗菌活性，除非在 4,5-二氢噻唑类似物的 2-芳基取代基上引入 2′-羟基。扫描电子显微镜（SEM）和脂肪酸暴露实验的结果表明，这些抗菌化合物会影响受试细菌的脂肪酸合成。
• Methods and compositions related to neuroactive thiazoline compounds
  申请人：Schmidt Eric W.

  公开号：US09751847B2

  公开（公告）日：2017-09-05

  In one aspect, the invention relates to compounds having a general structure: and methods of using same to modulate calcium release. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  在某个方面，本发明涉及具有一般结构的化合物：以及使用相同的方法来调节钙释放。本摘要旨在作为搜索特定领域的扫描工具，不旨在限制本发明。
• METHODS AND COMPOSITIONS RELATED TO NEUROACTIVE THIAZOLINE COMPOUNDS
  申请人：Schmidt Eric W.

  公开号：US20140018400A1

  公开（公告）日：2014-01-16

  In one aspect, the invention relates to compounds having a general structure: and methods of using same to modulate calcium release. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  在某个方面，本发明涉及具有一般结构的化合物：以及使用同样的方法来调节钙释放。本摘要旨在作为扫描工具，用于在特定技术领域进行搜索，不旨在限制本发明。
• Total Synthesis and Biological Investigation of Mindapyrroles A and B
  作者：Ryan A. Allen、William M. Wuest

  DOI：10.1002/cmdc.202300235

  日期：2023.9.15

  Antibiotics with novel and polypharmacological mechanisms of action are urgently needed. To this end, the total synthesis of mindapyrroles A and B was completed via a Friedel-Crafts alkylation. The antibacterial activity of these compounds was investigated against a panel of gram-positive and gram-negative pathogens, and their mechanism of action was determined to be different from their monomer pyoluteorin

  迫切需要具有新颖和多药理作用机制的抗生素。为此，通过Friedel-Crafts烷基化完成了敏达吡咯A和B的全合成。研究了这些化合物对一组革兰氏阳性和革兰氏阴性病原体的抗菌活性，并确定其作用机制与其单体幽门螺杆菌素不同。