(S)-2-(2-hydroxyphenyl)-4-hydroxymethyl-4,5-dihydrothiazole | 184649-71-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (S)-2-(2-hydroxyphenyl)-4-hydroxymethyl-4,5-dihydrothiazole
• 英文别名: 6-[(4S)-4-(Hydroxymethyl)-1,3-thiazolidin-2-ylidene]cyclohexa-2,4-dien-1-one；2-[(4S)-4-(hydroxymethyl)-4,5-dihydro-1,3-thiazol-2-yl]phenol
• CAS: 184649-71-6
• 化学式: C₁₀H₁₁NO₂S
• 分子量: 209.269
• InChiKey: CQCVSXXDUMTFCR-ZETCQYMHSA-N

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

• 作为产物：
  描述：

  在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以85%的产率得到(S)-2-(2-hydroxyphenyl)-4-hydroxymethyl-4,5-dihydrothiazole
  参考文献：
  名称：

  聚合的古铁青霉素为Ga 3+配合物的全合成

  摘要：

  含铁细胞piscibactin是参与致病细菌的铁摄取的主要毒力因子发光菌damselae亚种。piscicida和Anguillarum弧菌分别负责鱼类细菌光致细菌（巴氏杆菌病）和弧菌病。描述了使用l- / d-半胱氨酸作为手性试剂和梅德鲁姆酸的Ga 3+络合物的收敛全合成。酸敏感的β-羟基-2,4-二取代的噻唑啉部分和方便的保护基团的合成中的Staudinger还原/ Aza-Wittig工艺是该合成的关键步骤。

  DOI：

  10.1021/acs.orglett.0c03850

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。