[(S)-1-(4-Carbamoyl-thiazol-2-yl)-ethyl]-carbamic acid tert-butyl ester | 212009-09-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: [(S)-1-(4-Carbamoyl-thiazol-2-yl)-ethyl]-carbamic acid tert-butyl ester
• 英文别名: 1,1-Dimethylethyl N-[(1S)-1-[4-(aminocarbonyl)-2-thiazolyl]ethyl]carbamate；tert-butyl N-[(1S)-1-(4-carbamoyl-1,3-thiazol-2-yl)ethyl]carbamate
• CAS: 212009-09-1
• 化学式: C₁₁H₁₇N₃O₃S
• 分子量: 271.34
• InChiKey: MLCJNOOEQFHVFJ-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(S)-1-(4-Carbamoyl-thiazol-2-yl)-ethyl]-carbamic acid tert-butyl ester 在 劳森试剂 、 吡啶 、 potassium hydrogencarbonate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 2.33h， 生成
  参考文献：
  名称：

  Design, synthesis and anticancer mechanistic studies of linked azoles

  摘要：

  在此，我们报告了2,4-偶联咪唑含有分子的合成和生物活性评估。

  DOI：

  10.1039/c4md00387j
• 作为产物：
  描述：

  BOC-L-丙氨酸甲酯 在 劳森试剂 、 吡啶 、 ammonium hydroxide 、 potassium hydrogencarbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 乙醇 、 水 为溶剂， 反应 2.33h， 生成 [(S)-1-(4-Carbamoyl-thiazol-2-yl)-ethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Design, synthesis and anticancer mechanistic studies of linked azoles

  摘要：

  在此，我们报告了2,4-偶联咪唑含有分子的合成和生物活性评估。

  DOI：

  10.1039/c4md00387j

文献信息

• RITA Mimics: Synthesis and Mechanistic Evaluation of Asymmetric Linked Trithiazoles
  作者：Adrian L. Pietkiewicz、Yuqi Zhang、Marwa N. Rahimi、Michael Stramandinoli、Matthew Teusner、Shelli R. McAlpine

  DOI：10.1021/acsmedchemlett.6b00488

  日期：2017.4.13

  The established cytotoxic agent RITA contains a thiophene-furan-thiophene backbone and two terminal alcohol groups. Herein we investigate the effect of using thiazoles as the backbone in RITA-like molecules and modifying the terminal groups of these trithiazoles, thereby generating 41 unique structures. Incorporating side chains with varied steric bulk allowed us to investigate how size and a stereocenter impacted biological activity. Subjecting compounds to growth inhibition assays on HCT-116 cells showed that the most potent compounds 7d, 7e, and 7h had GI₅₀ values of 4.4, 4.4, and 3.4 μM, respectively, versus RITA (GI₅₀ of 800 nM). Analysis of these compounds in apoptosis assays proved that 7d, 7e, and 7h were as effective as RITA at inducing apoptosis. Evaluating the impact of 7h on proteins targeted by RITA (p53, c-Myc, and Mcl-1) indicated that it acts via a different mechanism of action to that of RITA. RITA suppressed Mcl-1 protein via p53, whereas compound 7h suppressed Mcl-1 expression via an alternative mechanism independent of p53.
• Synthesis and Antimicrobial Activity <i>in Vitro</i> of New Amino Acids and Peptides Containing Thiazole and Oxazole Moieties
  作者：Mincho Stanchev、Svoboda Tabakova、Georgi Videnov、Evgeny Golovinsky、Guenther Jung

  DOI：10.1002/(sici)1521-4184(19999)332:9<297::aid-ardp297>3.0.co;2-#

  日期：1999.9

  2-(Pyrrolidinyl)thiazole-4-carboxylic acid 5d, 2-(1-aminoalkyl)thiazole-4-carboxamides and hydrazides 8, 10 have been synthesized using alanine, valine, and proline as educts. In addition oxazole amino acids derived from leucine 20a and alanine 20b and some peptides 13, 14, 16 containing the 5-ring heterocyclic backbone modifications have been prepared. The thiazole and oxazole containing amino acids and peptides showed moderate antibacterial activity in vitro against various Gram-positive (Staphylococcus aureus, Bacillus cereus, etc.) and Gram-negative (Escherichia coli, Proteus vulgar is, etc.) bacteria, fungi (Candida albicans), and yeast (Saccharomyces cerevisae, etc.).