4-chloro-2-(5-nitrothiazol-2-ylcarbamoyl)phenyl benzoate | 315241-05-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 4-chloro-2-(5-nitrothiazol-2-ylcarbamoyl)phenyl benzoate
• 英文别名: 2-(benzoyloxy)-5-chlorobenzoic acid；2-Benzoyloxy-5-chlorobenzoic acid
• CAS: 315241-05-5
• 化学式: C₁₄H₉ClO₄
• 分子量: 276.676
• InChiKey: XGJWWTCRHZKZSB-UHFFFAOYSA-N

物化性质

• 沸点：
  491.2±35.0 °C(Predicted)
• 密度：
  1.402±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-chloro-2-(5-nitrothiazol-2-ylcarbamoyl)phenyl benzoate 在 咪唑 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 23.0h， 生成 6-氯黄酮
  参考文献：
  名称：

  通过分子内wittig反应的新型4H-chromen-4-ones合成

  摘要：

  由O-酰基（芳酰基）水杨酸的甲硅烷基酯与（三甲基甲硅烷基）亚甲基三苯基膦烷的甲硅烷基酯的反应顺序形成的酰基磷光烷在酯羰基上进行分子内的Wittig环化反应，得到良好或优异的4H-铬4--4-产量。

  DOI：

  10.1021/ol006518p
• 作为产物：
  描述：

  5-氯代水杨酸 、 苯甲酰氯 在 氢氧化钾 作用下， 以 水 为溶剂， 反应 0.5h， 生成 4-chloro-2-(5-nitrothiazol-2-ylcarbamoyl)phenyl benzoate
  参考文献：
  名称：

  通过分子内wittig反应的新型4H-chromen-4-ones合成

  摘要：

  由O-酰基（芳酰基）水杨酸的甲硅烷基酯与（三甲基甲硅烷基）亚甲基三苯基膦烷的甲硅烷基酯的反应顺序形成的酰基磷光烷在酯羰基上进行分子内的Wittig环化反应，得到良好或优异的4H-铬4--4-产量。

  DOI：

  10.1021/ol006518p

文献信息

• Structure–activity relationships of antitubercular salicylanilides consistent with disruption of the proton gradient via proton shuttling
  作者：Ill-Young Lee、Todd D. Gruber、Amanda Samuels、Minhan Yun、Bora Nam、Minseo Kang、Kathryn Crowley、Benjamin Winterroth、Helena I. Boshoff、Clifton E. Barry

  DOI：10.1016/j.bmc.2012.10.056

  日期：2013.1

  A series of salicylanilides was synthesized based on a high-throughput screening hit against Mycobacterium tuberculosis. A free phenolic hydroxyl on the salicylic acid moeity is required for activity, and the structure-activity relationship of the aniline ring is largely driven by the presence of electron withdrawing groups. We synthesized 94 analogs exploring substitutions of both rings and the linker region in this series and we have identified multiple compounds with low micromolar potency. Unfortunately, cytotoxicity in a murine macrophage cell line trends with antimicrobial activity, suggesting a similar mechanism of action. We propose that salicylanilides function as proton shuttles that kill cells by destroying the cellular proton gradient, limiting their utility as potential therapeutics. Published by Elsevier Ltd.
• Development of 5-nitrothiazole derivatives: Identification of leads against both replicative and latent Mycobacterium tuberculosis
  作者：Variam Ullas Jeankumar、Manoj Chandran、Ganesh Samala、Mallika Alvala、Pulla Venkat Koushik、Perumal Yogeeswari、Elena G. Salina、Dharmarajan Sriram

  DOI：10.1016/j.bmcl.2012.10.060

  日期：2012.12

  Twenty eight 5-nitrothiazole derivatives were synthesized and evaluated for in vitro activities against Mycobacterium tuberculosis (MTB), cytotoxicity against HEK 293T. Among the compounds, 5-nitro-N-(5-nitrothiazol-2-yl)furan-2-carboxamide (20) was found to be the most active compound in vitro with MICs of 5.48 mu M against log-phase culture of MTB and also non-toxic up to 100 mu M. (C) 2012 Elsevier Ltd. All rights reserved.