benzo[d]thiazol-2-yl(2,4-dimethylphenyl)methanone | 1394973-41-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzo[d]thiazol-2-yl(2,4-dimethylphenyl)methanone
• 英文别名: benzothiazol-2-yl(2,4-dimethylphenyl)methanone
• CAS: 1394973-41-1
• 化学式: C₁₆H₁₃NOS
• 分子量: 267.351
• InChiKey: RWIHRDMMYMUOOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.96
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  benzo[d]thiazol-2-yl(2,4-dimethylphenyl)methanone 、 (三氟甲基)三甲基硅烷 在 四甲基氟化铵 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 以45%的产率得到1-(benzo[d]thiazol-2-yl)-1-(2,4-dimethylphenyl)-2,2,2-trifluoroethan-1-ol
  参考文献：
  名称：

  Development of AC265347‐Inspired Calcium‐Sensing Receptor Ago‐Positive Allosteric Modulators

  摘要：

  AbstractThe calcium‐sensing receptor (CaSR) is a clinical target in the treatment of hyperparathyroidism and related diseases. However, clinical use of approved CaSR‐targeting drugs such as cinacalcet is limited due to adverse side effects including hypocalcaemia, nausea and vomiting, and in some instances, a lack of efficacy. The CaSR agonist and positive allosteric modulator (ago‐PAM), AC265347, is chemically distinct from clinically‐approved CaSR PAMs. AC265347 potently suppressed parathyroid hormone (PTH) release in rats with a lower propensity to cause hypocalcaemia compared to cinacalcet and may therefore offer benefits over current CaSR PAMs. Here we report a structure activity relationship (SAR) study seeking to optimise AC265347 as a drug candidate and disclose the discovery of AC265347‐like compounds with diverse pharmacology and improved physicochemical and drug‐like properties.

  DOI：

  10.1002/cmdc.202100368
• 作为产物：
  描述：

  2,4-二甲基苯乙烯 在 碘 、 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 生成 benzo[d]thiazol-2-yl(2,4-dimethylphenyl)methanone
  参考文献：
  名称：

  多路径耦合多米诺骨牌策略：无金属氧化环化，从多形式底物一锅合成2-酰基苯并噻唑

  摘要：

  已经开发了一种多途径偶联多米诺骨牌策略，用于通过多种不同的途径从多种形式的底物芳烃，芳基乙炔，2-羟基-芳族酮和甲醇中高效合成2-酰基苯并噻唑。通过逻辑耦合的氧化/杂环多米诺工艺，可以在一锅中合成多种不含金属的2-酰基苯并噻唑。

  DOI：

  10.1021/ol301921t

文献信息

• Concise Access to 2-Aroylbenzothiazoles by Redox Condensation Reaction between <i>o</i>-Halonitrobenzenes, Acetophenones, and Elemental Sulfur
  作者：Thanh Binh Nguyen、Karine Pasturaud、Ludmila Ermolenko、Ali Al-Mourabit

  DOI：10.1021/acs.orglett.5b01182

  日期：2015.5.15

  A wide range of 2-aroylbenzothiazoles 3 including some pharmacologically, relevant derivatives can be obtained in high yields by simply heating o-halonitrobenzenes 1, acetophenones 2, elemental sulfur, and N-methylmorpholine. This three-component nitro methyl Coupling was found to occur in an excellent atom-, step-, an redox-efficient manner in which elemental sulfur prayed the role of nucleophile building block and redox moderating agent to fulfill electronic requirements of the global reaction.