6-(4-苯基苯基)咪唑并[2,1-B] [1,3]噻唑-5-甲醛 | 82588-43-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 6-(4-苯基苯基)咪唑并[2,1-B] [1,3]噻唑-5-甲醛
• 中文别名: 6-(4-苯基苯基)咪唑并[2,1-B][1,3]噻唑-5-甲醛
• 英文名称: 6-([1,1'-biphenyl]-4-yl)imidazo[2,1-b]thiazole-5-carbaldehyde
• 英文别名: 5-Formyl-6-p-biphenylimidazo<2,1-b>thiazole；5-Formyl-6-p-biphenylimidazo[2,1-b]thiazole；6-Biphenyl-4-yl-imidazo[2,1-b]thiazole-5-carbaldehyde；6-(4-phenylphenyl)imidazo[2,1-b][1,3]thiazole-5-carbaldehyde
• CAS: 82588-43-0
• 化学式: C₁₈H₁₂N₂OS
• 分子量: 304.372
• InChiKey: FJLRPDKLIBVBFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(4-苯基苯基)咪唑并[2,1-B] [1,3]噻唑-5-甲醛 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 5-Hydroxymethyl-6-p-biphenylimidazo<2,1-b>thiazole
  参考文献：
  名称：

  潜在的抗肿瘤剂，VII. 5-取代的 6-苯基咪唑 [2,1-b] 噻唑

  摘要：

  报道了用于合成 5-甲酰基咪唑并 [2,1-b] 噻唑 7-12 的 Vilsmeier 反应，该反应在 6 位带有对取代的苯环。这些化合物用于合成缩氨基硫腙 7a-12a、甲苯磺酰腙7b-12b 和 5-羟甲基衍生物 13-18，进而用作制备甲基氨基甲酸 13a-18a、乙基氨基甲酸 13b-18b 和乙酸的起始原料酯 13c-18c。报告了 P-388 白血病测试的初步结果。

  DOI：

  10.1002/ardp.19823150511
• 作为产物：
  描述：

  2-溴-4-苯基乙酰苯 在 三氯氧磷 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 22.0h， 生成 6-(4-苯基苯基)咪唑并[2,1-B] [1,3]噻唑-5-甲醛
  参考文献：
  名称：

  DL5050, a Selective Agonist for the Human Constitutive Androstane Receptor

  摘要：

  The constitutive androstane receptor (CAR) is a xenobiotic sensor governing the transcription of genes involved in drug disposition, energy homeostasis, and cell proliferation. However, currently available human CAR (hCAR) agonists are nonselective, which commonly activate hCAR along with other nuclear receptors, especially the closely related human pregnane X receptor (hPXR). Using a well-known hCAR agonist CITCO as a template, we report our efforts in the discovery of a potent and highly selective hCAR agonist. Two of the new compounds of the series, 18 and 19 (DL5050), demonstrated excellent potency and selectivity for hCAR over hPXR. DL5050 preferentially induced the expression of CYP2B6 (target of hCAR) over CYP3A4 (target of hPXR) on both the mRNA and protein levels. The selective hCAR agonist DL5050 represents a valuable tool molecule to further define the biological functions of hCAR, and may also be used as a new lead in the discovery of hCAR agonists for various therapeutic applications.

  DOI：

  10.1021/acsmedchemlett.9b00079

文献信息

• An Efficient Synthesis of 2-Substituted Benzimidazoles via Photocatalytic Condensation of <i>o</i>-Phenylenediamines and Aldehydes
  作者：Jeshma Kovvuri、Burri Nagaraju、Ahmed Kamal、Ajay K. Srivastava

  DOI：10.1021/acscombsci.6b00107

  日期：2016.10.10

  method has been developed for the efficient synthesis of functionalized benzimidazoles. This protocol involves photocatalytic condensation of o-phenylenediamines with various aldehydes using the Rose Bengal as photocatalyst. The method was found to be general and was successfully employed for accessing pharmaceutically important benzimidazoles by the condensation of aromatic, heteroaromatic and aliphatic

  为了有效合成官能化的苯并咪唑，已经开发出一种光催化方法。该方案涉及使用玫瑰红作为光催化剂，将邻苯二胺与各种醛进行光催化缩合。发现该方法是通用的，并且以良好至优异的产率，通过芳族，杂芳族和脂族醛与邻苯二胺的缩合成功地用于制备药学上重要的苯并咪唑。值得注意的是，发现该方法对于反应性较低的杂环醛与邻苯二胺的缩合是有效的。
• DL5050, a Selective Agonist for the Human Constitutive Androstane Receptor
  作者：Dongdong Liang、Linhao Li、Caitlin Lynch、Benjamin Diethelm-Varela、Menghang Xia、Fengtian Xue、Hongbing Wang

  DOI：10.1021/acsmedchemlett.9b00079

  日期：2019.7.11

  The constitutive androstane receptor (CAR) is a xenobiotic sensor governing the transcription of genes involved in drug disposition, energy homeostasis, and cell proliferation. However, currently available human CAR (hCAR) agonists are nonselective, which commonly activate hCAR along with other nuclear receptors, especially the closely related human pregnane X receptor (hPXR). Using a well-known hCAR agonist CITCO as a template, we report our efforts in the discovery of a potent and highly selective hCAR agonist. Two of the new compounds of the series, 18 and 19 (DL5050), demonstrated excellent potency and selectivity for hCAR over hPXR. DL5050 preferentially induced the expression of CYP2B6 (target of hCAR) over CYP3A4 (target of hPXR) on both the mRNA and protein levels. The selective hCAR agonist DL5050 represents a valuable tool molecule to further define the biological functions of hCAR, and may also be used as a new lead in the discovery of hCAR agonists for various therapeutic applications.
• Potential Antitumor Agents, VII. 5-Substituted 6-Phenylimidazo[2,1-b]thiazoles
  作者：Aldo Andreani、Daniela Bonazzi、Mirella Rambaldi

  DOI：10.1002/ardp.19823150511

  日期：——

  The Vilsmeier reaction for the synthesis of the 5‐formylimidazo[2,1‐b]thiazoles 7–12 bearing a p‐substituted phenyl ring in position 6 is reported. These compounds were used for the synthesis of the thiosemicarbazones 7a‐12a, tosylhydrazones 7b‐12b and 5‐hydroxymethyl derivatives 13–18 which, in turn, were used as starting materials for preparing the methylcarbamic 13a‐18a, ethylcarbamic 13b‐18b and

  报道了用于合成 5-甲酰基咪唑并 [2,1-b] 噻唑 7-12 的 Vilsmeier 反应，该反应在 6 位带有对取代的苯环。这些化合物用于合成缩氨基硫腙 7a-12a、甲苯磺酰腙7b-12b 和 5-羟甲基衍生物 13-18，进而用作制备甲基氨基甲酸 13a-18a、乙基氨基甲酸 13b-18b 和乙酸的起始原料酯 13c-18c。报告了 P-388 白血病测试的初步结果。