6-(3-chlorophenyl)imidazo[2,1-b]thiazole | 353487-41-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-(3-chlorophenyl)imidazo[2,1-b]thiazole
• 英文别名: Cambridge id 5691481；6-(3-chlorophenyl)imidazo[2,1-b][1,3]thiazole
• CAS: 353487-41-9
• 化学式: C₁₁H₇ClN₂S
• 分子量: 234.709
• InChiKey: QHUKVWOTVKQXPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(3-chlorophenyl)imidazo[2,1-b]thiazole 在 溶剂黄146 、 三氯氧磷 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Human constitutive androstane receptor agonist DL5016: A novel sensitizer for cyclophosphamide-based chemotherapies

  摘要：

  The DNA alkylating prodrug cyclophosphamide (CPA), alone or in combination with other agents, is one of the most commonly used anti-cancer agents. As a prodrug, CPA is activated by cytochrome P450 2B6 (CYP2B6), which is transcriptionally regulated by the human constitutive androstane receptor (hCAR). Therefore, hCAR agonists represent novel sensitizers for CPA-based therapies. Among known hCAR agonists, compound 6-(4-chlorophenyl)imidazo-[2,1-b]thiazole-5-carbaldehyde-O-(3,4-dichlorobenzyl) oxime (CITCO) is the most potent and broadly utilized in biological studies. Through structural modification of CITCO, we have developed a novel compound DL5016 (32), which has an EC50 value of 0.66 mu M and E-MAX value of 4.9 when activating hCAR. DL5016 robustly induced the expression of hCAR target gene CYP2B6, at both the mRNA and protein levels, and caused translocation of hCAR from the cytoplasm to the nucleus in human primary hepatocytes. The effects of DL5016 were highlighted by dramatically enhancing the efficacy of CPA-based cytotoxicity to non-Hodgkin lymphoma cells. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.06.031
• 作为产物：
  描述：

  2-氨基噻唑 、 2'-溴-3-氯苯乙酮 以 乙醇 为溶剂， 反应 16.0h， 生成 6-(3-chlorophenyl)imidazo[2,1-b]thiazole
  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

• Metal-free regioselective bromination of imidazo-heteroarenes: the dual role of an organic bromide salt in electrocatalysis
  作者：Partha Pratim Sen、Vishal Jyoti Roy、Sudipta Raha Roy

  DOI：10.1039/d1gc01069g

  日期：——

  tetra-n-butylammonium bromide (TBAB), as a brominating agent and as an electrolyte for the regioselective bromination of several imidazo heteroaromatic motifs. Instead of using a transition metal/external oxidant, this methodology utilized electron holes and electrons by means of anodic oxidation and cathodic reduction to form the desired products in good to excellent yields at ambient temperature. The method is simple

  本文通过证明有机溴化物盐的双重作用来代表电化学转化，即四氮-丁基溴化铵 (TBAB)，作为溴化剂和电解质，用于几种咪唑杂芳族基序的区域选择性溴化。该方法不使用过渡金属/外部氧化剂，而是通过阳极氧化和阴极还原利用电子空穴和电子在环境温度下以良好至极好的产率形成所需的产物。该方法简单、环境友好且与各种官能团兼容。这种可持续的绿色溴化技术的意义在于，现成的低成本电极 (C(+)/C(-)) 可以重复使用多达 40 次而不会损失任何电化学活性。电氧化方法可以有效地扩大规模，也可以扩展到氯化。而且，
• [EN] COMPOUNDS FOR TREATING DUCHENNE MUSCULAR DYSTROPHY<br/>[FR] COMPOSÉS POUR TRAITER LA DYSTROPHIE MUSCULAIRE DE DUCHENNE
  申请人：SUMMIT CORP PLC

  公开号：WO2009013477A1

  公开（公告）日：2009-01-29

  Compounds of general formula (I), wherein X1, X2, X3, R1, R2, R3, Y and Z are as defined herein are useful for the treatment and prevention of Duchenne muscular dystrophy, Becker muscular dystrophy and cachexia.

  通式（I）的化合物，其中X1、X2、X3、R1、R2、R3、Y和Z的定义如本文所述，对于治疗和预防杜兴氏肌肉萎缩症、贝克氏肌肉萎缩症和消瘦症是有用的。
• COMPOUNDS FOR TREATING DUCHENNE MUSCULAR DYSTROPHY
  申请人：Summit Corporation Plc

  公开号：EP2167508A1

  公开（公告）日：2010-03-31