6-(4-chlorophenyl)-2-methylimidazo[2,1-b]thiazole | 113991-24-5

• 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-(4-chlorophenyl)-2-methylimidazo[2,1-b]thiazole
• 英文别名: 6-(4-Chlorophenyl)-2-methylimidazo[2,1-b][1,3]thiazole
• CAS: 113991-24-5
• 化学式: C₁₂H₉ClN₂S
• mdl: MFCD01456280
• 分子量: 248.736
• InChiKey: FQSQZUDPGREEHC-UHFFFAOYSA-N

物化性质

• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.083
• 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-(4-chlorophenyl)-2-methylimidazo[2,1-b]thiazole 在 sodium tetrahydroborate 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 16.0h， 生成 2-Methyl-6-p-chlorophenylimidazo<2,1-b>thiazol-5-ylmethyl m-Trifluoromethylphenylcarbamate
  参考文献：
  名称：

  Andreani, Aldo; Rambaldi, Mirella; Carloni, Patricia, Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 525 - 529

  摘要：

  DOI：

文献信息

• Photoinduced, Direct C(sp ² )−H Bond Azo Coupling of Imidazoheteroarenes and Imidazoanilines with Aryl Diazonium Salts Catalyzed by Eosin Y
  作者：Sumbal Saba、Caio R. Dos Santos、Bruno R. Zavarise、Aline A. S. Naujorks、Marcelo S. Franco、Alex R. Schneider、Marcos R. Scheide、Ricardo F. Affeldt、Jamal Rafique、Antonio L. Braga

  DOI：10.1002/chem.201905308

  日期：2020.4.6

  Herein, a greener approach to the eosin Y-Na2 catalyzed, C(sp2 )-H bond azo coupling of imidazoheteroarene with aryl diazonium salts is described, under acid free conditions. This direct photoredox process resulted in the corresponding azo products in good to excellent yields. Besides, this new approach could also be applicable to anilines, which is a poorly reactive substrate by other methods. The

  在本文中，描述了在无酸条件下，曙红Y-Na 2催化的咪唑杂芳烃的C（sp 2）-H键偶氮偶合与芳基重氮盐的更绿色的方法。这种直接的光氧化还原过程产生了相应的偶氮产物，收率良好至极好。此外，这种新方法也可适用于苯胺，而苯胺是其他方法反应性较差的底物。该反应的主要特征是它提供了高收率，并且是克级可缩放的，并且适用于生物学上相关的咪唑杂杂芳烃和-苯胺。
• 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。
• [EN] IMIDAZOTHIAZOLE COMPOUNDS AND METHODS FOR TREATING PLANT NEMATODE INFECTIONS<br/>[FR] COMPOSÉS ET PROCÉDÉS D'IMIDAZOTHIAZOLE POUR LE TRAITEMENT D'INFECTIONS PROVOQUÉES PAR DES NÉMATODES CHEZ UNE PLANTE
  申请人：GOVERNING COUNCIL UNIV TORONTO

  公开号：WO2021003571A1

  公开（公告）日：2021-01-14

  The present application relates to the treatment of nematode infections in a plant. For example, the application relates to the use of one or more compounds of Formula (I) as defined herein, or compositions comprising these compounds, for treatment of a nematode infection or a disease, disorder or condition arising from a nematode infection in a plant. (Formula I)

  本申请涉及植物中线虫感染的治疗。例如，本申请涉及使用本公式（I）中定义的一个或多个化合物，或包含这些化合物的组合物，用于治疗植物中的线虫感染或由线虫感染引起的疾病、紊乱或病况。
• Human constitutive androstane receptor agonist DL5016: A novel sensitizer for cyclophosphamide-based chemotherapies
  作者：Dongdong Liang、Linhao Li、Caitlin Lynch、Bryan Mackowiak、William D. Hedrich、Yong Ai、Yue Yin、Scott Heyward、Menghang Xia、Hongbing Wang、Fengtian Xue

  DOI：10.1016/j.ejmech.2019.06.031

  日期：2019.10

  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.