2-(1,3-Benzothiazol-2-ylthio)-1-biphenyl-4-ylethanone | 295361-68-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1,3-Benzothiazol-2-ylthio)-1-biphenyl-4-ylethanone
• 英文别名: 2-(1,3-benzothiazol-2-ylsulfanyl)-1-(4-phenylphenyl)ethanone
• CAS: 295361-68-1
• 化学式: C₂₁H₁₅NOS₂
• 分子量: 361.488
• InChiKey: MEEGNRHCRQNQSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1,3-Benzothiazol-2-ylthio)-1-biphenyl-4-ylethanone 、 2-氨基二苯甲酮 在 ytterbium(III) chloride 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以81%的产率得到2-((2-((1,1'-biphenyl)-4-yl)-4-phenylquinolin-3-yl)thio)benzo[d]thiazole
  参考文献：
  名称：

  Synthesis of 3-heteroarylthioquinoline derivatives and their in vitro antituberculosis and cytotoxicity studies

  摘要：

  A series of 3-heteroarylthioquinoline derivatives has been synthesized by the Friedlander annulation of 2-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]-1-aryl-1-ethanone/2-(1,3-benzothiazol-2-ylsulfanyl)-1-aryl-1-ethanone/1-aryl-2-[(2-phenyl-2H-1,2,3,4-tetraazol-5-yl)sulfanyl]-1-ethanone with 2-aminobenzophenone in good yields using YbCl3 as the catalyst. These compounds have been screened for their in vitro activity against Mycobacterium tuberculosis H37Rv (MTB) and among the 21 compounds screened, 2-[2-(4-bromophenyl)-4-phenyl-3-quinolyl]sulfanyl-5-methyl-1,3,4-thiadiazole (5d) and 2-[2-(4-chlorophenyl)-4-phenyl-3-quinolyl]sulfanyl-5-methyl-1,3,4-thiadiazole (5c) were found to be the most active compounds with MIC of 3.2 and 3.5 mu M respectively against MTB. The cytotoxic effects against mouse fibroblasts (NIH 3T3) in vitro were evaluated for 5c and 5d, which displayed no toxic effects (IC50 > 1000 mu M) against the mouse fibroblast cell line NIH 3T3. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.046
• 作为产物：
  描述：

  2-巯基苯并噻唑 、 2-溴-4-苯基乙酰苯 在 C₂₇H₂₂BrN₆Ni⁽¹⁺⁾*F₆P^(1-) 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以16%的产率得到2-(1,3-Benzothiazol-2-ylthio)-1-biphenyl-4-ylethanone
  参考文献：
  名称：

  机械化学逐步合成和催化吡啶官能化 N-杂环卡宾镍 (II) 配合物的 C-S 交叉偶联

  摘要：

  本文介绍了通过逐步研磨合成三种 N-杂环卡宾配合物。苯并咪唑盐（[H 2 L]Br 2和[H 2 L](PF 6 ) 2 ([ H 2 L ] = 1,1'-di(2-picolyl)-3,3'-methylenedibenzoimidazolium)）是初步准备。它们通过研磨与Ni(OAc) 2 ·4H 2 O反应得到三种镍配合物，[NiL]Br 2 ·CH 3 OH ( 1 )、[NiL]Br 2 ·2H 2 O ( 1' )和[NiL]( PF 6 ) 2·分别为0.5CH 3 CN ( 2 )。NH 4 PF 6与络合物1或1'一起研磨，或者KBr与络合物2一起研磨，进一步得到五配位络合物[NiLBr]PF 6 ( 3 ) 。配合物3也可以通过配合物1 / 1'和2的直接研磨获得。综合体3随后在 2-溴苯乙酮和 2-巯基苯并噻唑的 C-S 键交叉偶联中用作催化剂。从合成到催化反应的

  DOI：

  10.1039/d1dt03651c

文献信息

• Synthesis of 3-heteroarylthioquinoline derivatives and their in vitro antituberculosis and cytotoxicity studies
  作者：Selvam Chitra、Nidhin Paul、Shanmugam Muthusubramanian、Paramasivam Manisankar、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.ejmech.2011.07.046

  日期：2011.10

  A series of 3-heteroarylthioquinoline derivatives has been synthesized by the Friedlander annulation of 2-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]-1-aryl-1-ethanone/2-(1,3-benzothiazol-2-ylsulfanyl)-1-aryl-1-ethanone/1-aryl-2-[(2-phenyl-2H-1,2,3,4-tetraazol-5-yl)sulfanyl]-1-ethanone with 2-aminobenzophenone in good yields using YbCl3 as the catalyst. These compounds have been screened for their in vitro activity against Mycobacterium tuberculosis H37Rv (MTB) and among the 21 compounds screened, 2-[2-(4-bromophenyl)-4-phenyl-3-quinolyl]sulfanyl-5-methyl-1,3,4-thiadiazole (5d) and 2-[2-(4-chlorophenyl)-4-phenyl-3-quinolyl]sulfanyl-5-methyl-1,3,4-thiadiazole (5c) were found to be the most active compounds with MIC of 3.2 and 3.5 mu M respectively against MTB. The cytotoxic effects against mouse fibroblasts (NIH 3T3) in vitro were evaluated for 5c and 5d, which displayed no toxic effects (IC50 > 1000 mu M) against the mouse fibroblast cell line NIH 3T3. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Stepwise synthesis and catalysis in C–S cross-coupling of pyridine-functionalized N-heterocyclic carbene nickel(<scp>ii</scp>) complexes by mechanochemistry
  作者：Xiaoxiao Cui、Xiujia Hao、Fang Guo

  DOI：10.1039/d1dt03651c

  日期：——

  respectively. A five-coordinated complex [NiLBr]PF6 (3) was further obtained by grinding NH4PF6 with complex 1 or 1′, or grinding KBr with complex 2. Complex 3 can also be obtained by direct grinding of complexes 1/1′ and 2. Complex 3 was subsequently used as a catalyst in the C–S bond cross-coupling of 2-bromoacetophenone and 2-mercaptobenzothiazole. The entire procedure from the synthesis to the catalytic

  本文介绍了通过逐步研磨合成三种 N-杂环卡宾配合物。苯并咪唑盐（[H 2 L]Br 2和[H 2 L](PF 6 ) 2 ([ H 2 L ] = 1,1'-di(2-picolyl)-3,3'-methylenedibenzoimidazolium)）是初步准备。它们通过研磨与Ni(OAc) 2 ·4H 2 O反应得到三种镍配合物，[NiL]Br 2 ·CH 3 OH ( 1 )、[NiL]Br 2 ·2H 2 O ( 1' )和[NiL]( PF 6 ) 2·分别为0.5CH 3 CN ( 2 )。NH 4 PF 6与络合物1或1'一起研磨，或者KBr与络合物2一起研磨，进一步得到五配位络合物[NiLBr]PF 6 ( 3 ) 。配合物3也可以通过配合物1 / 1'和2的直接研磨获得。综合体3随后在 2-溴苯乙酮和 2-巯基苯并噻唑的 C-S 键交叉偶联中用作催化剂。从合成到催化反应的