3-(4-chlorophenyl)-4,6-dimethoxy-2-trichloroacetyl-1H-indole | 807618-98-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-(4-chlorophenyl)-4,6-dimethoxy-2-trichloroacetyl-1H-indole
• 英文别名: 3-(4-chlorophenyl)-4,6-dimethoxy-2-trichloroacetylindole
• CAS: 807618-98-0
• 化学式: C₁₈H₁₃Cl₄NO₃
• 分子量: 433.118
• InChiKey: XBOGCBOFMFEZEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.06
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  51.32
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-(4-chlorophenyl)-4,6-dimethoxy-2-trichloroacetyl-1H-indole 在 硝酸 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 以45%的产率得到3-(4-chlorophenyl)-4,6-dimethoxy-7-nitro-2-trichloroacetylindole
  参考文献：
  名称：

  某些4,6-二甲氧基吲哚的硝化作用

  摘要：

  可以使用吸附在二氧化硅上的硝酸硝化一系列在2或7位带有吸电子基团的3-取代的4,6-二甲氧基吲哚，分别得到7-硝基和2-硝基吲哚。 。1-氰基吲哚区域选择性地产生2-硝基吲哚而氰基基团消失。

  DOI：

  10.1016/j.tet.2004.08.086
• 作为产物：
  描述：

  3-(4-chlorophenyl)-4,6-dimethoxyindole 、 三氯乙酰氯 以 1,2-二氯乙烷 为溶剂， 反应 3.5h， 生成 3-(4-chlorophenyl)-4,6-dimethoxy-2-trichloroacetyl-1H-indole
  参考文献：
  名称：

  Synthesis and biological activity of novel mono-indole and mono-benzofuran inhibitors of bacterial transcription initiation complex formation

  摘要：

  Our ongoing research focused on targeting transcription initiation in bacteria has resulted in synthesis of several classes of mono-indole and mono-benzofuran inhibitors that targeted the essential protein-protein interaction between RNA polymerase core and sigma(70)/sigma(A) factors in bacteria. In this study, the reaction of indole-2-, indole-3-, indole-7- and benzofuran-2-glyoxyloyl chlorides with amines and hydrazines afforded a variety of glyoxyloylamides and glyoxyloylhydrazides. Similarly, condensation of 2- and 7-trichloroacetylindoles with amines and hydrazines delivered amides and hydrazides. The novel molecules were found to inhibit the RNA polymerase-sigma(70)/sigma(A) interaction as measured by ELISA, and also inhibited the growth of both Gram-positive and Gram-negative bacteria in culture. Structure-activity relationship (SAR) studies of the mono-indole and mono-benzofuran inhibitors suggested that the hydrophilic-hydrophobic balance is an important determinant of biological activity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.02.037

文献信息

• Synthesis and biological activity of novel bis-indole inhibitors of bacterial transcription initiation complex formation
  作者：Marcin Mielczarek、Ruth V. Devakaram、Cong Ma、Xiao Yang、Hakan Kandemir、Bambang Purwono、David StC. Black、Renate Griffith、Peter J. Lewis、Naresh Kumar

  DOI：10.1039/c4ob00460d

  日期：——

  mechanism of antibacterial activity. Several classes of structurally related bis-indole inhibitors of bacterial transcription initiation complex formation were synthesized and their antimicrobial activities were evaluated. Condensation of indole-7- and indole-2-carbohydrazides with 7- and 2-trichloroacetylindoles or indole-7- and indole-2-glyoxyloyl chlorides resulted in the successful synthesis of 7,7′-

  细菌对临床批准的抗生素的耐药性不断提高，导致当今临床医生的治疗选择令人震惊地减少。我们有针对性细菌RNA聚合酶之间的互动至关重要σ 70 / σ一用于开发显示出新的抗菌活性机理的先导分子。合成了几类细菌转录起始复合物形成的结构相关的双吲哚抑制剂，并对其抗菌活性进行了评估。吲哚-7-和吲哚-2-碳酰肼与7-和2-三氯乙酰吲哚或吲哚-7-和吲哚-2-乙氧基氯酰氯的缩合成功合成了7,7'-，2,2'-，2带有–CO–NH–NH–CO–和–CO–CO–NH–NH–CO–接头的1,7'和3,2'连接的双吲哚衍生物。吲哚-7-乙二酰氯与水合肼以不同比例反应，分别得到–CO–CO–NH–NH–CO–CO–双吲哚或酰肼衍生物。发现所得到的化合物是针对β'-CH-活性σ 70 /σ甲2.2在ELISA测定相互作用和抑制革兰氏阳性和革兰氏阴性细菌的生长。为了确定生物活性所需的合成抑制剂的结构特征，进行了结构-活性关系（SAR）研究。
• Approaches to calix[3]indoles from activated indole carboxylic acids
  作者：Bambang Purwono、Naresh Kumar、David StC. Black

  DOI：10.24820/ark.5550190.p011.637

  日期：——