2-[3'-(4''-chlorophenyl)-4',6'-dimethoxyindol-2'-yl]glyoxyloyl chloride | 180859-27-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-[3'-(4''-chlorophenyl)-4',6'-dimethoxyindol-2'-yl]glyoxyloyl chloride
• CAS: 180859-27-2
• 化学式: C₁₈H₁₃Cl₂NO₄
• 分子量: 378.212
• InChiKey: TUYKEMPVOHQNLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  68.39
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-[3'-(4''-chlorophenyl)-4',6'-dimethoxyindol-2'-yl]glyoxyloyl chloride 在 三乙胺 、 三氯氧磷 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 3.5h， 生成 (3-(4-chlorophenyl)-4,6-dimethoxy-1H-indol-2-yl)(5-(dimethylamino)-1,3,4-thiadiazol-2-yl) ketone
  参考文献：
  名称：

  2,5-二（7-吲哚基）-1,3,4-恶二唑以及2-和7-吲哚基2-（1,3,4-噻二唑基）酮的合成及生物学评价

  摘要：

  从容易获得的吲哚-7-乙二酰氯和7-三氯乙酰吲哚制备了一系列新型的肼桥联双吲哚，然后进行环脱水以生产2,5-二（7-吲哚基）-1,3,4-恶二唑和2， 2'-bi-1,3,4-恶二唑基与磷酰氯的乙酸乙酯溶液。该有效方案随后用于由相关的吲哚基-肼甲硫基酰胺合成2-和7-吲哚基2-（1,3,4-噻二唑基）酮。评估了合成的双吲哚的抗菌特性，特别是抑制RNA聚合酶和σ因子之间的蛋白质-蛋白质复合物形成及其对革兰氏阳性枯草芽孢杆菌和革兰氏阴性大肠杆菌的杀菌作用。

  DOI：

  10.1016/j.bmc.2014.01.025
• 作为产物：
  描述：

  草酰氯 、 3-(4-chlorophenyl)-4,6-dimethoxyindole 以 乙醚 为溶剂， 反应 3.0h， 生成 2-[3'-(4''-chlorophenyl)-4',6'-dimethoxyindol-2'-yl]glyoxyloyl chloride
  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。
• Reaction of some 4,6-dimethoxyindoles with oxalyl chloride
  作者：David StC. Black、Naresh Kumar、Darryl B. McConnell

  DOI：10.1016/0040-4020(96)00441-3

  日期：1996.6

  3-(4′-Chlorophenyl)-4,6-dimethoxyindole 1 undergoes reaction with oxalyl chloride to give the corresponding 2-and 7-glyoxyloyl chloride derivatives in differing proportions depending on the solvent and reaction temperature. The glyoxyloyl chlorides 2 and 3 were converted into the related glyoxylic acids, and also a wide range of glyoxylic esters and amides 4 and 5 respectively.

  使3-（4'-氯苯基）-4,6-二甲氧基吲哚1与草酰氯反应，以不同比例根据溶剂和反应温度得到相应的2-和7-乙二酰氯衍生物。乙醛酰氯2和3分别转化为相关的乙醛酸，也分别转化为各种乙醛酸酯和酰胺4和5。