3-(4-chlorophenyl)-4,6-dimethoxy-7-trichloroacetylindole

• 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-7-trichloroacetylindole
• 英文别名: 2,2,2-trichloro-1-[3-(4-chlorophenyl)-4,6-dimethoxy-1H-indol-7-yl]ethanone
• 化学式: C₁₈H₁₃Cl₄NO₃
• 分子量: 433.118
• InChiKey: QHMNIYDOHDOMEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-chlorophenyl)-4,6-dimethoxy-7-trichloroacetylindole 在 一水合肼 作用下， 反应 3.5h， 以79%的产率得到3-(4-chlorophenyl)-4,6-dimethoxy-1H-indole-7-carbohydrazide
  参考文献：
  名称：

  从吲哚到吡咯，呋喃，噻吩和吡啶：寻找细菌转录起始复合物形成的新型小分子抑制剂

  摘要：

  寻找能够抑制细菌中转录起始的小分子已导致使用各自的三氯乙酰基衍生物，碳酰肼和醛合成了N，N'-二取代的肼和亚胺-碳酰肼，它们由吲哚，吡啶，吡咯，呋喃和噻吩组成。由较小的杂环由连接的吲哚部分的代用CO NH Ñ Ç接头得到各种各样有效地靶向RNA聚合酶化合物的σ 70 / σ甲相互作用如通过ELISA测定和表现出增加的生长的抑制大肠杆菌相比枯草芽孢杆菌在培养中。通过分子建模和结构-活性关系（SAR）研究，确定了抗菌活性所需的合成转录起始抑制剂的结构特征。

  DOI：

  10.1016/j.bmc.2016.01.040
• 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 3.0h， 生成 3-(4-chlorophenyl)-4,6-dimethoxy-7-trichloroacetylindole
  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

文献信息

• The nitration of some 4,6-dimethoxyindoles
  作者：Ashley W. Jones、Bambang Purwono、Paul K. Bowyer、Peter S.R. Mitchell、Naresh Kumar、Stephen J. Nugent、Katrina A. Jolliffe、David StC. Black

  DOI：10.1016/j.tet.2004.08.086

  日期：2004.11

  A range of 3-substituted-4,6-dimethoxyindoles bearing electron-withdrawing groups in either the 2- or 7-position, can be nitrated using nitric acid adsorbed on silica, to give 7-nitro and 2-nitro-indoles, respectively. A 1-cyano-indole gives regioselectively the 2-nitro-indole with loss of the cyano group.

  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。
• 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。
• Synthesis and biological activity of novel mono-indole and mono-benzofuran inhibitors of bacterial transcription initiation complex formation
  作者：Marcin Mielczarek、Ruth V. Thomas、Cong Ma、Hakan Kandemir、Xiao Yang、Mohan Bhadbhade、David StC. Black、Renate Griffith、Peter J. Lewis、Naresh Kumar

  DOI：10.1016/j.bmc.2015.02.037

  日期：2015.4

  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.
• 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：——
• Synthesis of 7,7′-Linked-bis-Indoles via 7-Tryptamines
  作者：David StC. Black、Hakan Kandemir、Ibrahim F. Sengul、Christopher R. Gardner、Eryn L. Werry、Melissa L. Barron、Michael Kassiou

  DOI：10.3987/com-15-s(t)55

  日期：——

  The synthesis of 7-tryptamines was accomplished via the reduction of 7-nitrovinylindoles which were developed by the condensation of indole-7-carbaldehydes with nitromethane and ammonium acetate. 7-Tryptamines were subsequently used for the construction of 2,3-disubstituted and 3 -substituted 7,7'-linked-bis-indoles.