3-甲酰基-5-甲氧基-2-乙氧羰基-1H-吲哚 | 36820-78-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 3-甲酰基-5-甲氧基-2-乙氧羰基-1H-吲哚
• 中文别名: 3-甲酰基-5-甲氧基-1H-吲哚-2-羧酸乙酯
• 英文名称: ethyl 3-formyl-5-methoxy-1H-indole-2-carboxylate
• CAS: 36820-78-7
• 化学式: C₁₃H₁₃NO₄
• mdl: MFCD03848051
• 分子量: 247.251
• InChiKey: XQDZGHNVSBDTSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-甲酰基-5-甲氧基-2-乙氧羰基-1H-吲哚 在 对甲苯磺酸 、 间氯过氧苯甲酸 、 三甲基硅烷化重氮甲烷 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 3,5-dimethoxy-1H-indole-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  An efficient synthesis of LipidGreen and its derivatives via microwave assisted reaction and their live lipid imaging in zebrafish

  摘要：

  We have developed an efficient synthesis of LipidGreen. The conversion is achieved by selective methylation with trimethylsilyldiazomethane, selective deprotection by BBr3 and an improved microwave-assisted C-allylation procedure. Using this route, we have synthesized novel LipidGreen derivatives, and evaluated their live imaging abilities in zebrafish. In this series, Compound 7 is the most active, which is at least 10 fold more potent than LipidGreen. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.090
• 作为产物：
  描述：

  5-甲氧基吲哚-2-甲酸乙酯 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以99%的产率得到3-甲酰基-5-甲氧基-2-乙氧羰基-1H-吲哚
  参考文献：
  名称：

  An efficient synthesis of LipidGreen and its derivatives via microwave assisted reaction and their live lipid imaging in zebrafish

  摘要：

  We have developed an efficient synthesis of LipidGreen. The conversion is achieved by selective methylation with trimethylsilyldiazomethane, selective deprotection by BBr3 and an improved microwave-assisted C-allylation procedure. Using this route, we have synthesized novel LipidGreen derivatives, and evaluated their live imaging abilities in zebrafish. In this series, Compound 7 is the most active, which is at least 10 fold more potent than LipidGreen. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.090

文献信息

• Discovery of 3-Substituted 1<i>H</i>-Indole-2-carboxylic Acid Derivatives as a Novel Class of CysLT₁Selective Antagonists
  作者：Huayan Chen、Hui Yang、Zhilong Wang、Xin Xie、Fajun Nan

  DOI：10.1021/acsmedchemlett.5b00482

  日期：2016.3.10

  The indole derivative, 3-((E)-3-((3-((E)-2-(7-chloroquinolin-2yl)vinyl)phenyl)amino)-3-oxoprop-1-en-1-yl )-7-methoxy-1H-indole-2-carboxylic acid (17k), was identified as a novel and highly potent and selective CysLT1 antagonist with IC50 values of 0.0059 +/- 0.0011 and 15 +/- 4 muM for CysLT1 and CysLT2, respectively.

  吲哚衍生物3-（（E）-3-（（3-（（E）-2-（7-氯喹啉-2基）乙烯基）苯基）氨基）-3-氧代丙-1-烯-1-基） -7-甲氧基-1H-吲哚-2-羧酸（17k）被确定为一种新型且高效的选择性CysLT1拮抗剂，CysLT1和CysLT2的IC50值为0.0059 +/- 0.0011和15 +/- 4μM，分别。
• 1H-Indole Derivatives as Calcium Antagonists
  作者：Laura Garuti、Giuseppe Giovanninetti、Sergio Bova、Alberto Chiarini

  DOI：10.1002/ardp.19883210702

  日期：——

  Two short series of compounds with 1H‐indole skeleton, bearing hydantoin and piperazine nuclei respectively, were synthesized. Some compounds of these two series were tested for their calcium‐antagonistic activity on K+‐depolarized smooth muscle (rabbit auricolar artery and guinea‐pig taenia caeci) and their negative inotropic action on atrial muscle from guinea‐pig hearts.

  合成了两个具有 1H-吲哚骨架的短系列化合物，分别带有乙内酰脲和哌嗪核。测试了这两个系列中的一些化合物对 K + 去极化平滑肌（兔耳廓动脉和豚鼠绦虫）的钙拮抗活性及其对豚鼠心脏心房肌的负性肌力作用。
• Aziridinyl Quinone Antitumor Agents Based on Indoles and Cyclopent[<i>b</i>]indoles:  Structure−Activity Relationships for Cytotoxicity and Antitumor Activity
  作者：Edward B. Skibo、Chengguo Xing、Robert T. Dorr

  DOI：10.1021/jm010085u

  日期：2001.10.1

  DT-diaphorase substrate activity, DNA reductive alkylation, cytostatic/cytotoxic activity, and in vivo activity. As a result, generalizations have been made with respect with respect to the following: DT-diaphorase substrate design, DT-diaphorase-cytotoxicity quantitative structure-activity relationship (QSAR), and DNA reductive alkylating agent design. A saturating relationship exists between the substrate

  就其DT-心肌黄递酶底物活性，DNA还原烷基化作用，细胞抑制/细胞毒性活性和体内活性进行了研究，研究了由1-9系列代表的大量氮丙啶基醌。结果，关于以下方面进行了概括：DT-黄递酶底物设计，DT-黄递酶-细胞毒性定量结构-活性关系（QSAR）和DNA还原烷基化剂设计。在人重组DT-心肌黄递酶的底物特异性与人H460非小细胞肺癌细胞系中的细胞毒性之间存在饱和关系。这种关系的解释是，对于具有高DT-黄递酶底物特异性的底物，还原激活不再是速率限制。在吲哚和环戊[b]吲哚体系中，高DT-黄递质酶底物特异性是不希望的，因为其结果是失去了癌症的选择性，并增加了毒性。我们得出结论，这种类型的叠氮基醌应具有对DT-黄递酶的底物特异性（V（max）/ K（M））<10 x 10（-4）s（-1），以免毒性太大或非选择性。虽然系列1-9的细胞抑制活性和细胞毒性活性需要一些DNA烷基化，但烷基化过多会导致癌症选择
• Development of potent dipeptide-type SARS-CoV 3CL protease inhibitors with novel P3 scaffolds: Design, synthesis, biological evaluation, and docking studies
  作者：Pillaiyar Thanigaimalai、Sho Konno、Takehito Yamamoto、Yuji Koiwai、Akihiro Taguchi、Kentaro Takayama、Fumika Yakushiji、Kenichi Akaji、Shen-En Chen、Aurash Naser-Tavakolian、Arne Schön、Ernesto Freire、Yoshio Hayashi

  DOI：10.1016/j.ejmech.2013.07.037

  日期：2013.10

  We report the design and synthesis of a series of dipeptide-type inhibitors with novel P3 scaffolds that display potent inhibitory activity against SARS-CoV 3CLpro. A docking study involving binding between the dipeptidic lead compound 4 and 3CLpro suggested the modification of a structurally flexible P3 N-(3-methoxyphenyl)glycine with various rigid P3 moieties in 4. The modifications led to the identification

  我们报告了一系列具有新型 P3 支架的二肽型抑制剂的设计和合成，这些抑制剂对 SARS-CoV 3CLpro 显示出有效的抑制活性。一项涉及二肽先导化合物 4 和 3CLpro 之间结合的对接研究表明，用 4 中的各种刚性 P3 部分对结构灵活的 P3 N-(3-甲氧基苯基)甘氨酸进行修饰。这些修饰导致了几种有效衍生物的鉴定，包括 5c -k 和 5n 的抑制活性（Ki 或 IC50）在亚微摩尔至纳摩尔范围内。尤其是化合物 5h，显示出最有效的抑制活性，Ki 值为 0.006 μM。该效力比先导化合物 4 的效力高 65 倍 (Ki=0.39 μM)。此外，5h 的 Ki 值与等温滴定量热法 (ITC) 中观察到的结合亲和力 (16 nM) 非常吻合。围绕先导 4 中 P3 基团的 SAR 研究发现刚性吲哚-2-羰基单元是最佳 P3 部分之一 (5c)。进一步优化表明，吲哚单元4位的甲氧基取代非常有利于增强抑制效力。
• Design of C3-Alkenyl-Substituted 2-Indolylmethanols for Catalytic Asymmetric Interrupted Nazarov-Type Cyclization
  作者：Cong-Shuai Wang、Jia-Le Wu、Can Li、Lin-Zhi Li、Guang-Jian Mei、Feng Shi

  DOI：10.1002/adsc.201701521

  日期：2018.3.1

  The C3‐alkenyl‐substituted 2‐indolylmethanols have been designed as a new class of substrates for catalytic asymmetric interrupted Nazarov‐type cyclizations. In the presence of chiral phosphoric acid as a mild chiral Brønsted acid, the interrupted Nazarov‐type cyclization of C3‐alkenyl‐substituted 2‐indolylmethanols with nucleophiles occurred smoothly to construct cyclopenta[b]indole frameworks in

  C3-烯基取代的2-吲哚基甲醇被设计为催化不对称间断Nazarov型环化反应的新型底物。在存在手性磷酸作为温和的手性布朗斯台德酸的情况下，C3-烯基取代的2-吲哚基甲醇与亲核试剂的间断Nazarov型环化顺利发生，从而以通常优异的非对映异构和对映选择性（如上式）构建环戊[ b ]吲哚骨架到> 95：5 dr，> 99％ee）。