ethyl 7-acetyl-1H-indole-2-carboxylate | 90395-39-4

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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
• 英文名称: ethyl 7-acetyl-1H-indole-2-carboxylate
• 英文别名: Ethyl 7-acetylindole-2-carboxylate
• CAS: 90395-39-4
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: ZVBBXVOPPDQXSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 7-acetyl-1H-indole-2-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 1H-吲哚-2,7-二甲酸
  参考文献：
  名称：

  Investigations of SCIO-469-like compounds for the inhibition of p38 MAP kinase

  摘要：

  The p38 MAP kinase is implicated in the release of the pro-inflammatory cytokines TNF alpha and IL-1b. Inhibition of cytokine release may be a useful treatment for inflammatory conditions such as rheumatoid arthritis and Crohn's disease. A new lead structure for p38 MAP kinase inhibition was identified. Herein, we report the SAR of this new class of p38 inhibitors. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.023
• 作为产物：
  描述：

  乙烯基正丁醚 、 7-溴-1H-吲哚-2-甲酸乙酯 在 1,3-双(二苯基膦)丙烷 、 palladium diacetate 、 三乙胺 作用下， 以 乙醇 为溶剂， 以89 %的产率得到ethyl 7-acetyl-1H-indole-2-carboxylate
  参考文献：
  名称：

  [EN] 2-CARBOXYL-INDOLE INHIBITORS OF METALLO-BETA-LACTAMASES
  [FR] INHIBITEURS 2-CARBOXYL-INDOLE DE MÉTALLO-BÊTA-LACTAMASES

  摘要：

  The present invention relates to certain compounds that function as inhibitors of bacterial metallo-beta-lactamases. The present invention also relates to processes for the preparation of these compounds, to pharmaceutical compositions comprising them, and to their use in the treatment of a bacterial infection.

  公开号：

  WO2022248887A1

文献信息

• CBI analogues of the duocarmycins and CC-1065
  申请人：Boger L. Dale

  公开号：US20050026987A1

  公开（公告）日：2005-02-03

  An extensive series of CBI analogues of the duocarmycins and CC-1065 exploring substituent effects within the first indole DNA binding subunit is detailed. In general, substitution at the indole C5 position led to cytotoxic potency enhancements that can be ≧1000-fold providing simplified analogues containing a single DNA binding subunit that are more potent (IC 50 =2-3 pM) than CBI-TMI, duocarmycin SA, or CC-1065. The increases in cytotoxicity correlate well with accompanying increases in the rate and efficiency of DNA alkylation. This effect is more pronounced with the CBI versus DSA or CPI based analogues. Moreover, this effect is largely insensitive to the electronic character of the C5 substituent but is sensitive to the size, rigid length, and shape (sp, sp 2 , sp 3 hybridization) of this substituent consistent with expectation that the impact is due simply to its presence.

  一系列广泛的CBI类似物，包括二聚卡蜜素和CC-1065的类似物，探索了第一个吲哚DNA结合亚基中取代基效应的细节。一般来说，在吲哚C5位置的取代导致细胞毒性增强，可以达到≧1000倍，提供了更强效（IC50=2-3 pM）的含有单个DNA结合亚基的简化类似物，比CBI-TMI、二聚卡蜜素SA或CC-1065更有效。细胞毒性增加与DNA烷基化速率和效率的增加密切相关。与基于DSA或CPI的类似物相比，这种效应在CBI类似物中更为显著。此外，这种效应对于C5取代基的电子性质不太敏感，但对于取代基的大小、刚性长度和形状（sp、sp2、sp3杂化）敏感，这与预期一致，即这种影响仅仅是由于其存在。
• Synthetic studies on indoles and related compounds. XXV. The Friedel-Crafts acylation of ethyl 1H-indole-2-carboxylate. (2).
  作者：Masanobu TANI、Tsuyoshi AOKI、Sadao ITO、Shigenobu MATSUMOTO、Mami HIDESHIMA、Kaoru FUKUSHIMA、Ryoichi NOZAWA、Takako MAEDA、Mayumi TASHIRO、Yuusaku YOKOYAMA、Yasuoki MURAKAMI

  DOI：10.1248/cpb.38.3261

  日期：——

  The Friedel-Crafts acylation of ethyl 1H-indole-2-carboxylate (1) with various acylating reagents having a functional group or hetero atom and the acylation of some derivatives (6, 7, 8, and 9) of ethyl 1H-indole-2-carboxylate (1) with simple acylating reagents are described. Acylation occurred at the C3-position or on the benzene moiety (mainly at the C5-position) of the indole nucleus. The regioselectivity of the above acylation of indoles (1, 6, 7, 8, and 9) is discussed.

  本研究描述了 1H-吲哚-2-甲酸乙酯（1）与各种具有官能团或杂原子的酰化试剂的弗里德尔-卡夫酰化反应，以及 1H-吲哚-2-甲酸乙酯（1）的一些衍生物（6、7、8 和 9）与简单酰化试剂的酰化反应。酰化发生在吲哚核的 C3 位或苯分子上（主要是 C5 位）。讨论了上述吲哚（1、6、7、8 和 9）酰化反应的区域选择性。
• Synthetic Studies on Indoles and Related Compounds. XXXIII. Reaction of Ethyl Acylindole-2-carboxylates with Thallium Trinitrate.
  作者：Masanobu TANI、Shigenobu MATSUMOTO、Yoshiyuki AIDA、Shiho ARIKAWA、Atsuko NAKANE、Yuusaku YOKOYAMA、Yasuoki MURAKAMI

  DOI：10.1248/cpb.42.443

  日期：——

  Ethyl acylindole-2-carboxylates were treated with thallium trinitrate (TTN) in methanol, methyl orthoformate, methyl orthoformate/sulfuric acid, and acetic acid. The reactions in the former three methanolic solvents gave methyl indoleacetate derivatives via the Favorskii-type rearrangement reaction at the acyl group, whereas the reaction in acetic acid gave oxindole derivative with rearrangement of the C2-ethoxycarbonyl group. The TTN reaction was applied to a model compound leading to the synthesis of lysergic acid.

  酰基吲哚-2-羧酸乙酯在甲醇、原甲酸甲酯、原甲酸甲酯/硫酸和乙酸中与三硝酸铊（TTN）反应。在前三种甲醇溶剂中的反应是通过酰基上的 Favorski 型重排反应生成吲哚乙酸甲酯衍生物，而在乙酸中的反应是通过 C2-乙氧羰基的重排反应生成吲哚衍生物。TTN 反应被应用于一种模型化合物，导致麦角酸的合成。
• Monocyte chemoattractant protein-1 inhibitor compounds
  申请人：ZENECA LIMITED

  公开号：US20030119830A1

  公开（公告）日：2003-06-26

  The invention concerns the use of a compound of formula (I), in which Z, X, T, A, R 1 , R 2 , p and q have any of the meanings defined herein, and their pharmaceutically acceptable salts or in vivo hydrolysable esters, in the treatment of a disease or condition mediated by monocyte chemoattractant protein-1 (MCP-1). Certain of the components of formula (I) are novel and are provided, together with pharmaceutical compositions thereof, as further features of the invention.

  本发明涉及使用式（I）的化合物，其中Z，X，T，A，R1，R2，p和q具有本文所定义的任何含义，以及其药学上可接受的盐或体内水解酯，在治疗由单核细胞趋化蛋白-1（MCP-1）介导的疾病或状况中的应用。式（I）的某些组分是新颖的，并且作为本发明的进一步特征提供其制药组合物。
• Optimized Synthesis of Indole Carboxylate Metallo-β-Lactamase Inhibitor EBL-3183
  作者：Andrei Baran、Jevgenijs Kuzmins、Jevgenijs Kuznecovs、Alistair J. M. Farley、Tharindi Panduwawala、Anete Parkova、Pavel A. Donets、Jürgen Brem、Edgars Suna、Christopher J. Schofield、Kirill Shubin

  DOI：10.1021/acs.oprd.3c00002

  日期：——

  scale. The described process starts from a commercially available indole-2-carboxylate and employs an Ellman auxiliary approach coupled with ruthenium-catalyzed stereoselective reduction for the introduction of chirality. The key spirocyclic cyclobutane motif was assembled utilizing an epoxide building block, which was conveniently obtained in diastereomerically pure form. The amount and quality of the

  开发了一种用于制备金属-β-内酰胺酶抑制剂预选物 EBL-3183 的新合成路线，并以千克规模进行。所描述的过程从市售的 indole-2-carboxylate 开始，并采用 Ellman 辅助方法与钌催化的立体选择性还原相结合，以引入手性。关键的螺环环丁烷基序是利用环氧化物结构单元组装而成的，该结构单元可以方便地以非对映体纯形式获得。制备的最终靶标 EBL-3183 的数量和质量足以用于临床前研究。