2-碘-5-甲氧基-1H-吲哚-1-羧酸叔丁酯 | 99275-48-6

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 羧酸酯及其衍生物
• 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: 2-碘-5-甲氧基-1H-吲哚-1-羧酸叔丁酯
• 英文名称: tert-butyl 2-iodo-5-methoxy-1H-indole-1-carboxylate
• 英文别名: 1-t-butoxy-2-iodo-5-methoxyindole；tert-butyl 2-iodo-5-methoxyindole-1-carboxylate
• CAS: 99275-48-6
• 化学式: C₁₄H₁₆INO₃
• 分子量: 373.19
• InChiKey: RHFYEQRBIYQYPB-UHFFFAOYSA-N

物化性质

• 沸点：
  423.3±48.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-碘-5-甲氧基-1H-吲哚-1-羧酸叔丁酯 在 sodium methylate 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 为溶剂， 反应 0.25h， 生成 N-ethyl-N-[(2-iodo-5-methoxy-1H-indol-3-yl)methyl]ethanamine
  参考文献：
  名称：

  2-碘色胺和2-碘-5-甲氧基色胺的制备

  摘要：

  描述了吲哚和5-甲氧基吲哚的区域特异性碘化，以及将这些2-碘吲哚合成为相应的色胺的方法。

  DOI：

  10.1002/jhet.5570220260
• 作为产物：
  描述：

  N-BOC-5-甲氧基吲哚 在 碘 、 叔丁基锂 、 正戊烷 作用下， 生成 2-碘-5-甲氧基-1H-吲哚-1-羧酸叔丁酯
  参考文献：
  名称：

  2-碘色胺和2-碘-5-甲氧基色胺的制备

  摘要：

  描述了吲哚和5-甲氧基吲哚的区域特异性碘化，以及将这些2-碘吲哚合成为相应的色胺的方法。

  DOI：

  10.1002/jhet.5570220260

文献信息

• Discovery and optimization of a new class of pyruvate kinase inhibitors as potential therapeutics for the treatment of methicillin-resistant Staphylococcus aureus infections
  作者：Nag S. Kumar、Edie M. Dullaghan、B. Brett Finlay、Huansheng Gong、Neil E. Reiner、J. Jon Paul Selvam、Lisa M. Thorson、Sara Campbell、Nicholas Vitko、Anthony R. Richardson、Roya Zoraghi、Robert N. Young

  DOI：10.1016/j.bmc.2014.01.020

  日期：2014.3

  A novel series of bis-indoles derived from naturally occurring marine alkaloid 4 were synthesized and evaluated as inhibitors of methicillin-resistant Staphylococcus aureus (MRSA) pyruvate kinase (PK). PK is not only critical for bacterial survival which would make it a target for development of novel antibiotics, but it is reported to be one of the most highly connected 'hub proteins' in MRSA, and thus should be very sensitive to mutations and making it difficult for the bacteria to develop resistance. From the co-crystal structure of cis-3-4-dihydrohamacanthin B (4) bound to S. aureus PK we were able to identify the pharmacophore needed for activity. Consequently, we prepared simple direct linked bis-indoles such as 10b that have similar anti-MRSA activity as compound 4. Structure-activity relationship (SAR) studies were carried out on 10b and led us to discover more potent compounds such as 10c, 10d, 10k and 10m with enzyme inhibiting activities in the low nanomolar range that effectively inhibited the bacteria growth in culture with minimum inhibitory concentrations (MIC) for MRSA as low as 0.5 mu g/ml. Some potent PK inhibitors, such as 10b, exhibited attenuated antibacterial activity and were found to be substrates for an efflux mechanism in S. aureus. Studies comparing a wild type S. aureus with a construct (S. aureus LAC Delta pyk::ErmR) that lacks PK activity confirmed that bactericidal activity of 10d was PK-dependant. (C) 2014 Elsevier Ltd. All rights reserved.
• ANTI-BACTERIAL PYRUVATE KINASE MODULATOR COMPOUNDS, COMPOSITIONS, USES AND METHODS
  申请人：SIMON FRASER UNIVERSITY

  公开号：US20170216252A1

  公开（公告）日：2017-08-03

  Compounds of general formula I that are capable of inhibiting bacterial pyruvate kinase and/or bacterial growth. The compounds may find use as antibacterial agents in therapeutic and/or non-therapeutic contexts.
• Preparation of 2-iodotryptamine and 2-iodo-5-methoxytryptamine
  作者：Toni Kline

  DOI：10.1002/jhet.5570220260

  日期：1985.3

  The regiospecific iodination of indole and 5-methoxyindole, and the elaboration of these 2-iodoindoles to the corresponding tryptamines, are described.

  描述了吲哚和5-甲氧基吲哚的区域特异性碘化，以及将这些2-碘吲哚合成为相应的色胺的方法。
• A sonochemical approach to 3-(het)aryl substituted 1H-[1,3]oxazino[3,4-a]indol-1-one derivatives promoted by Pd/Cu-catalysts and ZnCl2
  作者：Gajjela Venkata Nageswara Rao、Srilaxmi Dandamudi、Mandava Bhuvan Tej、Satya Vani Chinnamaneni、Purna Chandra Rao Vasireddy、Ravikumar Kapavarapu、Mandava Venkata Basaveswara Rao、Manojit Pal

  DOI：10.1016/j.tetlet.2023.154659

  日期：2023.8