1-β-D-glucopyranosyl-1H-indole-3-acetic acid | 351346-16-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 1-β-D-glucopyranosyl-1H-indole-3-acetic acid
• 英文别名: 2-(1-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-1H-indol-3-yl)acetic acid；glucoindol A；N-beta-D-glucopyranosyl indole-3-acetic acid；2-[1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]indol-3-yl]acetic acid
• CAS: 351346-16-2
• 化学式: C₁₆H₁₉NO₇
• 分子量: 337.329
• InChiKey: MVSQEPAOMLRIRW-YMILTQATSA-N

物化性质

• 沸点：
  677.6±55.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  132
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-β-D-glucopyranosyl-1H-indole-3-acetic acid 在 劳森试剂 、 N-甲基吗啉 、 吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(3-((5-(furan-2-yl)thiazol-2-yl)methyl)-1H-indol-1-yl)-tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  [EN] THIAZOLE DERIVATIVES AS SGLT2 INHIBITORS AND PHARMACEUTICAL COMPOSITION COMPRISING SAME
  [FR] DÉRIVÉS DE THIAZOLE EN TANT QU'INHIBITEURS DE SGLT2 ET COMPOSITION PHARMACEUTIQUE COMPRENANT CEUX-CI

  摘要：

  公开号：

  WO2011159067A3
• 作为产物：
  描述：

  (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(3-(2-methoxy-2-oxoethyl)-1H-indol-1-yl)-tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 氢氧化钾 作用下， 以100%的产率得到1-β-D-glucopyranosyl-1H-indole-3-acetic acid
  参考文献：
  名称：

  水稻中吲哚-3-乙酸的代谢：N-β-d-吡喃葡萄糖基吲哚-3-乙酸及其结合物的鉴定和表征

  摘要：

  使用液相色谱-电喷雾电离-串联质谱 (LC-ESI-MS/MS) 在水稻 (Oryza sativa) 中寻找吲哚-3-乙酸 (IAA) 的结合物，以阐明 IAA 的未知代谢途径. 在大米提取物的碱性水解物中发现了 N-β-d-吡喃葡萄糖基吲哚-3-乙酸 (IAA-N-Glc)。对 3 周龄大米的定量分析表明，IAA-N-Glc 的总量与 IAA 的总量相等。基于 LC-ESI-MS/MS 的分析确定 IAA-N-Glc 的主要部分以与天冬氨酸和谷氨酸的结合形式存在。它们的水平与水稻营养生长过程中 IAA-N-Glc 的总量非常吻合。进一步的详细分析表明，两种结合物在根中高度积累。游离形式的 IAA-N-Glc 占种子总量的 60%，但在营养组织中未检测到。使用氘标记化合物的掺入研究表明 IAA-N-Glc 的氨基酸缀合物是由 IAA-氨基酸生物合成的。在拟南芥、莲藕和玉米的提取物中也发现了

  DOI：

  10.1016/j.phytochem.2007.05.040

文献信息

• INDOLEACETIC ACID DERIVATIVE AND PREPARATION METHOD AND PHARMACEUTICAL USE THEREOF
  申请人：Institute Chinese Materia Medica, China Academy of Chinese Medical Sciences

  公开号：US20200095271A1

  公开（公告）日：2020-03-26

  The present invention relates to an indoleacetic acid derivative and a preparation method and pharmaceutical use thereof. In particular, the present invention relates to a compound shown in general formula (I), a preparation method thereof, a pharmaceutical composition comprising the same, and a use thereof as a cough suppressant in treating a disease such as a cough. The definition of each substituent in the general formula (I) is the same as the definition in the specification.

  本发明涉及一种吲哚乙酸衍生物及其制备方法和药用。具体地，本发明涉及一种通式(I)所示的化合物，其制备方法，包含该化合物的药物组合物，以及其作为咳嗽镇咳剂用于治疗咳嗽等疾病的用途。通式(I)中的每个取代基的定义与说明书中的定义相同。
• Thiazole derivatives as SGLT2 inhibitors and pharmaceutical composition comprising same
  申请人：Lee Jinhwa

  公开号：US08586550B2

  公开（公告）日：2013-11-19

  The present invention relates to a novel compound with thiazole ring having an inhibitory activity against sodium-dependent glucose cotransporter 2 (SGLT2) being present in the intestine and kidney, and a pharmaceutical composition comprising the same as an active ingredient, which is useful for preventing or treating metabolic disorders, particularly diabetes.

  本发明涉及一种新型含噻唑环的化合物，具有对存在于肠和肾中的钠依赖性葡萄糖协同转运体2（SGLT2）的抑制活性，以及包含该化合物作为活性成分的药物组合物，可用于预防或治疗代谢性疾病，特别是糖尿病。
• Thiazole Derivatives as SGLT2 Inhibitors and Pharmaceutical Composition Comprising Same
  申请人：Lee Jinhwa

  公开号：US20130090298A1

  公开（公告）日：2013-04-11

  The present invention relates to a novel compound with thiazole ring having an inhibitory activity against sodium-dependent glucose cotransporter 2 (SGLT2) being present in the intestine and kidney, and a pharmaceutical composition comprising the same as an active ingredient, which is useful for preventing or treating metabolic disorders, particularly diabetes.

  本发明涉及一种新型含有噻唑环的化合物，具有对存在于肠和肾中的钠依赖性葡萄糖共转运体2（SGLT2）的抑制活性，以及包含该化合物作为活性成分的制药组合物，用于预防或治疗代谢性疾病，特别是糖尿病。
• Indoleacetic acid derivative and preparation method and pharmaceutical use thereof
  申请人：Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences

  公开号：US11008360B2

  公开（公告）日：2021-05-18

  The present invention relates to an indoleacetic acid derivative and a preparation method and pharmaceutical use thereof. In particular, the present invention relates to a compound shown in general formula (I), a preparation method thereof, a pharmaceutical composition comprising the same, and a use thereof as a cough suppressant in treating a disease such as a cough. The definition of each substituent in the general formula (I) is the same as the definition in the specification.

  本发明涉及一种吲哚乙酸衍生物及其制备方法和药物用途。特别是，本发明涉及通式（I）所示的一种化合物、其制备方法、由其组成的药物组合物，以及其在治疗咳嗽等疾病中作为镇咳剂的用途。通式（I）中各取代基的定义与说明书中的定义相同。
• Isolation, Structure Determination, and Sensory Activity of Mouth-Drying and Astringent Nitrogen-Containing Phytochemicals Isolated from Red Currants (<i>Ribes rubrum</i>)
  作者：Bernd Schwarz、Thomas Hofmann

  DOI：10.1021/jf0632076

  日期：2007.2.1

  Application of chromatographic separation and taste dilution analyses recently revealed, besides a series of flavon-3-ol glycosides and (E)/(Z)-aconitic acid, four nitrogen-containing phytochemicals as the key astringent and mouth-drying compounds in red currants (Ribes rubrum). The isolation and structure determination of the astringent indoles 3-carboxymethyl-indole-1-N-beta-D-glucopyranoside (1) and 3-methylcarboxymethyl-indole-1-N-beta-D-glucopyranoside (2), as well as the astringent, noncyanogenic nitriles 2-(4-hydroxybenzoyloxymethyl)-4-beta-D-glucopyranosyloxy-2(E)-butenenitrile (3) and 2-(4-hydroxy-3-methoxybenzoyloxymethyl)-4-beta-D-glucopyranosyloxy-2(E)-butenenitrile (4) by means of 1D/2D NMR, LC-MS/MS, and UV-vis spectroscopy are reported. The structures of compounds 1 and 2 were confirmed by synthesis. Using the recently developed half-tongue test, human recognition thresholds for the astringent and mouth-drying nitrogen compounds were determined to be between 0.0003 and 5.9 mu mol/L (water). In particular, the extraordinarily low threshold of 0.0003 mu mol/L evaluated for the indole 1 represents the lowest recognition threshold of any astringent phytochemical reported to date.