2-hydroxy-7-methyl-9H-carbazole

• 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: 2-hydroxy-7-methyl-9H-carbazole
• 英文别名: 2-hydroxy-7-methylcarbazole；2-Methyl-7-hydroxycarbazole；7-methyl-9H-carbazol-2-ol
• 化学式: C₁₃H₁₁NO
• 分子量: 197.236
• InChiKey: APAVSPUPFBJKBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  36
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 2-hydroxy-7-methyl-9H-carbazole 在 吡啶 作用下， 反应 3.0h， 以7.3 mg的产率得到Acetic acid 7-methyl-9H-carbazol-2-yl ester
  参考文献：
  名称：

  A New Alkaloid, 2-Hydroxy-7-methyl-9H-carbazole from Cimicifuga simplex

  摘要：

  A new alkaloid was isolated from the aerial parts of Cimicifuga simplex and was formulated as 2 - hydroxy - 7- methyl - 9H - carbazole on the basis of die spectroscopic evidence.

  DOI：

  10.3987/com-93-6472
• 作为产物：
  描述：

  2-methoxy-7-methylcarbazole 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 4.25h， 以87%的产率得到2-hydroxy-7-methyl-9H-carbazole
  参考文献：
  名称：

  2-Hydroxy-7-methylcarbazole、Glycozolicine、Mukoline、Mukolidine、Sansoakamine、Clausine-H 和 Clausine-K 的合成和 Clausine-TY 的结构修正

  摘要：

  Buchwald-Hartwig 胺化和钯 (II) 催化的氧化环化反应序列提供了获得一系列含氧三环咔唑的有效途径。在目前的工作中，这种方法被应用于天然存在的咔唑生物碱 2-羟基-7-甲基咔唑、甘唑啉、mukoline、mukolidine、sansoakamine、糖唑烷、clausine-H (clauszoline-C)、clausine-K ( clauszoline-J) 和 2-羟基-7-甲氧基咔唑-3-羧酸甲酯，最初提出作为 clausine-TY 的结构。后者的合成导致 clausine-TY 的结构重新分配。

  DOI：

  10.1002/ejoc.201402495

文献信息

• Novel substituted tricyclic compounds
  申请人：——

  公开号：US20030040538A1

  公开（公告）日：2003-02-27

  Compounds of the general formula (I) are useful in the treatment and prevention of &bgr;3-related diseases including diabetes, obesity and hyperlipidemia wherein R 1 is hydrogen, halogen, or hydroxyl; R 2 is C 1-4 alkyl or benzyl; R 3 is OR, halogen, trifluoromethyl, C 1-8 alkyl, lower acyl, NR 4 R 4′ , nitro, or cyano; R is hydrogen, C 1-8 alkyl, benzyl group, or optionally substituted lower acyl; R 4 and R 4′ are each independently hydrogen, C 1-4 alkyl, lower acyl, benzyl, or SO 2 R 5 ; R 5 is C 1-4 alkyl or benzyl; W is oxygen, a secondary nitrogen atom (NH), or sulfur; and * represents an asymmetric carbon atom. 1

  通式（I）的化合物在治疗和预防与β3相关的疾病，包括糖尿病、肥胖症和高脂血症方面具有用处，其中R1是氢、卤素或羟基；R2是C1-4烷基或苄基；R3是OR、卤素、三氟甲基、C1-8烷基、较低酰基、NR4R4'、硝基或氰基；R是氢、C1-8烷基、苄基或可选取代的较低酰基；R4和R4'各自独立地为氢、C1-4烷基、较低酰基、苄基或SO2R5；R5是C1-4烷基或苄基；W是氧、次级氮原子（NH）或硫；*代表不对称碳原子。
• Extracts of Cranberry and Methods of Using Thereof
  申请人：Alberte Randall S.

  公开号：US20100028469A1

  公开（公告）日：2010-02-04

  The present disclosure relates in part to extracts of cranberry ( Vaccinium macrocarpon ) comprising an enriched amount of certain compounds having anti-infective activity, e.g. antibacterial and/or antifungal activity, e.g. activity against C. albicans . Another aspect of the disclosure relates to combined cranberry and cinnamon extracts. In certain embodiments, these combined extracts have been optimized to control urinary tract infections caused by E. coli, S. aureus and C. albicans . Certain embodiments of the extract are enriched in bioactive compounds that have been shown to inhibit C. albicans adhesion and/or biofilm formation and its growth in vitro. In another aspect of the disclosure, the extracts are enriched in bioactives derived from cranberry and cinnamon that have been shown to inhibit the attachment and the growth of common urinary tract pathogens like E. coli, S. aureus and C. albicans.
• SMALL MOLECULE ANDROGEN RECEPTOR INHIBITORS AND METHODS OF USE THEREOF
  申请人：GEORGETOWN UNIVERSITY

  公开号：US20180215712A1

  公开（公告）日：2018-08-02

  Small molecule carbazole compounds for use as androgen receptor inhibitors are provided herein. Also provided herein are methods for using the carbazole compounds in treating prostate cancer, including castration-resistant prostate cancer and enzalutamide-resistant prostate cancer. The methods include administering to a subject an effective amount of a compound or composition as described herein.
• Synthesis of 2-Hydroxy-7-methylcarbazole, Glycozolicine, Mukoline, Mukolidine, Sansoakamine, Clausine-H, and Clausine-K and Structural Revision of Clausine-TY
  作者：Christian Schuster、Carsten Börger、Konstanze K. Julich-Gruner、Ronny Hesse、Anne Jäger、Györley Kaufmann、Arndt W. Schmidt、Hans-Joachim Knölker

  DOI：10.1002/ejoc.201402495

  日期：2014.8

  Buchwald–Hartwig amination and palladium(II)-catalyzed oxidative cyclization reaction sequence provided efficient access to a series of oxygenated tricyclic carbazoles. In the present work, this approach was applied to the total syntheses of the naturally occurring carbazole alkaloids 2-hydroxy-7-methylcarbazole, glycozolicine, mukoline, mukolidine, sansoakamine, glycozolidine, clausine-H (clauszoline-C)

  Buchwald-Hartwig 胺化和钯 (II) 催化的氧化环化反应序列提供了获得一系列含氧三环咔唑的有效途径。在目前的工作中，这种方法被应用于天然存在的咔唑生物碱 2-羟基-7-甲基咔唑、甘唑啉、mukoline、mukolidine、sansoakamine、糖唑烷、clausine-H (clauszoline-C)、clausine-K ( clauszoline-J) 和 2-羟基-7-甲氧基咔唑-3-羧酸甲酯，最初提出作为 clausine-TY 的结构。后者的合成导致 clausine-TY 的结构重新分配。
• A New Alkaloid, 2-Hydroxy-7-methyl-9H-carbazole from Cimicifuga simplex
  作者：Genjiro Kusano、Makio Shibano、Mayumi Idoji、Katsuhiko Minoura

  DOI：10.3987/com-93-6472

  日期：——

  A new alkaloid was isolated from the aerial parts of Cimicifuga simplex and was formulated as 2 - hydroxy - 7- methyl - 9H - carbazole on the basis of die spectroscopic evidence.