2-(1H-吡咯-1-基)苯醇 | 32277-91-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 2-(1H-吡咯-1-基)苯醇
• 中文别名: 苯酚,2-吡咯-1-基-
• 英文名称: 2-(1H-pyrrol-1-yl)phenol
• 英文别名: 1-(2-hydroxyphenyl)pyrrole；N-(2-hydroxyphenyl)pyrrole；2-pyrrol-1-ylphenol
• CAS: 32277-91-1
• 化学式: C₁₀H₉NO
• mdl: MFCD00128327
• 分子量: 159.188
• InChiKey: NZABOAAWARHJSH-UHFFFAOYSA-N

物化性质

• 熔点：
  48-50°C
• 沸点：
  138-140 °C(Press: 0.03 Torr)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-(1H-吡咯-1-基)苯醇 在 aluminum (III) chloride 、 水 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 1,2-二氯乙烷 为溶剂， 反应 48.25h， 生成 [1-(2-hydroxyphenyl)-1H-pyrrol-3-yl]phenylmethanone
  参考文献：
  名称：

  Decreasing acidity in a series of aldose reductase inhibitors: 2-Fluoro-4-(1H-pyrrol-1-yl)phenol as a scaffold for improved membrane permeation

  摘要：

  Targeting long-term diabetic complications, as well as inflammatory pathologies, aldose reductase inhibitors (ARIs) have been gaining attention over the years. In the present work, in order to address the poor membrane permeation of previously reported ARIs, derivatives of N-phenylpyrrole, bearing groups with putative pK(a) >= 7.4, were synthesized and evaluated for aldose reductase inhibitory activity. The 2-fluorophenol group proved the most promising moiety, and further modifications were explored. The most active compound (31), identified as a submicromolar inhibitor (IC50 = 0.443 mu M), was also selective against the homologous enzyme aldehyde reductase. Cross-docking revealed that 31 displays a peculiar interaction network that may be responsible for high affinity. Physicochemical profiling of 31 showed a pK(a) of 7.64, rendering it less than 50% ionized in the physiological pH range, with potentially favorable membrane permeation. The latter was supported from the successful inhibition of sorbitol formation in rat lenses and the ability to permeate rat jejunum. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.016
• 作为产物：
  描述：

  邻甲氧基苯胺 在 二氯苯酚溴酯 、 四丁基碘化铵 、 溶剂黄146 、 三乙胺 作用下， 以 氯苯 为溶剂， 反应 24.0h， 生成 2-(1H-吡咯-1-基)苯醇
  参考文献：
  名称：

  BN/BO-Ullazines 和 Bis-BO-Ullazines：BO 掺杂对芳香性和光电性能的影响

  摘要：

  我们已经实现了用两个 BO 单元或一个 BO 单元和一个 BN 单元对 ullazine 进行置换掺杂。这些 B 掺杂的 ullazing 的合成很简单，使用去甲基化和硼酸化环化作为关键步骤。BN/BO-ullazines ( 2 ) 和双-BO-ullazines ( 3 )的 Ullazine 核都非常接近于平面。通过紫外-可见光、荧光光谱、循环伏安法和密度泛函理论计算研究了它们的电子和光物理性质。

  DOI：

  10.1021/acs.joc.1c00777

文献信息

• Structure-activity relationships, biological evaluation and structural studies of novel pyrrolonaphthoxazepines as antitumor agents
  作者：Margherita Brindisi、Cristina Ulivieri、Gloria Alfano、Sandra Gemma、Francisco de Asís Balaguer、Tuhina Khan、Alessandro Grillo、Giulia Chemi、Grégory Menchon、Andrea E. Prota、Natacha Olieric、Daniel Lucena-Agell、Isabel Barasoain、J. Fernando Diaz、Angela Nebbioso、Mariarosaria Conte、Ludovica Lopresti、Stefania Magnano、Rebecca Amet、Paula Kinsella、Daniela M. Zisterer、Ola Ibrahim、Jeff O'Sullivan、Lucia Morbidelli、Roberta Spaccapelo、Cosima Baldari、Stefania Butini、Ettore Novellino、Giuseppe Campiani、Lucia Altucci、Michel O. Steinmetz、Simone Brogi

  DOI：10.1016/j.ejmech.2018.11.004

  日期：2019.1

  efforts we developed improved pyrrolonaphthoxazepines antitumor agents and their mode of action at the molecular level was elucidated. Compound 6j, one of the most potent analogues, was confirmed by X-ray as a colchicine-site MTA. A comprehensive structural investigation was performed for a complete elucidation of the structure-activity relationships. Selected pyrrolonaphthoxazepines were evaluated for

  微管靶向剂（MTA）是一类临床上成功的抗癌药物。对MTA的多药耐药性的出现要求开发具有多种机械性能的新型MTA。苯并a庚因最近被确定为一类新型的MTA。这些抗癌剂的抗肿瘤活性得到了彻底的表征，尽管它们的确切作用机理仍然难以捉摸。结合化学，生化，细胞，生物信息学和结构方面的努力，我们开发了改进的吡咯并萘并氧杂氮杂卓类抗肿瘤药，并阐明了它们在分子水平上的作用方式。化合物6jX射线证实它是最有效的类似物之一，是秋水仙碱的MTA。为了全面阐明结构-活性关系，进行了全面的结构研究。评价了选定的吡咯并萘并氧杂氮杂卓类化合物对多种癌细胞（包括耐多药细胞系）的细胞周期，凋亡和分化的影响。我们的结果将化合物6j定义为开发用于治疗耐药性肿瘤的有效化合物的潜在有用的最佳选择。
• [EN] HETEROCYCLIC CHROMENE-SPIROCYCLIC PIPERIDINE AMIDES AS MODULATORS OF ION CHANNELS<br/>[FR] AMIDES DE CHROMÈNE HÉTÉROCYCLIQUE-PIPÉRIDINE SPIROCYCLIQUE UTILES COMME MODULATEURS DES CANAUX IONIQUES
  申请人：VERTEX PHARMA

  公开号：WO2011140425A1

  公开（公告）日：2011-11-10

  The invention relates to heterocyclic chromene-spirocyclic piperidine amides useful as inhibitors of ion channels. The invention also provides pharmaceutically acceptable compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various disorders.

  本发明涉及杂环色烯-螺环哌啶酰胺，用作离子通道的抑制剂。本发明还提供了包含本发明化合物的药用可接受组合物，以及使用这些组合物治疗各种疾病的方法。
• [EN] BENZOXAZINES AS MODULATORS OF ION CHANNELS<br/>[FR] BENZOXAZINES COMME MODULATEURS DES CANAUX IONIQUES
  申请人：VERTEX PHARMA

  公开号：WO2013067248A1

  公开（公告）日：2013-05-10

  The invention relates to benzoxazines useful as inhibitors of ion channels. The invention also provides pharmaceutically acceptable compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various disorders.

  本发明涉及可用作离子通道抑制剂的苯并噁嗪。本发明还提供了包含本发明化合物的药用可接受组合物，以及使用这些组合物治疗各种疾病的方法。
• METHOD FOR PRODUCING AN ARENE WITH AN AROMATIC C-N BOND ORTHO TO AN AROMATIC C-O BOND
  申请人：THE ROYAL INSTITUTION FOR THE ADVANCEMENT OF LEARNING/MCGILL UNIVERSITY

  公开号：US20170066711A1

  公开（公告）日：2017-03-09

  A method for producing an arene with an aromatic C—N bond ortho to an aromatic C—O bond from a hydroxy arene comprising said aromatic C—O bond is provided. This method comprising the steps a) ortho-oxygenating the hydroxy arene to produce an ortho-quinone, b) condensating the ortho-quinone with a nitrogen nucleophile to generate a compound of Formula (IVa) or (IVb), and c) allowing 1,5-hydrogen atom shift of the compound of Formula (IVa) or (IVb), thereby producing arenes with a C—N bond ortho to a C—O bond of Formula (Va) and (Vb), respectively:

  提供一种从含有所述芳香C—O键的羟基芳烃制备具有芳香C—N键正交于芳香C—O键的芳烃的方法。该方法包括以下步骤：a) 对羟基芳烃进行正交氧化以产生一个正交醌，b) 将正交醌与氮亲核试剂缩合以生成化合物IVa或IVb的化合物，c) 允许化合物IVa或IVb发生1,5-氢原子转移，从而分别产生具有化合物Va和Vb的C—O键正交的C—N键的芳烃。
• [EN] PYRAZOLO[3,4-D]PYRIMIDIN-4(5H)-ONE DERIVATIVES AS PDE9 INHIBITORS<br/>[FR] UTILISATION DE DÉRIVÉS DE PYRAZOLO[3,4-D]PYRIMIDIN-4(5H)-ONE COMME INHIBITEURS DE PDE9
  申请人：CELON PHARMA SA

  公开号：WO2014016789A1

  公开（公告）日：2014-01-30

  A compound of the general formula (I) wherein R1 is selected from the group consisting of phenyl unsubstituted or substituted with 1 to 3 substituents selected from F, Cl, Br, I, CN, -O-C1-C3-alkyl, fluorinated -O-C1-C3-alkyl, -(CH2)mOH and 5-membered heterocyclic group with 1 or 2 heteroatoms selected from N, O and S; and 6- or 10-membered heteroaryl with 1 to 3 heteroatoms selected from O, N and S; R2 and R3 independently of each other represent H atom or straight or branched C1-C3 alkyl; R4 is selected from the group consisting of 4- to 6- membered cycloalkyl, wherein one of carbon atoms can be replaced by O atom, and which is unsubstituted or substituted with one or two halogen atoms,and straight or branched C1-C4 alkyl; Q represents a bond or C1-C3-alkylene, which can be optionally substituted by one to three C1-C3-alkyls; X is selected from the group consisting of O, NR5, and S(O)p; R5 represents H atom or C1-C3alkyl; m is 1, 2 or 3; p is 0, 1 or 2; and salts thereof, for use as a medicament, in particular for treating cognitive function disorders and neurodegenerative diseases.

  通用式（I）的化合物，其中R1选自苯基未取代或取代的基团，所取代基团可为1至3个取自F、Cl、Br、I、CN、-O-C1-C3-烷基、氟代-O-C1-C3-烷基、-(CH2)mOH和含有1或2个取自N、O和S的杂原子的5元杂环基；以及含有1至3个取自O、N和S的杂原子的6-或10-元杂芳基；R2和R3彼此独立地代表H原子或直链或支链的C1-C3烷基；R4选自4-至6-环脂肪族基团，其中一个碳原子可被氧原子取代，未取代或取代有一或两个卤素原子，以及直链或支链的C1-C4烷基；Q代表键或C1-C3-亚烷基，可选择性地被1至3个C1-C3-烷基取代；X选自O、NR5和S(O)p的基团；R5代表H原子或C1-C3烷基；m为1、2或3；p为0、1或2；以及其盐，用作药物，特别用于治疗认知功能障碍和神经退行性疾病。