1-(2-hydroxy-3-naphthyl)pyrrole | 177578-65-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(2-hydroxy-3-naphthyl)pyrrole
• 英文别名: 3-Pyrrol-1-ylnaphthalen-2-ol
• CAS: 177578-65-3
• 化学式: C₁₄H₁₁NO
• 分子量: 209.247
• InChiKey: IJBCRTNKJPJIRE-UHFFFAOYSA-N

物化性质

• 沸点：
  391.3±25.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• 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

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxy-3-naphthyl)pyrrole 在 sodium hydroxide 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 23.0h， 生成 Phenyl-(3-pyrrol-1-yl-naphthalen-2-yloxy)-acetic acid
  参考文献：
  名称：

  Pyrrolobenzothiazepinones and Pyrrolobenzoxazepinones:  Novel and Specific Non-Nucleoside HIV-1 Reverse Transcriptase Inhibitors with Antiviral Activity

  摘要：

  Two novel classes of pyrrolobenzothiazepinones and pyrrolobenzoxazepinones were investigated as potential anti-AIDS drugs. These compounds were found to inhibit HIV-1 reverse transcriptase (RT) enzyme in vitro and to prevent HIV-1 cytopathogenicity in T4 lymphocytes, without appreciable activity on HIV-2 cytopathic effects, and against HBV as well as calf-thymus DNA alpha-polymerase. Their potency is influenced by substituents at position 6 and on the fused aromatic ring. Specifically, small lipophilic substituents at C-6 were preferred, whereas substitutions on the benzo-fused ring were found to be detrimental to activity, with respect to the unsubstituted compounds. Modification of the pi-system at C-6 is well tolerated, although the replacement of the benzo-fused with a [2,3]naphtho-fused ring leads to a less active compound. Maximum potency and specificity is achieved with a phenyl and an ethyl group at position 6 of the pyrrolobenzoxazepinone system. In the enzymatic assay the oxazepinone derivative (+/-)-6-ethyl-6-phenylpyrrolo[2,1-d][1,5] 16e (IC50 = 0.25 mu M) was found to be more potent than nevirapine (IC50 = 0.5 mu M), tested in the same experimental conditions using rC . dG as a template-primer. In cell culture assay benzoxazepine 16e was active against HIV-1, both wild type and AZT-sensitive, and HIV-1 (IIIB) strains, but not against HIV-2. In enzyme assay although 16e inhibited HIV-1 RT, it was inactive against the nevirapine-resistant recombinant RT Y181C at 50 mu M. Molecular modeling studies suggest that these derivatives present a 3D pharmacophoric arrangement similar to that of other nonnucleoside inhibitors such as nevirapine.

  DOI：

  10.1021/jm950702c
• 作为产物：
  描述：

  2,5-二甲氧基四氢呋喃 、 3-氨基-2-萘酚 在 溶剂黄146 作用下， 以64 %的产率得到1-(2-hydroxy-3-naphthyl)pyrrole
  参考文献：
  名称：

  多孔有机聚合物负载的可回收铱催化剂用于无受体脱氢硅烷化：稠环氧杂硅环的合成

  摘要：

  通过催化方法将烷烃或芳烃中的特定C-H键直接转化为C-Si键引起了越来越多的研究兴趣。在此，我们报道了一种负载于萘啶基多孔有机聚合物上的新型铱催化剂的制备，并将其成功应用于2-芳基苯酚或醇和氢硅烷的脱氢硅烷化反应以得到稠环氧杂硅环。该合成方法表现出广泛的底物范围和良好的官能团兼容性，同时避免了氢受体的使用。此外，这种有机聚合物负载的铱催化剂可以很容易地从反应体系中回收并重复使用至少七次而没有明显的失活。该研究为进一步设计多相纳米催化剂提供了新的见解，并有助于硅取代功能分子的合成。

  DOI：

  10.1002/adsc.202400028

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。
• Design and synthesis of multifunctional microtubule targeting agents endowed with dual pro-apoptotic and anti-autophagic efficacy
  作者：Giuseppe Campiani、Tuhina Khan、Cristina Ulivieri、Leopoldo Staiano、Chiara Papulino、Stefania Magnano、Seema Nathwani、Anna Ramunno、Daniel Lucena-Agell、Nicola Relitti、Stefano Federico、Luca Pozzetti、Gabriele Carullo、Alice Casagni、Simone Brogi、Francesca Vanni、Paola Galatello、Magda Ghanim、Niamh McCabe、Stefania Lamponi、Massimo Valoti、Ola Ibrahim、Jeffrey O'Sullivan、Richard Turkington、Vincent P. Kelly、Ruben VanWemmel、J. Fernando Díaz、Sandra Gemma、Daniela Zisterer、Lucia Altucci、Maria Antonietta De Matteis、Stefania Butini、Rosaria Benedetti

  DOI：10.1016/j.ejmech.2022.114274

  日期：2022.5
• Pyrrolobenzothiazepinones and Pyrrolobenzoxazepinones:  Novel and Specific Non-Nucleoside HIV-1 Reverse Transcriptase Inhibitors with Antiviral Activity
  作者：Giuseppe Campiani、Vito Nacci、Isabella Fiorini、Maria P. De Filippis、Antonio Garofalo、Giovanni Greco、Ettore Novellino、Sergio Altamura、Laura Di Renzo

  DOI：10.1021/jm950702c

  日期：1996.1.1

  Two novel classes of pyrrolobenzothiazepinones and pyrrolobenzoxazepinones were investigated as potential anti-AIDS drugs. These compounds were found to inhibit HIV-1 reverse transcriptase (RT) enzyme in vitro and to prevent HIV-1 cytopathogenicity in T4 lymphocytes, without appreciable activity on HIV-2 cytopathic effects, and against HBV as well as calf-thymus DNA alpha-polymerase. Their potency is influenced by substituents at position 6 and on the fused aromatic ring. Specifically, small lipophilic substituents at C-6 were preferred, whereas substitutions on the benzo-fused ring were found to be detrimental to activity, with respect to the unsubstituted compounds. Modification of the pi-system at C-6 is well tolerated, although the replacement of the benzo-fused with a [2,3]naphtho-fused ring leads to a less active compound. Maximum potency and specificity is achieved with a phenyl and an ethyl group at position 6 of the pyrrolobenzoxazepinone system. In the enzymatic assay the oxazepinone derivative (+/-)-6-ethyl-6-phenylpyrrolo[2,1-d][1,5] 16e (IC50 = 0.25 mu M) was found to be more potent than nevirapine (IC50 = 0.5 mu M), tested in the same experimental conditions using rC . dG as a template-primer. In cell culture assay benzoxazepine 16e was active against HIV-1, both wild type and AZT-sensitive, and HIV-1 (IIIB) strains, but not against HIV-2. In enzyme assay although 16e inhibited HIV-1 RT, it was inactive against the nevirapine-resistant recombinant RT Y181C at 50 mu M. Molecular modeling studies suggest that these derivatives present a 3D pharmacophoric arrangement similar to that of other nonnucleoside inhibitors such as nevirapine.
• Recyclable Iridium Catalyst Supported on Porous Organic Polymer for Acceptorless Dehydrogenative Silylation: Synthesis of Ring‐Fused Oxasilacycles
  作者：Jiayi Xian、Xing Sheng、Yi Lin、Zhenning Sun、Chaohan Chen、Kun Zhou、Chao Peng、Bin Li、Xiuwen Chen、Feng Xie

  DOI：10.1002/adsc.202400028

  日期：2024.4.23

  alkanes or aromatics via catalytic methods has attracted growing research interest. Herein, we report the preparation of a new iridium catalyst supported on a naphthyridine‐based porous organic polymer and its successful application in the dehydrogenative silylation of 2‐arylphenols or alcohol and hydrosilanes to access ring‐fused oxasilacycles. The synthetic method exhibits broad substrate scope and good

  通过催化方法将烷烃或芳烃中的特定C-H键直接转化为C-Si键引起了越来越多的研究兴趣。在此，我们报道了一种负载于萘啶基多孔有机聚合物上的新型铱催化剂的制备，并将其成功应用于2-芳基苯酚或醇和氢硅烷的脱氢硅烷化反应以得到稠环氧杂硅环。该合成方法表现出广泛的底物范围和良好的官能团兼容性，同时避免了氢受体的使用。此外，这种有机聚合物负载的铱催化剂可以很容易地从反应体系中回收并重复使用至少七次而没有明显的失活。该研究为进一步设计多相纳米催化剂提供了新的见解，并有助于硅取代功能分子的合成。