naphthalen-2-yl(1H-pyrrol-3-yl)methanone | 220968-60-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: naphthalen-2-yl(1H-pyrrol-3-yl)methanone
• 英文别名: 3-(2-naphthalenoyl)-1H-pyrrole；Naphthalen-2yl(1H-pyrrol-3-yl)methanone
• CAS: 220968-60-5
• 化学式: C₁₅H₁₁NO
• 分子量: 221.258
• InChiKey: NKQDJPURKURBRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  naphthalen-2-yl(1H-pyrrol-3-yl)methanone 在 tris[2-(methoxyethoxy)ethyl]amine 、 sodium hydride 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 1.0h， 生成 [3-(Naphthalene-2-carbonyl)-pyrrol-1-yl]-acetic acid
  参考文献：
  名称：

  Substituted Pyrrol-1-ylacetic Acids That Combine Aldose Reductase Enzyme Inhibitory Activity and Ability To Prevent the Nonenzymatic Irreversible Modification of Proteins from Monosaccharides

  摘要：

  Starting from the known inhibitory activity of (3-benzoylpyrrol-1-yl)acetic acid (1) and (2-benzoylpyrrol-1-yl)acetic acid (II), a series of 3-aroyl and 2,4-bis-aroyl derivatives (54-75) were synthesized and tested for inhibition of aldose reductase, an enzyme involved in the appearance of diabetic complications. It was found that a number of the tested compounds exhibited considerable activity in the micromolar range. Important structural features for the potent compounds is the presence of substituents with relatively low Hammett sigma values and/ or moieties which increase their overall aromatic area. The most active derivative was the [2,4-bis(4-methoxybenzoyl)pyrrol-1-yl] acetic acid (75), with potency favorably compared to known ARIs such as tolrestat, epalrestat, zopolrestat, and fidarestat. Four selected derivatives were also evaluated for their ability to interfere with the oxidative modification of serum albumin in an in vitro experimental glycation model of diabetes mellitus. All of them showed considerable activity, comparable to the known inhibitor trolox. Our results, taken together, indicate that compound 75 combines favorably two biological activities directly connected to a number of pathological conditions related to the chronic diabetes mellitus.

  DOI：

  10.1021/jm0209477
• 作为产物：
  描述：

  [1-(Benzenesulfonyl)pyrrol-3-yl]-naphthalen-2-ylmethanone 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 生成 naphthalen-2-yl(1H-pyrrol-3-yl)methanone
  参考文献：
  名称：

  1-苯磺酰基-1 H-吡咯的Friedel-crafts酰化制备3-芳酰基吡咯的研究

  摘要：

  在这项工作中，我们研究了氯化铝催化的1-苯磺酰基-1 H-吡咯与一系列11种芳酰氯的反应。形成的产物不是分离的，而是水解成目标3-芳基吡咯的总产率，通常高于50％。但是，在富含π电子的1-苯基-1 H-吡咯-3-羰基氯和1-甲基-1 H-吲哚-3-羰基氯的情况下，发生了显着的C-2取代，导致分离出相应的1-苯磺酰基-2-芳酰基吡咯作为主要或唯一产品。从1-三异丙基硅烷基-1 H-吡咯开始合成所需的C-3异构体。

  DOI：

  10.1002/jhet.5570350619

文献信息

• Useful aroyl aminoacyl pyrrole compounds
  申请人：Ortho-McNeil Pharmaceutical, Inc.

  公开号：US06573267B2

  公开（公告）日：2003-06-03

  This invention is directed to aroyl aminoacyl pyrroles pharmaceutically useful as agents and modulators for the treatment of central nervous system disorders and a method for the treatment of central nervous system disorders including, but not limited to, use of the compounds of the present invention as anticonvulsant agents and modulators, antiepileptic agents and modulators, neuroprotective agents and modulators, muscle relaxant agents and modulators and as agents and modulators for the treatment of neuropathic pain.

  该发明涉及作为治疗中枢神经系统疾病的药物有用的芳酰氨基酰吡咯烷类化合物，以及治疗中枢神经系统疾病的方法，包括但不限于使用本发明化合物作为抗惊厥剂和调节剂、抗癫痫剂和调节剂、神经保护剂和调节剂、肌肉松弛剂和调节剂，以及治疗神经病性疼痛的药物和调节剂。
• A study of the friedel-crafts acylation of 1-benzenesulfonyl-1<i>H</i>-pyrrole in the preparation of 3-aroylpyrroles
  作者：Ioannis Nicolaou、Vassilis J. Demopoulos

  DOI：10.1002/jhet.5570350619

  日期：1998.11

  In this work, we studied the aluminum chloride catalyzed reaction of 1-benzenesulfonyl-1H-pyrrole with a series of eleven aroyl chlorides. The products formed were not isolated, but hydrolyzed to the target 3-aroylpyrroles in overall yields, usually, higher than 50%. However, in the cases with the π electron rich 1-phenyl-1H-pyrrole-3-carbonyl chloride and 1-methyl-1H-indole-3-carbonyl chloride significant

  在这项工作中，我们研究了氯化铝催化的1-苯磺酰基-1 H-吡咯与一系列11种芳酰氯的反应。形成的产物不是分离的，而是水解成目标3-芳基吡咯的总产率，通常高于50％。但是，在富含π电子的1-苯基-1 H-吡咯-3-羰基氯和1-甲基-1 H-吲哚-3-羰基氯的情况下，发生了显着的C-2取代，导致分离出相应的1-苯磺酰基-2-芳酰基吡咯作为主要或唯一产品。从1-三异丙基硅烷基-1 H-吡咯开始合成所需的C-3异构体。
• US6573267B2
  申请人：——

  公开号：US6573267B2

  公开（公告）日：2003-06-03
• Antimalarial Activity of Natural and Synthetic Prodiginines
  作者：Kancharla Papireddy、Martin Smilkstein、Jane Xu Kelly、Shweta、Shaimaa M. Salem、Mamoun Alhamadsheh、Stuart W. Haynes、Gregory L. Challis、Kevin A. Reynolds

  DOI：10.1021/jm200543y

  日期：2011.8.11

  Prodiginines are a family of linear and cyclic oligopyrrole red-pigmented compounds. Herein we describe the in vitro antimalarial activity of four natural (IC50 = 1.7–8.0 nM) and three sets of synthetic prodiginines against Plasmodium falciparum. Set 1 compounds replaced the terminal nonalkylated pyrrole ring of natural prodiginines and had diminished activity (IC50 > 2920 nM). Set 2 and set 3 prodiginines

  Prodiginines 是一系列线性和环状低聚吡咯红色颜料化合物。在此，我们描述了四种天然 (IC 50 = 1.7–8.0 nM) 和三组合成 prodiginine 对恶性疟原虫的体外抗疟活性。第 1 组化合物取代了天然 prodiginines 的末端非烷基化吡咯环并且活性降低 (IC 50 > 2920 nM)。第 2 组和第 3 组 prodiginine 分别在右手端吡咯的 3 或 5 位被单取代或双取代。使用烷基或芳基取代基观察到有效的体外活性 (IC 50 = 0.9–16.0 nM)。在P. yoelii中评估了 Metacycloprodiginine 和更有效的合成类似物使用口服给药的鼠专利感染。每种类似物在每天 25 (mg/kg) 给药后将寄生虫血症降低了 90% 以上，并且在某些情况下可以治愈。最有利的特征是 5 (mg/kg)/天的寄生虫减少 92%，25 (mg/kg)/天的寄生虫减少
• Substituted Pyrrol-1-ylacetic Acids That Combine Aldose Reductase Enzyme Inhibitory Activity and Ability To Prevent the Nonenzymatic Irreversible Modification of Proteins from Monosaccharides
  作者：Ioannis Nicolaou、Vassilis J. Demopoulos

  DOI：10.1021/jm0209477

  日期：2003.1.1

  Starting from the known inhibitory activity of (3-benzoylpyrrol-1-yl)acetic acid (1) and (2-benzoylpyrrol-1-yl)acetic acid (II), a series of 3-aroyl and 2,4-bis-aroyl derivatives (54-75) were synthesized and tested for inhibition of aldose reductase, an enzyme involved in the appearance of diabetic complications. It was found that a number of the tested compounds exhibited considerable activity in the micromolar range. Important structural features for the potent compounds is the presence of substituents with relatively low Hammett sigma values and/ or moieties which increase their overall aromatic area. The most active derivative was the [2,4-bis(4-methoxybenzoyl)pyrrol-1-yl] acetic acid (75), with potency favorably compared to known ARIs such as tolrestat, epalrestat, zopolrestat, and fidarestat. Four selected derivatives were also evaluated for their ability to interfere with the oxidative modification of serum albumin in an in vitro experimental glycation model of diabetes mellitus. All of them showed considerable activity, comparable to the known inhibitor trolox. Our results, taken together, indicate that compound 75 combines favorably two biological activities directly connected to a number of pathological conditions related to the chronic diabetes mellitus.