萘-1-基(1H-吡咯-3-基)甲酮 | 162934-76-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 萘-1-基(1H-吡咯-3-基)甲酮
• 英文名称: naphthalen-1-yl(1H-pyrrol-3-yl)methanone
• 英文别名: 3-(naphthalen-1-yl)carbonyl-1H-pyrrole
• CAS: 162934-76-1
• 化学式: C₁₅H₁₁NO
• 分子量: 221.258
• InChiKey: SRFPXOWDJKQVJQ-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于氯仿、二氯甲烷、乙酸乙酯、甲醇

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

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  萘-1-基(1H-吡咯-3-基)甲酮 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以95%的产率得到1H-pyrrol-3-yl(thiophen-2-yl)methanone
  参考文献：
  名称：

  The Regioselective Photoinduced Aroylation at the 3-Position of Pyrrole Derivatives

  摘要：

  Irradiation of arenecarbothioamide with pyrrole or indole derivatives gave regioselectively 3-aroylpyrrole or -indole derivatives, respectively.

  DOI：

  10.3987/com-95-7317
• 作为产物：
  描述：

  萘-1-基(1-甲苯磺酰-1H-吡咯-3-基)甲酮 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 12.0h， 以96%的产率得到萘-1-基(1H-吡咯-3-基)甲酮
  参考文献：
  名称：

  1-烷基-3-（1-萘基）吡咯：一类新的大麻素

  摘要：

  描述了一系列1-烷基-3-（1-萘基）吡咯的设计和合成。分子模型研究被用来辅助这些化合物的设计。在合成过程中，对N-芳基磺酰基吡咯的Friedel-Crafts反应进行了重新研究。对标题化合物（4）进行药理评估，获得的数据已使这些吡咯能够被分类为大麻素。

  DOI：

  10.1016/0040-4039(95)00016-6

文献信息

• 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。
• [EN] IMIDAZOLE DERIVATIVES HAVING AN INHIBITORY ACTIVITY FOR FARNESYL TRANSFERASE AND PROCESS FOR PREPARATION THEREOF<br/>[FR] DERIVES D'IMIDAZOLE A ACTIVITE INHIBITRICE DE FARNESYLE TRANSFERASE ET LEUR PROCEDE DE PREPARATION
  申请人：LG CHEMICAL LTD.

  公开号：WO1999028315A1

  公开（公告）日：1999-06-10

  (EN) The present invention relates to a novel imidazole derivative represented by formula (1) which shows an inhibitory activity against farnesyl transferase or pharmaceutically acceptable salts or isomers thereof, in which A, n1 and Y are defined in the specification; to a process for preparation of the compound of formula (1); to intermediates which are used in the preparation of the compound of formula (1); and to a pharmaceutical composition comprising the compound of formula (1) as an active ingredient.(FR) La présente invention concerne un nouveau dérivé d'imidazole représenté par la formule (1) présentant une activité inhibitrice contre la farnésyle transférase, ou ses sels ou isomères acceptables sur le plan pharmaceutique, formule dans laquelle A, n1 et Y sont définis dans le description de l'invention; un procédé de préparation du composé de la formule (1); des intermédiaires utilisés dans la préparation du composé de la formule (1); et une composition pharmaceutique comprenant le composé de la formule (1) en tant que principe actif.

  (中) 本发明涉及一种新的咪唑衍生物，其表示为式（1），该衍生物对法尼酰转移酶具有抑制活性，或其药学上可接受的盐或异构体，其中A、n1和Y在规范中定义；制备式（1）化合物的方法；用于制备式（1）化合物的中间体；以及包含式（1）化合物作为活性成分的药物组合物。
• Imidazole derivatives having an inhibitory activity for farnesyl transferase and process for preparation thereof
  申请人：LG Chemical Ltd.

  公开号：US20020137769A1

  公开（公告）日：2002-09-26

  The present invention relates to novel imidazole derivatives which show an inhibitory activity against farnesyl transferase, pharmaceutically acceptable salts or isomers thereof and pharmaceutical compositions comprising such imidazole derivatives. More particularly, the present invention relates to intermediate compounds which are used in the preparation of the imidazole derivatives of the invention. Related processes also are disclosed.

  本发明涉及新型咪唑衍生物，其对法尼酰转移酶具有抑制活性，其药学上可接受的盐或异构体以及包含此类咪唑衍生物的制药组合物。更具体地说，本发明涉及用于制备本发明咪唑衍生物的中间化合物。相关的制备过程也被揭示。
• Farnesyl transferase inhibitors having a piperidine structure and process for preparation thereof
  申请人：LG Chemical Ltd.

  公开号：US06436960B1

  公开（公告）日：2002-08-20

  The present invention relates to a novel piperidine derivative represented by formula (1) which shows an inhibitory activity against farnesyl transferase or pharmaceutically acceptable salts thereof, in which A, E and G are defined in the specification; to a process for preparation of the compound of formula (1); to an intermediate which is used in the preparation of the compound of formula (1); and to a pharmaceutical composition comprising the compound of formula (1) as an active ingredient.

  本发明涉及一种新的哌啶衍生物，其化学式表示为（1），该衍生物对法尼酰转移酶具有抑制活性，或其药学上可接受的盐，其中A、E和G在规范中定义；以及制备化合物（1）的方法；用于制备化合物（1）的中间体；以及包含化合物（1）作为活性成分的制药组合物。
• 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.