2-(1H-吡咯-1-基)噻吩-3-羧酸 | 79242-76-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 2-(1H-吡咯-1-基)噻吩-3-羧酸
• 中文别名: 2,6-二乙基-4-甲基苯胺
• 英文名称: 2-(1H-pyrrol-1-yl)thiophene-3-carboxylic acid
• 英文别名: 2-(1-pyrrolyl)-3-thienylcarboxylic acid；acide (pyrrolyl-1)-2 theonique-3；2-pyrrol-1-ylthiophene-3-carboxylic acid
• CAS: 79242-76-5
• 化学式: C₉H₇NO₂S
• 分子量: 193.226
• InChiKey: HGVFZWBIJVXWGG-UHFFFAOYSA-N

物化性质

• 沸点：
  375.6±27.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P330,P362,P403+P233,P501
• 危险性描述：
  H302,H312,H332

反应信息

• 作为反应物：
  描述：

  2-(1H-吡咯-1-基)噻吩-3-羧酸 在 sodium azide 、 三乙胺 、 三氯氧磷 作用下， 以 水 、 丙酮 为溶剂， 反应 2.17h， 生成 azoture de (formyl-2 pyrrolyl-1)-2 theonyle-3
  参考文献：
  名称：

  Rault, Sylvain; Effi, Yamien; Sevricourt, Michel Cugnon de, Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 17 - 21

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基噻吩-3-甲腈 在 sodium hydroxide 、 水 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 2-(1H-吡咯-1-基)噻吩-3-羧酸
  参考文献：
  名称：

  Novel Selective and Partial Agonists of 5-HT₃ Receptors. Part 1. Synthesis and Biological Evaluation of Piperazinopyrrolothienopyrazines

  摘要：

  A series of piperazinopyrrolo[1,2-a]thieno[3,2-e]- and -[2,3-e]pyrazine derivatives were prepared and evaluated in order to determine the necessary requirements for high affinity on the 5-HT3 receptors and high selectivity versus other 5-HT receptor subtypes. Various substitutions on the piperazine and the thiophene ring of the pyrrolothienopyrazine moieties were systematically explored as well as replacement of the piperazine by other cyclic amines. The best compounds are in the nanomolar range of affinity for 5-HT3 receptors with high to very high selectivity (up to 10 000 for 14b). These high-affinity compounds have in common a benzyl- or allylpiperazine substituent with no substitutions on the thiophene ring. Five of these compounds (1a, 4b, 13a,b, and 14b) have been evaluated on the Von Bezold-Jarisch reflex and were characterized as partial agonists. One of them, 13a, has shown in vivo at very low dose a potent anxiolytic-like activity in the light/dark test.

  DOI：

  10.1021/jm950543x

文献信息

• Novel antagonists of serotonin-4 receptors: Synthesis and biological evaluation of pyrrolothienopyrazines
  作者：Stéphane Lemaître、Alban Lepailleur、Ronan Bureau、Sabrina Butt-Gueulle、Véronique Lelong-Boulouard、Pascal Duchatelle、Michel Boulouard、Aline Dumuis、Cyril Daveu、Frank Lezoualc’h、Bruno Pfeiffer、François Dauphin、Sylvain Rault

  DOI：10.1016/j.bmc.2008.11.045

  日期：2009.3

  of a 5-HT4 receptor antagonist pharmacophore, a series of pyrrolo[1,2-a]thieno[3,2-e] and pyrrolo[1,2-a]thieno[2,3-e] pyrazine derivatives were designed, prepared, and evaluated to determine the properties necessary for high-affinity binding to 5-HT4 receptors. The compounds were synthesized by substituting the chlorine atom of the pyrazine ring with various N-alkyl-4-piperidinylmethanolates. They

  根据5-HT 4受体拮抗剂药效团的定义，一系列吡咯并[1,2- a ]噻吩并[3,2- e ]和吡咯并[1,2- a ]噻吩并[2,3- e ]设计，制备和评估吡嗪衍生物，以确定与5-HT 4受体高亲和力结合所需的性质。通过用各种N-烷基-4-哌啶基甲醇盐取代吡嗪环的氯原子来合成化合物。在结合测定中以[ 3 H] GR113808（1）作为5-HT 4受体放射性配体对它们进行了评估。亲和力值（K i（或抑制百分比）受到芳环上的取代基和侧哌啶链上的取代基的影响。三环上的甲基会显着增加亲和力，而N-丙基或N-丁基会产生具有纳摩尔亲和力的化合物。在最有效的配体中，选择34d用于进一步的药理研究并在体内进行评估。该化合物在稳定表达5-HT 4（a）受体的COS-7细胞中充当拮抗剂/弱部分激动剂，并作为一种外周镇痛药而引起了人们的极大兴趣。
• [EN] PIPERIDINE-2, 6-DIONE DERIVATIVES WHICH BIND TO CEREBLON, AND METHODS OF USE THEREOF<br/>[FR] DÉRIVÉS DE PIPÉRIDINE-2, 6-DIONE QUI SE LIENT AU CÉRÉBLON, ET PROCÉDÉS D'UTILISATION DE CEUX-CI
  申请人：CAPTOR THERAPEUTICS S A

  公开号：WO2021105335A1

  公开（公告）日：2021-06-03

  The present invention provides novel compounds which bind to cereblon, and methods of use thereof. The compounds are represented by Formulas (Ia), (Ib), (IIa) and (IIb), below: Formula (Ia), Formula (Ib), Formula (IIa), Formual (IIb).

  本发明提供了结合到 cereblon 的新化合物，以及其使用方法。这些化合物由以下公式（Ia）、（Ib）、（IIa）和（IIb）表示：公式（Ia）、公式（Ib）、公式（IIa）、公式（IIb）。
• Active manganese dioxide promoted cyclization of ortho-(1H-pyrrol-1-yl)aryl and heteroaryl carboxylic acids to 5H-pyrrolo[1,2-a][3,1]benzoxazin-5-one derivatives
  作者：Fedora Grande、Antonella Brizzi、Antonio Garofalo、Francesca Aiello

  DOI：10.1016/j.tet.2013.09.072

  日期：2013.11

  1]benzoxazin-5-one and six of its substituted derivatives have been prepared by active manganese dioxide promoted oxidative cyclization of the corresponding 2-(1H-pyrrol-1-yl)benzoic acids, under mild conditions, in moderate yields. The method was successfully extended to the cyclization of some ortho-(1H-pyrrol-1-yl)heteroaryl carboxylic acids and 2-(1H-indol-1-yl)benzoic acids.

  迄今未知内酯5 ħ -吡咯并[1,2-一个] [3,1]苯并恶嗪-5-酮和其取代的衍生物的6已经制备由活性二氧化锰促进了相应的2-（1-氧化合环ħ -在温和条件下以中等收率得到吡咯-1-基）苯甲酸。该方法已成功地扩展到某些邻-（1 H-吡咯-1-基）杂芳基羧酸和2-（1 H-吲哚-1-基）苯甲酸的环化反应。
• Spiro-tricyclicaromatic succinimide derivatives as inhibitors of aldose
  申请人：Alcon Laboratories, Inc.

  公开号：US04537892A1

  公开（公告）日：1985-08-27

  Disclosed are substituted or unsubstituted planar tricyclic fluorene or nuclear analogs thereof, spiro-coupled to a five-membered ring containing a secondary amide, and the pharmaceutically acceptable salts thereof. These compounds are useful, inter alia, in the treatment of diabetes. Also disclosed are processes for the preparation of such compounds; pharmaceutical compositions comprising such compounds; and methods of treatment comprising administering such compounds and compositions when indicated for, inter alia, long term, prophylactic treatment of the diabetes syndrome.

  本发明涉及替代或未替代的平面三环芴或其核类似物，与含有次级酰胺的五元环螺合，以及其药学上可接受的盐。这些化合物在糖尿病治疗中有用，此外还揭示了制备这些化合物的方法；包含这些化合物的制药组合物；以及在适用于糖尿病综合症的长期预防性治疗方面指示时，施用这些化合物和组合物的治疗方法。
• Spiro-tricyclicaromatic succinimide derivatives
  申请人：Alcon Laboratories, Inc.

  公开号：US05070100A1

  公开（公告）日：1991-12-03

  Disclosed are substituted or unsubstituted planar tricyclic fluorene or nuclear analogs thereof, spiro-coupled to a five-membered ring containing a secondary amide, and the pharmaceutically acceptable salts thereof. These compounds are useful, inter alia in the treatment of diabetes. Also disclosed are processes for the preparation of such compounds; pharmaceutical compositions comprising such compounds; and methods of treatment comprising administering such compounds and compositions when indicated for, inter alia, long term, prophylactic treatment of the diabetes syndrome. A particularly preferred class of compounds comprise difluoro-dialkoxy substituted spiro-(9H-fluorene-9,4'-imidazolidine)-2,40 ,5-diones.

  本发明涉及取代或未取代的平面三环芴或其核类似物，与含有二级酰胺的五元环螺合的化合物以及其药学上可接受的盐。这些化合物可用于治疗糖尿病等疾病。本发明还涉及制备这些化合物的方法；包含这些化合物的制药组合物；以及在适当时用于长期预防性治疗糖尿病综合症等情况下，通过给予这些化合物和组合物的治疗方法。其中一类特别优选的化合物包括二氟二烷氧基取代的螺-(9H-芴-9,4'-咪唑啉)-2,4,5-二酮。