5-chlorothiophene-3-carbonyl chloride | 113471-08-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 5-chlorothiophene-3-carbonyl chloride
• 英文别名: 5-Chlor-thiophen-(3)-carbonsaeurechlorid
• CAS: 113471-08-2
• 化学式: C₅H₂Cl₂OS
• 分子量: 181.042
• InChiKey: DCLHJPCKHFKQGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-chlorothiophene-3-carbonyl chloride 在 potassium permanganate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 正丁基锂 、 水 、 碳酸氢钠 、 sodium carbonate 、 magnesium sulfate 、 三苯基膦 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 生成 2-Amino-5-(5-chlorothiophen-3-yl)-3-methyl-5-(3-pyrimidin-5-ylphenyl)imidazol-4-one
  参考文献：
  名称：

  New pyrazolyl and thienyl aminohydantoins as potent BACE1 inhibitors: Exploring the S2′ region

  摘要：

  The proteolytic enzyme beta-secretase (BACE1) plays a central role in the synthesis of the pathogenic beta-amyloid in Alzheimer's disease. SAR studies of the S2' region of the BACE1 ligand binding pocket with pyrazolyl and thienyl P2' side chains are reported. These analogs exhibit low nanomolar potency for BACE1, and demonstrate >50-to 100-fold selectivity for the structurally related aspartyl proteases BACE2 and cathepsin D. Small groups attached at the nitrogen of the P2' pyrazolyl moiety, together with the P3 pyrimidine nucleus projecting into the S3 region of the binding pocket, are critical components to ligand's potency and selectivity. P2' thiophene side chain analogs are highly potent BACE1 inhibitors with excellent selectivity against cathepsin D, but only modest selectivity against BACE2. The cell-based activity of these new analogs tracked well with their increased molecular binding with EC50 values of 0.07-0.2 mu M in the ELISA assay for the most potent analogs. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.057
• 作为产物：
  描述：

  5-氯-3-噻吩甲酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 5-chlorothiophene-3-carbonyl chloride
  参考文献：
  名称：

  钴 (III) 催化的 1,3-烯炔和醛的连续 C−H 键加成立体选择性合成烯醇

  摘要：

  报道了一种高效、立体选择性的共催化三组分合成丙二烯醇的方法。该方法通过 C−H 键激活和顺序加成到 1,3-烯炔和各种醛来引入两个 C−C σ 键。揭示了一种合理的机制和进一步的转变。

  DOI：

  10.1002/anie.202202364

文献信息

• [EN] CHLOROTHIOPHENE-AMIDES AS INHIBITORS OF COAGULATION FACTORS XA AND THROMBIN<br/>[FR] CHLOROTHIOPHÈNE-AMIDES UTILISÉS COMME INHIBITEURS DES FACTEURS DE COAGULATION XA ET DE LA THROMBINE
  申请人：SANOFI AVENTIS

  公开号：WO2009103440A1

  公开（公告）日：2009-08-27

  The present invention relates to compounds of the formula I wherein R1; R2; R3; R4; R5, R13, R16, X and M have the meanings indicated in the claims. The compounds of formula I are valuable pharmacologically active compounds. They exhibit a strong anti-thrombotic effect and are suitable, for example, for the therapy and prophylaxis of cardio-vascular disorders like thromboembolic diseases or restenoses. They are reversible inhibitors of the blood clotting enzymes factor Xa (FXa) and thrombin and can in general be applied in conditions in which an undesired activity of factor Xa and/or thrombin are present or for the cure or prevention of which an inhibition of factor Xa and thrombin are intended. The invention furthermore relates to processes for the preparation of compounds of the formula I, their use, in particular as active ingredients in pharmaceuticals, and pharmaceutical preparations comprising them.

  本发明涉及具有式I的化合物，其中R1; R2; R3; R4; R5, R13, R16, X和M具有权利要求中所指示的含义。式I的化合物是有价值的药理活性化合物。它们表现出强大的抗血栓作用，例如，适用于治疗和预防心血管疾病，如血栓栓塞疾病或再狭窄。它们是血液凝块酶因子Xa（FXa）和凝血酶的可逆抑制剂，通常可应用于存在因子Xa和/或凝血酶不良活性的情况，或者用于治疗或预防需要抑制因子Xa和凝血酶的情况。此外，本发明还涉及制备式I化合物的方法，它们的用途，特别是作为药物中的活性成分，以及包含它们的药物制剂。
• [EN] PROCESSES FOR THE PREPARATION OF 5-CHLORO-N-({(5S)-2-OXO-3-[4-(3-OXO-4-MORPHOLINYL) PHENYL]-1,3-OXAZOLIDIN-5-YL}METHYL)-2-THIOPHENE-CARBOXAMIDE AND INTERMEDIATES THEREOF<br/>[FR] PROCÉDÉS DE PRÉPARATION DU 5-CHLORO-N-({(5S)-2-OXO-3-[4-(3-OXO-4- MORPHOLINYL) PHÉNYL]-1,3-OXAZOLIDIN-5-YL}MÉTHYL)-2-THIOPHÈNE-CARBOMAXIDE ET DE SES INTERMÉDIAIRES
  申请人：SYMED LABS LTD

  公开号：WO2013046211A1

  公开（公告）日：2013-04-04

  TThe present invention provides processes for the preparation of 5-chloro-N-((5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-2-thiophene-carboxamide (I) and intermediates thereof. Also provides novel intermediates and their use in the synthesis of oxazolidine derivatives.

  本发明提供了用于制备5-氯-N-((5S)-2-氧代-3-[4-(3-氧代-4-吗啉基)苯基]-1,3-噁唑烷-5-基}甲基)-2-噻吩甲酰胺(I)及其中间体的方法。还提供了新型中间体及其在噁唑烷衍生物合成中的应用。
• Syntheses of 2-aryl-4-(3-thienyl)imidazole derivatives with antiinflammatory properties.
  作者：MAMORU SUZUKI、SADAO MAEDA、KAZUO MATSUMOTO、TOHRU ISHIZUKA、YOSHIO IWASAWA

  DOI：10.1248/cpb.34.3111

  日期：——

  A series of 2-substituted 4-(3-thienyl)imidazoles (6, 11, and 14) was synthesized and evaluated for antiinflammatory activity. Among them, 6g, 14a, and 14g exhibited strong activity, comparable to that of ibuprofen. The acute toxicity and the ulcerogenicity were low as compared with those of standard acidic antiinflammatory agents. The structure-activity relationships are discussed.

  研究人员合成了一系列 2-取代的 4-(3-噻吩基)咪唑（6、11 和 14），并对其抗炎活性进行了评估。其中，6g、14a 和 14g 具有很强的活性，与布洛芬的活性相当。与标准酸性消炎药相比，它们的急性毒性和致溃疡性较低。本文讨论了结构-活性关系。
• CHLOROTHIOPHENE-AMIDES AS INHIBITORS OF COAGULATION FACTORS XA AND THROMBIN
  申请人：FOLLMANN Markus

  公开号：US20110112075A1

  公开（公告）日：2011-05-12

  The present invention relates to compounds of the formula I, wherein R1; R2; R3; R4; R5, R13, R16, X and M have the meanings indicated in the claims. The compounds of formula I are valuable pharmacologically active compounds. They exhibit a strong anti-thrombotic effect and are suitable, for example, for the therapy and prophylaxis of cardio-vascular disorders like thromboembolic diseases or restenoses. They are reversible inhibitors of the blood clotting enzymes factor Xa (FXa) and thrombin and can in general be applied in conditions in which an undesired activity of factor Xa and/or thrombin are present or for the cure or prevention of which an inhibition of factor Xa and thrombin are intended. The invention furthermore relates to processes for the preparation of compounds of the formula I, their use, in particular as active ingredients in pharmaceuticals, and pharmaceutical preparations comprising them.

  本发明涉及式I的化合物，其中R1; R2; R3; R4; R5，R13，R16，X和M具有所述权利要求中指示的含义。式I的化合物是有价值的药理活性化合物。它们具有强烈的抗血栓作用，例如，它们适用于治疗和预防心血管疾病，如血栓栓塞性疾病或再狭窄。它们是血凝酶酶因子Xa（FXa）和凝血酶的可逆抑制剂，并且通常可以应用于存在因子Xa和/或凝血酶不良活性或为治愈或预防而意图抑制因子Xa和凝血酶的情况。此外，本发明还涉及式I化合物的制备方法，它们的用途，特别是作为药物中的活性成分，以及包含它们的制剂。
• Discovery of <i>N</i>-Arylsulfonyl-Indole-2-Carboxamide Derivatives as Galectin-3 and Galectin-8 C-Terminal Domain Inhibitors
  作者：Haoming Zhang、Xiaoyu Wang、Yanjun Wan、Liheng Liu、Jie Zhou、Pingping Li、Bailing Xu

  DOI：10.1021/acsmedchemlett.3c00261

  日期：2023.9.14

  = 2.06 μM), which are the most potent and selective noncarbohydrate-based inhibitors toward gal-3/8 isoforms to date. The molecular docking investigations suggested that the unique amino acids Arg144 in galectin-3 and Ser213 in galectin-8C could contribute to their potency and selectivity. The scratch wound assay demonstrated that Cpd53 and Cpd57 were able to inhibit the MRC-5 lung fibroblast cells

  半乳糖凝集素 3 和半乳糖凝集素 8 均通过识别含半乳糖的糖蛋白参与细胞粘附、迁移、凋亡、血管生成和炎症过程。抑制半乳糖凝集素 3/8 活性是治疗癌症和组织纤维化的潜在方法。在此，一系列新型N-芳基磺酰基-5-芳氧基-吲哚-2-甲酰胺衍生物被公开为半乳糖凝集素 3 和半乳糖凝集素 8 C 端结构域的双重抑制剂，具有低微摩尔水平的K d值（Cpd 53 ， gal -3： K d = 4.12 μM，gal-8C： K d = 6.04 μM；Cpd 57 ，gal-3： K d = 12.8 μM，gal-8C： K d = 2.06 μM），它们是最有效和选择性的迄今为止针对 gal-3/8 亚型的非碳水化合物抑制剂。分子对接研究表明，galectin-3 中的独特氨基酸 Arg144 和 galectin-8C 中的 Ser213 可能有助于其效力和选择性。划痕试验表明，化合物53和化合物57也能够抑制