3-氰基噻吩-2-羧酸 | 58231-00-8

• 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: 3-氰基噻吩-2-羧酸
• 英文名称: 3-cyanothiophene-2-carboxylic acid
• CAS: 58231-00-8
• 化学式: C₆H₃NO₂S
• mdl: MFCD01859848
• 分子量: 153.161
• InChiKey: AHKYFPXBUQSQAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 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：
  89.3
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H312,H315,H319,H332,H335
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  3-氰基噻吩-2-羧酸 在 盐酸 作用下， 以 ammonium hydroxide 、 溶剂黄146 为溶剂， 生成 噻吩-2,3-二羧酸
  参考文献：
  名称：

  Aromatic dicarboxamides

  摘要：

  N-(4-氨基苯基)-芳香二羧酰亚胺，例如式##STR1##的化合物或其盐是抗癫痫药物。

  公开号：

  US04025505A1
• 作为产物：
  描述：

  2-甲酸甲酯-3-氰基噻吩 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 0.75h， 以90%的产率得到3-氰基噻吩-2-羧酸
  参考文献：
  名称：

  DNA Binding Ligands Targeting Drug-Resistant Bacteria:  Structure, Activity, and Pharmacology

  摘要：

  We describe the lead optimization and structure-activity relationship of DNA minor-groove binding ligands, a novel class of antibacterial molecules. These compounds have been shown to target A/T-rich sites within the bacterial genome and, as a result, inhibit DNA replication and RNA transcription. The optimization was focused on N-terminal aromatic heterocycles and C-terminal amines and resulted in compounds with improved in vivo tolerability and excellent in vitro antibacterial potency (MIC greater than or equal to 0.031 mug/mL) against a broad range of Grainpositive pathogens, including drug-resistant strains such as methicillin-resistant Stapylococcus aureus (MRSA), penicillin-resistant Streptococcus pneumoniae (PRSP), and vancomycin-resistant Enterococcus faecalis (VRE). In a first proof-of-concept study, a selected compound (35) showed in vivo efficacy in a mouse peritonitis model against methicillin-sensitive S. aureus infection with an ED50 value of 30 mg/kg.

  DOI：

  10.1021/jm030097a

文献信息

• Substituted 3-aryl-5-aryl-[1,2,4]-oxadiazoles and analogs as activators of caspases and inducers of apoptosis and the use thereof
  申请人：——

  公开号：US20030045546A1

  公开（公告）日：2003-03-06

  The present invention is directed to substituted 3-aryl-5-aryl-[1,2,4]-oxadiazoles and analogs thereof, represented by the Formula I: 1 wherein Ar 1 , Ar 3 , A, B and D are defined herein. The present invention also relates to the discovery that compounds having Formula I are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention may be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明涉及取代的3-芳基-5-芳基-[1,2,4]-噁二唑及其类似物，由以下式I表示： 1 其中Ar1，Ar3，A，B和D在此处定义。本发明还涉及发现具有式I的化合物是caspase的激活剂和凋亡诱导剂。因此，本发明的caspase激活剂和凋亡诱导剂可用于诱导在各种临床病况中发生未受控制的异常细胞生长和扩散的细胞死亡。
• Phosphorylamides, their preparation and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05840917A1

  公开（公告）日：1998-11-24

  A phosphorylamide derivative represented by the general formula (I): ##STR1## wherein R represents an amino group that may be substituted, or a salt thereof, possesses potent antibacterial activity against Helicobacter bacterium, especially Helicobacter pylori, and is useful for prevention or treatment of digestive diseases caused by Helicobacter bacterium, solely or in combination with an antacid or an acid secretion inhibitor.

  一种由通式（I）表示的磷酰胺衍生物：##STR1## 其中R代表可能被取代的氨基团或其盐，对幽门螺杆菌，特别是幽门螺杆菌，具有强效的抗菌活性，并可用于单独或与抗酸剂或酸分泌抑制剂联合预防或治疗由幽门螺杆菌引起的消化系统疾病。
• Redox-Neutral Photocatalytic C−H Carboxylation of Arenes and Styrenes with CO2
  作者：Matthias Schmalzbauer、Thomas D. Svejstrup、Florian Fricke、Peter Brandt、Magnus J. Johansson、Giulia Bergonzini、Burkhard König

  DOI：10.1016/j.chempr.2020.08.022

  日期：2020.10

  Carbon dioxide (CO2) is an attractive one-carbon (C1) building block in terms of sustainability and abundance. However, its low reactivity limits applications in organic synthesis as typically high-energy reagents are required to drive transformations. Here, we present a redox-neutral C─H carboxylation of arenes and styrenes using a photocatalytic approach. Upon blue-light excitation, the anthrolate

  就可持续性和丰富性而言，二氧化碳（CO 2）是有吸引力的一碳（C1）构建基块。但是，其低反应性限制了有机合成中的应用，因为通常需要高能试剂来驱动转化。在这里，我们介绍了使用光催化方法的芳烃和苯乙烯的氧化还原中性CH羧基化。在蓝光激发下，邻苯二甲酸根阴离子光催化剂能够将许多芳族化合物还原为相应的自由基阴离子，这些自由基阴离子会与CO 2反应得到羧酸。高通量筛选和计算分析表明，底物的电子亲和力和亲核性之间的正确平衡至关重要。这种新颖的方法使许多芳族化合物能够羧基化，包括许多经典的羧化化学中不容忍的化合物。超过50个使用CO 2或酮进行C-H官能化的例子说明了广泛的适用性。该方法为常见的芳烃的增值提供了新的机会，并可能在后期的CH羧基化中得到应用。
• Importance of Binding Site Hydration and Flexibility Revealed When Optimizing a Macrocyclic Inhibitor of the Keap1–Nrf2 Protein–Protein Interaction
  作者：Fabio Begnini、Stefan Geschwindner、Patrik Johansson、Lisa Wissler、Richard J. Lewis、Emma Danelius、Andreas Luttens、Pierre Matricon、Jens Carlsson、Stijn Lenders、Beate König、Anna Friedel、Peter Sjö、Stefan Schiesser、Jan Kihlberg

  DOI：10.1021/acs.jmedchem.1c01975

  日期：2022.2.24

  Upregulation of the transcription factor Nrf2 by inhibition of the interaction with its negative regulator Keap1 constitutes an opportunity for the treatment of disease caused by oxidative stress. We report a structurally unique series of nanomolar Keap1 inhibitors obtained from a natural product-derived macrocyclic lead. Initial exploration of the structure-activity relationship of the lead, followed

  通过抑制与其负调节因子 Keap1 的相互作用来上调转录因子 Nrf2 构成了治疗由氧化应激引起的疾病的机会。我们报告了从天然产物衍生的大环铅中获得的一系列结构独特的纳摩尔级 Keap1 抑制剂。对先导化合物的构效关系进行初步探索，然后进行结构导向优化，使抑制效力提高了 100 倍。纳摩尔抑制剂的大环核心定位三个药效团单元，用于与 Keap1 的关键残基（包括 R415、R483 和 Y572）进行有效相互作用。配体优化导致配位水分子从 Keap1 结合位点移位，并显着改变热力学曲线。此外，R415 和 R483 的微小重组伴随着配体之间亲和力的重大差异。因此，本研究表明在设计高亲和力配体时考虑 Keap1 结合位点的水合作用和灵活性的重要性。
• Method of using substituted 3-aryl-5-aryl-[1,2,4]-oxadiazoles and analogs as activators of caspases and inducers of apoptosis and the use thereof
  申请人：Cytovia, Inc.

  公开号：US07435750B2

  公开（公告）日：2008-10-14

  The present invention is directed to substituted 3-aryl-5-aryl-[1,2,4]-oxadiazoles and analogs thereof, represented by the Formula I: wherein Ar1, Ar3, A, B and D are defined herein. The present invention also relates to the discovery that compounds having Formula I are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention may be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明涉及被公式I所代表的取代的3-芳基-5-芳基-[1,2,4]-噁二唑及其类似物，其中Ar1、Ar3、A、B和D在此被定义。本发明还涉及发现具有公式I的化合物是caspase的激活剂和凋亡诱导剂。因此，本发明的caspase激活剂和凋亡诱导剂可用于在各种临床病症中诱导细胞死亡，其中出现了异常细胞的不受控制的生长和扩散。