3-(5-nitrothiophen-2-yl)propenoic acid | 17163-22-3

• 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: 3-(5-nitrothiophen-2-yl)propenoic acid
• 英文别名: 3-(5-nitro-2-thienyl)acrylic acid；3-(5-nitro-thiophen-2-yl)-acrylic acid；3-<5-Nitro-thienyl-(2)>-acrylsaeure；3-(5-Nitro-2-thienyl)acrylsaeure；3-(5-nitrothiophen-2-yl)prop-2-enoic acid
• CAS: 17163-22-3
• 化学式: C₇H₅NO₄S
• 分子量: 199.187
• InChiKey: IIJCRPJUZLOCIE-UHFFFAOYSA-N

物化性质

• 熔点：
  251-252 °C (decomp)(Solv: ethanol (64-17-5))
• 沸点：
  392.2±32.0 °C(Predicted)
• 密度：
  1.576±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于二氯甲烷、DMSO、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 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-(5-nitrothiophen-2-yl)propenoic acid 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 3-(5-nitrothiophen-2-yl)-N-(5-phenyl-1H-1,2,4-triazol-3-yl)prop-2-enamide
  参考文献：
  名称：

  Synthesis and preliminary biological evaluation of novel N-(3-aryl-1,2,4-triazol-5-yl) cinnamamide derivatives as potential antimycobacterial agents: An operational Topliss Tree approach

  摘要：

  A series of novel N-(3-aryl-1,2,4-triazol-5-yl) cinnamamide derivatives were designed on basis of structural similarity to the known FAS II inhibitors. Topliss operational method was used to optimize the potency of molecules. The minimum inhibitory concentration (MIC) of all synthesized compounds was determined against Mycobacterium tuberculosis H(37)R(v) using resazurin microtitre assay (REMA) plate method. The synthesized compounds exhibit antimycobacterial activity in the range of 5-95 mu M with a good safety profile. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.076
• 作为产物：
  描述：

  (5-nitro-2-thienyl)methylenemalonic acid 在 乙酸酐 作用下， 反应 0.25h， 生成 3-(5-nitrothiophen-2-yl)propenoic acid
  参考文献：
  名称：

  [EN] PROPENAMIDE THIOPHENE DERIVATIVES AS FLAVIVIRUS INHIBITORS AND THEIR USE
  [FR] DÉRIVÉS DE THIOPHÈNE PROPÉNAMIDE UTILISÉS COMME INHIBITEURS DE FLAVIVIRUS ET LEUR UTILISATION

  摘要：

  本发明涉及新的黄病毒抑制剂，包括所述抑制剂的组合物和用于治疗与病毒感染有关的疾病的方法，例如由于黄病毒感染引起的疾病，包括给予所述抑制剂。

  公开号：

  WO2017102014A1

文献信息

• Studies on the Synthesis of New Antimicrobials. II. Syntheses of 3-(5-Nitro-2-thienyl) acrylic Acid Derivatives and their Some Antibacterial Activities
  作者：Ryuichi Kimura、Takahiro Yabuuchi、Masakatsu Hisaki

  DOI：10.1248/cpb.10.1232

  日期：——

  3-(5-Nitro-2-thienyl) acrylic acid was synthesized in good yield by direct nitration of 3-(2-thienyl) acrylic acid obtained from 2-thiophenecarboxaldehyde without proceeding through 5-nitro-2-thiophenecarboxaldehyde diacetate. By condensation of the acid with various amines, alcohols or phenols, its amide and ester derivatives were prepared. 2-Bromo-3-(5-nitro-2-thienyl) acrylic acid esters were also obtained by bromination of the corresponding esters. Antibacterial activity of these compounds was tested on some bacteria in vitro.

  通过直接硝化由 2-噻吩甲醛得到的 3-(2-噻吩基)丙烯酸，而不经过 5-硝基-2-噻吩甲醛二乙酸酯，合成了 3-(5-硝基-2-噻吩基)丙烯酸，收率很高。通过该酸与各种胺、醇或酚的缩合，制备出了其酰胺和酯衍生物。通过对相应的酯进行溴化处理，还得到了 2-溴-3-（5-硝基-2-噻吩基）丙烯酸酯。对这些化合物的抗菌活性进行了体外测试。
• 一类截短侧耳素芳杂环丙烯酸酯类化合物及其合成方法和应用
  申请人：西安康远晟生物医药科技有限公司

  公开号：CN114573502A

  公开（公告）日：2022-06-03

  本发明提供一类截短侧耳素芳杂环丙烯酸酯类化合物及其制备方法和应用，其结构式为
• NEW FLUORESCENT CROSSLINKED AROMATIC POLYAMIDES CONTAINING THIOPHENEAND FURANE IN THEIR BACKBONE
  作者：C. O SÁNCHEZ、P SOBARZO、N GATICA、D MAC-LEOD-CAREY

  DOI：10.4067/s0717-97072015000300014

  日期：——

  New fluorescent crosslinked aromatic polyamides containing phenylen, thiophene and furane groups in the main chain were synthesized by self-condensation from 3-(5-aminothiophen-2-yl) propenoic acid, 3-(5-aminofuran-2-yl) propenoic acid and 3-(4-((5-aminothiophen-2-yl) methyleneamino) phenyl) propenoic acid using the phosphorylation method and triphenylphosphite as initiator. The amino compounds were obtained from 3-(5-nitrothiophen-2-yl) propenoic acid, 3-(5-nitrofuran-2-yl) propenoic acid and 3-(4-((5-nitrothiophen-2-yl) methyleneamino) phenyl) propenoic by selective reduction of each nitro group and was confirmed by H-1-NMR and FT-IR spectroscopy. Crosslinking of polyamides ocurr by mechanism between vinyl side groups reacts with the vinyl carbon of another chain, giving rise to interchain linear crosslinking. Depending on the structure the polymers have higher degree of crosslinking. Some vinyl groups react by thermal treatmentat 200 degrees C. Partially crosslinked polyamides with high emission fluorescence were obtained. Consequently amide bond formation, crosslinking and conjugation are the main factors that influence the fluorescence process. While polymers have several factors that affect the fluorescence, we believe that the most significant is the crosslinking of vinyl bonds. Subsequent thermal treatment of polyamides provoked crosslinking increase and fluorescence loss. The effect of the chemical structure was correlated with the thermal decomposition. Polyamides were characterized by UV-visible, FT-IR and 1H-NMR spectroscopy, inherent viscosity and thermogravimetric analysis (TGA). The synthesized polyamides exhibited potential for heat sensitive devices application since the fluorescence can be activated or quenched according to a heating process.
• [EN] PROPENAMIDE THIOPHENE DERIVATIVES AS FLAVIVIRUS INHIBITORS AND THEIR USE<br/>[FR] DÉRIVÉS DE THIOPHÈNE PROPÉNAMIDE UTILISÉS COMME INHIBITEURS DE FLAVIVIRUS ET LEUR UTILISATION
  申请人：UNIV D'AIX-MARSEILLE

  公开号：WO2017102014A1

  公开（公告）日：2017-06-22

  The present invention deals with new flavivirus inhibitors, compositions comprising said inhibitors and methods for the treatment of disorders related to a viral infection, such as a disease due to a flavivirus infection, comprising administering said inhibitors.

  本发明涉及新的黄病毒抑制剂，包括所述抑制剂的组合物和用于治疗与病毒感染有关的疾病的方法，例如由于黄病毒感染引起的疾病，包括给予所述抑制剂。
• Synthesis and preliminary biological evaluation of novel N-(3-aryl-1,2,4-triazol-5-yl) cinnamamide derivatives as potential antimycobacterial agents: An operational Topliss Tree approach
  作者：Manoj D. Kakwani、Nutan H. Palsule Desai、Arundhati C. Lele、Muktikant Ray、M.G.R. Rajan、Mariam S. Degani

  DOI：10.1016/j.bmcl.2011.08.076

  日期：2011.11

  A series of novel N-(3-aryl-1,2,4-triazol-5-yl) cinnamamide derivatives were designed on basis of structural similarity to the known FAS II inhibitors. Topliss operational method was used to optimize the potency of molecules. The minimum inhibitory concentration (MIC) of all synthesized compounds was determined against Mycobacterium tuberculosis H(37)R(v) using resazurin microtitre assay (REMA) plate method. The synthesized compounds exhibit antimycobacterial activity in the range of 5-95 mu M with a good safety profile. (C) 2011 Elsevier Ltd. All rights reserved.

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