2-hydroxy-3-(4-nitrophenyl)acrylic acid | 141666-15-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-hydroxy-3-(4-nitrophenyl)acrylic acid
• 英文别名: 2-Hydroxy-3-(4-nitrophenyl)prop-2-enoic acid；2-hydroxy-3-(4-nitrophenyl)prop-2-enoic acid
• CAS: 141666-15-1
• 化学式: C₉H₇NO₅
• 分子量: 209.158
• InChiKey: FUKCXXJPBOBGMI-UHFFFAOYSA-N

物化性质

• 熔点：
  186 °C (decomp)(Solv: toluene (108-88-3))
• 沸点：
  403.8±45.0 °C(Predicted)
• 密度：
  1.558±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 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：
  103
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-hydroxy-3-(4-nitrophenyl)acrylic acid 在 sodium tetrahydroborate 、 乙酰氯 作用下， 以 甲醇 为溶剂， 反应 0.17h， 生成 3-(4-Nitro-phenyl)-propane-1,2-diol
  参考文献：
  名称：

  Chemocontrolled reduction of aromatic α-ketoesters by NaBH4: Selective synthesis of α-hydroxy esters or 1,2-diols

  摘要：

  alpha-hydroxyesters 5a-g or diols 6a-g have been obtained in high yields by reduction of aromatic alpha-ketoesters 4 once or twice respectively by using NaBH4 as the reducer under suitable conditions. The use of a solvent that does not interact with the reagent allowed the double reduction to occur with only a slight excess of borohydride in very mild conditions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00154-8
• 作为产物：
  描述：

  2-methyl-4(4-nitrophenylmethylene)-2-oxazolin-5-one 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 以67%的产率得到2-hydroxy-3-(4-nitrophenyl)acrylic acid
  参考文献：
  名称：

  双臂二氮杂-对环芳烃前体的多克合成。具有 Zn2+、Cu2+ 和 Co2+ 离子的络合物

  摘要：

  已开发出多步合成策略，以多克规模获得 N-4-硝基苯基-丙酮酰-氨基酯。随后由硝基催化氢化促进的多米诺反应生成二氮杂对环芳烷 3、13 和 14。已通过 UV-vis 和 H NMR 光谱方法研究了与 Zn、Cu 和 Co 离子的络合。

  DOI：

  10.3998/ark.5550190.0012.316

文献信息

• Compounds and Their Salts Specific to the PPAR Receptors and the EGF Receptors and Their Use in the Medical Field
  申请人：Naccari Giancarlo

  公开号：US20090048343A1

  公开（公告）日：2009-02-19

  The present invention relates to compounds comprising the general formula (I), in which R 1 and R 2 , which may be identical or different, are selected from the group comprising —H or a linear or branched alkyl group having from 1 to 6 carbon atoms or together form an aromatic or aliphatic ring with 5 or 6 atoms; Y and Z, which may be identical or different, are selected from the group comprising —H, —OH, —COOH, —OR 3 , —CH(OR 3 )COOH, in which R 3 is selected from H, phenyl, benzyl, —CF 3 or —CF 2 CF 3 , vinyl, allyl and a linear or branched alkyl group having from 1 to 6 carbon atoms.

  本发明涉及具有一般式（I）的化合物，其中R1和R2，可以相同也可以不同，选自包括-H或具有1至6个碳原子的直链或支链烷基基团，或者共同形成具有5或6个原子的芳香或脂肪环的群；Y和Z，可以相同也可以不同，选自包括-H，-OH，-COOH，-OR3，-CH(OR3)COOH的群，其中R3选自H，苯基，苄基，-CF3或-CF2CF3，乙烯基，烯丙基和具有1至6个碳原子的直链或支链烷基基团。
• Evaluation of α-hydroxycinnamic acids as pyruvate carboxylase inhibitors
  作者：Daniel J. Burkett、Brittney N. Wyatt、Mallory Mews、Anson Bautista、Ryan Engel、Chris Dockendorff、William A. Donaldson、Martin St. Maurice

  DOI：10.1016/j.bmc.2019.07.027

  日期：2019.9

  5 μM respectively. Compound 8v is a competitive inhibitor with respect to pyruvate (Ki = 0.74 μM) and a mixed-type inhibitor with respect to ATP, indicating that it targets the unique carboxyltransferase (CT) domain of PC. Furthermore, compound 8v does not significantly inhibit human carbonic anhydrase II, matrix metalloproteinase-2, malate dehydrogenase or lactate dehydrogenase.

  通过基于结构的药物设计项目（SBDD），发现了有效的丙酮酸羧化酶小分子抑制剂（PC）。制备了一系列α-酮酸（7）和α-羟基肉桂酸（8），并在两种测定中评估了其对PC的抑制作用。两种最有效的抑制剂是3,3'-（1,4-亚苯基）双[2-羟基-2-丙酸]（8u）和2-羟基-3-（喹啉-2-基）丙酸（8v））的IC 50值分别为3.0±1.0μM和4.3±1.5μM。化合物8v是相对于丙酮酸（K i = 0.74μM）和针对ATP的混合型抑制剂，表明它靶向PC的独特羧基转移酶（CT）域。此外，化合物8v不会显着抑制人碳酸酐酶II，基质金属蛋白酶-2，苹果酸脱氢酶或乳酸脱氢酶。
• Compounds and their salts specific to the PPAR receptors and the EGF receptors and their use in the medical field
  申请人：Giuliani International Limited

  公开号：US08153841B2

  公开（公告）日：2012-04-10

  The present invention relates to compounds comprising the general formula (I), in which R1 and R2, which may be identical or different, are selected from the group comprising —H or a linear or branched alkyl group having from 1 to 6 carbon atoms or together form an aromatic or aliphatic ring with 5 or 6 atoms; Y and Z, which may be identical or different, are selected from the group comprising —H, —OH, —COOH, —OR3, —CH(OR3)COOH, in which R3 is selected from H, phenyl, benzyl, —CF3 or —CF2CF3, vinyl, allyl and a linear or branched alkyl group having from 1 to 6 carbon atoms.

  本发明涉及具有通式（I）的化合物，其中R1和R2可能相同或不同，选自包括-H或具有1至6个碳原子的线性或支链烷基或共同形成具有5或6个原子的芳香或脂肪环的群体; Y和Z可能相同或不同，选自包括-H，-OH，-COOH，-OR3，-CH（OR3）COOH，其中R3选自H，苯基，苄基，-CF3或-CF2CF3，乙烯基，丙烯基和具有1至6个碳原子的线性或支链烷基。
• Compounds and their Salts Specific to the PPAR Receptors and the EGF Receptors and their Use in the Medical Field
  申请人：Naccari Giancarlo

  公开号：US20130005813A1

  公开（公告）日：2013-01-03

  The present invention relates to compounds comprising the general formula (I), in which R 1 and R 2 , which may be identical or different, are selected from the group comprising —H or a linear or branched alkyl group having from 1 to 6 carbon atoms or together form an aromatic or aliphatic ring with 5 or 6 atoms; Y and Z, which may be identical or different, are selected from the group comprising —H, —OH, —COOH, —OR 3 , —CH(OR 3 )COOH, in which R 3 is selected from H, phenyl, benzyl, —CF 3 or —CF 2 CF 3 , vinyl, allyl and a linear or branched alkyl group having from 1 to 6 carbon atoms.

  本发明涉及通式（I）的化合物，其中R1和R2可以相同或不同，选自包括-H或具有1到6个碳原子的线性或支链烷基或共同形成具有5或6个原子的芳香或脂肪环的群体；Y和Z可以相同或不同，选自包括-H、-OH、-COOH、-OR3、-CH（OR3）COOH的群体，其中R3选自H、苯基、苄基、-CF3或-CF2CF3、乙烯基、丙烯基和具有1到6个碳原子的线性或支链烷基。
• COMPOUNDS AND THEIR SALTS SPECIFIC TO THE PPAR RECEPTORS AND THE EGF RECEPTORS AND THEIR USE IN THE MEDICAL FIELD
  申请人：Nogra Pharma Limited

  公开号：EP1910270B3

  公开（公告）日：2016-05-11