(E)-3-(2-nitrovinyl)benzoic acid | 5006-03-1

• 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: (E)-3-(2-nitrovinyl)benzoic acid
• 英文别名: m-(2-nitrovinyl)-benzoic acid；3-(trans-2-nitro-vinyl)-benzoic acid；3-(trans-2-Nitro-vinyl)-benzoesaeure；1-(3-Carboxyphenyl)-2-nitroethene；3-[(E)-2-nitroethenyl]benzoic acid
• CAS: 5006-03-1
• 化学式: C₉H₇NO₄
• 分子量: 193.159
• InChiKey: GGKIXJPRNNYPLG-SNAWJCMRSA-N

物化性质

• 熔点：
  193-194 °C
• 沸点：
  407.1±28.0 °C(Predicted)
• 密度：
  1.387±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 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：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-(2-nitrovinyl)benzoic acid 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 7.5h， 生成 m-(2-nitrovinyl)-benzoyl-alanine mercaptopropionic acid adduct
  参考文献：
  名称：

  Studies on peptides. CXXII. N-Succinimidyl-p-(2-nitrovinyl)-benzoate and its m-isomer, as heterobifunctional conjugatin reagents for immunoassay.

  摘要：

  N-琥珀酰亚胺基对位和间位（2-硝基乙烯基）苯甲酸酯（SNVB）被引入作为免疫测定中的异双功能偶联剂。这些试剂在酸性介质中与SH化合物（如半胱氨酸或巯基丙酸）顺利反应，然后在略碱性条件下与丙氨酸反应，生成相应的苯甲�丙氨酸衍生物。基于这些模型实验，讨论了这些试剂在实际应用中的可行性。

  DOI：

  10.1248/cpb.32.5036
• 作为产物：
  描述：

  硝基甲烷 、 3-羧基苯甲醛 生成 (E)-3-(2-nitrovinyl)benzoic acid
  参考文献：
  名称：

  THE POLAR EFFECT OF THE β-NITROVINYL GROUP

  摘要：

  苯酚和苯甲酸的甲基和对位β-硝基乙烯衍生物已被合成。测定了每种化合物的酸度常数pK_a，并从这些值中得到了β-硝基乙烯基团的以下Hammett西格玛常数：σ_meta = 0.34，σ_para = 0.26，σ⁻ = 0.88。讨论了这些值与β-硝基乙烯基团对亲电取代的定向效应之间的关系。

  DOI：

  10.1139/v57-204

文献信息

• [EN] INHIBITOR COMPOUNDS<br/>[FR] COMPOSÉS À TITRE D'INHIBITEURS
  申请人：AZERIA THERAPEUTICS LTD

  公开号：WO2020212697A1

  公开（公告）日：2020-10-22

  The present invention relates to compounds of Formula (I) that function as inhibitors of serum and glucocorticoid regulated kinase (SGK) activity: Formula (I) wherein X1, X2, Y1, Y2, Y3, Y4, R2, R3, Y and Z are each as defined herein. The present invention also relates to processes for the preparation of these compounds, to pharmaceutical compositions comprising them, and to their use in the treatment of proliferative disorders, such as cancer, as well as other diseases or conditions in which SGK activity is implicated.

  本发明涉及作为血清和糖皮质激素调节激酶（SGK）活性抑制剂的化合物的公式（I）：公式（I）其中X1、X2、Y1、Y2、Y3、Y4、R2、R3、Y和Z分别如本文所定义。本发明还涉及制备这些化合物的方法，包括含有它们的药物组合物，以及它们在治疗增殖性疾病（如癌症）以及其他涉及SGK活性的疾病或症状中的用途。
• Carboxylate Salt Bridge-Mediated Enamine Catalysis: Expanded Michael Reaction Substrate Scope and Facile Access to Antidepressant (<i>R</i>)-Pristiq
  作者：Thomas C. Nugent、Hussein Ali El Damrany Hussein、Shahzad Ahmed、Foad Tehrani Najafian、Ishtiaq Hussain、Tony Georgiev、Mahmoud Khalaf Aljoumhawy

  DOI：10.1002/adsc.201700801

  日期：2017.8.17

  We report broad guidance on how to catalyze enantioselective aldehyde additions to nitroalkene or maleimide Michael electrophiles in the presence of unprotected acidic spectator groups, e.g., carboxylic acids, acetamides, phenols, catechols, and maleimide NH groups. Remarkably, these l‐threonine and l‐serine potassium salt‐catalyzed reactions proceed even when the nucleophilic and electrophilic Michael

  我们报告了如何在未保护的酸性旁观者基团（例如羧酸，乙酰胺，苯酚，儿茶酚和马来酰亚胺NH基团）的存在下，如何催化对硝基烯或马来酰亚胺Michael亲电试剂加成对映选择性醛的广泛指导。值得注意的是，这些l-苏氨酸和l即使亲核和亲电迈克尔伙伴同时包含酸性旁观者基团，丝氨酸钾盐催化的反应也会继续进行。这些发现开始解决了在酸性部分存在下对映选择性催化反应的历史不相容性，并同时侵犯了通常与细胞环境有关的观众群体的耐受性。从催化剂使能的烯胺到迈克尔·亲电试剂的羧酸盐桥被认为有助于扩大迈克尔·底物的分布。这些努力的实际成果是以新合成路线合成抗抑郁药（R）-Pristiq，（-）- O-去甲基甲基文拉法辛，由于不需要保护基，因此迄今已知的最高收率。
• Synthesis and biological evaluation of novel inhibitors against 1,3,8-trihydroxynaphthalene reductase from Magnaporthe grisea
  作者：Haifeng Chen、Xinya Han、Nian Qin、Lin Wei、Yue Yang、Li Rao、Bo Chi、Lingling Feng、Yanliang Ren、Jian Wan

  DOI：10.1016/j.bmc.2016.01.053

  日期：2016.3

  1,3,8-Trihydroxynaphthalene reductase (3HNR) is an essential enzymes that is involved in fungal melanin biosynthesis. Based on the structural informations of active site of 3HNR, a series of β-nitrostyrene compounds were rationally designed and synthesized. The enzymatic activities of these compounds showed that most of them exhibited high inhibitory activities (<5.0 μM) against 3HNR; compound 3-2

  1,3,8-三羟基萘还原酶（3HNR）是参与真菌黑色素生物合成的必需酶。根据3HNR活性位点的结构信息，合理设计合成了一系列β-硝基苯乙烯化合物。这些化合物的酶促活性表明，它们中的大多数对3HNR表现出高抑制活性（<5.0μM）。化合物3-2表现出最高的抑制活性（IC 50  = 0.29μM）。特别地，这些化合物中的一些对稻瘟病菌具有中等的杀真菌活性。化合物3-4显示出对稻瘟病菌的高体内活性（EC 50  = 9.5 ppm）。此外，化合物3-2以分子为代表，选择该化合物与3HNR活性位点周围残基的可能结合方式。阳性结果表明，β-硝基苯乙烯衍生物最有可能成为发现稻瘟病新药的诱因。
• Biological evaluation and SAR analysis of novel covalent inhibitors against fructose-1,6-bisphosphatase
  作者：Xinya Han、Yunyuan Huang、Lin Wei、Haifeng Chen、Yanrong Guo、Zilong Tang、Wei Hu、Qinfei Xia、Qi Wang、Jufen Yan、Yanliang Ren

  DOI：10.1016/j.bmc.2020.115624

  日期：2020.9

  Fructose-1,6-bisphosphatase (FBPase) is an attractive target for affecting the GNG pathway. In our previous study, the C128 site of FBPase has been identified as a new allosteric site, where several nitrovinyl compounds can bind to inhibit FBPase activity. Herein, a series of nitrostyrene derivatives were further synthesized, and their inhibitory activities against FBPase were investigated in vitro. Most of the prepared nitrostyrene compounds exhibit potent FBPase inhibition (IC50 10 mu M). Specifically, when the substituents of F, Cl, OCH3, CF3, OH, COOH, or 2-nitrovinyl were installed at the R-2 (meta-) position of the benzene ring, the FBPase inhibitory activities of the resulting compounds increased 4.5-55 folds compared to those compounds with the same groups at the R-1 (para-) position. In addition, the preferred substituents at the R-3 position were Cl or Br, thus compound HS36 exhibited the most potent inhibitory activity (IC50 = 0.15 mu M). The molecular docking and site-directed mutation suggest that C128 and N125 are essential for the binding of HS36 and FBPase, which is consistent with the C128-N125-S123 allosteric inhibition mechanism. The reaction enthalpy calculations show that the order of the reactions of compounds with thiol groups at the R-3 position is Cl H > CH3. CoMSIA analysis is consistent with our proposed binding mode. The effect of compounds HS12 and HS36 on glucose production in primary mouse hepatocytes were further evaluated, showing that the inhibition was 71% and 41% at 100 mu M, respectively.
• SALTS OF PAROXETINE
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP1091958A1

  公开（公告）日：2001-04-18