1-nitro-3-(2-chloro-2-nitroethenyl)benzene | 127143-24-2

• 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: 1-nitro-3-(2-chloro-2-nitroethenyl)benzene
• 英文别名: (Z)-(2-chloro-2-nitroethenyl)-3-nitrobenzene；(Z)-1-(2-chloro-2-nitrovinyl)-3-nitrobenzene；1-[(Z)-2-chloro-2-nitroethenyl]-3-nitrobenzene
• CAS: 127143-24-2
• 化学式: C₈H₅ClN₂O₄
• 分子量: 228.592
• InChiKey: JIDCHUYSPMETFP-VMPITWQZSA-N

物化性质

• 沸点：
  350.7±37.0 °C(Predicted)
• 密度：
  1.526±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 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：
  91.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-nitro-3-(2-chloro-2-nitroethenyl)benzene 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 8-allyl-3-nitro-2-(3-nitrophenyl)-4H-1-benzopyran-4-one
  参考文献：
  名称：

  新型黄酮8-乙酸衍生物作为氨基肽酶N / CD13的可逆抑制剂的合成和生物学评估。

  摘要：

  在肿瘤细胞中过表达的细胞表面氨肽酶N（APN / CD13）在血管生成中起关键作用。然而，缺乏该蛋白的有效的，选择性的，尤其是非细胞毒性的抑制剂，并且目前的工作是为了开发与APN / CD13结合的新一代非细胞毒性的抑制剂。在这种情况下，我们合成了一系列新的黄酮8-乙酸衍生物。在本文所述和评估的化合物中，2'，3-二硝基黄酮8-乙酸（19b）被证明是最有效的，其IC（50）为25 microM，是Bestatin（1）的2.5倍。 ），这是APN / CD13的天然已知抑制剂。但是，与Bestatin（1）相反，二硝基黄酮19b不会对培养的人类模型细胞产生任何细胞毒性。在B苯基的3'-或4'-位上存在其他取代基，例如NO（2）或OCH（3），或存在空间限制（化合物24和29），都不能提高选择性和效力。黄酮19b对APN / CD13的亲和力无法用其他蛋白酶回收，例如基质金属蛋白酶9（MMP-9），血管紧张素转化酶（ACE

  DOI：

  10.1021/jm021109f
• 作为产物：
  描述：

  间硝基苯甲醛 在 (二氯碘)-苯 、 ammonium acetate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 1-nitro-3-(2-chloro-2-nitroethenyl)benzene
  参考文献：
  名称：

  Biological evaluation and SAR analysis of novel covalent inhibitors against fructose-1,6-bisphosphatase

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2020.115624

文献信息

• A Convenient Synthesis of 3-Chloro-3,4-dihydro-4-hydroxy-3-nitro-2-phenyl-2<i>H</i>-1-benzopyrans
  作者：Daniel Dauzonne、Pierre Demerseman

  DOI：10.1055/s-1990-26791

  日期：——

  The novel title compounds 5 are prepared by a simple and efficient two-step procedure starting from substituted benzaldehydes 1. A convenient route to the (2-chloro-2-nitroethenyl)benzenes 3 required as intermediates in the synthesis is reported.

  以取代苯甲醛1为起始原料，通过简便高效的两步法制备了新颖标题化合物5。报道了一条便捷的途径，用于合成为合成所需的中间体——(2-氯-2-硝基乙烯基)苯3。
• Synthesis and Biological Evaluation of 5-Arylfuro(2,3-d)pyrimidines as Novel Dihydrofolate Reductase Inhibitors.
  作者：Farid WAHID、Claude MONNERET、Daniel DAUZONNE

  DOI：10.1248/cpb.47.156

  日期：——

  A series of about fifty novel 5-arylfuro[2,3-d]pyrimidine derivatives were synthesized as potential inhibitors of dihydrofolate reductase (DHFR) arising from different species. Weak enzyme inhibition was observed for most of the compounds, with only a few reaching IC50 values less than 30 microM. With regards to antibacterial and anti-malarial potency, only seven compounds showed a modest in vitro

  合成了一系列约五十种新颖的5-芳基呋喃[2,3-d]嘧啶衍生物，作为潜在的抑制剂，其来自不同物种的二氢叶酸还原酶（DHFR）。对于大多数化合物，酶抑制作用较弱，只有少数达到的IC50值小于30 microM。关于抗菌和抗疟疾效力，只有七种化合物显示出对某些细菌菌株的适度体外活性，只有三种产物证明对恶性疟原虫具有显着活性。
• A convenient procedure for the preparation of 5,6-dihydro-6-nitro-5-phenylfuro[2,3-d]pyrimidin-4(3H)-ones and 5-phenylfuro[2,3-d]pyrimidin-4(3H)-ones
  作者：Daniel Dauzonne、Anne Adam-Launay

  DOI：10.1016/s0040-4020(01)92249-5

  日期：1992.4

  Z-(2-chloro-2-nitroethenyl)benzenes with 4,6-dihydroxypyrimidine provides 5,6-dihydro-6-nitro-5-phenylfuro[2,3-d]pyrimidin-4(3H)-ones at room temperature. Involving the same starting materials, but using DBU in refluxing ethanol instead of triethylamine, the so far unknown 5-phenylfuro[2,3-d]pyrimidin-4(3H-ones are obtained

  Z-（2-氯-2-硝基乙烯基）苯与4,6-二羟基嘧啶的三乙胺促进的缩合反应提供5,6-二氢-6-硝基-5-苯基呋喃[2,3-d]嘧啶-4（3 H）-在室温下一个。使用相同的起始原料，但在回流的乙醇中使用DBU代替三乙胺，获得了迄今未知的5-苯基呋喃[2,3-d]嘧啶-4（3 H -ones）
• Aleksiev, D. I.; Ivanova, S., Phosphorus, Sulfur and Silicon and the Related Elements, 1995, vol. 101, # 1-4, p. 109 - 116
  作者：Aleksiev, D. I.、Ivanova, S.

  DOI：——

  日期：——
• (2-chloro-2-nitroethenyl)benzenes as synthons: a general method for the preparation of 2,3-dihydro- 2-nitro-3-phenyl-4H-furo [3,2-c] [1]benzopyran-4-ones and 3-phenyl-4H-furo[3,2-c][1]benzopyran-4-ones
  作者：Daniel Dauzonne、Hubert Josien、Pierre Demerseman

  DOI：10.1016/s0040-4020(01)89053-0

  日期：1990.1