3,5-dinitrocinnamic acid | 137348-83-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3,5-dinitrocinnamic acid
• 英文别名: (E)-3-(3,5-dinitrophenyl)prop-2-enoic acid
• CAS: 137348-83-5
• 化学式: C₉H₆N₂O₆
• 分子量: 238.156
• InChiKey: RTQOYSSNAMTQMS-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 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：
  129
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,5-dinitrocinnamic acid 在 吡啶 、 4-二甲氨基吡啶 、 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 35.0h， 生成 ((2R,3S,4S,4aR,10bS)-3,4,8,10-tetrahydroxy-9-methoxy-6-oxo-2,3,4,4a,6,10b-hexahydropyrano[3,2-c]isochromen-2-yl)methyl (E)-3-(3,5-dinitrophenyl)acrylate
  参考文献：
  名称：

  Synthesis and in vitro and in vivo antitumour activity study of 11-hydroxyl esterified bergenin/cinnamic acid hybrids

  摘要：

  Fourteen bergenin/cinnamic acid hybrids were synthesized, characterized and evaluated for their anti-tumour activity both in vitro and in vivo. The most potent compound, 5c, arrested HepG2 cells (IC50 = 4.23 +/- 0.79 mu M) in the G2/M phase and induced cellular apoptosis. Moreover, compound 5c was also found to suppress the tumour growth in Heps xenograft-bearing mice with low toxicity. In the mechanistic study, 5c administration ignited a mitochondria-mediated apoptosis pathway of HepG2 cell death. Furthermore, 5c activated Akt-dependent pathways and further decreased the expression of the Bc1-2 family of proteins. The downstream mitochondrial p53 translocation was also significantly activated, accompanied by an increase of the caspase-9, caspase-3 activation. These data imply that bergenin/cinnamic acid hybrids could serve as novel Akt/Bcl-2 inhibitors for further preclinical studies. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.03.053
• 作为产物：
  描述：

  丙二酸 、 3,5-二硝基苯甲醛 在 哌啶 、 吡啶 作用下， 反应 6.0h， 生成 3,5-dinitrocinnamic acid
  参考文献：
  名称：

  [EN] SUBSTITUTED 1,2,4-OXADIAZOLE, ITS APPLICATION AND A PHARMACEUTICAL PREPARATION COMPRISING IT
  [FR] 1,2,4-OXADIAZOLE SUBSTITUÉ, SON APPLICATION ET PRÉPARATION PHARMACEUTIQUE LE COMPRENANT

  摘要：

  基于通式I的取代1,2,4-噁二唑，其中Y = S或CH2，R = 苯基或在2,3,4和5位上被一个或多个电子受体基团或电子给体基团取代的苯基。这些化合物可以通过简单的合成方法制备，并具有低毒性和高效抗结核分枝杆菌的特性，包括多重耐药菌株。本发明还揭示了一种含有通式I的取代1,2,4-噁二唑作为活性物质的药物制剂，以及将这种取代1,2,4-噁二唑用作抗结核药物的用途。

  公开号：

  WO2020128675A1

文献信息

• Mehta; Musso; White, European Journal of Medicinal Chemistry, 1985, vol. 20, # 5, p. 443 - 446
  作者：Mehta、Musso、White

  DOI：——

  日期：——
• Methyl 3,5-Dinitro-trans-cinnamate
  作者：C. V. K. Sharma、K. Panneerselvam、G. R. Desiraju、T. Pilati

  DOI：10.1107/s010827019500237x

  日期：1995.7.15

  The title compound, C10H8N2O6, forms C-H ... O hydrogen-bonded inversion dimers in the crystal with a calculated (AM1) energy of -8.2 kcal mol(-1) (1 cal = 4.184 J). These dimers in turn form a planar sheet structure which is stacked along the [100] direction.
• SUBSTITUTED 1,2,4-OXADIAZOLE, ITS APPLICATION AND A PHARMACEUTICAL PREPARATION COMPRISING IT
  申请人：SVENOX PHARMACEUTICALS LLC

  公开号：US20210403443A1

  公开（公告）日：2021-12-30

  Disclosed are compounds effective against tuberculosis based on substituted 1,2,4-oxadiazoles of general formula I, where Y═S or CH 2 and R=phenyl- or phenyl-substituted in positions 2, 3, 4, and 5 by one or several electron-acceptor groups or electron-donor groups. These compounds can be produced by easy syntheses and are characterized by low toxicity and high efficacy against mycobacteria, including multiresistant strains thereof. Also disclosed are a pharmaceutical preparation containing substituted 1,2,4-oxadiazole of formula I as an active substance as well as the use of this substituted 1,2,4-oxadiazole as an antituberculosis drug.
• Synthesis and in vitro and in vivo antitumour activity study of 11-hydroxyl esterified bergenin/cinnamic acid hybrids
  作者：Chengyuan Liang、Shaomeng Pei、Weihui Ju、Minyi Jia、Danni Tian、Yonghong Tang、Gennian Mao

  DOI：10.1016/j.ejmech.2017.03.053

  日期：2017.6

  Fourteen bergenin/cinnamic acid hybrids were synthesized, characterized and evaluated for their anti-tumour activity both in vitro and in vivo. The most potent compound, 5c, arrested HepG2 cells (IC50 = 4.23 +/- 0.79 mu M) in the G2/M phase and induced cellular apoptosis. Moreover, compound 5c was also found to suppress the tumour growth in Heps xenograft-bearing mice with low toxicity. In the mechanistic study, 5c administration ignited a mitochondria-mediated apoptosis pathway of HepG2 cell death. Furthermore, 5c activated Akt-dependent pathways and further decreased the expression of the Bc1-2 family of proteins. The downstream mitochondrial p53 translocation was also significantly activated, accompanied by an increase of the caspase-9, caspase-3 activation. These data imply that bergenin/cinnamic acid hybrids could serve as novel Akt/Bcl-2 inhibitors for further preclinical studies. (C) 2017 Elsevier Masson SAS. All rights reserved.
• [EN] SUBSTITUTED 1,2,4-OXADIAZOLE, ITS APPLICATION AND A PHARMACEUTICAL PREPARATION COMPRISING IT<br/>[FR] 1,2,4-OXADIAZOLE SUBSTITUÉ, SON APPLICATION ET PRÉPARATION PHARMACEUTIQUE LE COMPRENANT
  申请人：SVENOX PHARMACEUTICALS LLC

  公开号：WO2020128675A1

  公开（公告）日：2020-06-25

  Substances effective against tuberculosis based on substituted 1,2,4-oxadiazoles of general formula I, where Y = S or CH2 and R = phenyl- or phenyl- substituted in positions 2, 3, 4, and 5 by one or several electron-acceptor groups or electron-donor groups. These compounds can be produced by easy syntheses and are characterized by low toxicity and high efficacy against mycobacteria, including multiresistant strains thereof. The invention also discloses a pharmaceutical preparation containing substituted 1,2,4-oxadiazole of formula I as active substance as well as the use of this substituted 1,2,4-oxadiazole as an antituberculosis drug.

  基于通式I的取代1,2,4-噁二唑，其中Y = S或CH2，R = 苯基或在2,3,4和5位上被一个或多个电子受体基团或电子给体基团取代的苯基。这些化合物可以通过简单的合成方法制备，并具有低毒性和高效抗结核分枝杆菌的特性，包括多重耐药菌株。本发明还揭示了一种含有通式I的取代1,2,4-噁二唑作为活性物质的药物制剂，以及将这种取代1,2,4-噁二唑用作抗结核药物的用途。