cis-N-[2-((E)-phenylvinyl)-1,3-dioxan-5-yl]benzamide

• 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: cis-N-[2-((E)-phenylvinyl)-1,3-dioxan-5-yl]benzamide
• 英文别名: N-[cis-2-((E)-styryl)-1,3-dioxan-5-yl]benzamide；(cis)-2-(E)-phenylpropenyl-5-benzoylamino-1,3-dioxane
• 化学式: C₁₉H₁₉NO₃
• 分子量: 309.365
• InChiKey: VLJJNYMWPICDPY-JZYAGYNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  trans-N-[2-((E)-phenylvinyl)-1,3-dioxan-5-yl]benzamide 在 盐酸 作用下， 反应 12.0h， 生成 cis-N-[2-((E)-phenylvinyl)-1,3-dioxan-5-yl]benzamide
  参考文献：
  名称：

  致力于化学预防剂的发展。第1部分：新型2，5-二取代的二氧杂环烷烃的设计，合成和抗炎活性。

  摘要：

  设计并通过立体选择性合成方法合成了一类新的2,5-二取代-二氧杂环戊烷作为癌症的化学预防剂。使用二甲苯诱导的小鼠耳朵水肿模型测试了这些化合物的抗炎活性。这些化合物中的某些具有比阿司匹林更好的抗炎活性，这表明它们可以进一步发展为潜在的抗炎药先导化合物。另外，这些抗炎药的治疗并未延长小鼠的尾巴出血时间。还分析了这些化合物之间的结构/活性关系。

  DOI：

  10.1016/j.bmc.2007.05.013

文献信息

• 5-Benzoylamino-1,3-dioxacyclanes, the method for preparing the same and their use as PKC inhibitor
  申请人：Zen Hayley

  公开号：US20050043396A1

  公开（公告）日：2005-02-24

  The present invention discloses a series of benzoylamino-1,3-dioxacyclane compounds, of which compounds 1-21 were prepared via transacetalisation reaction between N-benzoylaminoglycol and 1,1,3,3-tetramethoxypropane; while compounds 22-48 were prepared via stereospecific acetalisation reaction between N-benzoylamino glycol and aromatic aldehyde, and if necessary, the nitro groups were reduced and further be salified with propane diacid and L-Arg or L-Lys. These compounds possess the structural type of PKC inhibitor and positive anti-inflammatory effect, and can be applied in medical fields as PKC inhibitor for corresponding therapy.

  本发明公开了一系列苯甲酰氨基-1,3-二氧杂环丁烷化合物，其中化合物1-21是通过N-苯甲酰氨基乙醇与1,1,3,3-四甲氧基丙烷之间的缩酮化反应制备的；而化合物22-48是通过N-苯甲酰氨基乙醇与芳香醛之间的立体特异性缩醛化反应制备的，如果有必要，可以将硝基还原，并进一步与丙烷二酸和L-精氨酸或L-赖氨酸成盐。这些化合物具有PKC抑制剂的结构类型和积极的抗炎效果，并且可以作为PKC抑制剂应用于医学领域的相应治疗。
• Toward the development of chemoprevention agents. Part II: Chemo-enzymatic synthesis and anti-inflammatory activities of a new class of 5-amino-2-substitutedphenyl-1,3-dioxacycloalkanes
  作者：Keli Gu、Lanrong Bi、Ming Zhao、Chao Wang、Jingfang Ju、Shiqi Peng

  DOI：10.1016/j.bmc.2007.06.018

  日期：2007.9

  A new series of optically pure 5-amino-2-substitutedphenyl-1,3-dioxacyclozilkanes were designed and synthesized via a chemo-enzymatic combined method to develop new chemoprevention agents. Twenty-four of newly synthesized compounds significantly inhibited xylene-induced rat ear edema and exhibited comparable or better anti-inflammatory activities than the reference drug aspirin. Treatment of these anti-inflammatory agents did not prolong the tail bleeding time in rat. In addition, 5-amino-2-substitutedphenyl- I 3-dioxacycloalkanes exhibited good membrane permeability based on in vitro Caco-2 cell monolayer permeability assay. Furthermore, some preliminary structure-activity relationships were further analyzed among these compounds. Taken together, 5-amino-2-substitutedphenyl-1,3-dioxacycloalkanes may represent a new class of anti-inflammatory drugs with safer pharmacological profile. (c) 2007 Elsevier Ltd. All rights reserved.