(2S,4R,5R)-(2-phenyl-4-methyl-1,3-dioxan-5-yl)amine | 133710-95-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: (2S,4R,5R)-(2-phenyl-4-methyl-1,3-dioxan-5-yl)amine
• 英文别名: (2S,4R,5R)-4-methyl-2-phenyl-1,3-dioxan-5-amine
• CAS: 133710-95-9
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: FJCXCMWNVJCQIE-IEBDPFPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,4R,5R)-(2-phenyl-4-methyl-1,3-dioxan-5-yl)amine 、 苯甲酰氯 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 3.0h， 生成 N-[(2S,4R,5R)-2-phenyl-4-methyl-1,3-dioxan-5-yl]benzamide
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2007.06.018
• 作为产物：
  描述：

  N-[(2S,4R,5R)-2-phenyl-4-methyl-1,3-dioxan-5-yl]phenylacetamide 在 盐酸 、 penicillin acylase 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 (2S,4R,5R)-(2-phenyl-4-methyl-1,3-dioxan-5-yl)amine
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2007.06.018

文献信息

• Toward the development of chemoprevention agents (III): Synthesis and anti-inflammatory activities of a new class of 5-glycylamino-2-substituted-phenyl-1,3-dioxacycloalkanes
  作者：Lanrong Bi、Ming Zhao、Keli Gu、Chao Wang、Jingfang Ju、Shiqi Peng

  DOI：10.1016/j.bmc.2007.11.017

  日期：2008.2.15

  A new series of 5-glycylamino-2-substituted-phenyl-1,3-dioxacycloalkanes were designed and synthesized. The anti-inflammatory activities of these compounds were tested using the xylene-induced mouse ear edema model. Sixteen of these new compounds exhibited comparable or better anti-inflammatory activities than aspirin suggesting that they can be further developed as potential anti-inflammatory drug leads. In addition, treatment with these anti-inflammatory agents did not prolong tail bleeding time in mice. The structure/activity relationships were also analyzed among these compounds. Considering their good efficacy and safety profiles, some 5-glycylamino-2-substituted-phenyl-1,3-dioxacycloalkanes are worthy to be explored further in assessing the possible link between anti-inflammation and cancer prevention. (C) 2007 Elsevier Ltd. All rights reserved.
• 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.