(3aR,4R,7R,7aR)-7-hydroxy-2,2-dimethyl-5-(4'-phenoxybenzenesulfonyl)hexahydro[1,3]dioxolo[4,5-c]-4-carboxylic acid benzyloxyamide | 642089-93-8

• 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: (3aR,4R,7R,7aR)-7-hydroxy-2,2-dimethyl-5-(4'-phenoxybenzenesulfonyl)hexahydro[1,3]dioxolo[4,5-c]-4-carboxylic acid benzyloxyamide
• 英文别名: (3aR,4R,7R,7aR)-7-hydroxy-2,2-dimethyl-5-(4'-phenoxybenzenesulfonyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridine-4-carboxylic acid benzyloxyamide；(3aR,4R,7R,7aR)-7-hydroxy-2,2-dimethyl-5-(4-phenoxyphenyl)sulfonyl-N-phenylmethoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide
• CAS: 642089-93-8
• 化学式: C₂₈H₃₀N₂O₈S
• 分子量: 554.621
• InChiKey: WWZUFKHAEVWBEN-VEYUFSJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  132
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (3aR,4R,7R,7aR)-7-hydroxy-2,2-dimethyl-5-(4'-phenoxybenzenesulfonyl)hexahydro[1,3]dioxolo[4,5-c]-4-carboxylic acid benzyloxyamide 在 palladium on activated charcoal Muromac 、 氢气 作用下， 以 甲醇 为溶剂， 反应 2.5h， 生成 (2R,3R,4R,5R)-3,4,5-trihydroxy-1-(4'-phenoxybenzenesulfonyl)-piperidine-2-carboxylic acid hydroxamide
  参考文献：
  名称：

  Azasugar-Based MMP/ADAM Inhibitors as Antipsoriatic Agents

  摘要：

  As a part of synthetic studies on MMP (matrix metalloproteinase)/ADAM (a disintegrin and metalloproteinase) inhibitors, we have preliminarily communicated that azasugar-based compound la exhibited a potential inhibitory activity on some metalloprotease-catalyzed proteolytic reactions. To find promising candidates for the topical treatment of psoriasis, we investigated stability in aqueous solution of compound la and its derivative 1b and then optimized the P1' substuent (2-5). In the present study, we synthesized novel derivatives of compound-la and evaluated their inhibitory activity toward MMP-1, -3, and -9, TACE, and HB-EGF shedding, from a viewpoint of versatility of azasugars as a functional scaffold. As a result, it was found that compound 1b demonstrated desirable inhibitory activity as an antipsoriatic agent, and some of the derivatives showed selective inhibitory activity. In addition, it was found that compound 1b exhibited a significant therapeutic effect on a mouse TPA-induced epidermal hyperplasia. model. Therefore, compound 1b could become a promising candidate as a practical antipsoriatic agent.

  DOI：

  10.1021/jm0304313
• 作为产物：
  描述：

  4-苯氧基苯磺酰氯 在 4-二甲氨基吡啶 、 sodium hydroxide 、 cerium(III) chloride 、 草酸 、 potassium carbonate 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.51h， 生成 (3aR,4R,7R,7aR)-7-hydroxy-2,2-dimethyl-5-(4'-phenoxybenzenesulfonyl)hexahydro[1,3]dioxolo[4,5-c]-4-carboxylic acid benzyloxyamide
  参考文献：
  名称：

  Azasugar-Based MMP/ADAM Inhibitors as Antipsoriatic Agents

  摘要：

  As a part of synthetic studies on MMP (matrix metalloproteinase)/ADAM (a disintegrin and metalloproteinase) inhibitors, we have preliminarily communicated that azasugar-based compound la exhibited a potential inhibitory activity on some metalloprotease-catalyzed proteolytic reactions. To find promising candidates for the topical treatment of psoriasis, we investigated stability in aqueous solution of compound la and its derivative 1b and then optimized the P1' substuent (2-5). In the present study, we synthesized novel derivatives of compound-la and evaluated their inhibitory activity toward MMP-1, -3, and -9, TACE, and HB-EGF shedding, from a viewpoint of versatility of azasugars as a functional scaffold. As a result, it was found that compound 1b demonstrated desirable inhibitory activity as an antipsoriatic agent, and some of the derivatives showed selective inhibitory activity. In addition, it was found that compound 1b exhibited a significant therapeutic effect on a mouse TPA-induced epidermal hyperplasia. model. Therefore, compound 1b could become a promising candidate as a practical antipsoriatic agent.

  DOI：

  10.1021/jm0304313

文献信息

• Novel azasugar derivative and drug containing the same as the active ingredient
  申请人：Tsukida Takahiro

  公开号：US20050137221A1

  公开（公告）日：2005-06-23

  A novel azasugar derivative, and a drug containing the same as an active ingredient are disclosed. The drug is useful for treatment of keratinocyte-proliferative diseases.

  本发明揭示了一种新型的氮杂糖衍生物以及含有该衍生物作为活性成分的药物。该药物可用于治疗角质形成细胞增殖性疾病。
• Azasugar derivative and drug containing the same as the active ingredient
  申请人：Carna Biosciences Inc.

  公开号：US07223779B2

  公开（公告）日：2007-05-29

  A novel azasugar derivative, and a drug containing the same as an active ingredient are disclosed. The drug is useful for treatment of keratinocyte-proliferative diseases.

  本发明揭示了一种新的氮杂糖衍生物，以及包含该衍生物作为活性成分的药物。该药物可用于治疗角质形成细胞增殖性疾病。
• NOVEL AZASUGAR DERIVATIVE AND DRUG CONTAINING THE SAME AS THE ACTIVE INGREDIENT
  申请人：Carna Biosciences Inc.

  公开号：EP1516872A1

  公开（公告）日：2005-03-23

  A novel azasugar derivative, and a drug containing the same as an active ingredient are disclosed. The drug is useful for treatment of keratinocyte-proliferative diseases.

  本发明公开了一种新型天苏糖衍生物和一种含有天苏糖衍生物作为活性成分的药物。该药物可用于治疗角质细胞增生性疾病。
• EP1516872
  申请人：——

  公开号：——

  公开（公告）日：——
• US7223779B2
  申请人：——

  公开号：US7223779B2

  公开（公告）日：2007-05-29