6-methyl-benzo[1,3]dioxole-5-sulfonic acid 3-hydrazinocarbonyl-phenyl ester | 930088-11-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 6-methyl-benzo[1,3]dioxole-5-sulfonic acid 3-hydrazinocarbonyl-phenyl ester
• 英文别名: [3-(Hydrazinecarbonyl)phenyl] 6-methyl-1,3-benzodioxole-5-sulfonate
• CAS: 930088-11-2
• 化学式: C₁₅H₁₄N₂O₆S
• 分子量: 350.352
• InChiKey: BPFJAVCBYIFGMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  125
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-methyl-benzo[1,3]dioxole-5-sulfonic acid 3-hydrazinocarbonyl-phenyl ester 、 4-氰基苯甲醛 在 盐酸 作用下， 以 乙醇 为溶剂， 以94%的产率得到LASSBio-774
  参考文献：
  名称：

  Synthesis and anti-platelet activity of novel arylsulfonate–acylhydrazone derivatives, designed as antithrombotic candidates

  摘要：

  In this work, we describe a new class of promising anti-platelet drug candidates with significant antithrombotic activity in vivo. This new series of compounds was structurally planned by modification of known thrombin inhibitors based on the use of acylhydrazone subunit, as a non-peptide scaffold, and variations at PI moiety. Three different families of arylsulfonate-acylhydrazone derivatives were designed. The bioassays indicated the first class of derivatives represented by 4f (LASSBio-693) and 4j (LASSBio-743), which were active in inhibiting the platelet aggregation induced by thrombin. The second class represented by compounds 4e (LASSBio-774) and 4h (LASSBio-480) that selectively inhibit the platelet aggregation involving TXA(2) formation. Finally, the third class of derivatives was identified acting as a novel symbiotic agent able to inhibit the platelet aggregation induced by collagen or AA and by thrombin, represented by compounds 4b (LASSBio-694) and 4g (LASSBio-770). (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.03.032
• 作为产物：
  描述：

  3-(6-methyl-benzo[1,3]dioxole-5-sulfonyloxy)-benzoic acid methyl ester 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以78%的产率得到6-methyl-benzo[1,3]dioxole-5-sulfonic acid 3-hydrazinocarbonyl-phenyl ester
  参考文献：
  名称：

  Synthesis and anti-platelet activity of novel arylsulfonate–acylhydrazone derivatives, designed as antithrombotic candidates

  摘要：

  In this work, we describe a new class of promising anti-platelet drug candidates with significant antithrombotic activity in vivo. This new series of compounds was structurally planned by modification of known thrombin inhibitors based on the use of acylhydrazone subunit, as a non-peptide scaffold, and variations at PI moiety. Three different families of arylsulfonate-acylhydrazone derivatives were designed. The bioassays indicated the first class of derivatives represented by 4f (LASSBio-693) and 4j (LASSBio-743), which were active in inhibiting the platelet aggregation induced by thrombin. The second class represented by compounds 4e (LASSBio-774) and 4h (LASSBio-480) that selectively inhibit the platelet aggregation involving TXA(2) formation. Finally, the third class of derivatives was identified acting as a novel symbiotic agent able to inhibit the platelet aggregation induced by collagen or AA and by thrombin, represented by compounds 4b (LASSBio-694) and 4g (LASSBio-770). (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.03.032