1,2,3-Trimethoxy-10-methylmercapto-6,7-dihydro-5H-benzoheptalen-9-on | 1935-00-8

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 英文名称: 1,2,3-Trimethoxy-10-methylmercapto-6,7-dihydro-5H-benzoheptalen-9-on
• 英文别名: 1,2,3-trimethoxy-10-methylsulfanyl-6,7-dihydro-5H-benzo[a]heptalen-9-one
• CAS: 1935-00-8
• 化学式: C₂₀H₂₂O₄S
• 分子量: 358.458
• InChiKey: LUYGHURNISJMBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  70.1
• 氢给体数：
  0
• 氢受体数：
  5

上下游信息

反应信息

• 作为产物：
  描述：

  Desacetamido-colchicein 在 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 1,2,3-Trimethoxy-10-methylmercapto-6,7-dihydro-5H-benzoheptalen-9-on
  参考文献：
  名称：

  Discovery of structurally simplified analogs of colchicine as an immunosuppressant

  摘要：

  We have discovered a new class of colchicine-derived therapeutic agents for immune diseases including rejection of organ-transplantation and autoimmune disease. Compound 2, which had been developed to overcome poor pharmacokinetic properties of compound 1, a first-generation colchicine analog, turned out to show toxicity such as intestinal toxicity and loss of weight during in vivo tests. The deletion of 7-carboxamide group and middle ring-truncation in colchicine allowed us to have structurally simplified analogs with strong immunosuppressive activity. Herein, we report non-alkaloid tricyclic compound 7 and 12 as immunosuppressants which exhibited a strong immunosuppressive in vivo efficacy on the T-dependent antibody response, the Zymosan A-induced arthritis model and the Carrageenan-induced edema model. Compound 7 and 12 revealed less toxicity than the previous lead compound 2, and their minimum lethal doses (MLD) were proved to exceed 100 mg/kg. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.007

文献信息

• Novel tricyclic derivatives and their use
  申请人：Chang Dong Jo

  公开号：US20070021427A1

  公开（公告）日：2007-01-25

  The present invention relates to tricyclic colchicine derivatives represented by the formulas (I) or (II), pharmaceutically acceptable salts thereof, and a method for providing an immuno-suppressive or immuno-modulating effect, an anti-proliferative effect, an anti-inflammatory effect or a method for treating cancer comprising administering to a patient an effective amount of one or more colchicine derivatives:

  本发明涉及三环秋水仙素衍生物，其公式表示为(I)或(II)，以及其药学上可接受的盐，以及提供免疫抑制或免疫调节作用、抗增殖作用、抗炎作用或治疗癌症的方法，包括向患者施用一种或多种秋水仙素衍生物的有效量。
• Drugs with improved hydrophobicity for incorporation in medical devices
  申请人：Abraxis BioScience, LLC

  公开号：EP2896412A1

  公开（公告）日：2015-07-22

  The invention provides a medical device comprising a hydrophobic analog of a medicament known to inhibit cell proliferation and migration. The invention also provides a method of treating a narrowing in a body passageway comprising placing an implantable medical device comprising a hydrophobic analog of a medicament known to inhibit cell proliferation and migration. The medicaments can be incorporated within or coated on the device. The invention further provides hydrophobic analogs of medicaments known to inhibit cell proliferation and migration.

  本发明提供了一种医疗装置，其中包含一种已知可抑制细胞增殖和迁移的药物的疏水性类似物。本发明还提供了一种治疗身体通道狭窄的方法，该方法包括放置一种可植入的医疗设备，该设备包含一种已知可抑制细胞增殖和迁移的疏水性类似药剂。这些药剂可以掺入装置中，也可以涂在装置上。本发明进一步提供了已知可抑制细胞增殖和迁移的药物疏水性类似物。
• DRUGS WITH IMPROVED HYDROPHOBICITY FOR INCORPORATION IN MEDICAL DEVICES
  申请人：Abraxis BioScience, LLC

  公开号：EP1861070B1

  公开（公告）日：2018-01-17
• TRICYCLIC DERIVATIVES OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF, THEIR PREPARATIONS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：JE IL Pharmaceutical Co., Ltd.

  公开号：EP1646608B1

  公开（公告）日：2011-03-02
• Discovery of structurally simplified analogs of colchicine as an immunosuppressant
  作者：Dong-Jo Chang、Wan-Joo Kim

  DOI：10.1016/j.bmcl.2014.05.007

  日期：2014.7

  We have discovered a new class of colchicine-derived therapeutic agents for immune diseases including rejection of organ-transplantation and autoimmune disease. Compound 2, which had been developed to overcome poor pharmacokinetic properties of compound 1, a first-generation colchicine analog, turned out to show toxicity such as intestinal toxicity and loss of weight during in vivo tests. The deletion of 7-carboxamide group and middle ring-truncation in colchicine allowed us to have structurally simplified analogs with strong immunosuppressive activity. Herein, we report non-alkaloid tricyclic compound 7 and 12 as immunosuppressants which exhibited a strong immunosuppressive in vivo efficacy on the T-dependent antibody response, the Zymosan A-induced arthritis model and the Carrageenan-induced edema model. Compound 7 and 12 revealed less toxicity than the previous lead compound 2, and their minimum lethal doses (MLD) were proved to exceed 100 mg/kg. (C) 2014 Elsevier Ltd. All rights reserved.