2-methoxy-5-(3-(2,3,4-trimethoxyphenyl)prop-1-en-1-yl)cyclohepta-2,4,6-trien-1-one | 1616515-32-2

• 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: 2-methoxy-5-(3-(2,3,4-trimethoxyphenyl)prop-1-en-1-yl)cyclohepta-2,4,6-trien-1-one
• CAS: 1616515-32-2
• 化学式: C₂₀H₂₂O₅
• 分子量: 342.392
• InChiKey: ZQWDZGGDHRPYPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  环庚三烯酚酮 在 platinum(IV) oxide 、 硫酸 、 氢气 、 palladium diacetate 、 potassium carbonate 、 溶剂黄146 、 三苯基膦 、 silver carbonate 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 为溶剂， 生成 2-methoxy-5-(3-(2,3,4-trimethoxyphenyl)prop-1-en-1-yl)cyclohepta-2,4,6-trien-1-one
  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

• 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.