Domesticin | 476-71-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 阿朴菲
• 英文名称: Domesticin
• 英文别名: (+)-domesticine；Domesticine；(12S)-18-methoxy-13-methyl-5,7-dioxa-13-azapentacyclo[10.7.1.02,10.04,8.016,20]icosa-1(20),2,4(8),9,16,18-hexaen-19-ol
• CAS: 476-71-1
• 化学式: C₁₉H₁₉NO₄
• 分子量: 325.364
• InChiKey: ZMNSHBTYBQNBPV-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  苯甲酸酐 、 Domesticin 在 4-二甲氨基吡啶 、 三乙胺 作用下， 生成 [(12S)-18-methoxy-13-methyl-5,7-dioxa-13-azapentacyclo[10.7.1.02,10.04,8.016,20]icosa-1(20),2,4(8),9,16,18-hexaen-19-yl] benzoate
  参考文献：
  名称：

  Cytotoxicity of aporphines in human colon cancer cell lines HCT-116 and Caco-2: An SAR study

  摘要：

  A series of synthetic aporphine derivatives structurally related to domesticine and nantenine (ring A, N6 and ring C truncated analogs), was evaluated in MTS cytotoxicity assays against the human colon cancer cell lines, HCT-116 and Caco-2. In general, the C1 position of ring A is tolerant of alkoxy substituents as well as a benzoyl ester functionality. Other modifications evaluated resulted in a decrease in cytotoxic activity. The most potent compounds identified had IC(50) values in the range 23-38 mu M, comparable to the known cytotoxic agent, etoposide. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.005
• 作为产物：
  描述：

  ethyl (12S)-19-hydroxy-18-methoxy-5,7-dioxa-13-azapentacyclo[10.7.1.02,10.04,8.016,20]icosa-1(20),2,4(8),9,16,18-hexaene-13-carboxylate 在 lithium aluminium tetrahydride 、 三乙酰氧基硼氢化钠 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 Domesticin
  参考文献：
  名称：

  Cytotoxicity of aporphines in human colon cancer cell lines HCT-116 and Caco-2: An SAR study

  摘要：

  A series of synthetic aporphine derivatives structurally related to domesticine and nantenine (ring A, N6 and ring C truncated analogs), was evaluated in MTS cytotoxicity assays against the human colon cancer cell lines, HCT-116 and Caco-2. In general, the C1 position of ring A is tolerant of alkoxy substituents as well as a benzoyl ester functionality. Other modifications evaluated resulted in a decrease in cytotoxic activity. The most potent compounds identified had IC(50) values in the range 23-38 mu M, comparable to the known cytotoxic agent, etoposide. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.005

文献信息

• Johns,S.R. et al., Australian Journal of Chemistry, 1966, vol. 19, p. 2331 - 2338
  作者：Johns,S.R. et al.

  DOI：——

  日期：——
• Slavikova, Leonora; Slavik, Jiri; Dolejs, Ladislav, Collection of Czechoslovak Chemical Communications, 1985, vol. 50, # 4, p. 854 - 860
  作者：Slavikova, Leonora、Slavik, Jiri、Dolejs, Ladislav

  DOI：——

  日期：——
• Cytotoxicity of aporphines in human colon cancer cell lines HCT-116 and Caco-2: An SAR study
  作者：Shashikanth Ponnala、Sandeep Chaudhary、Antonio González-Sarrias、Navindra P. Seeram、Wayne W. Harding

  DOI：10.1016/j.bmcl.2011.06.005

  日期：2011.8

  A series of synthetic aporphine derivatives structurally related to domesticine and nantenine (ring A, N6 and ring C truncated analogs), was evaluated in MTS cytotoxicity assays against the human colon cancer cell lines, HCT-116 and Caco-2. In general, the C1 position of ring A is tolerant of alkoxy substituents as well as a benzoyl ester functionality. Other modifications evaluated resulted in a decrease in cytotoxic activity. The most potent compounds identified had IC(50) values in the range 23-38 mu M, comparable to the known cytotoxic agent, etoposide. (C) 2011 Elsevier Ltd. All rights reserved.