tert-butyl-3-[3-(dimethylamino)-5,11-dioxo-5H-indeno[1,2-c]isoquinolin-6-(11H)-yl]propylcarbamate | 1383663-21-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: tert-butyl-3-[3-(dimethylamino)-5,11-dioxo-5H-indeno[1,2-c]isoquinolin-6-(11H)-yl]propylcarbamate
• 英文别名: tert-butyl N-[3-[3-(dimethylamino)-5,11-dioxoindeno[1,2-c]isoquinolin-6-yl]propyl]carbamate
• CAS: 1383663-21-5
• 化学式: C₂₆H₂₉N₃O₄
• 分子量: 447.534
• InChiKey: VZFRHMMCRUFHCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  79
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl-3-[3-(dimethylamino)-5,11-dioxo-5H-indeno[1,2-c]isoquinolin-6-(11H)-yl]propylcarbamate 在 盐酸 作用下， 以 乙醚 、 氯仿 为溶剂， 反应 1.0h， 以95%的产率得到6-(3-aminopropyl)-3-(dimethylamino)-5H-indeno[1,2-c]isoquinoline-5,11-(6H)-dione
  参考文献：
  名称：

  Identification, Synthesis, and Biological Evaluation of the Metabolites of 3-Amino-6-(3′-aminopropyl)-5H-indeno[1,2-c]isoquinoline-5,11-(6H)dione (AM6–36), a Promising Rexinoid Lead Compound for the Development of Cancer Chemotherapeutic and Chemopreventive Agents

  摘要：

  Activation of the retinoid X receptor (RXR), which is involved in cell proliferation, differentiation, and apoptosis, is a strategy for cancer chemotherapy and chemoprevention, and 3-amino-6-(3'-aminopropyl)-5H-indeno[1,2-c]isoquinoline-5,11-(6H)dione (AM6-36) (3) is among the few RXR ligands known. The presently reported studies of 3 include its binding to human plasma proteins, metabolic stability using human liver microsomes, metabolism by human liver microsomes and hepatocytes, and in vivo disposition in rat serum, liver, and mammary tissue. Compound 3 was 75% bound to human plasma proteins, and its metabolic stability was much greater than propranolol. One phase I metabolite was formed by human liver microsomes, seven phase I and II metabolites were formed by human hepatoc-ytes, and five metabolites were detected in rat serum and liver after oral administration. The putative metabolites predicted using LC-MS-MS were synthesized to confirm their structures and to provide sufficient material for investigation of induction of RXRE transcriptional activity and inhibition of NF kappa B.

  DOI：

  10.1021/jm3006806
• 作为产物：
  描述：

  6-(3-aminopropyl)-3-nitro-5H-indeno[1,2-c]isoquinoline-5,11(6H)-dione hydrochloride 在 palladium 10% on activated carbon 、 氢气 、 sodium cyanoborohydride 、 三乙胺 作用下， 以 甲醇 、 氯仿 、 溶剂黄146 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 4.0h， 生成 tert-butyl-3-[3-(dimethylamino)-5,11-dioxo-5H-indeno[1,2-c]isoquinolin-6-(11H)-yl]propylcarbamate
  参考文献：
  名称：

  Identification, Synthesis, and Biological Evaluation of the Metabolites of 3-Amino-6-(3′-aminopropyl)-5H-indeno[1,2-c]isoquinoline-5,11-(6H)dione (AM6–36), a Promising Rexinoid Lead Compound for the Development of Cancer Chemotherapeutic and Chemopreventive Agents

  摘要：

  Activation of the retinoid X receptor (RXR), which is involved in cell proliferation, differentiation, and apoptosis, is a strategy for cancer chemotherapy and chemoprevention, and 3-amino-6-(3'-aminopropyl)-5H-indeno[1,2-c]isoquinoline-5,11-(6H)dione (AM6-36) (3) is among the few RXR ligands known. The presently reported studies of 3 include its binding to human plasma proteins, metabolic stability using human liver microsomes, metabolism by human liver microsomes and hepatocytes, and in vivo disposition in rat serum, liver, and mammary tissue. Compound 3 was 75% bound to human plasma proteins, and its metabolic stability was much greater than propranolol. One phase I metabolite was formed by human liver microsomes, seven phase I and II metabolites were formed by human hepatoc-ytes, and five metabolites were detected in rat serum and liver after oral administration. The putative metabolites predicted using LC-MS-MS were synthesized to confirm their structures and to provide sufficient material for investigation of induction of RXRE transcriptional activity and inhibition of NF kappa B.

  DOI：

  10.1021/jm3006806