7-(3,5-dibromophenyl)-2-hydroxy-7,11-dihydrobenzo[h]furo[3,4-b]quinolin-8(10H)-one | 1309571-52-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7-(3,5-dibromophenyl)-2-hydroxy-7,11-dihydrobenzo[h]furo[3,4-b]quinolin-8(10H)-one
• 英文别名: 11-(3,5-Dibromophenyl)-4-hydroxy-14-oxa-17-azatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2(7),3,5,8,12(16)-hexaen-13-one
• CAS: 1309571-52-5
• 化学式: C₂₁H₁₃Br₂NO₃
• 分子量: 487.147
• InChiKey: FWGWURLCLVRGMZ-UHFFFAOYSA-N

物化性质

• 沸点：
  655.4±55.0 °C(Predicted)
• 密度：
  1.91±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-羟乙酰乙酸内酯 、 1-氨基-7-萘酚 、 3,5-二溴苯甲醛 以 乙醇 为溶剂， 以50%的产率得到7-(3,5-dibromophenyl)-2-hydroxy-7,11-dihydrobenzo[h]furo[3,4-b]quinolin-8(10H)-one
  参考文献：
  名称：

  Anticancer Properties of an Important Drug Lead Podophyllotoxin Can Be Efficiently Mimicked by Diverse Heterocyclic Scaffolds Accessible via One-Step Synthesis

  摘要：

  Structural simplification of an antimitotic natural product podophyllotoxin with mimetic heterocyclic scaffolds constructed using multicomponent reactions led to the identification of compounds exhibiting low nanomolar antiproliferative and apoptosis-inducing properties. The most potent compounds were found in the dihydropyridopyrazole, dihydropyridonaphthalene, dihydropyridoindole, and dihydropyridopyrimidine scaffold series. Biochemical mechanistic studies, performed with dihydropyridopyrazole compounds showed that these heterocycles inhibit in vitro tubulin polymerization and disrupt the formation of mitotic spindles in dividing cells at low nanomolar concentrations, in a manner similar to podophyllotoxin itself. Separation of a racemic dihydropyridonaphthalene into individual enantiomers demonstrated that only the optical antipode matching the absolute configuration of podophyllotoxin possessed potent anticancer activity. Computer modeling, performed using the podophyllotoxin binding site on P-tubulin, provided a theoretical understanding of these successful experimental findings.

  DOI：

  10.1021/jm200410r

文献信息

• LIPID PRODRUGS FOR USE IN DRUG DELIVERY
  申请人：New Mexico Tech University Research Park Corporation

  公开号：EP3773734A1

  公开（公告）日：2021-02-17
• [EN] LIPID PRODRUGS FOR USE IN DRUG DELIVERY<br/>[FR] PROMÉDICAMENTS LIPIDIQUES DESTINÉS À ÊTRE UTILISÉS DANS L'ADMINISTRATION DE MÉDICAMENTS
  申请人：NEW MEXICO TECH UNIV RESEARCH PARK COPORATION

  公开号：WO2019200043A1

  公开（公告）日：2019-10-17

  The present disclosure describes the synthesis and use of lipid prodrugs that self-assemble into lipid microbubbles or liposomes. The prodrug-loaded microbubbles or liposomes can be activated intracellularly using an external stimulus, for example, using ultrasound waves.