ortho-quinonemethide | 1439356-89-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 喜树碱
• 英文名称: ortho-quinonemethide
• 英文别名: (19S)-19-ethyl-19-hydroxy-8-methylidene-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,10,15(20)-hexaene-7,14,18-trione
• CAS: 1439356-89-4
• 化学式: C₂₁H₁₆N₂O₅
• 分子量: 376.368
• InChiKey: CNZMUNMUDGFPBU-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  96.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  10-hydroxyl-9-L-prolinol (+)methylcamptothecin 在 sodium hypochlorite 作用下， 以92.1%的产率得到ortho-quinonemethide
  参考文献：
  名称：

  Cyclane-aminol 10-hydroxycamptothecin analogs as novel DNA topoisomerase I inhibitors induce apoptosis selectively in tumor cells

  摘要：

  A novel series of cyclane-aminol 10-hydroxycamptothecin (HCPT) analogs was designed and synthesized through the Mannich reaction using HCPT as the lead compound, such as 10-hydroxyl-9-L-prolinol (+) methylcamptothecin (PRPT), 10-hydroxyl-9-(4'-hydroxy) piperidinylmethylcamptothecin (PPPT), and 10-hydroxy-9(4'-hydroxyethyl)-piperazinylmethycamptothecin (QPPT). Three kinds of new cyclane-aminols were introduced into the structure of HCPT, which modified strong cytotoxic HCPT into cyclane-aminol HCPT analogs with moderate cytotoxicity and improved selectivity toward DNA topoisomerase I inhibition in tumor cells. Special metabolic pathways for cyclane-aminol HCPT analogs in rats were discovered, which differed from other HCPT analogs. Cyclane-aminol HCPT analogs can capture O-2(-) and cause an increase in intracellular hydrogen peroxide levels with selective induction of apoptosis in tumor cells rather than in normal peripheral blood mononuclear cells. Among them, PPPT has a much better druggability than topotecan (TPT) and has the potential to be developed into an antitumor agent. (C) 2014 Wolters Kluwer Health vertical bar Lippincott Williams & Wilkins.

  DOI：

  10.1097/cad.0000000000000083

文献信息

• DERIVATIVES OF CAMPTOTHECIN, A METHOD OF PRODUCING THEM AND THEIR USE
  申请人：INSTYTUT CHEMII ORGANICZNEJ POLSKIEJ AKADEMII NAUK

  公开号：US20150266888A1

  公开（公告）日：2015-09-24

  The subject of the present invention are water-soluble derivatives of camptothecin, their synthesis and use. These compounds exhibit preferable biological properties for use in anti-neoplasm therapy.
• US9682992B2
  申请人：——

  公开号：US9682992B2

  公开（公告）日：2017-06-20