Ethyl 2-chloro-3-fluoro-5-oxo-5H-benzo[4,5]thiazolo[3,2-a][1,8]naphthyridine-6-carboxylate | 105686-24-6

• 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: Ethyl 2-chloro-3-fluoro-5-oxo-5H-benzo[4,5]thiazolo[3,2-a][1,8]naphthyridine-6-carboxylate
• 英文别名: ethyl 2-chloro-3-fluoro-5-oxo-[1,3]benzothiazolo[3,2-a][1,8]naphthyridine-6-carboxylate
• CAS: 105686-24-6
• 化学式: C₁₇H₁₀ClFN₂O₃S
• 分子量: 376.795
• InChiKey: UNYLVECBXTUFND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  84.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Ethyl 2-chloro-3-fluoro-5-oxo-5H-benzo[4,5]thiazolo[3,2-a][1,8]naphthyridine-6-carboxylate 在 aluminum (III) chloride 作用下， 以 N-甲基吡咯烷酮 、 二氯甲烷 为溶剂， 生成 3-Fluoro-6-(4-methylpiperazine-1-carbonyl)-2-morpholin-4-yl-[1,3]benzothiazolo[3,2-a][1,8]naphthyridin-5-one
  参考文献：
  名称：

  Discovery of CX-5461, the First Direct and Selective Inhibitor of RNA Polymerase I, for Cancer Therapeutics

  摘要：

  Accelerated proliferation of solid tumor and hematologic cancer cells is linked to accelerated transcription of rDNA by the RNA polymerase I (Pol I) enzyme to produce elevated levels of rRNA (rRNA). Indeed, upregulation of Pol I, frequently caused by mutational alterations among tumor suppressors and oncogenes, is required for maintenance of the cancer phenotype and forms the basis for seeking selective inhibitors of Pot I as anticancer therapeutics. 2-(4-Methyl-[1,4]diazepan-1-yl)-5-oxo-5H-7-thia-1,11b-diaza-benzo[c]fluorene-6-carboxylic acid (5-methyl-pyrazin-2-ylmethyl)-amide (CX-5461, 7c) has been identified as the first potent, selective, and orally bioavailable inhibitor of RNA Pot I transcription with in vivo activity in tumor growth efficacy models. The preclinical data support the development of CX-5461 as an anticancer drug with potential for activity in several types of cancer.

  DOI：

  10.1021/ml300110s
• 作为产物：
  描述：

  2-(2-苯并噻唑)乙酸乙酯 、 2,6-二氯-5-氟代烟酰氯 在 三乙胺 、 magnesium chloride 作用下， 生成 Ethyl 2-chloro-3-fluoro-5-oxo-5H-benzo[4,5]thiazolo[3,2-a][1,8]naphthyridine-6-carboxylate
  参考文献：
  名称：

  Discovery of CX-5461, the First Direct and Selective Inhibitor of RNA Polymerase I, for Cancer Therapeutics

  摘要：

  Accelerated proliferation of solid tumor and hematologic cancer cells is linked to accelerated transcription of rDNA by the RNA polymerase I (Pol I) enzyme to produce elevated levels of rRNA (rRNA). Indeed, upregulation of Pol I, frequently caused by mutational alterations among tumor suppressors and oncogenes, is required for maintenance of the cancer phenotype and forms the basis for seeking selective inhibitors of Pot I as anticancer therapeutics. 2-(4-Methyl-[1,4]diazepan-1-yl)-5-oxo-5H-7-thia-1,11b-diaza-benzo[c]fluorene-6-carboxylic acid (5-methyl-pyrazin-2-ylmethyl)-amide (CX-5461, 7c) has been identified as the first potent, selective, and orally bioavailable inhibitor of RNA Pot I transcription with in vivo activity in tumor growth efficacy models. The preclinical data support the development of CX-5461 as an anticancer drug with potential for activity in several types of cancer.

  DOI：

  10.1021/ml300110s

文献信息

• QUINOLONE ANALOGS AND METHODS RELATED THERETO
  申请人：NAGASAWA Johnny Yasuo

  公开号：US20090093455A1

  公开（公告）日：2009-04-09

  The present invention provides novel quinolone compounds and pharmaceutical composition thereof which may inhibit cell proliferation and/or induce cell apoptosis. The present invention also provides methods of preparing such compounds and compositions, and methods of making and using the same.

  本发明提供了新型喹诺酮化合物及其药物组合物，可以抑制细胞增殖和/或诱导细胞凋亡。本发明还提供了制备这种化合物和组合物的方法，以及制备和使用它们的方法。
• Methods of preparing quinolone analogs
  申请人：Chua C. Peter

  公开号：US20070032652A1

  公开（公告）日：2007-02-08

  The present invention relates to the preparation of compounds which are capable of inducing cell death such as apoptotic cell death (apoptosis), and/or for reducing a cell proliferative disorder.

  本发明涉及制备能够诱导细胞死亡，如凋亡细胞死亡（细胞凋亡），和/或用于减少细胞增殖紊乱的化合物。
• [EN] QUINOLONE ANALOGS AND METHODS RELATED THERETO<br/>[FR] ANALOGUES DE QUINOLONE ET PROCÉDÉS ASSOCIÉS
  申请人：CYLENE PHARMACEUTICALS INC

  公开号：WO2009046383A1

  公开（公告）日：2009-04-09

  The present invention provides novel quinolone compounds and pharmaceutical composition thereof which may inhibit cell proliferation and/or induce cell apoptosis. The present invention also provides methods of preparing such compounds and compositions, and methods of making and using the same.

  本发明提供了新型的喹诺酮化合物及其制药组合物，可抑制细胞增殖和/或诱导细胞凋亡。本发明还提供了制备这种化合物和组合物的方法，以及使用它们的方法。
• METHODS OF PREPARING QUINOLONE ANALOGS
  申请人：CHUA Peter C.

  公开号：US20090082565A1

  公开（公告）日：2009-03-26

  The present invention relates to the preparation of compounds which are capable of inducing cell death such as apoptotic cell death (apoptosis), and/or for reducing a cell proliferative disorder.

  本发明涉及制备能够诱导细胞死亡，例如凋亡细胞死亡（凋亡），和/或减少细胞增殖紊乱的化合物。
• Facile and efficient generation of quinolone amides from esters using aluminum chloride
  作者：Michael K. Schwaebe、David M. Ryckman、Johnny Y. Nagasawa、Fabrice Pierre、Anne Vialettes、Mustapha Haddach

  DOI：10.1016/j.tetlet.2010.12.108

  日期：2011.3

  Quinolone esters are readily converted into the corresponding amides using aluminum chloride at room temperature in excellent yields and purities. The method is both general and scalable to multi-kilogram quantities. (C) 2011 Elsevier Ltd. All rights reserved.