(S)-5-methoxy-1-((R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3-oxo-1,3-dihydroisobenzofuran-4-yl benzoate | 1314077-43-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 邻苯二甲酸异喹啉类
• 英文名称: (S)-5-methoxy-1-((R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3-oxo-1,3-dihydroisobenzofuran-4-yl benzoate
• 英文别名: [(1S)-5-methoxy-1-[(5R)-4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3-oxo-1H-2-benzofuran-4-yl] benzoate
• CAS: 1314077-43-4
• 化学式: C₂₈H₂₅NO₈
• 分子量: 503.508
• InChiKey: CDFNXANKOIRXPT-PKTZIBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  92.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  那可汀 在 sodium azide 、 potassium carbonate 、 sodium iodide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (S)-5-methoxy-1-((R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3-oxo-1,3-dihydroisobenzofuran-4-yl benzoate
  参考文献：
  名称：

  [EN] SYNTHESIS AND CHARACTERIZATION OF SECOND GENERATION BENZOFURANONE RING SUBSTITUTED NOSCAPINE ANALOGS
  [FR] SYNTHÈSE ET CARACTÉRISATION D'ANALOGUES DE NOSCAPINE À CYCLE BENZOFURANONE SUBSTITUÉ DE DEUXIÈME GÉNÉRATION

  摘要：

  本文描述了式(I)化合物及其在癌症治疗中作为微管调节剂的用途：

  公开号：

  WO2012171002A1

文献信息

• Synthesis and Characterization of Second Generation Benzofuranone Ring Substituted Noscapine Analogs
  申请人：Aneja Ritu

  公开号：US20140121233A1

  公开（公告）日：2014-05-01

  Compound of Formula (I) and use thereof as microtubule modulating agents in the treatment of cancer are described herein.

  本文描述了化合物I的组合物及其在癌症治疗中作为微管调节剂的用途。
• Second generation benzofuranone ring substituted noscapine analogs: Synthesis and biological evaluation
  作者：Ram Chandra Mishra、Prasanthi Karna、Sushma Reddy Gundala、Vaishali Pannu、Richard A. Stanton、Kamlesh Kumar Gupta、M. Hope Robinson、Manu Lopus、Leslie Wilson、Maged Henary、Ritu Aneja

  DOI：10.1016/j.bcp.2011.03.029

  日期：2011.7

  Microtubules, composed of alpha/beta tubulin heterodimers, represent a validated target for cancer chemotherapy. Thus, tubulin- and microtubule-binding antimitotic drugs such as taxanes and vincas are widely employed for the chemotherapeutic management of various malignancies. Although quite successful in the clinic, these drugs are associated with severe toxicity and drug resistance problems. Noscapinoids represent an emerging class of microtubule-modulating anticancer agents based upon the parent molecule noscapine, a naturally occurring non-toxic cough-suppressant opium alkaloid. Here we report in silico molecular modeling, chemical synthesis and biological evaluation of novel analogs derived by modification at position-7 of the benzofuranone ring system of noscapine. The synthesized analogs were evaluated for their tubulin polymerization activity and their biological activity was examined by their antiproliferative potential using representative cancer cell lines from varying tissue-origin [A549 (lung), CEM (lymphoma), MIA PaCa-2 (pancreatic), MCF-7 (breast) and PC-3 (prostate)]. Cell-cycle studies were performed to explore their ability to halt the cell-cycle and induce subsequent apoptosis. The varying biological activity of these analogs that differ in the nature and bulk of substituent at position-7 was rationalized utilizing predictive in silico molecular modeling. (C) 2011 Elsevier Inc. All rights reserved.
• [EN] SYNTHESIS AND CHARACTERIZATION OF SECOND GENERATION BENZOFURANONE RING SUBSTITUTED NOSCAPINE ANALOGS<br/>[FR] SYNTHÈSE ET CARACTÉRISATION D'ANALOGUES DE NOSCAPINE À CYCLE BENZOFURANONE SUBSTITUÉ DE DEUXIÈME GÉNÉRATION
  申请人：UNIV GEORGIA STATE

  公开号：WO2012171002A1

  公开（公告）日：2012-12-13

  Compounds of Formula (I) and use thereof as microtubule modulating agents in the treatment of cancer are described herein:

  本文描述了式(I)化合物及其在癌症治疗中作为微管调节剂的用途：