(3E)-6[(Tert-butyldiphenylsilyl)oxy]hex-3-ene-1-YL methanesulfonate | 1383153-81-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (3E)-6[(Tert-butyldiphenylsilyl)oxy]hex-3-ene-1-YL methanesulfonate
• 英文别名: [(E)-6-[tert-butyl(diphenyl)silyl]oxyhex-3-enyl] methanesulfonate
• CAS: 1383153-81-8
• 化学式: C₂₃H₃₂O₄SSi
• 分子量: 432.656
• InChiKey: HIPBTRJVRPPRNQ-AATRIKPKSA-N

物化性质

• 沸点：
  521.0±50.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.88
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3E)-6[(Tert-butyldiphenylsilyl)oxy]hex-3-ene-1-YL methanesulfonate 在 吡啶 、 sodium azide 、 四丁基氟化铵 、 水 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 生成 [(E)-6-[[14-[2-(dimethylamino)ethyl]-8-oxo-4,14,15-triazatetracyclo[7.6.1.02,7.013,16]hexadeca-1(15),2(7),3,5,9,11,13(16)-heptaen-10-yl]amino]hex-3-enyl] methanesulfonate
  参考文献：
  名称：

  Synthesis and biological evaluation of new cytotoxic indazolo[4,3-gh]isoquinolinone derivatives

  摘要：

  A series of indazolo[4,3-gh]isoquinolinones derivatives have been synthesized to decrease cardiotoxic side effects in comparison to Mitoxantrone. The antiproliferative effects of different side chains were investigated and tested on at least four different cell lines of cervix, ovarian, CNS, NSCLC (non-small-cell lung cancer) and colon carcinoma. In addition to antiproliferative activities, influence on cell cycle and intercalation behavior have been tested. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.022

文献信息

• Design, Synthesis, and Biological Evaluation of <i>N</i>-Alkylated Deoxynojirimycin (DNJ) Derivatives for the Treatment of Dengue Virus Infection
  作者：Wenquan Yu、Tina Gill、Lijuan Wang、Yanming Du、Hong Ye、Xiaowang Qu、Ju-Tao Guo、Andrea Cuconati、Kang Zhao、Timothy M. Block、Xiaodong Xu、Jinhong Chang

  DOI：10.1021/jm300171v

  日期：2012.7.12

  We recently described the discovery of oxygenated N-alkyl deoxynojirimycin (DNJ) derivative 7 (CM-10-18) with antiviral activity against dengue virus (DENY) infection both in vitro and in vivo. This imino sugar was promising but had an EC50 against DENY in BHK cells of 6.5 mu M, which limited its use in in vivo. Compound 7 presented structural opportunities for activity relationship analysis, which we exploited and report here. These structure activity relationship studies led to analogues 2h, 2l, 3j, 3l, 3v, and 4b-4c with nanomolar antiviral activity (EC50 = 0.3-0.5 mu M) against DENY infection, while maintaining low cytotoxicity (CC50 > 500 mu M, SI > 1000). In male Sprague-Dawley rats, compound 3l was well tolerated at a dose up to 200 mg/kg and displayed desirable PK profiles, with significantly improved bioavailability (F = 92 +/- 4%).
• Synthesis and biological evaluation of new cytotoxic indazolo[4,3-gh]isoquinolinone derivatives
  作者：Manochehr Shahabi、Eva Schirmer、Karem Shanab、Theerachart Leepasert、Jana Ruzicka、Wolfgang Holzer、Helmut Spreitzer、Babette Aicher、Peter Schmidt、Lars Blumenstein、Gilbert Müller、Eckhard Günther

  DOI：10.1016/j.bmcl.2013.01.022

  日期：2013.3

  A series of indazolo[4,3-gh]isoquinolinones derivatives have been synthesized to decrease cardiotoxic side effects in comparison to Mitoxantrone. The antiproliferative effects of different side chains were investigated and tested on at least four different cell lines of cervix, ovarian, CNS, NSCLC (non-small-cell lung cancer) and colon carcinoma. In addition to antiproliferative activities, influence on cell cycle and intercalation behavior have been tested. (C) 2013 Elsevier Ltd. All rights reserved.