2-(3-bromo-4-methylphenyl)-1,3-dioxolane | 124717-60-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(3-bromo-4-methylphenyl)-1,3-dioxolane
• 英文别名: 3-bromo-4-methylbenzaldehyde ethylene acetal；1,3-Dioxolane, 2-(3-bromo-4-methylphenyl)-
• CAS: 124717-60-8
• 化学式: C₁₀H₁₁BrO₂
• 分子量: 243.1
• InChiKey: YTQXPAWDHPRBBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-bromo-4-methylphenyl)-1,3-dioxolane 在 盐酸 、 正丁基锂 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 3.5h， 生成 4-methyl-3-(methylsulfonyl)benzaldehyde
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of a Novel Series of 2,3,5,6,7,9-Hexahydrothieno[3,2-b]quinolin-8(4H)-one 1,1-Dioxide K_ATP Channel Openers:  Discovery of (−)-(9S)-9-(3-Bromo-4-fluorophenyl)-2,3,5,6,7,9- hexahydrothieno[3,2-b]quinolin-8(4H)-one 1,1-Dioxide (A-278637), a Potent K_ATP Opener That Selectively Inhibits Spontaneous Bladder Contractions

  摘要：

  Structure-activity relationships were investigated on a novel series of sulfonyldihydropyridine-containing K-ATP openers. Ring sizes, absolute stereochemistry, and aromatic substitution were evaluated for K-ATP activity in guinea pig bladder cells using a fluorescence-based membrane potential assay and in a pig bladder strip assay. The inhibition of spontaneous bladder contractions in vitro was also examined for a select group of compounds. All compounds studied showed greater potency to inhibit spontaneous bladder contractions relative to their potencies to inhibit contractions elicited by electrical stimulation. In an anesthetized pig model of myogenic bladder overactivity, compound 14 and (-)-cromakalim 1 were found to inhibit spontaneous bladder contractions in vivo at plasma concentrations lower than those that affected hemodynamic parameters. Compound 14 showed approximately 5-fold greater selectivity than I in vivo and supports the concept that bladder-selective K-ATP channel openers may have utility in the treatment of overactive bladder.

  DOI：

  10.1021/jm030356w
• 作为产物：
  描述：

  3-溴-4-甲基苯甲醛 、 乙二醇 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以94%的产率得到2-(3-bromo-4-methylphenyl)-1,3-dioxolane
  参考文献：
  名称：

  植物抗肿瘤剂。29.喜树碱的D环和E环修饰的类似物的合成和生物学活性。

  摘要：

  描述了由对甲苯甲醛分11个步骤的五环喜树碱类似物3和4的全合成。化合物3的整体形状与有效的天然喜树碱（1a）相同。尽管从三维的角度来看3和1b（外消旋，（20RS）-喜树碱）具有近乎空间的同一性，但9KB和9PS细胞毒性试验表明3的活性至少比1b降低了40-60倍，且异构体4不活泼。同样，对拓扑异构酶I活性的抑制研究表明，对3的活性很小，对4的活性却没有。显然，吡啶酮环D对于抗肿瘤活性是必不可少的。描述了喜树碱的三个E环修饰类似物2d-f，其中的净变化是E环中的O被N取代。

  DOI：

  10.1021/jm00165a014

文献信息

• Triaromatic vitamin D analogues
  申请人：——

  公开号：US20030195259A1

  公开（公告）日：2003-10-16

  The invention relates, as novel and useful industrial products, to triaromatic compounds, which are vitamin D analogues, of general formula (I): 1 and also to a method for preparing them and to their use in pharmaceutical compositions intended for use in human or veterinary medicine, or alternatively in cosmetic compositions.

  该发明涉及一种新颖且有用的工业产品，即一般式(I)的三芳基化合物，它们是维生素D类似物，同时涉及一种制备它们的方法以及它们在用于人类或兽医药物的制剂中的使用，或者在化妆品制剂中的使用。
• Plant antitumor agents. 29. Synthesis and biological activity of ring D and ring E modified analogs of camptothecin
  作者：Allan W. Nicholas、Mansukh C. Wani、Govindarajan Manikumar、Monroe E. Wall、Kurt W. Kohn、Yves Pommier

  DOI：10.1021/jm00165a014

  日期：1990.3

  activity for 3 and no activity for 4. It is evident that the pyridone ring D is essential for antitumor activity. Three E ring modified analogues of camptothecin, 2d-f, are described in which the net change is replacement of O by N in ring E. Compared to (20S)-camptothecin (1a) or (20RS)-camptothecin (1b), the ring E modified analogues 2d-f display little or no cytotoxic activity, greatly reduced effect

  描述了由对甲苯甲醛分11个步骤的五环喜树碱类似物3和4的全合成。化合物3的整体形状与有效的天然喜树碱（1a）相同。尽管从三维的角度来看3和1b（外消旋，（20RS）-喜树碱）具有近乎空间的同一性，但9KB和9PS细胞毒性试验表明3的活性至少比1b降低了40-60倍，且异构体4不活泼。同样，对拓扑异构酶I活性的抑制研究表明，对3的活性很小，对4的活性却没有。显然，吡啶酮环D对于抗肿瘤活性是必不可少的。描述了喜树碱的三个E环修饰类似物2d-f，其中的净变化是E环中的O被N取代。
• NICHOLAS, ALLAN W.;WANI, MANSUKH C.;MANIKUMAR, GOVINDARAJAN;WALL, MONROE +, J. MED. CHEM., 33,(1990) N, C. 972-978
  作者：NICHOLAS, ALLAN W.、WANI, MANSUKH C.、MANIKUMAR, GOVINDARAJAN、WALL, MONROE +

  DOI：——

  日期：——
• POTASSIUM CHANNEL OPENERS
  申请人：Abbott Laboratories

  公开号：EP1194429A1

  公开（公告）日：2002-04-10
• ANALOGUES DE LA VITAMINE D
  申请人：GALDERMA RESEARCH & DEVELOPMENT

  公开号：EP1456160B1

  公开（公告）日：2010-01-20